14 days in Caribbean Itinerary

14 days in Caribbean Itinerary

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Route & dates

14 days in Caribbean Itinerary

Start: San Francisco, United States
Fly:  10​h 30​min
1
Havana, Cuba
— 3 nights
Fly:  2​h 45​min
2
Santo Domingo, Dominican Republic
— 2 nights
shuttle:  2​h
3
Punta Cana, Dominican Republic
— 2 nights
Fly:  4​h 30​min
4
San Juan, Puerto Rico
— 3 nights
Fly:  9​h 15​min
5
Soufriere, St. Lucia
— 2 nights
Fly:  13​h 15​min
End: San Francisco, United States

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.
Havana is known for historic sites, museums, nightlife, beaches, and parks. Your plan includes some of its best attractions: don't miss a visit to El Malecon, explore the different monuments and memorials at Christopher Columbus Cemetery (Cemetario de Colon), get to know the fascinating history of Old Havana, and steep yourself in history at Fortaleza de San Carlos de la Cabana.

To find more things to do, ratings, photos, and other tourist information, refer to the Havana day trip planner .

San Francisco, USA to Havana is an approximately 10.5-hour flight. The time zone difference moving from Pacific Standard Time to Cuba Standard Time is 3 hours. In November, Havana is a bit warmer than San Francisco - with highs of 83°F and lows of 65°F. Wrap up your sightseeing on the 27th (Wed) early enough to travel to Santo Domingo.

Things to do in Havana

Historic Sites Museums Neighborhoods
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Plaza de la Catedral ©
Plaza de la Catedral

2
nights
Santo Domingo, Dominican Republic

Santo Domingo ©
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Start off your visit on the 28th (Thu): make a trip to Zona Colonial and then steep yourself in history at Fortaleza Ozama. Get ready for a full day of sightseeing on the 29th (Fri): appreciate the history behind Columbus Lighthouse (Faro A Colon), then contemplate in the serene atmosphere at Catedral Primada de America, then step into the grandiose world of Alcazar de Colon, and finally observe the fascinating underwater world at National Aquarium.

To find photos, maps, where to stay, and tourist information, go to the Santo Domingo online journey planner .

Getting from Havana to Santo Domingo by flight takes about 3 hours. Due to the time zone difference, you'll lose 1 hour traveling from Havana to Santo Domingo. Finish your sightseeing early on the 29th (Fri) so you can take a shuttle to Punta Cana.

Things to do in Santo Domingo

Historic Sites Parks Zoos & Aquariums
Highlights from your plan
Alcazar de Colon ©
Alcazar de Colon
Zona Colonial ©
Zona Colonial
Catedral Primada de America
Catedral Primada de America

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 30th (Sat): tee off at Punta Espada Golf Course and then stroll through Bavaro Beach. Keep things going the next day: make a trip to Jesus Maestro Parish and then step off the mainland to explore Saona Island.

For where to stay, other places to visit, and other tourist information, you can read our Punta Cana trip itinerary builder app .

You can take a shuttle from Santo Domingo to Punta Cana in 2 hours. Alternatively, you can drive; or take a bus. In November, plan for daily highs up to 85°F, and evening lows to 74°F. Wrap up your sightseeing on the 1st (Sun) to allow time to travel to San Juan.

Things to do in Punta Cana

Parks Outdoors Beaches
Highlights from your plan
Bavaro Beach ©
Bavaro Beach
Saona Island ©
Saona Island
Punta Espada Golf Course ©
Punta Espada Golf Course

3
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Step out of San Juan to go to El Yunque National Forest and see El Yunque Rain Forest, which is approximately 1h 10 min away. Next up on the itinerary: contemplate the long history of Old San Juan, admire the masterpieces at Museo de Las Americas, stop by Coqui el Original, and appreciate the extensive heritage of Sitio Histórico de San Juan.

To see photos, other places to visit, traveler tips, and tourist information, use the San Juan route planner.

Traveling by flight from Punta Cana to San Juan takes 4.5 hours. Alternatively, you can do a combination of shuttle and flight; or do a combination of bus and ferry. December in San Juan sees daily highs of 85°F and lows of 75°F at night. Cap off your sightseeing on the 4th (Wed) early enough to travel to Soufriere.

Things to do in San Juan

Parks Historic Sites Wildlife

Side Trip

El Yunque Rain Forest
Highlights from your plan
El Yunque Rain Forest ©
El Yunque Rain Forest
Old San Juan ©
Old San Juan
Sitio Histórico de San Juan ©
Sitio Histórico de San Juan

2
nights
Soufriere, St. Lucia

Soufriere ©
Home to some of Saint Lucia's landmark buildings and natural features, Soufriere provides travelers with an engaging and direct route into the center of island life.
Kick off your visit on the 5th (Thu): admire the natural beauty at Diamond Falls Botanical Gardens and then take your sightseeing to a higher altitude at Gros Piton. On your second day here, witness a stunning natural landmark at Sulphur Springs, then stop by St. Lucia Rum Shop, then contemplate the waterfront views at Rodney Bay, and finally contemplate the waterfront views at Marigot Bay.

For other places to visit, where to stay, and more tourist information, read Soufriere trip planning website .

Traveling by flight from San Juan to Soufriere takes 9.5 hours. December in Soufriere sees daily highs of 85°F and lows of 76°F at night. Wrap up your sightseeing by early afternoon on the 7th (Sat) to allow time for travel back home.

Things to do in Soufriere

Parks Nature Neighborhoods

Side Trips

St. Lucia, Rodney Bay
Highlights from your plan
Diamond Falls Botanical Gardens ©
Diamond Falls Botanical Gardens
Rodney Bay ©
Rodney Bay
Marigot Bay ©
Marigot Bay

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