55 days in United States, Mexico & Cuba Itinerary

55 days in United States, Mexico & Cuba Itinerary

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Route & dates

55 days in United States, Mexico & Cuba Itinerary

Start: Sydney, Australia
Fly:  17 h 45 min
1
Los Angeles, United States
— 4 nights
Drive:  1 h 45 min
2
Santa Barbara, United States
— 2 nights
Drive:  3 h 45 min
3
San Diego, United States
— 4 nights
Fly:  6 h 15 min
4
New Orleans, United States
— 3 nights
+2
Fly + Foot + Bus:  6 h 15 min
5
Tulum, Mexico
— 4 nights
Bus:  1 h
6
Playa del Carmen, Mexico
— 3 nights
Drive:  1 h
7
Cancun, Mexico
— 2 nights
Drive:  1 h 15 min
8
Isla Mujeres, Mexico
— 1 night
+3
Ferry + Bus + Foot + Fly:  3 h 30 min
9
Havana, Cuba
— 3 nights
Fly:  7 h 15 min
10
New York City, United States
— 4 nights
Bus + Fly:  3 h
11
Boston, United States
— 4 nights
Fly:  4 h
12
Chicago, United States
— 4 nights
Fly + Bus:  4 h
13
Nashville, United States
— 2 nights
Drive:  3 h 30 min
14
Memphis, United States
— 2 nights
Bus + Fly:  7 h 45 min
15
Las Vegas, United States
— 4 nights
Fly:  4 h
16
San Francisco, United States
— 5 nights
Fly:  17 h
End: Sydney, Australia

4
nights
Los Angeles, United States

Los Angeles ©
Surrounded by mountain ranges, forests, valleys, beaches, and deserts, the metropolitan area of Los Angeles is home to over 17 million people.
Explore Los Angeles' surroundings by going to Anaheim (Disneyland Park & Disney California Adventure Park). There's much more to do: find something for the whole family at Universal Studios Hollywood, don't miss a visit to Santa Monica Pier, admire the landmark architecture of Walt Disney Concert Hall, and look and learn at Griffith Observatory.

For more things to do, reviews, maps, and more tourist information, read our Los Angeles day trip planner .

Sydney, Australia to Los Angeles is an approximately 18-hour flight. You can also do a combination of train and flight; or do a combination of bus and flight. You'll gain 18 hours traveling from Sydney to Los Angeles due to the time zone difference. In May, daytime highs in Los Angeles are 28°C, while nighttime lows are 17°C. Wrap up your sightseeing on the 11th (Mon) early enough to drive to Santa Barbara.

Things to do in Los Angeles

Theme Parks Museums Fun & Games

Side Trips

Anaheim, Santa Monica Pier
Highlights from your plan
Diorama-museum of Bhagavad-gita ©
Diorama-museum of Bhagavad-gita
Disneyland Park ©
Disneyland Park
Universal Studios Hollywood ©
Universal Studios Hollywood

2
nights
Santa Barbara, United States

Nestled between the Pacific Ocean and the Santa Ynez Mountains, Santa Barbara is a solid vacation destination with its wide beaches, renowned wineries, and some of California's finest shopping and dining options.
Start off your visit on the 12th (Tue): contemplate the long history of Old Mission Santa Barbara, explore the world behind art at Santa Barbara Museum of Art, and then get lost in a book at Camarillo Public Library. On your second day here, learn about wildlife with up-close encounters at Santa Barbara Zoo and then awaken your taste buds at some of the top wineries in the area.

To find where to stay, ratings, maps, and other tourist information, read Santa Barbara trip planner .

Traveling by car from Los Angeles to Santa Barbara takes 2 hours. Alternatively, you can take a bus; or take a train. Plan for a bit cooler nights when traveling from Los Angeles in May since evenings lows in Santa Barbara dip to 13°C. Wrap up your sightseeing on the 13th (Wed) to allow time to drive to San Diego.

Things to do in Santa Barbara

Tours Historic Sites Parks

Side Trip

Camarillo Public Library
Highlights from your plan
Wine Tours & Tastings
Camarillo Public Library ©
Camarillo Public Library
Old Mission Santa Barbara ©
Old Mission Santa Barbara

4
nights
San Diego, United States

San Diego ©
Divided into neighborhoods with distinct characters and cultural heritages, San Diego sits just north of the Mexican border and offers visitors a blend of tourist attractions, including a lively nightlife, diverse cuisine, and a thriving musical scene.
Change things up with a short trip to Self Realization Fellowship Hermitage & Meditation Gardens in Encinitas (about 30 minutes away). Next up on the itinerary: get to know the resident critters at San Diego Zoo, take in nature's colorful creations at Botanical Building and Lily Pond, examine the collection at USS Midway Museum, and pause for some photo ops at Cabrillo National Monument.

To see more things to do, reviews, and tourist information, you can read our San Diego online visit planner .

Getting from Santa Barbara to San Diego by car takes about 4 hours. Other options: do a combination of bus and flight; or fly. Plan for a bit warmer nights when traveling from Santa Barbara in May since evenings lows in San Diego dip to 19°C. Finish your sightseeing early on the 17th (Sun) to allow enough time to travel to New Orleans.

Things to do in San Diego

Parks Zoos & Aquariums Fun & Games

Side Trip

Self Realization Fellowship Hermitage & Meditation Gardens
Highlights from your plan
AxeVentures ©
AxeVentures
San Diego Zoo ©
San Diego Zoo
Balboa Park ©
Balboa Park

3
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: examine the collection at The National WWII Museum, make a trip to Jackson Square, get to know the fascinating history of French Quarter, and wander the streets of Garden District.

For ratings, photos, other places to visit, and more tourist information, refer to the New Orleans trip planner .

Traveling by flight from San Diego to New Orleans takes 6.5 hours. Alternatively, you can drive; or take a bus. The time zone changes from Pacific Standard Time to Central Standard Time, which is usually a 2 hour difference. Traveling from San Diego in May, expect a bit warmer with lows of 24°C in New Orleans. Wrap up your sightseeing on the 21st (Thu) early enough to travel to Tulum.

Things to do in New Orleans

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

4
nights
Tulum, Mexico

The only Mayan site built to overlook the ocean, Tulum remains a coastal paradise preserving the last vestiges of a pre-Hispanic civilization.
Explore Tulum's surroundings by going to Cobá Zona Arqueológica Cobá (in Coba) and Sian Ka'an Biosphere Reserve (in Sian Ka'an). The adventure continues: explore the ancient world of Tulum Archaeological Site, explore the galleries of MiNiAtUrE art Gallery, Head underground at Cenotes Sac Actun, and indulge in some personalized pampering at some of the best spas.

To find traveler tips, more things to do, maps, and tourist information, refer to the Tulum trip planner.

Traveling by combination of flight and bus from New Orleans to Tulum takes 6.5 hours. Alternatively, you can drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from New Orleans to Tulum. Traveling from New Orleans in May, expect nights in Tulum to be about the same, around 25°C, while days are somewhat warmer, around 34°C. Finish your sightseeing early on the 25th (Mon) to allow enough time to take a bus to Playa del Carmen.

Things to do in Tulum

Outdoors Adventure Tours

Side Trips

Sian Ka'an Biosphere Reserve, Cobá Zona Arqueológica Cobá
Highlights from your plan
Climbing Tours
Tulum Archaeological Site ©
Tulum Archaeological Site
Sian Ka'an Biosphere Reserve ©
Sian Ka'an Biosphere Reserve

3
nights
Playa del Carmen, Mexico

The tourist hub of the popular Mayan Riviera, upscale Playa del Carmen remains the jewel of Mexico's Caribbean coastline.
Playa del Carmen is known for theme parks, adventure, wildlife, nightlife, and nature. Your plan includes some of its best attractions: get in on the family fun at Xcaret, make a trip to Quinta Avenida, discover the deep blue sea with a scuba or snorkeling tour, and whizz through the canopy at some of the top local zipline courses and adventure parks.

For traveler tips, other places to visit, where to stay, and more tourist information, go to the Playa del Carmen day trip planning app .

You can take a bus from Tulum to Playa del Carmen in an hour. Another option is to drive. Expect a daytime high around 34°C in May, and nighttime lows around 25°C. Finish your sightseeing early on the 28th (Thu) to allow enough time to drive to Cancun.

Things to do in Playa del Carmen

Outdoors Tours Adventure
Highlights from your plan
Skydiving
Xcaret ©
Xcaret
Scuba & Snorkeling

2
nights
Cancun, Mexico

Few destinations in Mexico dazzle visitors quite like Cancun, a modern resort town filled with glitzy hotels sitting on picturesque and well-developed Caribbean beaches.
Start off your visit on the 29th (Fri): head outdoors with Outdoor Activities and then buy something for everyone on your list at La Isla Shopping Village. Get ready for a full day of sightseeing on the 30th (Sat): head outdoors with Outdoor Activities and then steep yourself in history at El Rey Archaeological Zone.

To find where to stay, other places to visit, photos, and tourist information, go to the Cancun online trip itinerary builder .

Getting from Playa del Carmen to Cancun by car takes about an hour. Other options: take a bus. In May in Cancun, expect temperatures between 35°C during the day and 28°C at night. Finish up your sightseeing early on the 30th (Sat) so you can go by car to Isla Mujeres.

Things to do in Cancun

Outdoors Tours Wildlife
Highlights from your plan
Swim with Dolphins
La Isla Shopping Village ©
La Isla Shopping Village
Zipline

1
night
Isla Mujeres, Mexico

Isla Mujeres ©
Tiny municipal seat of an eponymous island, each season Isla Mujeres swells to bursting with international tourists coming here to swim, snorkel, dive, fish, and sail.
Kick off your visit on the 31st (Sun): explore the ancient world of Punta Sur, take in the architecture and atmosphere at Iglesia Del Sagrado Corazon, and then tour the pleasant surroundings at Playa Norte.

For photos, where to stay, reviews, and more tourist information, read our Isla Mujeres tour itinerary planner .

You can drive from Cancun to Isla Mujeres in 1.5 hours. May in Isla Mujeres sees daily highs of 35°C and lows of 28°C at night. Finish your sightseeing early on the 31st (Sun) to allow enough time to travel to Havana.

Things to do in Isla Mujeres

Beaches Parks Outdoors
Highlights from your plan
Playa Norte ©
Playa Norte
Punta Sur ©
Punta Sur
Iglesia Del Sagrado Corazon ©
Iglesia Del Sagrado Corazon

3
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: make a trip to Malecón of Havana, contemplate the long history of Castillo de la Real Fuerza, get the lay of the land with Walking tours, and take an in-depth tour of Museum of the Revolution (Museo de la Revolucion).

To see maps, where to stay, traveler tips, and tourist information, read Havana online trip itinerary planner .

Getting from Isla Mujeres to Havana by combination of ferry and flight takes about 3.5 hours. Traveling from Isla Mujeres in May, plan for slightly colder nights in Havana, with lows around 24°C. Cap off your sightseeing on the 3rd (Wed) early enough to travel to New York City.

Things to do in Havana

Tours Historic Sites Museums
Highlights from your plan
Photography Tours
Malecón of Havana ©
Malecón of Havana
Fortaleza de San Carlos de la Cabana ©

4
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: go for a walk through Central Park, take a stroll through Times Square, don't miss a visit to Statue of Liberty National Monument, and admire the landmark architecture of Rockefeller Center.

For ratings, reviews, photos, and more tourist information, read New York City trip planner .

You can fly from Havana to New York City in 7.5 hours. Another option is to fly. Expect slightly colder temperatures when traveling from Havana in June; daily highs in New York City reach 31°C and lows reach 21°C. Finish your sightseeing early on the 8th (Mon) to allow enough time to travel to Boston.

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

4
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.
Explore the numerous day-trip ideas around Boston: Falmouth (Shining Sea Bikeway, Cornelia Carey Sanctuary (The Knob), & more), Stanley park (in Westfield) and Cape Cod Canal (in Buzzards Bay). There's much more to do: examine the collection at Heritage Museums & Gardens, admire the masterpieces at Sandwich Glass Museum, explore the different monuments and memorials at Mount Auburn Cemetery, and get advice or help at Boston Public Library.

To see reviews, maps, more things to do, and more tourist information, use the Boston trip itinerary builder tool .

Traveling by combination of bus and flight from New York City to Boston takes 3 hours. Alternatively, you can fly; or drive. Traveling from New York City in June, plan for slightly colder nights in Boston, with lows around 18°C. Finish up your sightseeing early on the 12th (Fri) so you can travel to Chicago.

Things to do in Boston

Parks Museums Historic Sites

Side Trips

Falmouth, Sandwich, Cape Cod Canal, Mount Auburn Cemetery, Stanley park
Highlights from your plan
Stanley park ©
Stanley park
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Museum of Fine Arts ©
Museum of Fine Arts

4
nights
Chicago, United States

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, parks, nightlife, zoos & aquariums, and childrens museums. Your plan includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, get to know the resident critters at Lincoln Park Zoo, tour the pleasant surroundings at Millennium Park, and admire the striking features of 360 Chicago Observation Deck.

To see maps, traveler tips, more things to do, and other tourist information, use the Chicago road trip tool .

You can fly from Boston to Chicago in 4 hours. Other options are to do a combination of bus and flight; or drive. Due to the time zone difference, you'll gain 1 hour traveling from Boston to Chicago. Expect a daytime high around 32°C in June, and nighttime lows around 20°C. Finish your sightseeing early on the 16th (Tue) so you can travel to Nashville.

Things to do in Chicago

Museums Parks Childrens Museums

Side Trip

Ernest Hemingway Birthplace
Highlights from your plan
BATL-The Backyard Axe Throwing League ©
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry

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.
On the 17th (Wed), see the interesting displays at Country Music Hall of Fame and Museum, have some family-friendly fun at BATL - The Backyard Axe Throwing League, and then indulge your taste buds at Food & Drink. On your second day here, catch a live performance at Grand Ole Opry, then test your team's savvy at The Escape Game Nashville (Berry Hill), then take in the history at Lotz House Museum, and finally brush up on your knowledge of spirits at Nelson's Green Brier Distillery.

To find photos, ratings, other places to visit, and more tourist information, go to the Nashville travel route planner .

You can fly from Chicago to Nashville in 4 hours. Other options are to do a combination of subway, bus, and flight; or drive. When traveling from Chicago in June, plan for a bit warmer days in Nashville, with highs around 36°C, while nights are about the same with lows around 22°C. Finish your sightseeing early on the 18th (Thu) so you can drive to Memphis.

Things to do in Nashville

Fun & Games Museums Tours

Side Trip

Lotz House Museum
Highlights from your plan
The Escape Game Nashville (Berry Hill) ©
BATL - The Backyard Axe Throwing League ©
Lotz House Museum ©
Lotz House Museum

2
nights
Memphis, United States

Memphis ©
The largest city on the Mississippi River, Memphis bills itself as both the "Birthplace of Rock" and "Home of the Blues." With such a rich musical heritage, it shouldn't come as a surprise that Elvis Presley chose to live in Memphis during his later years.
Start off your visit on the 19th (Fri): see the interesting displays at Graceland, then admire the masterpieces at Belz Museum of Asian & Judaic Art, then look for gifts at Lansky, and finally don't miss a visit to Beale Street. Get ready for a full day of sightseeing on the next day: test your team's savvy at popular escape rooms, make a trip to The Peabody Ducks, then appreciate the history behind National Civil Rights Museum - Lorraine Motel, and finally contemplate the long history of Sun Studio.

For traveler tips, ratings, photos, and other tourist information, read our Memphis online day trip planner .

Drive from Nashville to Memphis in 3.5 hours. Alternatively, you can take a bus; or fly. In June in Memphis, expect temperatures between 37°C during the day and 25°C at night. Wrap up your sightseeing on the 20th (Sat) to allow time to travel to Las Vegas.

Things to do in Memphis

Museums Historic Sites Fun & Games
Highlights from your plan
Graceland
Graceland
Room Escape Games

4
nights
Las Vegas, United States

Las Vegas ©
Nicknamed the "Entertainment Capital of the World," Las Vegas sits in the middle of a desert in the southern section of Nevada.
Take a break from Las Vegas with a short trip to Hoover Dam in Boulder City, about 50 minutes away. The adventure continues: ponder the design of Fountains of Bellagio, examine the collection at The Neon Museum, admire the natural beauty at Bellagio Conservatory & Botanical Gardens, and try your luck at Bellagio Hotel and Casino.

To find ratings, other places to visit, reviews, and tourist information, read our Las Vegas sightseeing planning tool .

You can fly from Memphis to Las Vegas in 8 hours. Alternatively, you can do a combination of bus and flight; or drive. Traveling from Memphis to Las Vegas, you'll gain 2 hours due to the time zone difference. Traveling from Memphis in June, things will get somewhat warmer in Las Vegas: highs are around 46°C and lows about 29°C. Wrap up your sightseeing on the 24th (Wed) to allow time to travel to San Francisco.

Things to do in Las Vegas

Parks Fun & Games Shopping

Side Trip

Hoover Dam
Highlights from your plan
Fountains of Bellagio ©
Fountains of Bellagio
The Strip ©
The Strip

5
nights
San Francisco, United States

San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
San Francisco is known for nature, museums, nightlife, parks, and shopping. Your plan includes some of its best attractions: don't miss a visit to Golden Gate Bridge, take in the waterfront at Fisherman's Wharf, wander the streets of SoMa, and walk around Golden Gate Park.

For where to stay, more things to do, maps, and more tourist information, read San Francisco day trip planner.

You can fly from Las Vegas to San Francisco in 4 hours. Other options are to do a combination of flight and train; or drive. Traveling from Las Vegas in June, things will get cooler in San Francisco: highs are around 25°C and lows about 15°C. Wrap up your sightseeing by early afternoon on the 29th (Mon) to allow enough time to travel back home.

Things to do in San Francisco

Parks Museums Historic Sites
Highlights from your plan
Beer Tastings & Tours
Golden Gate Bridge ©
Golden Gate Bridge
Alcatraz Island ©
Alcatraz Island

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