57 days in United States, Montreal & Havana Itinerary

57 days in United States, Montreal & Havana Itinerary

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Route & dates

Start: New York City, United States
Fly:  5 h 30 min
1
Niagara Falls, United States
— 2 nights
+4
Train + Tram + Foot + Ferry + Fly:  5 h 30 min
2
Montreal, Canada
— 2 nights
Fly + Drive:  7 h 30 min
3
Acadia National Park, United States
— 1 night
Drive:  3 h 30 min
4
Portland, United States
— 2 nights
Drive:  5 h 15 min
5
Saratoga Springs, United States
— 1 night
Bus:  45 min
6
Albany, United States
— 2 nights
Drive:  3 h 30 min
7
Salem, United States
— 3 nights
Train:  45 min
8
Boston, United States
— 3 nights
Train:  1 h
9
Plymouth, United States
— 1 night
Drive:  2 h 30 min
10
Hartford, United States
— 1 night
Drive:  2 h 30 min
11
New York City, United States
— 5 nights
Train:  2 h
12
Philadelphia, United States
— 2 nights
Drive:  2 h 30 min
13
Gettysburg, United States
— 2 nights
Drive:  1 h 30 min
14
Baltimore, United States
— 1 night
Train:  1 h
15
Washington DC, United States
— 2 nights
Drive:  1 h
16
Mount Vernon, United States
— 1 night
Drive:  2 h 30 min
17
Williamsburg, United States
— 2 nights
Train:  1 h
18
Richmond, United States
— 1 night
Bus:  1 h 15 min
19
Charlottesville, United States
— 1 night
Fly:  5 h 30 min
20
Louisville, United States
— 2 nights
Drive:  3 h
21
Nashville, United States
— 2 nights
Drive:  4 h 30 min
22
Great Smoky Mountains National Park, United States
— 1 night
Drive:  2 h 30 min
23
Asheville, United States
— 1 night
Fly:  4 h
24
Atlanta, United States
— 1 night
Fly:  3 h
25
Charleston, United States
— 2 nights
Drive:  2 h 30 min
26
Savannah, United States
— 1 night
Fly:  6 h 30 min
27
New Orleans, United States
— 2 nights
+2
Fly + Taxi + Bus:  7 h
28
St. Augustine, United States
— 1 night
+2
Fly + Tram + Train:  4 h 30 min
29
Fort Lauderdale, United States
— 1 night
Bus:  1 h
30
Miami, United States
— 1 night
Fly:  4 h
31
Havana, Cuba
— 5 nights
Fly:  7 h 15 min
End: New York City, United States

2
nights
Niagara Falls, United States

Niagara Falls ©
The city of Niagara Falls houses the U.S.
Your day-by-day itinerary now includes Genesee Country Village & Museum as well as Bridal Veil Falls. Kick off your visit on the 9th (Sat): take in the dramatic scenery at Bridal Veil Falls, explore the fascinating underground world of Cave of the Winds, then take in panoramic vistas at Niagara Falls Observation Tower, then see the interesting displays at Niagara Power Project Visitors Center, and finally trek along Niagara Gorge Trail. Get ready for a full day of sightseeing on the next day: admire the masterpieces at Genesee Country Village & Museum and then admire the masterpieces at Castellani Art Museum of Niagara University.

To see more things to do, ratings, traveler tips, and other tourist information, you can read our Niagara Falls trip itinerary builder website.

New York City to Niagara Falls is an approximately 5.5- hour flight. You can also do a combination of bus and flight; or drive. Traveling from New York City in May, you can expect nighttime temperatures to be slightly colder in Niagara Falls, with lows of 49°F. Wrap up your sightseeing by early afternoon on the 10th (Sun) to allow enough time to travel to Montreal.

Things to do in Niagara Falls

Parks Museums Nature

Side Trips

Genesee Country Village & Museum, Niagara Power Project Visitors Center
Find places to stay May 8 — 10:
Highlights from your plan
Cave of the Winds ©
Cave of the Winds
Genesee Country Village & Museum ©
Genesee Country Village & Museum
Niagara Power Project Visitors Center ©
Niagara Power Project Visitors Center

2
nights
Montreal, Canada

Montreal ©
Quebec's economic and cultural capital, Montreal serves as the province's major point of entry, known for its rich history and high standard of living.
Your day-by-day itinerary now includes Pointe-a-Calliere, Montreal Archaeology and History Complex, Musee des beaux-arts de Montreal, Musee Redpath, and other attractions you added. Kick off your visit on the 11th (Mon): take an in-depth tour of Pointe-a-Calliere, Montreal Archaeology and History Complex, take in the architecture and atmosphere at St. Patrick's Basilica, learn more about the world around you at Musee Redpath, pause for some serene contemplation at Notre-Dame Basilica, then pause for some photo ops at Church of Saint-Leon-de-Westmount, and finally admire the masterpieces at Musee des beaux-arts de Montreal. Keep things going the next day: get a new perspective on nature at Biodome de Montreal, get engrossed in the history at Chateau Ramezay Historic Site and Museum of Montreal, and then see the interesting displays at Grevin Montreal.

Plan a Montreal trip in moments using our itinerary builder.

You can do a combination of train and flight from Niagara Falls to Montreal in 5.5 hours. Alternatively, you can drive; or take a train. In May, daily temperatures in Montreal can reach 68°F, while at night they dip to 50°F. Wrap up your sightseeing by early afternoon on the 12th (Tue) to allow enough time to travel to Acadia National Park.

Things to do in Montreal

Museums Historic Sites
Find places to stay May 10 — 12:
Highlights from your plan
Grevin Montreal ©
Grevin Montreal
Musee des beaux-arts de Montreal ©
Musee des beaux-arts de Montreal
Notre-Dame Basilica ©
Notre-Dame Basilica

1
night
Acadia National Park, United States

Acadia National Park ©
The first national park east of the Mississippi River, Acadia National Park draws visitors with its rugged landscape of ocean shoreline, low-slung granite mountains, dense woodlands, and pristine lakes.
Start off your visit on the 13th (Wed): tour the pleasant surroundings at Sieur de Monts Spring, trek along The Bowl Trail, then hike along Heart of Acadia Loop, then get engrossed in the history at Somesville Historical Museum and Gardens, and finally head outdoors with Dorr Mountain.

For reviews, where to stay, and more tourist information, read Acadia National Park driving holiday planner.

You can do a combination of flight and car from Montreal to Acadia National Park in 7.5 hours. Alternatively, you can drive; or do a combination of flight and bus. Plan for a bit cooler temperatures traveling from Montreal in May, with highs in Acadia National Park at 60°F and lows at 43°F. Finish up your sightseeing early on the 13th (Wed) so you can go by car to Portland.

Things to do in Acadia National Park

Parks Outdoors Trails

Side Trip

Somesville Historical Museum and Gardens
Find places to stay May 12 — 13:
Highlights from your plan
The Bowl Trail ©
The Bowl Trail
Heart of Acadia Loop ©
Heart of Acadia Loop
Sieur de Monts Spring ©
Sieur de Monts Spring

2
nights
Portland, United States

Portland ©
Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Your list of things to see and do now includes Fishing Charters & Tours, Eastern Promenade, DiMillo's Old Port Marina, and other attractions. Start off your visit on the 14th (Thu): enjoy breathtaking views from Portland Observatory, visit Old Port, learn about winemaking at Maine Mead Works, then browse the collection at Tate House Museum, then explore the world behind art at Portland Museum of Art, and finally go for a stroll along the water at DiMillo's Old Port Marina. Get ready for a full day of sightseeing on the next day: step off the mainland to explore Casco Bay Islands, stroll through Eastern Promenade, and then see what you can catch with a fishing tour.

To find photos, other places to visit, maps, and tourist information, use the Portland sightseeing site.

You can drive from Acadia National Park to Portland in 3.5 hours. Alternatively, you can do a combination of car and bus; or take a bus. In May, plan for daily highs up to 64°F, and evening lows to 45°F. Wrap up your sightseeing on the 15th (Fri) to allow time to drive to Saratoga Springs.

Things to do in Portland

Outdoors Parks Tours
Find places to stay May 13 — 15:
Highlights from your plan
Portland Museum of Art ©
Portland Museum of Art
Old Port ©
Old Port
Tate House Museum ©
Tate House Museum

1
night
Saratoga Springs, United States

Saratoga Springs ©
Named for the restorative mineral springs in the area, Saratoga Springs began its life as a resort town.
Your day-by-day itinerary now includes Saratoga Race Course, National Museum of Racing and Hall of Fame and Saratoga Spa State Park. Kick off your visit on the 16th (Sat): examine the collection at The Saratoga Automobile Museum, admire the majestic nature at Saratoga Spa State Park, then see the interesting displays at National Museum of Racing and Hall of Fame, and finally try your luck at Saratoga Race Course.

To see photos, reviews, and tourist information, read our Saratoga Springs route planner.

Traveling by car from Portland to Saratoga Springs takes 5.5 hours. Alternatively, you can do a combination of bus and flight; or do a combination of flight and bus. Traveling from Portland in May, plan for somewhat warmer nights in Saratoga Springs, with lows around 56°F. Cap off your sightseeing on the 16th (Sat) early enough to catch the bus to Albany.

Things to do in Saratoga Springs

Museums Casinos Parks
Find places to stay May 15 — 16:
Highlights from your plan
The Saratoga Automobile Museum ©
The Saratoga Automobile Museum
National Museum of Racing and Hall of Fame ©
National Museum of Racing and Hall of Fame
Saratoga Spa State Park ©
Saratoga Spa State Park

2
nights
Albany, United States

Albany ©
Albany is the capital of the U.S. Your day-by-day itinerary now includes Albany Institute of History & Art, Shaker Heritage Society and Ten Broeck Mansion.

To find more things to do, where to stay, other places to visit, and tourist information, refer to the Albany itinerary builder site.

You can take a bus from Saratoga Springs to Albany in an hour. Other options are to drive; or take a train. Traveling from Saratoga Springs in May, expect little chillier with lows of 49°F in Albany. You will have some time to spend on the 18th (Mon) before leaving for Salem.

Things to do in Albany

Museums Historic Sites Parks
Find places to stay May 16 — 18:
Highlights from your plan
New York State Museum ©
New York State Museum
Schuyler Mansion ©
Schuyler Mansion
Albany Institute of History & Art ©
Albany Institute of History & Art

3
nights
Salem, United States

Salem ©
Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
Deepen your sense of the past at sights like Old Burying Point Cemetery and Derby Wharf Light Station. Appreciate the collections at Phillips House and Witch House. There's much more to do: admire the masterpieces at Count Orlok's Nightmare Gallery, go for a stroll along the water at Pickering Wharf, sample the tasty concoctions at Notch Brewery & Tap Room, and get to know the fascinating history of Wicked Good Books.

To find ratings, where to stay, more things to do, and more tourist information, read Salem online trip builder.

You can drive from Albany to Salem in 3.5 hours. Other options are to do a combination of flight and train; or take a bus. In May, plan for daily highs up to 67°F, and evening lows to 48°F. Wrap up your sightseeing by early afternoon on the 21st (Thu) to allow enough time to take a train to Boston.

Things to do in Salem

Museums Historic Sites Breweries & Distilleries
Find places to stay May 18 — 21:
Highlights from your plan
Salem Old Town Hall ©
Salem Old Town Hall
Old Burying Point Cemetery ©
Old Burying Point Cemetery
Witch Dungeon Museum ©
Witch Dungeon Museum

3
nights
Boston, United States

Boston ©
Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Your list of things to see and do now includes The Paul Revere House, Samuel Adams Brewery, Newbury Street, and other attractions. Get some cultural insight at North End and Boston Tea Party Ships & Museum. Step off the beaten path and head to Old State House and The Mapparium. There's more to do: contemplate in the serene atmosphere at Trinity Church and steep yourself in history at Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill.

For other places to visit, traveler tips, maps, and tourist information, read our Boston trip builder tool.

Traveling by train from Salem to Boston takes an hour. Alternatively, you can drive; or take a bus. In May, daily temperatures in Boston can reach 67°F, while at night they dip to 50°F. You'll have a few hours on the 24th (Sun) to wrap things up before traveling to Plymouth.

Things to do in Boston

Museums Historic Sites Neighborhoods
Find places to stay May 21 — 24:
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Tea Party Ships & Museum ©
Boston Tea Party Ships & Museum
North End ©
North End

1
night
Plymouth, United States

Plymouth ©
Rightly calling itself "America's Hometown," Plymouth holds a prominent place in the nation's history and culture as the site of the first Puritan colony.
Your day-by-day itinerary now includes Plimoth Plantation as well as Richard Sparrow House. Kick off your visit on the 24th (Sun): take in the exciting artwork at Richard Sparrow House, get engrossed in the history at Plimoth Plantation, then see the interesting displays at Plimoth Grist Mill, and finally get engrossed in the history at The Jenney. Get ready for a full day of sightseeing on the next day: take an in-depth tour of Pilgrim Hall Museum, contemplate the long history of Mayflower II, then pause for some photo ops at Plymouth Rock, then get advice or help at Mayflower Society House and Library, and finally walk around Pilgrim Memorial State Park.

For traveler tips, ratings, where to stay, and tourist information, use the Plymouth holiday site.

Take a train from Boston to Plymouth in an hour. Alternatively, you can drive; or take a bus. In May, daily temperatures in Plymouth can reach 68°F, while at night they dip to 47°F. Finish your sightseeing early on the 25th (Mon) to allow enough time to drive to Hartford.

Things to do in Plymouth

Museums Historic Sites Shopping
Find places to stay May 24 — 25:
Highlights from your plan
Plimoth Grist Mill ©
Plimoth Grist Mill
Plimoth Plantation ©
Plimoth Plantation
The Jenney ©
The Jenney

1
night
Hartford, United States

Hartford ©
Hartford is the capital of the U.S. Your day-by-day itinerary now includes Old State House, Wadsworth Atheneum Museum of Art and The Mark Twain House & Museum. On the 26th (Tue), browse the exhibits of The Mark Twain House & Museum, admire the masterpieces at Wadsworth Atheneum Museum of Art, and then get a sense of history and politics at Old State House.

To find other places to visit, where to stay, photos, and tourist information, read Hartford route planning app.

Traveling by car from Plymouth to Hartford takes 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In May, daily temperatures in Hartford can reach 72°F, while at night they dip to 51°F. Wrap up your sightseeing by early afternoon on the 26th (Tue) to allow time for the car ride to New York City.

Things to do in Hartford

Museums Historic Sites
Find places to stay May 25 — 26:
Highlights from your plan
The Mark Twain House & Museum ©
The Mark Twain House & Museum
Wadsworth Atheneum Museum of Art ©
Wadsworth Atheneum Museum of Art
Old State House ©
Old State House

5
nights
New York City, United States

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Your day-by-day itinerary now includes Museum of Sex, The Strand Bookstore and Madame Morbid's Trolley Tours. Deepen your sense of the past at sights like The Met Cloisters and Ellis Island. Get some cultural insight at The Metropolitan Museum of Art and New York Public Library. Venture out of the city with trips to Magazzino Italian Art (in Cold Spring) and Hyde Park (Home of Franklin D. Roosevelt, Vanderbilt Mansion National Historic Site, &more). There's much more to do: admire the masterpieces at Frick Collection, enjoy breathtaking views from Empire State Building, pause for some photo ops at Statue of Liberty National Monument, and take in nature's colorful creations at Brooklyn Botanic Garden.

To see other places to visit, traveler tips, reviews, and tourist information, read our New York City trip itinerary planner.

You can drive from Hartford to New York City in 2.5 hours. Other options are to take a bus; or take a train. In May in New York City, expect temperatures between 69°F during the day and 55°F at night. Wrap up your sightseeing by early afternoon on the 31st (Sun) to allow enough time to take a train to Philadelphia.

Things to do in New York City

Museums Historic Sites Parks

Side Trips

Hyde Park, Brooklyn, Magazzino Italian Art, New York Botanical Garden
Find places to stay May 26 — 31:
Highlights from your plan
The Met Cloisters ©
The Met Cloisters
Home of Franklin D. Roosevelt ©
Home of Franklin D. Roosevelt

2
nights
Philadelphia, United States

Philadelphia ©
Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S.
Your day-by-day itinerary now includes United States Mint. On your second day here, get a sense of history and politics at City Hall Visitor Center, take in the spiritual surroundings of Cathedral Basilica of Saints Peter and Paul, take in the architecture and atmosphere at Christ Church, get engrossed in the history at National Liberty Museum, then appreciate the history behind Liberty Bell Center, and finally engage your brain at Penn Museum.

Take the guesswork out of planning a Philadelphia vacation by using our trip itinerary maker.

You can take a train from New York City to Philadelphia in 2 hours. Other options are to drive; or take a bus. In May in Philadelphia, expect temperatures between 74°F during the day and 56°F at night. Finish your sightseeing early on the 2nd (Tue) to allow enough time to drive to Gettysburg.

Things to do in Philadelphia

Historic Sites Museums Childrens Museums
Find places to stay May 31 — Jun 2:
Highlights from your plan
City Hall Visitor Center ©
City Hall Visitor Center
Eastern State Penitentiary ©
Eastern State Penitentiary
Independence Hall ©
Independence Hall

2
nights
Gettysburg, United States

Gettysburg ©
Located near the memorial park marking the site of one of the largest Civil War battles, the town of Gettysburg sits in a landscape of rolling green hills with views of the Blue Ridge Mountains in the distance.
Your list of things to see and do now includes Little Round Top, Gettysburg Museum of History, Eisenhower National Historic Site, and other attractions. On the 3rd (Wed), appreciate the extensive heritage of Shriver House Museum, steep yourself in history at Jennie Wade House, contemplate the long history of Eisenhower National Historic Site, then see the interesting displays at Gettysburg Museum of History, and finally get engrossed in the history at Gettysburg Lincoln Railroad Station. Get ready for a full day of sightseeing on the next day: contemplate the long history of Little Round Top, contemplate the long history of Dobbin House Tavern, witness the site of a historic battle at Gettysburg National Military Park, stroll the grounds of Gettysburg National Cemetery, then get your game on at 1863 Escape, and finally witness the site of a historic battle at Gettysburg National Military Park Museum & Visitor Center.

For traveler tips, maps, where to stay, and tourist information, you can read our Gettysburg online sightseeing planner.

Traveling by car from Philadelphia to Gettysburg takes 2.5 hours. Alternatively, you can do a combination of train and flight; or do a combination of train and bus. In June in Gettysburg, expect temperatures between 81°F during the day and 62°F at night. Cap off your sightseeing on the 4th (Thu) early enough to go by car to Baltimore.

Things to do in Gettysburg

Historic Sites Museums Parks
Find places to stay Jun 2 — 4:
Highlights from your plan
Jennie Wade House ©
Jennie Wade House
Gettysburg National Military Park ©
Gettysburg National Military Park

1
night
Baltimore, United States

Baltimore ©
A major center for tourism and travel, Baltimore is famous as the city where amateur poet Francis Scott Key wrote the lyrics for the United States' national anthem.
Your day-by-day itinerary now includes The Walters Art Museum, Fort McHenry National Monument and Historic Shrine and Baltimore Museum of Art. On the 5th (Fri), admire the masterpieces at Baltimore Museum of Art, explore the wealth of natural beauty at Fort McHenry National Monument and Historic Shrine, examine the collection at Geppi's Entertainment Museum, then appreciate the extensive heritage of Federal Hill Park, and finally admire the masterpieces at The Walters Art Museum.

To see traveler tips, other places to visit, maps, and other tourist information, use the Baltimore tour planning app.

Traveling by car from Gettysburg to Baltimore takes 1.5 hours. Alternatively, you can do a combination of car and subway; or fly. Traveling from Gettysburg in June, plan for somewhat warmer nights in Baltimore, with lows around 69°F. Finish your sightseeing early on the 5th (Fri) so you can take a train to Washington DC.

Things to do in Baltimore

Museums Parks Historic Sites
Find places to stay Jun 4 — 5:
Highlights from your plan
The Walters Art Museum ©
The Walters Art Museum
Baltimore Museum of Art ©
Baltimore Museum of Art

2
nights
Washington DC, United States

Washington DC ©
The capital of the United States, the District of Columbia contains the lion's share of the country's most treasured monuments, memorials, and public museums.
You've added The Phillips Collection, Ford's Theatre, National Gallery of Art, and other attractions to your itinerary. Get ready for a full day of sightseeing on the next day: stroll through Hillwood Estate, Museum & Gardens, take in nature's colorful creations at U.S. National Arboretum, contemplate the long history of President Lincoln's Cottage, explore the world behind art at National Gallery of Art, then get a new perspective on nature at Smithsonian National Museum of Natural History, and finally get engrossed in the history at Ford's Theatre.

To find maps, ratings, reviews, and tourist information, read our Washington DC trip builder.

Take a train from Baltimore to Washington DC in an hour. Alternatively, you can take a bus; or drive. In June in Washington DC, expect temperatures between 86°F during the day and 69°F at night. Wrap up your sightseeing on the 7th (Sun) early enough to drive to Mount Vernon.

Things to do in Washington DC

Museums Historic Sites Parks
Find places to stay Jun 5 — 7:
Highlights from your plan
National Gallery of Art ©
National Gallery of Art
Smithsonian National Museum of Natural History ©
Smithsonian American Art Museum ©
Smithsonian American Art Museum

1
night
Mount Vernon, United States

Mount Vernon ©
Mount Vernon is a census-designated place (CDP) and unincorporated community in Fairfax County, Virginia, United States. For reviews, other places to visit, more things to do, and more tourist information, use the Mount Vernon online journey builder.

Getting from Washington DC to Mount Vernon by car takes about an hour. Other options: take a bus. Traveling from Washington DC in June, you can expect nighttime temperatures to be slightly colder in Mount Vernon, with lows of 63°F. Wrap up your sightseeing by early afternoon on the 8th (Mon) to allow time for the car ride to Williamsburg.

Things to do in Mount Vernon

Historic Sites Museums

Side Trip

Historic Port Tobacco Village
Find places to stay Jun 7 — 8:
Highlights from your plan
George Washington's Mount Vernon ©
George Washington's Mount Vernon

2
nights
Williamsburg, United States

Williamsburg ©
Founded in 1632 as a fortified settlement on the high ground between two rivers, Williamsburg served as a colonial capital of Virginia for over 80 years.
Your day-by-day itinerary now includes Historic Jamestowne, Colonial Williamsburg, Busch Gardens Williamsburg, and other attractions you added. Here are some ideas for day two: see the interesting displays at Virginia Musical Museum, do a tasting at Williamsburg Winery, contemplate the long history of Jamestown Settlement, then contemplate the long history of Bassett Hall, then admire the masterpieces at DeWitt Wallace Decorative Arts Museum, and finally don't miss a visit to Colonial Williamsburg Capitol Building.

To see traveler tips and other tourist information, you can read our Williamsburg day trip tool.

Drive from Mount Vernon to Williamsburg in 2.5 hours. Alternatively, you can do a combination of bus and train; or do a combination of bus, flight, and taxi. In June, daily temperatures in Williamsburg can reach 87°F, while at night they dip to 68°F. Wrap up your sightseeing on the 10th (Wed) early enough to take a train to Richmond.

Things to do in Williamsburg

Historic Sites Museums Wineries
Find places to stay Jun 8 — 10:
Highlights from your plan
Jamestown Settlement ©
Jamestown Settlement
Historic Jamestowne ©
Historic Jamestowne
Governor's Palace ©
Governor's Palace

1
night
Richmond, United States

Richmond ©
The capital city of Virginia, Richmond has diverse architecture, a large collection of monuments, and world-class museums that reveal the city's important role in American history.
Your day-by-day itinerary now includes American Civil War Museum- Historic Tredegar, White House of the Confederacy and Virginia Museum of Fine Arts. Start off your visit on the 11th (Thu): explore the world behind art at Virginia Museum of Fine Arts, take an in-depth tour of Agecroft Hall & Gardens, then brush up on your military savvy at White House of the Confederacy, and finally learn about all things military at American Civil War Museum- Historic Tredegar.

For reviews, maps, photos, and more tourist information, read our Richmond vacation maker.

Traveling by train from Williamsburg to Richmond takes an hour. Alternatively, you can drive. June in Richmond sees daily highs of 86°F and lows of 66°F at night. Wrap up your sightseeing on the 11th (Thu) early enough to take a bus to Charlottesville.

Things to do in Richmond

Museums Historic Sites
Find places to stay Jun 10 — 11:
Highlights from your plan
Virginia Museum of Fine Arts ©
Virginia Museum of Fine Arts
White House of the Confederacy ©
White House of the Confederacy
American Civil War Museum- Historic Tredegar ©

1
night
Charlottesville, United States

Charlottesville ©
Situated at the foothills of the Blue Ridge Mountains, Charlottesville is perhaps best known as the home of three of the United States' founding fathers, including Thomas Jefferson.
Your day-by-day itinerary now includes Trump Winery as well as Monticello.

To find other places to visit, ratings, maps, and more tourist information, refer to the Charlottesville sightseeing planning tool.

Traveling by bus from Richmond to Charlottesville takes 1.5 hours. Alternatively, you can drive. In June, daytime highs in Charlottesville are 84°F, while nighttime lows are 64°F. Wrap up your sightseeing by early afternoon on the 12th (Fri) to allow time for travel to Louisville.

Things to do in Charlottesville

Historic Sites Parks Wineries
Find places to stay Jun 11 — 12:
Highlights from your plan
Monticello ©
Monticello
James Monroe's Highland ©
James Monroe's Highland
Mulberry Row ©
Mulberry Row

2
nights
Louisville, United States

Louisville ©
Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Your list of things to see and do now includes Frazier History Museum, Churchill Downs, Old Louisville, and other attractions. On the 13th (Sat), examine the collection at Louisville Slugger Museum & Factory, wander the streets of Frankfort Ave, contemplate the long history of Historic Locust Grove, then examine the collection at Kentucky Derby Museum, and finally whizz through the canopy at Louisville Mega Cavern. On the 14th (Sun), you'll have a packed day of sightseeing: get thoroughly spooked out with Old Louisville, then try to win big at Churchill Downs, and then examine the collection at Frazier History Museum.

To find more things to do, where to stay, ratings, and tourist information, go to the Louisville trip itinerary builder app.

Traveling by flight from Charlottesville to Louisville takes 5.5 hours. Alternatively, you can do a combination of shuttle and flight; or drive. Expect a daytime high around 86°F in June, and nighttime lows around 67°F. Wrap up your sightseeing by early afternoon on the 14th (Sun) to allow enough time to drive to Nashville.

Things to do in Louisville

Museums Tours Historic Sites
Find places to stay Jun 12 — 14:
Highlights from your plan
Louisville Slugger Museum & Factory ©
Louisville Slugger Museum & Factory
Kentucky Derby Museum ©
Kentucky Derby Museum
Churchill Downs ©
Churchill Downs

2
nights
Nashville, United States

Nashville ©
Known as the capital of country music, the thriving city of Nashville combines old-world southern charm with a progressive urban flair.
Your list of things to see and do now includes Cheekwood, Wildhorse Saloon, Belle Meade Plantation, and other attractions. On the 15th (Mon), you'll have a packed day of sightseeing: see the interesting displays at Musicians Hall of Fame and Museum, admire the masterpieces at Frist Art Museum, take in the history at Lotz House Museum, then whizz through the canopy at Soar Adventure Tower, then admire the natural beauty at Gaylord Opryland Resort Gardens, and finally steep yourself in history at Belle Meade Plantation.

To find more things to do, maps, traveler tips, and tourist information, use the Nashville route planner.

You can drive from Louisville to Nashville in 3 hours. Other options are to take a bus; or fly. You'll gain 1 hour traveling from Louisville to Nashville due to the time zone difference. Expect a daytime high around 88°F in June, and nighttime lows around 67°F. On the 16th (Tue), wrap the sightseeing up by early afternoon so you can travel to Great Smoky Mountains National Park.

Things to do in Nashville

Museums Historic Sites Parks

Side Trip

Franklin
Find places to stay Jun 14 — 16:
Highlights from your plan
Lotz House Museum ©
Lotz House Museum
Belle Meade Plantation ©
Belle Meade Plantation
Cheekwood ©
Cheekwood

1
night
Great Smoky Mountains National Park, United States

Great Smoky Mountains National Park ©
Great Smoky Mountains National Park contains some of the highest mountains east of the Mississippi River, but it's the ease of access that makes this national park the United States' most visited.
Start off your visit on the 17th (Wed): look for all kinds of wild species at Roaring Fork, appreciate the extensive heritage of Noah Bud Ogle Cabin, identify plant and animal life at Quiet Walkways, then make a trip to Elkmont Ghost Town, and finally admire the sheer force of Spruce Flats Falls.

To see more things to do, photos, ratings, and tourist information, read our Great Smoky Mountains National Park online trip planner.

Explore your travel options from Nashville to Great Smoky Mountains National Park with the Route module. You'll lose 1 hour traveling from Nashville to Great Smoky Mountains National Park due to the time zone difference. In June, daytime highs in Great Smoky Mountains National Park are 86°F, while nighttime lows are 66°F. Finish your sightseeing early on the 17th (Wed) so you can travel to Asheville.

Things to do in Great Smoky Mountains National Park

Parks Wildlife Historic Sites

Side Trip

Great Smoky Mountains National Park
Find places to stay Jun 16 — 17:
Highlights from your plan
Roaring Fork ©
Roaring Fork
Noah Bud Ogle Cabin ©
Noah Bud Ogle Cabin
Quiet Walkways ©
Quiet Walkways

1
night
Asheville, United States

Asheville ©
Asheville nestles between two major mountain ranges in the scenic western section of North Carolina.
Your day-by-day itinerary now includes Grovewood Village, The North Carolina Arboretum and Biltmore. Start off your visit on the 18th (Thu): get engrossed in the history at Smith-McDowell House Museum, view the masterpieces at Lexington Glassworks, stop by Battery Park Book Exchange and Champagne Bar, learn about winemaking at Biltmore, then admire the natural beauty at The North Carolina Arboretum, and finally steep yourself in history at Grovewood Village.

For photos, other places to visit, where to stay, and tourist information, you can read our Asheville travel route planning app.

Explore your travel options from Great Smoky Mountains National Park to Asheville with the Route module. In June, daily temperatures in Asheville can reach 83°F, while at night they dip to 62°F. Wrap up your sightseeing on the 18th (Thu) to allow time to travel to Atlanta.

Things to do in Asheville

Museums Historic Sites Shopping
Find places to stay Jun 17 — 18:
Highlights from your plan
The North Carolina Arboretum ©
The North Carolina Arboretum
Biltmore ©
Biltmore
Grovewood Village ©
Grovewood Village

1
night
Atlanta, United States

Atlanta ©
Georgia’s largest city and capital, Atlanta is a thriving metropolis anchored by its southern roots.
Your day-by-day itinerary now includes Georgia Aquarium as well as Swan House. Start off your visit on the 19th (Fri): see the interesting displays at World of Coca-Cola, contemplate the long history of Martin Luther King Jr. National Historic Site, then steep yourself in history at Margaret Mitchell House, then steep yourself in history at Swan House, and finally admire nature's wide array of creatures at Georgia Aquarium.

To find reviews, more things to do, where to stay, and other tourist information, read our Atlanta tour planning tool.

Getting from Asheville to Atlanta by flight takes about 4 hours. Other options: drive; or do a combination of bus and flight. Plan for a bit warmer nights when traveling from Asheville in June since evenings lows in Atlanta dip to 70°F. Wrap up your sightseeing on the 19th (Fri) to allow time to travel to Charleston.

Things to do in Atlanta

Museums Historic Sites Parks
Find places to stay Jun 18 — 19:
Highlights from your plan
World of Coca-Cola ©
World of Coca-Cola
Martin Luther King Jr. National Historic Site ©
Martin Luther King Jr. National Historic Site
Margaret Mitchell House ©
Margaret Mitchell House

2
nights
Charleston, United States

Charleston ©
Many visitors describe their Charleston holiday as a warm embrace by an old, dear friend--who lived about 200 years ago.
You've added Fort Sumter National Monument, Wild Blue Ropes Adventure Park, Boone Hall Plantation, and other attractions to your itinerary. Kick off your visit on the 20th (Sat): take in nature's colorful creations at Magnolia Plantation & Gardens, contemplate the long history of Boone Hall Plantation, take an in-depth tour of Confederate Museum, learn more about the world around you at The Charleston Museum, then take a memorable tour with Wild Blue Ropes Adventure Park, and finally contemplate the long history of Fort Sumter National Monument.

To find more things to do, reviews, traveler tips, and tourist information, refer to the Charleston trip planning website.

You can fly from Atlanta to Charleston in 3 hours. Other options are to drive; or take a bus. In June, plan for daily highs up to 87°F, and evening lows to 73°F. On the 21st (Sun), wrap the sightseeing up by early afternoon so you can drive to Savannah.

Things to do in Charleston

Historic Sites Museums Parks

Side Trip

Boone Hall Plantation
Find places to stay Jun 19 — 21:
Highlights from your plan
Boone Hall Plantation ©
Boone Hall Plantation
The Charleston Museum ©
The Charleston Museum
Fort Sumter National Monument ©
Fort Sumter National Monument

1
night
Savannah, United States

Savannah ©
Georgia's oldest city, Savannah displays its colonial history proudly on every corner.
To see maps, other places to visit, ratings, and other tourist information, read our Savannah travel site.

Traveling by car from Charleston to Savannah takes 2.5 hours. Alternatively, you can take a bus. In June, daily temperatures in Savannah can reach 89°F, while at night they dip to 72°F. Wrap up your sightseeing on the 22nd (Mon) to allow time to travel to New Orleans.

Things to do in Savannah

Museums Parks Historic Sites
Find places to stay Jun 21 — 22:
Highlights from your plan
Wormsloe Historic Site ©
Wormsloe Historic Site
Telfair Academy ©
Telfair Academy
Davenport House Museum ©
Davenport House Museum

2
nights
New Orleans, United States

New Orleans ©
Known for its Creole cuisine, rich musical tradition, and nearby swamps and plantations, New Orleans is one of the nation's oldest cities.
Your day-by-day itinerary now includes New Orleans Pharmacy Museum, Garden District, Jean Lafitte National Historical Park and Preserve, and other attractions you added. On the 23rd (Tue), examine the collection at New Orleans Museum of Art, appreciate the extensive heritage of French Quarter, and then explore the wealth of natural beauty at Jean Lafitte National Historical Park and Preserve. Here are some ideas for day two: learn about all things military at The National WWII Museum, visit Garden District, see the interesting displays at New Orleans Pharmacy Museum, steep yourself in history at Hermann-Grima House, then partake in some friendly competition at Escape My Room New Orleans, and finally appreciate the extensive heritage of Jackson Square.

For ratings, reviews, and other tourist information, you can read our New Orleans travel planner.

You can fly from Savannah to New Orleans in 6.5 hours. Other options are to do a combination of taxi and flight; or drive. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. While traveling from Savannah, expect little chillier days and a bit warmer nights in New Orleans, ranging from highs of 83°F to lows of 83°F. Cap off your sightseeing on the 24th (Wed) early enough to travel to St. Augustine.

Things to do in New Orleans

Museums Historic Sites Neighborhoods
Find places to stay Jun 22 — 24:
Highlights from your plan
Garden District ©
Garden District
Escape My Room New Orleans ©
Escape My Room New Orleans
The National WWII Museum ©
The National WWII Museum

1
night
St. Augustine, United States

St. Augustine ©
St. You've added World Golf Hall of Fame, St. Augustine Distillery, Old St. Augustine Village, and other attractions to your itinerary. Kick off your visit on the 25th (Thu): steep yourself in history at Fountain of Youth Archaeological Park, take in the architecture and atmosphere at Memorial Presbyterian Church, examine the collection at Villa Zorayda Museum, get engrossed in the history at Old Florida Museum, then get engrossed in the history at The Oldest Store Museum, and finally get engrossed in the history at St. Augustine History Museum. On your second day here, take an in-depth tour of Spanish Military Hospital Museum, get engrossed in the history at Medieval Torture Museum, then steep yourself in history at Old St. Augustine Village, then brush up on your knowledge of spirits at St. Augustine Distillery, and finally examine the collection at World Golf Hall of Fame.

For reviews, photos, other places to visit, and other tourist information, read our St. Augustine tour itinerary site.

You can do a combination of flight and bus from New Orleans to St. Augustine in 7 hours. Alternatively, you can fly; or drive. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. Plan for little chillier nights when traveling from New Orleans in June since evenings lows in St. Augustine dip to 73°F. Finish your sightseeing early on the 26th (Fri) to allow enough time to travel to Fort Lauderdale.

Things to do in St. Augustine

Museums Historic Sites Breweries & Distilleries
Find places to stay Jun 24 — 26:
Highlights from your plan
St. Augustine Distillery ©
St. Augustine Distillery
Villa Zorayda Museum ©
Villa Zorayda Museum
Memorial Presbyterian Church ©
Memorial Presbyterian Church

1
night
Fort Lauderdale, United States

Fort Lauderdale ©
Known as the "Venice of America" because of its extensive network of navigable waterways, Fort Lauderdale welcomes over 10 million annual visitors, most of them attracted by the city's popular beaches and marinas.
Your day-by-day itinerary now includes Bonnet House Museum and Gardens as well as Sawgrass Recreation Park. Kick off your visit on the 27th (Sat): indulge in some personalized pampering at some of the best spas, then do sightseeing your way with Sawgrass Recreation Park, and then examine the collection at Bonnet House Museum and Gardens.

To see more things to do, other places to visit, maps, and more tourist information, you can read our Fort Lauderdale trip itinerary maker.

Traveling by combination of flight and train from St. Augustine to Fort Lauderdale takes 4.5 hours. Alternatively, you can drive; or do a combination of bus and flight. June in Fort Lauderdale sees daily highs of 89°F and lows of 77°F at night. Wrap up your sightseeing on the 27th (Sat) to allow time to take a bus to Miami.

Things to do in Fort Lauderdale

Museums Spas Tours
Find places to stay Jun 26 — 27:
Highlights from your plan
Bonnet House Museum and Gardens ©
Bonnet House Museum and Gardens
Sawgrass Recreation Park ©
Sawgrass Recreation Park
Spas

1
night
Miami, United States

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Your day-by-day itinerary now includes Vizcaya Museum and Gardens, Deering Estate and Airboat In Everglades.

For where to stay, reviews, photos, and other tourist information, read our Miami trip itinerary maker tool.

Traveling by bus from Fort Lauderdale to Miami takes an hour. Alternatively, you can drive; or take a train. In June, daily temperatures in Miami can reach 89°F, while at night they dip to 77°F. Finish up your sightseeing early on the 28th (Sun) so you can travel to Havana.

Things to do in Miami

Museums Wildlife Tours
Find places to stay Jun 27 — 28:
Highlights from your plan
Lock & Load Museum ©
Lock & Load Museum
Vizcaya Museum and Gardens ©
Vizcaya Museum and Gardens
Perez Art Museum Miami ©
Perez Art Museum Miami

5
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Your day-by-day itinerary now includes Museo del Chocolate, Fortaleza de San Carlos de la Cabana, El Morro, and other attractions you added. Do some cultural sightseeing at Finca Vigía and Church and Convent of St. Francis of Asisi. You'll discover tucked-away gems like Plaza de Armas and Palacio De Los Capitanes Generales. Next up on the itinerary: get to know the fascinating history of Malecón of Havana, steep yourself in history at Castillo de la Real Fuerza, and wander the streets of Vedado.

Plan my day in Havana using traveler tips and tourist information provided by Inspirock.

Traveling by flight from Miami to Havana takes 4 hours. Alternatively, you can do a combination of train and flight. Traveling from Miami in June, you can expect nighttime temperatures to be a bit cooler in Havana, with lows of 72°F. Wrap up your sightseeing by early afternoon on the 3rd (Fri) to allow enough time to travel back home.

Things to do in Havana

Historic Sites Museums Neighborhoods
Find places to stay Jun 28 — Jul 3:
Highlights from your plan
Old Square (Plaza Vieja) ©
Old Square (Plaza Vieja)
Finca Vigía ©
Finca Vigía
Fortaleza de San Carlos de la Cabana ©
Fortaleza de San Carlos de la Cabana

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