15 days in Caribbean Itinerary

15 days in Caribbean Itinerary

Created using Inspirock Caribbean trip builder

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Fly
1
San Juan, Puerto Rico
— 2 nights
Fly
2
Culebra, Puerto Rico
— 2 nights
Fly
3
Punta Cana, Dominican Republic
— 2 nights
Shuttle
4
Santo Domingo, Dominican Republic
— 2 nights
Drive
5
Cap-Haitien, Haiti
— 2 nights
Fly
6
Havana, Cuba
— 3 nights
Fly

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San Juan, Puerto Rico

— 2 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.
On the 7th (Mon), get to know the fascinating history of Paseo de la Princesa, see what you can catch with a fishing tour, and then appreciate the history behind Holocaust Memorial Monument. On your second day here, contemplate the long history of Catedral Basilica Menor de San Juan Bautista, then steep yourself in history at Sitio Histórico de San Juan, and then get to know the fascinating history of Old San Juan.

To find other places to visit, more things to do, reviews, and tourist information, read our San Juan vacation website.

Atlanta, USA to San Juan is an approximately 6.5-hour flight. The time zone difference when traveling from Atlanta to San Juan is 1 hour. Traveling from Atlanta in June, you can expect nighttime temperatures to be a bit warmer in San Juan, with lows of 78°F. Finish your sightseeing early on the 8th (Tue) to allow enough time to travel to Culebra.

Things to do in San Juan

Historic Sites · Neighborhoods · Tours · Outdoors
Find places to stay Jun 6 — 8:

Culebra, Puerto Rico

— 2 nights

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Start off your visit on the 9th (Wed): enjoy the sand and surf at Zoni Beach, see some colorful creatures with a scuba or snorkeling tour, and then kick back and relax at Playa Punta Soldado Beach. On the next day, kick back and relax at Flamenco Beach.

To find traveler tips, where to stay, maps, and more tourist information, go to the Culebra trip itinerary maker tool.

Getting from San Juan to Culebra by flight takes about 2 hours. Other options: do a combination of car and ferry; or do a combination of shuttle and ferry. In June, daytime highs in Culebra are 89°F, while nighttime lows are 79°F. Wrap up your sightseeing on the 10th (Thu) to allow time to travel to Punta Cana.

Things to do in Culebra

Outdoors · Beaches · Parks · Tours
Find places to stay Jun 8 — 10:

Punta Cana, Dominican Republic

— 2 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.
Start off your visit on the 11th (Fri): stroll through Bavaro Beach and then enjoy the sand and surf at Macao Beach. Keep things going the next day: get close to the beloved marine mammals with a swim-with-the-dolphins experience and then contemplate in the serene atmosphere at Basilica Catedral Nuestra Senora de la Altagracia.

To see reviews, photos, maps, and more tourist information, you can read our Punta Cana day trip website.

You can fly from Culebra to Punta Cana in 6.5 hours. Alternatively, you can do a combination of ferry, taxi, and bus; or do a combination of ferry, taxi, shuttle, and bus. In June, plan for daily highs up to 87°F, and evening lows to 76°F. Wrap up your sightseeing on the 13th (Sun) early enough to take a shuttle to Santo Domingo.

Things to do in Punta Cana

Outdoors · Beaches · Parks · Tours

Side Trip

Find places to stay Jun 10 — 13:

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 13th (Sun), steep yourself in history at Fortaleza Ozama, step into the grandiose world of Alcazar de Colon, then take in the architecture and atmosphere at Basilica Cathedral of Santa Maria la Menor, and finally appreciate the extensive heritage of Chu Chu Colonial. Get ready for a full day of sightseeing on the next day: take in the dramatic natural features at The 3 Eyes National Park.

For more things to do, ratings, traveler tips, and other tourist information, go to the Santo Domingo day trip site.

You can take a shuttle from Punta Cana to Santo Domingo in 2 hours. Alternatively, you can drive; or fly. Wrap up your sightseeing on the 15th (Tue) early enough to drive to Cap-Haitien.

Things to do in Santo Domingo

Nature · Parks · Historic Sites · Neighborhoods
Find places to stay Jun 13 — 15:

Cap-Haitien, Haiti

— 2 nights

Cap

Haiti's second city, Cap-Haitien offers an atmosphere at odds with what you'll find in the capital.
On the 15th (Tue), pause for some serene contemplation at Cathedrale Notre Dame de Cap Haitien and then get a dose of the wild on A Paradise Cove Escape and Haitian Village Experience. On the next day, explore the historical opulence of Sans Souci Palace, then make a trip to Citadelle Laferrière, and then steep yourself in history at National History Park - Citadel, Sans Souci, Ramiers.

For ratings, traveler tips, where to stay, and more tourist information, go to the Cap-Haitien holiday builder site.

Getting from Santo Domingo to Cap-Haitien by car takes about 5.5 hours. Other options: do a combination of flight and bus; or take a bus. Due to the time zone difference, you'll gain 1 hour traveling from Santo Domingo to Cap-Haitien. In June in Cap-Haitien, expect temperatures between 86°F during the day and 80°F at night. Finish up your sightseeing early on the 17th (Thu) so you can travel to Havana.

Things to do in Cap-Haitien

Historic Sites · Tours · Outdoors · Wildlife

Side Trips

Find places to stay Jun 15 — 17:

Havana, Cuba

— 3 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.
Kick off your visit on the 17th (Thu): pause for some photo ops at Neptune Statue and then contemplate the long history of Christopher Columbus Cemetery (Cemetario de Colon). Get ready for a full day of sightseeing on the next day: get outside with Outdoor Activities, take a stroll through Callejon de Hamel, and then appreciate the extensive heritage of Malecón of Havana.

To find other places to visit, maps, photos, and more tourist information, you can read our Havana holiday maker tool.

Fly from Cap-Haitien to Havana in 15.5 hours. Expect a bit cooler evenings in Havana when traveling from Cap-Haitien in June, with lows around 72°F. You'll have a few hours on the 20th (Sun) to wrap things up before traveling home.

Things to do in Havana

Outdoors · Historic Sites · Tours · Wildlife
Find places to stay Jun 17 — 20:

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.