22 days in Caribbean Itinerary

22 days in Caribbean Itinerary

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Route & dates

22 days in Caribbean Itinerary

Start: Yellowstone National Park, United States
Drive + Fly:  12​h
1
San Juan, Puerto Rico
— 3 nights
Fly:  30​min
2
Culebra, Puerto Rico
— 3 nights
Fly + Drive:  2​h 15​min
3
Isla de Vieques, Puerto Rico
— 5 nights
Fly:  3​h
4
Philipsburg, St. Maarten-St. Martin
— 5 nights
Fly + Shuttle:  4​h 15​min
5
Punta Cana, Dominican Republic
— 2 nights
Fly:  6​h
6
Havana, Cuba
— 3 nights
Fly + Drive:  19​h 15​min
End: Yellowstone National Park, United States

3
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Go for a jaunt from San Juan to El Yunque National Forest to see El Yunque Rain Forest about 1h 10 min away. There's much more to do: get to know the fascinating history of Old San Juan, appreciate the history behind Paseo de los Presidentes, skim along the rocks with a canyoning and rapelling tour, and indulge your taste buds at Food & Drink.

For maps, photos, more things to do, and tourist information, read our San Juan planning website .

Yellowstone National Park, USA to San Juan is an approximately 12-hour combination of car and flight. The time zone changes from Mountain Standard Time to Atlantic Standard Time, which is usually a 3 hour difference. Traveling from Yellowstone National Park in April, things will get much hotter in San Juan: highs are around 87°F and lows about 75°F. Cap off your sightseeing on the 11th (Sat) early enough to catch the flight to Culebra.

Things to do in San Juan

Parks Outdoors Tours

Side Trip

El Yunque Rain Forest
Find places to stay Apr 8 — 11:
Highlights from your plan
Old San Juan ©
Old San Juan
El Yunque Rain Forest ©
El Yunque Rain Forest
Condado Beach ©
Condado Beach

3
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.
Culebra is known for beaches, wildlife, nature, outdoors, and adventure. Your plan includes some of its best attractions: kick back and relax at Flamenco Beach, tour the pleasant surroundings at Tamarindo Beach, step off the mainland to explore Culebrita Island, and enjoy the sea views from Culebrita Lighthouse.

To see photos, other places to visit, more things to do, and tourist information, you can read our Culebra trip website .

Culebra is just a short distance from San Juan. In April, daytime highs in Culebra are 85°F, while nighttime lows are 76°F. Finish your sightseeing early on the 14th (Tue) so you can travel to Isla de Vieques.

Things to do in Culebra

Parks Outdoors Beaches
Find places to stay Apr 11 — 14:
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Culebrita Island ©
Culebrita Island
Zoni Beach ©
Zoni Beach

5
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.
Isla de Vieques is known for nature, beaches, adventure, wildlife, and nightlife. Your plan includes some of its best attractions: explore the activities along Sun Bay Beach, tour the pleasant surroundings at Secret Beach, kick back and relax at La Chiva, and trot along with a tour on horseback.

To see other places to visit, traveler tips, and more tourist information, go to the Isla de Vieques trip maker tool .

Traveling by combination of flight and car from Culebra to Isla de Vieques takes 2.5 hours. Alternatively, you can ride a ferry. In April, daily temperatures in Isla de Vieques can reach 85°F, while at night they dip to 75°F. Cap off your sightseeing on the 19th (Sun) early enough to travel to Philipsburg.

Things to do in Isla de Vieques

Outdoors Parks Beaches
Find places to stay Apr 14 — 19:
Highlights from your plan
Sun Bay Beach ©
Sun Bay Beach
Vieques National Wildlife Refuge ©
Vieques National Wildlife Refuge
La Chiva ©
La Chiva

5
nights
Philipsburg, St. Maarten-St. Martin

Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Philipsburg is known for shopping, beaches, wildlife, adventure, and museums. Your plan includes some of its best attractions: enjoy the sand and surf at Maho Beach, make a trip to Frontstreet, tour the pleasant surroundings at Orient Bay Beach, and try to win big at Casino Royale.

For other places to visit, more things to do, reviews, and other tourist information, go to the Philipsburg trip site .

Traveling by flight from Isla de Vieques to Philipsburg takes 3 hours. Expect a daytime high around 84°F in April, and nighttime lows around 75°F. Wrap up your sightseeing on the 24th (Fri) to allow time to travel to Punta Cana.

Things to do in Philipsburg

Outdoors Parks Beaches

Side Trips

Sint Maarten, Saint-Martin, Maho, Orient Bay Beach, WAKE N' GLISSE
Find places to stay Apr 19 — 24:
Highlights from your plan
Speed Boats Tours
Orient Bay Beach ©
Orient Bay Beach
Mullet Bay Beach ©
Mullet Bay Beach

2
nights
Punta Cana, Dominican Republic

Punta Cana ©
In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.
Start off your visit on the 25th (Sat): play a few rounds at Punta Espada Golf Course and then stroll through Bavaro Beach. Get ready for a full day of sightseeing on the 26th (Sun): look for gifts at HARRISON'S Fine Caribbean Jewelers and then head off the coast to Saona Island.

To find traveler tips, ratings, maps, and other tourist information, go to the Punta Cana sightseeing planner.

You can do a combination of flight and shuttle from Philipsburg to Punta Cana in 4.5 hours. Another option is to fly. In April, daily temperatures in Punta Cana can reach 86°F, while at night they dip to 74°F. Finish your sightseeing early on the 26th (Sun) so you can travel to Havana.

Things to do in Punta Cana

Parks Outdoors Nature
Find places to stay Apr 24 — 26:
Highlights from your plan
Bavaro Beach ©
Bavaro Beach
Saona Island ©
Saona Island
Punta Espada Golf Course ©
Punta Espada Golf Course

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.
On the 27th (Mon), contemplate the long history of Fortaleza de San Carlos de la Cabana, then make a trip to Plaza de Armas, and then get to know the fascinating history of Old Havana. On your second day here, wander the streets of Christopher Columbus Cemetery (Cemetario de Colon), get to know the fascinating history of Malecón of Havana, then don't miss a visit to Plaza de la Catedral, and finally make a trip to El Capitolio.

For ratings, photos, maps, and tourist information, you can read our Havana trip planner .

You can fly from Punta Cana to Havana in 6 hours. Alternatively, you can do a combination of shuttle and flight. The time zone changes from Atlantic Standard Time to Cuba Standard Time, which is usually a -1 hour difference. Traveling from Punta Cana in April, Havana is a bit cooler at night with lows of 67°F. Finish your sightseeing early on the 29th (Wed) to allow enough time to travel back home.

Things to do in Havana

Historic Sites Neighborhoods
Find places to stay Apr 26 — 29:
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Fortaleza de San Carlos de la Cabana ©

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