40 days in United States & Cuba Itinerary

40 days in United States & Cuba Itinerary

Created using Inspirock route planner

This plan was created by another user.  Make it your plan

Route & dates

40 days in United States & Cuba Itinerary

Start: Auckland, New Zealand
Fly:  21​h
1
New Orleans, United States
— 4 nights
Fly:  4​h 15​min
2
Miami, United States
— 2 nights
Fly:  4​h
3
Havana, Cuba
— 2 nights
Drive:  4​h 15​min
4
Trinidad, Cuba
— 2 nights
Drive:  3​h 45​min
5
Cayo Coco, Cuba
— 2 nights
Drive + Fly:  7​h 45​min
6
Miami, United States
— 2 nights
bus:  45​min
7
Fort Lauderdale, United States
— 1 night
Drive:  3​h
8
Cocoa Beach, United States
— 2 nights
Drive:  1​h 15​min
9
Orlando, United States
— 2 nights
Drive:  4​h 45​min
10
Savannah, United States
— 2 nights
Drive:  2​h 15​min
11
Charleston, United States
— Few hours
Drive:  2​h 15​min
12
Myrtle Beach, United States
— 3 nights
Drive:  7​h 15​min
13
Gatlinburg, United States
— 3 nights
Drive:  4​h 30​min
14
Roanoke, United States
— 2 nights
Drive:  4​h 15​min
15
Washington DC, United States
— 3 nights
Drive:  2​h
16
Wilmington, United States
— 1 night
Drive:  2​h 15​min
17
New York City, United States
— 5 nights
Fly:  22​h
End: Auckland, New Zealand


Learn more about your trip

4
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.
New Orleans is known for historic sites, museums, nightlife, parks, and classes. Your plan includes some of its best attractions: learn about all things military at The National WWII Museum, stroll around New Orleans City Park, get to know the fascinating history of French Quarter, and examine the collection at Blaine Kern's Mardi Gras World.

To see ratings, other places to visit, reviews, and other tourist information, you can read our New Orleans route app .

Auckland, New Zealand to New Orleans is an approximately 21-hour flight. You can also do a combination of flight and bus; or do a combination of flight and train. The time zone difference moving from New Zealand Standard Time (NZST) to Central Standard Time (CST) is minus 18 hours. Traveling from Auckland in May, expect New Orleans to be a bit warmer, temps between 24°C and 24°C. Wrap up your sightseeing on the 21st (Fri) early enough to travel to Miami.

Things to do in New Orleans

Historic Sites Parks Neighborhoods
Highlights from your plan
Garden District ©
Garden District
The National WWII Museum
The National WWII Museum
St. Louis Cathedral ©
St. Louis Cathedral

2
nights
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.
On the 21st (Fri), examine the collection at Vizcaya Museum and Gardens and then browse the different shops at Bayside Marketplace. On the 22nd (Sat), you'll have a packed day of sightseeing: kick back and relax at South Beach, then have fun at Lock & Load Miami, and then admire the masterpieces at Wynwood Walls.

To see maps, ratings, photos, and more tourist information, refer to the Miami visit app .

Fly from New Orleans to Miami in 4.5 hours. Alternatively, you can do a combination of flight and bus; or drive. Traveling from New Orleans to Miami, you'll lose 1 hour due to the time zone difference. Expect a bit warmer weather when traveling from New Orleans in May: highs in Miami hover around 36°C, while lows dip to 27°C. Finish your sightseeing early on the 23rd (Sun) to allow enough time to travel to Havana.

Things to do in Miami

Museums Shopping Beaches

Side Trip

South Beach
Highlights from your plan
Vizcaya Museum and Gardens ©
Vizcaya Museum and Gardens
South Beach ©
South Beach
Bayside Marketplace ©
Bayside Marketplace

2
nights
Havana, Cuba

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Havana is known for historic sites, nightlife, museums, beaches, and classes. Your plan includes some of its best attractions: appreciate the extensive heritage of Malecón of Havana, make a trip to Old Havana, steep yourself in history at Old Square (Plaza Vieja), and get engrossed in the history at Fototeca de Cuba.

Inspirock's itinerary builder makes planning a Havana trip simple and quick.

You can fly from Miami to Havana in 4 hours. Alternatively, you can do a combination of train and flight. Traveling from Miami in May, you can expect nighttime temperatures to be slightly colder in Havana, with lows of 24°C. Finish up your sightseeing early on the 25th (Tue) so you can go by car to Trinidad.

Things to do in Havana

Historic Sites Tours Museums
Highlights from your plan
Walking tours
Malecón of Havana ©
Malecón of Havana
El Capitolio ©
El Capitolio

2
nights
Trinidad, Cuba

Trinidad ©
Built on sugar and seemingly preserved in molasses, the town of Trinidad attracts visitors with its well-aged 19th century architecture and rustic charm, showcasing the sounds, scents, and sights of days gone by.
Start off your visit on the 26th (Wed): take in the awesome beauty at Topes de Collantes, then see the interesting displays at Romance Museum, then kick back and relax at Ancon Beach, and finally tour the pleasant surroundings at Valle de los Ingenios. On the next day, make a trip to Trinidad de Cuba, examine the collection at Colonial Architecture Museum, see the interesting displays at Colonial Architecture Museum, then see the interesting displays at Museo de Historia Municipal, and finally view the masterpieces at Galerie D'Art Calleyro.

To see photos, other places to visit, where to stay, and other tourist information, read our Trinidad day trip site .

You can drive from Havana to Trinidad in 4.5 hours. Other options are to take a shuttle; or take a bus. In May, daily temperatures in Trinidad can reach 37°C, while at night they dip to 26°C. Finish your sightseeing early on the 27th (Thu) to allow enough time to drive to Cayo Coco.

Things to do in Trinidad

Parks Wildlife Museums

Side Trips

Trinidad de Cuba, Topes de Collantes
Highlights from your plan
Valle de los Ingenios ©
Valle de los Ingenios
Topes de Collantes ©
Topes de Collantes
Ancon Beach ©
Ancon Beach

2
nights
Cayo Coco, Cuba

Cayo Coco
White sand beaches and calm waters have led to booming tourism in Cayo Coco, one of the main islands of the Jardines Del Rey archipelago.
On the 28th (Fri), head off the coast to Cayo Media Luna, then kick back and relax at Playa Pilar, and then kick back and relax at Cayo Guillermo.

For traveler tips, other places to visit, where to stay, and more tourist information, you can read our Cayo Coco journey tool .

Traveling by car from Trinidad to Cayo Coco takes 4 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of bus and train. In May, daily temperatures in Cayo Coco can reach 35°C, while at night they dip to 26°C. Wrap up your sightseeing on the 29th (Sat) to allow time to travel to Miami.

Things to do in Cayo Coco

Parks Beaches Outdoors

Side Trip

Cayo Guillermo
Highlights from your plan
Playa Pilar
Playa Pilar
Cayo Guillermo ©
Cayo Guillermo
Cayo Media Luna ©
Cayo Media Luna

2
nights
Miami, United States

Miami ©
On the 29th (Sat), examine the collection at Vizcaya Museum and Gardens, then have fun at Lock & Load Miami, then see the interesting displays at Lock & Load Museum, and finally don't miss a visit to Bayside Marketplace. Get ready for a full day of sightseeing on the 30th (Sun): contemplate in the serene atmosphere at St Patrick Catholic Church, then get some thrills on the water with a speed boat tour, and then make a trip to Wynwood Walls.

To see traveler tips, reviews, where to stay, and other tourist information, read Miami trip maker .

The Route module can help you plan travel from Cayo Coco to Miami. Wrap up your sightseeing on the 31st (Mon) early enough to take a bus to Fort Lauderdale.

Things to do in Miami

Museums Outdoors Shopping
Highlights from your plan
Lock & Load Museum ©
Lock & Load Museum
Vizcaya Museum and Gardens ©
Vizcaya Museum and Gardens
Bayside Marketplace ©
Bayside Marketplace

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.
You've now added Little Havana to your itinerary. Start off your visit on the 31st (Mon): shop like a local with E Las Olas Blvd and then wander the streets of Little Havana.

To find maps, where to stay, more things to do, and other tourist information, refer to the Fort Lauderdale trip builder .

Getting from Miami to Fort Lauderdale by bus takes about an hour. Other options: drive; or take a train. May in Fort Lauderdale sees daily highs of 35°C and lows of 27°C at night. Finish up your sightseeing early on the 1st (Tue) so you can go by car to Cocoa Beach.

Things to do in Fort Lauderdale

Neighborhoods Shopping

Side Trip

Little Havana
Highlights from your plan
Little Havana ©
Little Havana
E Las Olas Blvd ©
E Las Olas Blvd

2
nights
Cocoa Beach, United States

Cocoa Beach ©
Situated in one of Florida's busiest vacation areas, Cocoa Beach burst onto the world scene in the 1960s, when it became a popular setting for parades honoring the nation's "Apollo" astronauts.
Cocoa Beach is known for adventure, beaches, shopping, fun & games, and parks. Your plan includes some of its best attractions: tour the pleasant surroundings at Cocoa Beach, stroll around Lori Wilson Park, test your team's savvy at popular escape rooms, and work some fitness into your day at Manatee Sanctuary Park.

To see maps, photos, ratings, and other tourist information, go to the Cocoa Beach trip itinerary builder .

Drive from Fort Lauderdale to Cocoa Beach in 3 hours. Alternatively, you can take a bus; or fly. In June, daytime highs in Cocoa Beach are 36°C, while nighttime lows are 28°C. On the 3rd (Thu), wrap the sightseeing up by early afternoon so you can drive to Orlando.

Things to do in Cocoa Beach

Parks Outdoors Beaches

Side Trips

Parker Brothers Concepts, Manatee Sanctuary Park
Highlights from your plan
Cocoa Beach ©
Cocoa Beach
Room Escape Games
Ron Jon Surf Shop ©
Ron Jon Surf Shop

2
nights
Orlando, United States

Orlando ©
For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Start off your visit on the 3rd (Thu): have some family-friendly fun at The Escape Game Orlando.

To see maps, other places to visit, photos, and other tourist information, refer to the Orlando trip planning site .

You can drive from Cocoa Beach to Orlando in 1.5 hours. Other options are to take a shuttle; or do a combination of bus and shuttle. In June, daily temperatures in Orlando can reach 38°C, while at night they dip to 26°C. Finish your sightseeing early on the 5th (Sat) to allow enough time to drive to Savannah.

Things to do in Orlando

Theme Parks Fun & Games Nightlife
Highlights from your plan
Happily Ever After Fireworks ©
Happily Ever After Fireworks
Walt Disney World Resort ©
Walt Disney World Resort
The Escape Game Orlando ©
The Escape Game Orlando

2
nights
Savannah, United States

Georgia's oldest city, Savannah displays its colonial history proudly on every corner.
Kick off your visit on the 5th (Sat): go on a hair-raising tour with a ghost and vampire tour, then take in the spiritual surroundings of Cathedral of St. John the Baptist, and then don't miss a visit to River Street Savannah. On the next day, see majestic marine mammals with a dolphin and whale watching tour, then stroll the grounds of Colonial Park Cemetery, then walk around Forsyth Park, and finally wander the streets of Savannah Historic District.

For ratings, maps, traveler tips, and other tourist information, use the Savannah visit planner.

Drive from Orlando to Savannah in 5 hours. Alternatively, you can take a train; or fly. Expect a daytime high around 37°C in June, and nighttime lows around 26°C. Finish your sightseeing early on the 7th (Mon) to allow enough time to drive to Charleston.

Things to do in Savannah

Tours Historic Sites Wildlife

Side Trip

Dolphin & Whale Watching
Highlights from your plan
Ghost & Vampire Tours
Savannah Historic District ©
Savannah Historic District
Cathedral of St. John the Baptist ©

few
hours
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.
Charleston is known for parks, historic sites, shopping, wildlife, and nightlife. Your plan includes some of its best attractions: take in nature's colorful creations at Magnolia Plantation & Gardens, contemplate the long history of Charleston Fire Department, Station 2/3, get up close to creatures of the deep with a dolphin and whale watching tour, and deepen your knowledge of military history at Fort Sumter National Monument.

To see other places to visit, more things to do, and more tourist information, you can read our Charleston day trip app .

Drive from Savannah to Charleston in 2.5 hours. Alternatively, you can take a bus. May in Charleston sees daily highs of 32°C and lows of 20°C at night. Cap off your sightseeing on the 1st (Tue) early enough to go by car to Wilmington.

Things to do in Charleston

Tours Outdoors Parks

3
nights
Myrtle Beach, United States

Myrtle Beach ©
Myrtle Beach is a coastal city on the east coast of the United States in Horry County, South Carolina. Change things up with a short trip to Brookgreen Gardens in Murrells Inlet (about 30 minutes away). The adventure continues: surround yourself with nature on a nature and wildlife tour, get a new perspective on things with Boat Tours & Water Sports, wander the streets of Broadway at the Beach, and see the interesting displays at Warbird Park.

To find traveler tips, maps, and other tourist information, refer to the Myrtle Beach trip builder .

You can drive from Charleston to Myrtle Beach in 2.5 hours. Alternatively, you can take a bus. In June in Myrtle Beach, expect temperatures between 35°C during the day and 26°C at night. Wrap up your sightseeing on the 10th (Thu) to allow time to travel to Gatlinburg.

Things to do in Myrtle Beach

Outdoors Parks Tours

Side Trip

Brookgreen Gardens
Highlights from your plan
Myrtle Beach ©
Myrtle Beach
Brookgreen Gardens ©
Brookgreen Gardens
Nature & Wildlife Tours

3
nights
Gatlinburg, United States

Gatlinburg ©
Nestled in the lush, wooded forests of the Great Smoky Mountains National Park, Gatlinburg is Tennessee’s premier mountain resort destination.
Start off your visit on the 11th (Fri): get up close and personal with brilliant marine life at Ripley's Aquarium of the Smokies, then brush up on your knowledge of spirits at Sugarlands Distilling Company, then learn about winemaking at Tennessee Homemade Wines, and finally get interesting insight from Tours. Keep things going the next day: explore the wealth of natural beauty at Great Smoky Mountains National Park, get great views at Gatlinburg SkyLift Park, and then brush up on your knowledge of spirits at Ole Smoky Tennessee Moonshine.

For ratings, maps, other places to visit, and more tourist information, you can read our Gatlinburg trip planner .

You can do a combination of flight and taxi from Myrtle Beach to Gatlinburg in 4.5 hours. Alternatively, you can do a combination of flight and car; or drive. Traveling from Myrtle Beach in June, you can expect nighttime temperatures to be little chillier in Gatlinburg, with lows of 22°C. Finish up your sightseeing early on the 13th (Sun) so you can go by car to Roanoke.

Things to do in Gatlinburg

Parks Nature Zoos & Aquariums
Highlights from your plan
Sugarlands Distilling Company ©
Sugarlands Distilling Company
Zipline
Great Smoky Mountains National Park ©

2
nights
Roanoke, United States

Roanoke is an independent city in the U.S. Start off your visit on the 13th (Sun): examine the collection at Virginia Museum of Transportation, then look for gifts at Chocolatepaper, and then stroll around Mill Mountain Star & Park. Get ready for a full day of sightseeing on the next day: sample some tasty brews at a beer tour and tasting, then browse for treasures at Black Dog Salvage, and then contemplate in the serene atmosphere at St. John's Episcopal Church.

To find where to stay, more things to do, and other tourist information, refer to the Roanoke route website .

Traveling by car from Gatlinburg to Roanoke takes 4.5 hours. Alternatively, you can do a combination of taxi and flight; or do a combination of car and flight. In June, plan for daily highs up to 34°C, and evening lows to 20°C. Finish up your sightseeing early on the 15th (Tue) so you can travel to Washington DC.

Things to do in Roanoke

Tours Museums Shopping
Highlights from your plan
Beer Tastings & Tours
Mill Mountain Star & Park ©
Mill Mountain Star & Park
O. Winston Link Museum ©
O. Winston Link Museum

3
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.
On the 16th (Wed), ponder the world of politics at United States Capitol, see the interesting displays at National Air and Space Museum, then admire the masterpieces at National Gallery of Art, and finally appreciate the history behind Vietnam Veterans Memorial. Here are some ideas for day two: get engrossed in the history at United States Holocaust Memorial Museum, then learn more about the world around you at Smithsonian National Museum of Natural History, then appreciate the history behind Washington Monument, and finally explore the activities along Tidal Basin.

For maps, where to stay, and tourist information, read Washington DC online day trip planner .

Do a combination of flight, bus, and subway from Roanoke to Washington DC in 4 hours. Alternatively, you can drive; or do a combination of car, flight, bus, and subway. In June in Washington DC, expect temperatures between 35°C during the day and 24°C at night. Wrap up your sightseeing on the 18th (Fri) early enough to take a train to Wilmington.

Things to do in Washington DC

Museums Nature Parks
Highlights from your plan
National Air and Space Museum ©
National Air and Space Museum
National Gallery of Art ©
National Gallery of Art
Tidal Basin ©
Tidal Basin

1
night
Wilmington, United States

Wilmington ©
Wilmington is the largest city in the state of Delaware, United States, built on the site of Fort Christina, the first Swedish settlement in North America. On the 18th (Fri), take in the history at Brandywine Battlefield, then take in nature's colorful creations at Nemours Estate, then get engrossed in the history at Hagley Museum and Library, and finally get engrossed in the history at Winterthur Museum, Garden & Library.

To see reviews, maps, and more tourist information, go to the Wilmington vacation builder .

Getting from Washington DC to Wilmington by train takes about 1.5 hours. Other options: drive; or take a bus. Traveling from Washington DC in June, expect slightly colder with lows of 20°C in Wilmington. Finish up your sightseeing early on the 19th (Sat) so you can catch the train to New York City.

Things to do in Wilmington

Historic Sites Parks Museums

Side Trips

Brandywine Battlefield, Winterthur Museum, Garden & Library
Highlights from your plan
Nemours Estate ©
Nemours Estate
Winterthur Museum, Garden & Library ©
Hagley Museum and Library ©
Hagley Museum and Library

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.
New York City is known for museums, nightlife, shopping, historic sites, and parks. Your plan includes some of its best attractions: take in the pleasant sights at Central Park, make a trip to Rockefeller Center, pause for some photo ops at 9/11 Memorial, and take in panoramic vistas at Top of the Rock.

For photos, where to stay, reviews, and tourist information, read New York City trip planner .

Traveling by train from Wilmington to New York City takes 2 hours. Alternatively, you can drive; or take a bus. In June in New York City, expect temperatures between 31°C during the day and 21°C at night. Finish your sightseeing early on the 24th (Thu) so you can travel back home.

Things to do in New York City

Museums Parks Historic Sites
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

Similar Plans

44 days in New York City, California & Florida BY A USER FROM UNITED STATES November, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: November, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 39 days in United States BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular sights PREFERENCES: June, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Fast-paced 60 days in Washington DC BY A USER FROM CHILE January, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: January, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 23 days in United States & Papeete BY A USER FROM ITALY July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular & hidden gems PREFERENCES: July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Fast-paced 38 days in United States BY A USER FROM UNITED STATES November, teens, culture, relaxing, beaches, historic sites, museums, shopping, popular sights PREFERENCES: November, teens, culture, relaxing, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 4 days in Orlando & Savannah BY A USER FROM UNITED STATES November, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular sights PREFERENCES: November, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Fast-paced 32 days in United States BY A USER FROM UNITED KINGDOM July, teens, kids, culture, outdoors, relaxing, historic sites, museums, shopping, slow & easy, popular & hidden gems PREFERENCES: July, teens, kids, culture, outdoors, relaxing, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 10 days in Charleston, Savannah & Kansas City BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 7 days in United States BY A USER FROM UNITED STATES November, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: November, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 8 days in New York City BY A USER FROM UNITED STATES April, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, hidden gems PREFERENCES: April, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium 3 days in Savannah BY A USER FROM UNITED STATES March, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, hidden gems PREFERENCES: March, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium 22 days in New York City & Los Angeles BY A USER FROM AUSTRALIA March, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: March, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium
View more plans