21 days in Dominican Republic, Puerto Rico & Jamaica Itinerary

21 days in Dominican Republic, Puerto Rico & Jamaica Itinerary

Created using Inspirock Caribbean journey maker

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Fly
1
Punta Cana, Dominican Republic
— 2 nights
Shuttle
2
Santo Domingo, Dominican Republic
— 2 nights
Fly
3
San Juan, Puerto Rico
— 2 nights
Fly
4
Culebra, Puerto Rico
— 4 nights
Fly
5
Isla de Vieques, Puerto Rico
— 5 nights
Fly
6
Ocho Rios, Jamaica
— 2 nights
Fly

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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.
Explore Punta Cana's surroundings by going to La Romana (Teeth Of The Dog & Altos de Chavon Regional Museum of Archaeology). There's much more to do: stroll through Bavaro Beach, look for gifts at Nino's Liquors, enjoy the sand and surf at Macao Beach, and step off the mainland to explore Saona Island.

To see ratings, photos, and other tourist information, you can read our Punta Cana trip planner.

Ankara, Turkey to Punta Cana is an approximately 18.5-hour flight. You'll gain 7 hours traveling from Ankara to Punta Cana due to the time zone difference. Traveling from Ankara in May, expect nights in Punta Cana to be a bit warmer, around 28°C, while days are much hotter, around 35°C. Wrap up your sightseeing on the 4th (Wed) to allow time to take a shuttle to Santo Domingo.

Things to do in Punta Cana

Parks · Outdoors · Beaches · Golf

Side Trips

Find places to stay May 1 — 4:

Santo Domingo, Dominican Republic

— 2 nights
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Kick off your visit on the 5th (Thu): step into the grandiose world of Alcazar de Colon, don't miss a visit to Zona Colonial, and then admire the masterpieces at Amber Museum. On the 6th (Fri), you'll have a packed day of sightseeing: delve into the distant past at Monasterio de San Francisco, then pause for some photo ops at Columbus Lighthouse (Faro A Colon), then steep yourself in history at Fortaleza Ozama, and finally make a trip to Santo Domingo Skyline.

To find traveler tips, other places to visit, ratings, and tourist information, read Santo Domingo trip itinerary maker site.

Take a shuttle from Punta Cana to Santo Domingo in 2 hours. Alternatively, you can drive; or fly. Finish your sightseeing early on the 6th (Fri) so you can fly to San Juan.

Things to do in Santo Domingo

Historic Sites · Museums · Shopping
Find places to stay May 4 — 6:

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.
Start off your visit on the 7th (Sat): indulge in some culinary diversions at a local gastronomic tour, take a stroll through Old San Juan, and then appreciate the history behind Paseo de los Presidentes. Here are some ideas for day two: scramble along the landscape with a canyoning and rapelling tour, tour the pleasant surroundings at Condado Beach, and then make a trip to Plaza de la Catedral.

To find ratings, traveler tips, where to stay, and other tourist information, read San Juan day trip app.

You can fly from Santo Domingo to San Juan in 3 hours. Another option is to ride a ferry. In May, daily temperatures in San Juan can reach 36°C, while at night they dip to 28°C. Finish your sightseeing early on the 8th (Sun) to allow enough time to fly to Culebra.

Things to do in San Juan

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

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.
Culebra is known for beaches, wildlife, and outdoors. Your trip includes some of its best attractions: kick back and relax at Flamenco Beach, stroll through Playa Tamarindo, step off the mainland to explore Culebrita, and get advice or help at Culebra Public Library.

You can plan Culebra trip in no time by asking Inspirock to help create your itinerary.

You can fly from San Juan to Culebra in 2 hours. Alternatively, you can do a combination of car and ferry; or do a combination of shuttle, taxi, and ferry. In May, daytime highs in Culebra are 36°C, while nighttime lows are 29°C. Finish your sightseeing early on the 12th (Thu) to allow enough time to fly to Isla de Vieques.

Things to do in Culebra

Parks · Beaches · Outdoors · Nature
Find places to stay May 8 — 12:

Isla de Vieques, Puerto Rico

— 5 nights

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.
Isla de Vieques is known for beaches, nature, and adventure. Your trip includes some of its best attractions: tour the pleasant surroundings at Balneario Sun Bay, get outside with Outdoor Activities, head off the coast to Vieques Island, and admire the landmark architecture of Puerto Ferro Lighthouse.

For maps, photos, other places to visit, and other tourist information, read our Isla de Vieques trip planning tool.

Fly from Culebra to Isla de Vieques in 3.5 hours. Alternatively, you can ride a ferry. In May, daily temperatures in Isla de Vieques can reach 34°C, while at night they dip to 28°C. Finish your sightseeing early on the 17th (Tue) to allow enough time to fly to Ocho Rios.

Things to do in Isla de Vieques

Outdoors · Parks · Beaches · Wildlife
Find places to stay May 12 — 17:

Ocho Rios, Jamaica

— 2 nights
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
On the 18th (Wed), admire the sheer force of Dunn's River Falls and Park and then take in the dramatic scenery at Blue Hole. On the 19th (Thu), you'll have a packed day of sightseeing: pause for some serene contemplation at Our Lady of Fatima Catholic Church, contemplate the long history of Rose Hall Great House, and then stop by White Witch Golf Course.

To find where to stay, traveler tips, ratings, and other tourist information, read Ocho Rios online itinerary planner.

Getting from Isla de Vieques to Ocho Rios by flight takes about 11 hours. The time zone difference moving from Atlantic Standard Time to Eastern Standard Time is minus 1 hour. May in Ocho Rios sees daily highs of 37°C and lows of 29°C at night. Wrap up your sightseeing by early afternoon on the 20th (Fri) to allow enough time to fly back home.

Things to do in Ocho Rios

Parks · Outdoors · Nature · Golf

Side Trip

Find places to stay May 17 — 20:

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.

Puerto Rico travel guide

4.5
Historic Walking Areas · Beaches · Surfing, Windsurfing & Kitesurfing
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.

Jamaica travel guide

4.1
Waterfalls · Beaches · Nightlife
The third most populous English-speaking country in the Americas, Jamaica remains a member of the Commonwealth of Nations, with the British monarch its official head of state. Jamaica tourism thrives thanks to the island nation's reputation for natural beauty, outstanding cuisine, and lively music scene. The country's landscape is as diverse as its population, its tropical climate supporting varied ecosystems that include everything from savannahs to rugged mountain slopes. For most visitors, a holiday in Jamaica is a largely outdoor affair, with hiking, fishing, golfing, camping, snorkeling, horseback riding, and kite surfing among the most popular things to do.