21 days in Los Angeles, New York City & Caribbean Itinerary

21 days in Los Angeles, New York City & Caribbean Itinerary

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Route & dates

21 days in Los Angeles, New York City & Caribbean Itinerary

Start: Brisbane, Australia
Fly:  16​h
1
Los Angeles, United States
— 3 nights
Fly:  8​h 45​min
2
New York City, United States
— 3 nights
Fly:  6​h 30​min
3
Culebra, Puerto Rico
— 2 nights
Fly + Drive:  2​h 15​min
4
Isla de Vieques, Puerto Rico
— 2 nights
Fly:  3​h
5
Shoal Bay Village, Anguilla
— 1 night
taxi + Fly:  30​min
6
St. Jean, St. Barthelemy
— 2 nights
Fly:  3​h
7
Santo Domingo, Dominican Republic
— 1 night
Fly:  2​h 45​min
8
Havana, Cuba
— 3 nights
Fly:  26​h
End: Brisbane, Australia


Learn more about your trip

3
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.
Head to Abbot Kinney Boulevard and Melrose Trading Postfor plenty of shopping. Get a sense of the local culture at Montana Avenue and Annenberg Community Beach House. When in Los Angeles, make a side trip to see Third Street Promenade in Santa Monica, approximately 30 minutes away. Next up on the itinerary: get a taste of the local shopping with Hammer Museum, take in the exciting artwork at Annenberg Space for Photography, examine the collection at The Getty Center, and look for gifts at Amoeba Music.

To see reviews, ratings, traveler tips, and tourist information, read Los Angeles trip itinerary tool .

Brisbane, Australia to Los Angeles is an approximately 16-hour flight. You can also do a combination of flight and train. You'll gain 18 hours traveling from Brisbane to Los Angeles due to the time zone difference. Expect little chillier temperatures when traveling from Brisbane in March; daily highs in Los Angeles reach 27°C and lows reach 14°C. Finish up your sightseeing early on the 10th (Tue) so you can travel to New York City.

Things to do in Los Angeles

Shopping Museums Historic Sites

Side Trip

Santa Monica
Highlights from your plan
Abbot Kinney Boulevard ©
Abbot Kinney Boulevard
The Getty Center ©
The Getty Center
Santa Monica Pier ©
Santa Monica Pier

3
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.
For shopping fun, head to Fifth Avenue or The Strand Bookstore. Popular historic sites such as 9/11 Memorial and Ellis Island are in your itinerary. There's much more to do: explore the world behind art at The Metropolitan Museum of Art, take in the architecture and atmosphere at St. Patrick's Cathedral, ponder the world of politics at New York City Hall, and take in panoramic vistas at Empire State Building.

For more things to do, ratings, and other tourist information, go to the New York City holiday builder .

You can fly from Los Angeles to New York City in 9 hours. Alternatively, you can do a combination of flight and bus; or drive. Due to the time zone difference, you'll lose 3 hours traveling from Los Angeles to New York City. While traveling from Los Angeles, expect much colder days and a bit cooler nights in New York City, ranging from highs of 11°C to lows of 1°C. Finish up your sightseeing early on the 14th (Sat) so you can travel to Culebra.

Things to do in New York City

Museums Historic Sites Parks
Highlights from your plan
9/11 Memorial ©
9/11 Memorial
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
Ellis Island ©
Ellis Island

2
nights
Culebra, Puerto Rico

Culebra ©
With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Kick off your visit on the 15th (Sun): stroll through Playa Punta Soldado Beach and then enjoy the sand and surf at Flamenco Beach. Keep things going the next day: tour the pleasant surroundings at Carlos Rosario Beach, then stop by Zinkowski Art Studio, then browse the collection at Culebra Public Library, and finally enjoy the sand and surf at Zoni Beach.

To find where to stay, ratings, photos, and other tourist information, go to the Culebra trip builder tool .

Traveling by flight from New York City to Culebra takes 6.5 hours. Alternatively, you can do a combination of bus and flight; or do a combination of flight, shuttle, and ferry. You'll lose 1 hour traveling from New York City to Culebra due to the time zone difference. Traveling from New York City in March, things will get much hotter in Culebra: highs are around 34°C and lows about 26°C. Wrap up your sightseeing on the 16th (Mon) early enough to travel to Isla de Vieques.

Things to do in Culebra

Outdoors Parks Beaches
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach
Playa Punta Soldado Beach ©
Playa Punta Soldado Beach

2
nights
Isla de Vieques, Puerto Rico

Isla de Vieques ©
For sixty years until 2003, most of the Isla de Vieques was closed off to the public, with the US Navy using the island's beaches and surrounding waters for drills and testing of new military machinery, such as bombs.
Start off your visit on the 17th (Tue): enjoy the sea views from Puerto Ferro Lighthouse, delve into the distant past at El Hombre de Puerto Ferro, and then tour the pleasant surroundings at Sun Bay. Here are some ideas for day two: look for gifts at Isla Vida, then take in the exciting artwork at Siddhia Hutchinson Fine Art Gallery, then tour the pleasant surroundings at Media Luna Beach, and finally kick back and relax at La Chiva.

To see maps, traveler tips, other places to visit, and tourist information, go to the Isla de Vieques vacation site .

Traveling by combination of flight and car from Culebra to Isla de Vieques takes 2.5 hours. Alternatively, you can ride a ferry. In March in Isla de Vieques, expect temperatures between 34°C during the day and 26°C at night. Cap off your sightseeing on the 18th (Wed) early enough to travel to Shoal Bay Village.

Things to do in Isla de Vieques

Outdoors Parks Beaches
Highlights from your plan
Sun Bay Beach ©
Sun Bay Beach
Media Luna Beach ©
Media Luna Beach
La Chiva ©
La Chiva

1
night
Shoal Bay Village, Anguilla

Shoal Bay Village ©
On the 19th (Thu), stop by Irie Life, enjoy the sand and surf at Rendezvous Bay Beach, and then kick back and relax at Shoal Bay.

To see other places to visit and other tourist information, read Shoal Bay Village day trip planning app .

Getting from Isla de Vieques to Shoal Bay Village by flight takes about 3 hours. Other options: do a combination of flight and ferry. March in Shoal Bay Village sees daily highs of 34°C and lows of 26°C at night. Wrap up your sightseeing on the 19th (Thu) to allow time to travel to St. Jean.

Things to do in Shoal Bay Village

Outdoors Parks Beaches

Side Trips

Irie Life, Rendezvous Bay Beach
Highlights from your plan
Shoal Bay ©
Shoal Bay
Rendezvous Bay Beach ©
Rendezvous Bay Beach

2
nights
St. Jean, St. Barthelemy

St. Jean ©
Start off your visit on the 20th (Fri): kick back and relax at Colombier Beach and then kick back and relax at St. Jean Beach. On the 21st (Sat), you'll have a packed day of sightseeing: steep yourself in history at Corossol, kick back and relax at Grand Cul de Sac Beach, then enjoy the sand and surf at Anse de Grande Saline, and finally look for gifts at Sea Spice.

For where to stay, traveler tips, more things to do, and more tourist information, read St. Jean trip planning tool .

St. Jean is very close to Shoal Bay Village. Wrap up your sightseeing on the 21st (Sat) to allow time to travel to Santo Domingo.

Things to do in St. Jean

Outdoors Parks Beaches

Side Trips

St. Barthelemy, Grand Cul de Sac Beach
Highlights from your plan
St. Jean Beach ©
St. Jean Beach
Colombier Beach ©
Colombier Beach
Grand Cul de Sac Beach ©
Grand Cul de Sac Beach

1
night
Santo Domingo, Dominican Republic

Santo Domingo ©
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
On the 22nd (Sun), appreciate the history behind Columbus Lighthouse (Faro A Colon), contemplate in the serene atmosphere at Catedral Primada de America, view the masterpieces at Amber Museum, then step into the grandiose world of Alcazar de Colon, and finally steep yourself in history at Fortaleza Ozama.

To see traveler tips, photos, maps, and other tourist information, refer to the Santo Domingo trip itinerary maker site .

Fly from St. Jean to Santo Domingo in 3 hours. Wrap up your sightseeing on the 22nd (Sun) to allow time to travel to Havana.

Things to do in Santo Domingo

Historic Sites Museums Shopping
Highlights from your plan
Alcazar de Colon ©
Alcazar de Colon
Catedral Primada de America
Catedral Primada de America
Fortaleza Ozama ©
Fortaleza Ozama

3
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Visit El Malecon and Christopher Columbus Cemetery (Cemetario de Colon) for their historical value. Get some cultural insight at Fortaleza de San Carlos de la Cabana and El Morro. There's much more to do: appreciate the extensive heritage of Old Havana, steep yourself in history at Casa de la Amistad, take an in-depth tour of Museum of the Revolution (Museo de la Revolucion), and make a trip to Plaza de Armas.

Find out how to plan Havana trip without stress by asking Inspirock to help create an itinerary.

Fly from Santo Domingo to Havana in 3 hours. You'll gain 1 hour traveling from Santo Domingo to Havana due to the time zone difference. March in Havana sees daily highs of 32°C and lows of 19°C at night. Wrap up your sightseeing on the 25th (Wed) early enough to travel back home.

Things to do in Havana

Historic Sites Museums Neighborhoods
Highlights from your plan
El Malecon ©
El Malecon
Fortaleza de San Carlos de la Cabana ©

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