11 days in Puerto Rico, Dominican Republic & Cuba Itinerary

11 days in Puerto Rico, Dominican Republic & Cuba Itinerary

Created using Inspirock Caribbean travel route builder

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1
Culebra, Puerto Rico
— 2 nights
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2
San Juan, Puerto Rico
— 2 nights
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3
Isla de Vieques, Puerto Rico
— 2 nights
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4
Santo Domingo, Dominican Republic
— 1 night
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5
Havana, Cuba
— 3 nights
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2
nights
Culebra, Puerto Rico

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Here are some ideas for day two: tour the pleasant surroundings at Playa Punta Soldado Beach and then enjoy the sand and surf at Flamenco Beach.

To find reviews, where to stay, maps, and tourist information, you can read our Culebra holiday app.

New York City, USA to Culebra is an approximately 9-hour flight. Due to the time zone difference, you'll lose 1 hour traveling from New York City to Culebra. Expect much warmer temperatures when traveling from New York City in April; daily highs in Culebra reach 85°F and lows reach 76°F. Finish up your sightseeing early on the 18th (Sat) so you can travel to San Juan.

Things to do in Culebra

Outdoors · Parks · Beaches

2
nights
San Juan, Puerto Rico

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
On the 19th (Sun), contemplate the long history of Depigment Art, then take in the exciting artwork at La Casa de los Contrafuertes, and then appreciate the extensive heritage of Old San Juan. On your second day here, appreciate the extensive heritage of Sitio Histórico de San Juan, then stop by The Butterfly People, then revel in the low prices at Coach Outlet Store, and finally browse the exhibits of Galeria Botello.

To see maps, traveler tips, and tourist information, read San Juan trip planner.

Fly from Culebra to San Juan in 2 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and shuttle. April in San Juan sees daily highs of 87°F and lows of 75°F at night. Finish up your sightseeing early on the 20th (Mon) so you can travel to Isla de Vieques.

Things to do in San Juan

Shopping · Historic Sites · Museums · Neighborhoods

2
nights
Isla de Vieques, Puerto Rico

Isla Nena

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 21st (Tue): take in the exciting artwork at Siddhia Hutchinson Fine Art Gallery, then look for gifts at Isla Vida, then hunt for treasures at Fish Market, and finally get great views at Puerto Ferro Lighthouse. On your second day here, kick back and relax at La Chiva, view the masterpieces at Serenity Point Yoga & Visionary Arts Space, and then get a new perspective on things with Boat Tours & Water Sports.

To see more things to do, where to stay, ratings, and other tourist information, refer to the Isla de Vieques trip planner.

Traveling by flight from San Juan to Isla de Vieques takes 2 hours. Alternatively, you can do a combination of car and ferry; or do a combination of shuttle and 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 22nd (Wed) early enough to travel to Santo Domingo.

Things to do in Isla de Vieques

Shopping · Museums · Outdoors · Parks

1
night
Santo Domingo, Dominican Republic

Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Start off your visit on the 23rd (Thu): don't miss a visit to Columbus Lighthouse (Faro A Colon), explore the historical opulence of Alcazar de Colon, and then browse the eclectic array of goods at Mercado Modelo.

To find ratings, traveler tips, other places to visit, and more tourist information, go to the Santo Domingo road trip planning website.

Fly from Isla de Vieques to Santo Domingo in 5.5 hours. Alternatively, you can do a combination of ferry and taxi. Finish your sightseeing early on the 23rd (Thu) to allow enough time to travel to Havana.

Things to do in Santo Domingo

Shopping · Museums · Historic Sites

3
nights
Havana, Cuba

Rome of the Caribbean

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Get a sense of the local culture at Malecón of Havana and Old Square (Plaza Vieja). Do your shopping at Yuniel Delgado Studio and Espacio de Arte Triana & Usich. And it doesn't end there: make a trip to Plaza de la Catedral, appreciate the extensive heritage of Old Havana, steep yourself in history at Fortaleza de San Carlos de la Cabana, and take a stroll through Christopher Columbus Cemetery (Cemetario de Colon).

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

Traveling by flight from Santo Domingo to Havana takes 5.5 hours. Traveling from Santo Domingo to Havana, you'll gain 1 hour due to the time zone difference. April in Havana sees daily highs of 87°F and lows of 67°F at night. Finish up your sightseeing early on the 26th (Sun) so you can travel back home.

Things to do in Havana

Historic Sites · Museums · Shopping · Neighborhoods

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
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

4.3
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.