16 days in Puerto Rico, Dominican Republic & Cuba Itinerary

16 days in Puerto Rico, Dominican Republic & Cuba Itinerary

Created using Inspirock Caribbean trip planner

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1
San Juan, Puerto Rico
— 3 nights
Fly
2
Culebra, Puerto Rico
— 4 nights
Fly
3
Punta Cana, Dominican Republic
— 3 nights
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4
Santo Domingo, Dominican Republic
— 2 nights
Fly
5
Havana, Cuba
— 2 nights
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San Juan, Puerto Rico

— 3 nights

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S. jurisdiction and one of the oldest in the Americas.
Old San Juan and Sitio Histórico de San Juan will appeal to history buffs. Visiting El Yunque Rain Forest and Pine Grove Beach will get you outdoors. The adventure continues: explore the world behind art at Museo de Arte de Puerto Rico, get a sense of history and politics at The Capitol of Puerto Rico, and contemplate the long history of La Fortaleza - Palacio de Santa Catalina.

To find more things to do, ratings, traveler tips, and tourist information, you can read our San Juan online journey planner.

Dublin, Ireland to San Juan is an approximately 15.5-hour flight. The time zone difference moving from Greenwich Mean Time (GMT) to Atlantic Standard Time (AST) is minus 4 hours. In March, San Juan is much warmer than Dublin - with highs of 34°C and lows of 26°C. Finish your sightseeing early on the 1st (Thu) so you can travel to Culebra.

Things to do in San Juan

Parks · Wildlife · Nature · Historic Sites

Side Trips

Find places to stay Mar 29 — Apr 1:

Culebra, Puerto Rico

— 4 nights

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Your itinerary includes some good beach time at Flamenco Beach and Zoni Beach. Visiting Culebrita and Culebra National Wildlife Refuge will get you outdoors. The adventure continues: enjoy the sand and surf at Playa Carlos Rosario, browse the collection at Culebra Public Library, tour the pleasant surroundings at Tamarindo Beach, and visit a coastal fixture at Culebrita Lighthouse.

To find ratings, other places to visit, reviews, and more tourist information, go to the Culebra trip planner.

Traveling by flight from San Juan to Culebra takes 2 hours. Alternatively, you can do a combination of car and ferry; or do a combination of shuttle and ferry. In April in Culebra, expect temperatures between 34°C during the day and 28°C at night. Wrap up your sightseeing on the 5th (Mon) early enough to travel to Punta Cana.

Things to do in Culebra

Parks · Beaches · Outdoors · Nature
Find places to stay Apr 1 — 5:

Punta Cana, Dominican Republic

— 3 nights
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.
Kick off your visit on the 6th (Tue): stop by Coralina Tropical Shop, identify plant and animal life at El Tour Caribe, and then enjoy the sand and surf at Bavaro Beach. Get ready for a full day of sightseeing on the next day: fulfill a lifelong dream with a swim-with-the-dolphins experience, enjoy the sand and surf at Macao Beach, and then look for gifts at HARRISON'S Fine Caribbean Jewelers.

For more things to do, photos, where to stay, and tourist information, read our Punta Cana tour planning site.

Getting from Culebra to Punta Cana by flight takes about 6.5 hours. Other options: do a combination of ferry, taxi, and bus; or do a combination of ferry, taxi, shuttle, and bus. April in Punta Cana sees daily highs of 35°C and lows of 27°C at night. Finish your sightseeing early on the 8th (Thu) so you can take a shuttle to Santo Domingo.

Things to do in Punta Cana

Outdoors · Tours · Wildlife · Beaches
Find places to stay Apr 5 — 8:

Santo Domingo, Dominican Republic

— 2 nights
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
On the 8th (Thu), steep yourself in history at Alcazar de Colon and then contemplate the long history of Fortaleza Ozama. Keep things going the next day: ponder the world of politics at Palacio National and then make a trip to Zona Colonial.

To find maps, other places to visit, and more tourist information, refer to the Santo Domingo driving holiday planner.

Traveling by shuttle from Punta Cana to Santo Domingo takes 2 hours. Alternatively, you can drive; or fly. Finish up your sightseeing early on the 10th (Sat) so you can travel to Havana.

Things to do in Santo Domingo

Historic Sites
Find places to stay Apr 8 — 10:

Havana, Cuba

— 2 nights

Rome of the Caribbean

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Visit Old Havana and Old Square (Plaza Vieja) for their historical value. Malecón of Havana and Fortaleza de San Carlos de la Cabana are good opportunities to explore the local culture. Next up on the itinerary: stop by Christopher Columbus Cemetery (Cemetario de Colon), steep yourself in history at El Morro, don't miss a visit to Plaza de la Catedral, and admire the striking features of Casa de la Amistad.

For where to stay, more things to do, photos, and more tourist information, you can read our Havana trip planner.

You can fly from Santo Domingo to Havana in 5.5 hours. You'll gain 1 hour traveling from Santo Domingo to Havana due to the time zone difference. In April, daily temperatures in Havana can reach 36°C, while at night they dip to 22°C. Cap off your sightseeing on the 12th (Mon) early enough to travel back home.

Things to do in Havana

Historic Sites · Neighborhoods
Find places to stay Apr 10 — 12:

Puerto Rico travel guide

4.5
Historic Walking Areas · Beaches · Forests
A U.S. territory encompassing one big island and several smaller ones, Puerto Rico appeals to visitors from around the globe with its rich history, pleasant climate, natural beauty, and renowned local cuisine. Most tourists take a vacation in Puerto Rico for that classic seaside experience, though the island offers much more than just sun and sand. Tours of Puerto Rico usually start in the city of San Juan, which boasts a trendy bar scene and plenty of art museums for visitors looking to add a bit of culture to their vacation. A short drive from the island's urban centers, pristine rainforests serve as peaceful retreats from the city bustle and ensure plenty of chances to spot wildlife and take exhilarating nature walks.

Dominican Republic travel guide

4.1
Beaches · Islands · Zipline
Sharing the island of Hispaniola with Haiti, friendly Dominican Republic offers two distinct coastlines, one bathed by the Caribbean Sea and the other by the Atlantic Ocean. Nearly 1,600 km (1,000 mi) of palm-shaded beaches figure highly on most Dominican Republic itineraries, allowing visitors to design their vacation around a range of water-based activities. The sun-kissed country benefits from pleasant temperatures throughout the year, so it's no surprise that holidays in Dominican Republic remain a popular choice for visitors from distant and colder corners of the world. A big producer of coffee, cocoa, rum, sugarcane, and tobacco, the country provides a vibrant cultural experience in multicultural cities and quaint countryside.

Cuba travel guide

4.4
Beaches · Historic Walking Areas · Landmarks
The largest island in the Caribbean, Cuba lies just 140 km (90 mi) south of Florida and captivates a growing number of Western visitors with its tropical landscapes and cultural attractions. Sightseeing in Cuba inevitably begins in Havana, a city of photogenic architecture, lively nightlife, and a passion for baseball. The country's smaller colonial towns usually feature central squares, ideal places to meet the locals under wrought-iron street lamps. Savvy visitors escape the cities during their Cuba holidays, devoting plenty of time to the country's charming countryside, where you can get the feel for this diverse land by conversing with friendly tobacco farmers and small-scale fruit producers.