21 days in Dominican Republic, Puerto Rico & Jamaica Itinerary

21 days in Dominican Republic, Puerto Rico & Jamaica Itinerary

Created using Inspirock Caribbean visit planner

Make it your trip
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.
Venture out of the city with trips to La Romana (Teeth Of The Dog & Altos de Chavon Regional Museum of Archaeology). There's still lots to do: head off the coast to Saona Island, make a trip to Jesus Maestro Parish, stop by Nino's Liquors, and kick back and relax at Bavaro Beach.

To see photos, ratings, more things to do, and tourist information, you can read our Punta Cana trip planner.

Ankara, Turkey to Punta Cana is an approximately 18.5-hour flight. Due to the time zone difference, you'll gain 7 hours traveling from Ankara to Punta Cana. Traveling from Ankara in December, expect Punta Cana to be much warmer, temps between 34°C and 26°C. Finish up your sightseeing early on the 27th (Mon) so you can catch the shuttle to Santo Domingo.

Things to do in Punta Cana

Outdoors · Parks · Beaches · Nature

Side Trips

Find places to stay Dec 24 — 27:

Santo Domingo, Dominican Republic

— 2 nights
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 (Tue): contemplate the long history of Alcazar de Colon, don't miss a visit to Zona Colonial, and then explore the world behind art at Amber Museum. On the 29th (Wed), you'll have a packed day of sightseeing: explore the ancient world of Monasterio de San Francisco, appreciate the history behind Columbus Lighthouse (Faro A Colon), then steep yourself in history at Fortaleza Ozama, and finally make a trip to Santo Domingo Skyline.

To see other places to visit, where to stay, more things to do, and more tourist information, refer to the Santo Domingo trip app.

You can take a shuttle from Punta Cana to Santo Domingo in 2 hours. Other options are to drive; or fly. Finish your sightseeing early on the 29th (Wed) to allow enough time to fly to San Juan.

Things to do in Santo Domingo

Historic Sites · Museums · Shopping
Find places to stay Dec 27 — 29:

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 30th (Thu), indulge in some culinary diversions at a local gastronomic tour, then get to know the fascinating history of Old San Juan, and then pause for some photo ops at Paseo de los Presidentes. Here are some ideas for day two: skim along the rocks with a canyoning and rapelling tour, then stroll through Condado Beach, and then make a trip to Plaza de la Catedral.

Plan my trip to San Juan with suggested itineraries provided by Inspirock.

Getting from Santo Domingo to San Juan by flight takes about 3 hours. Other options: ride a ferry. In December in San Juan, expect temperatures between 34°C during the day and 28°C at night. Wrap up your sightseeing on the 31st (Fri) early enough to fly to Culebra.

Things to do in San Juan

Outdoors · Tours · Historic Sites · Parks
Find places to stay Dec 29 — 31:

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: tour the pleasant surroundings at Flamenco Beach, step off the mainland to explore Culebrita, get advice or help at Culebra Public Library, and enjoy the sand and surf at Playa Tamarindo.

To find ratings, photos, other places to visit, and more tourist information, use the Culebra route maker.

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, taxi, and ferry. In December in Culebra, expect temperatures between 34°C during the day and 28°C at night. Wrap up your sightseeing on the 4th (Tue) to allow time to fly to Isla de Vieques.

Things to do in Culebra

Parks · Outdoors · Beaches · Wildlife
Find places to stay Dec 31 — Jan 4:

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: kick back and relax at Balneario Sun Bay, add some adventure to your tour with a kayaking and canoeing tour, have fun at Vieques Gun Club & Sporting Clays, and stroll through Playa La Chiva.

To see more things to do, traveler tips, maps, and other tourist information, you can read our Isla de Vieques trip planner.

You can fly from Culebra to Isla de Vieques in 3.5 hours. Alternatively, you can ride a ferry. Expect a daytime high around 32°C in January, and nighttime lows around 26°C. Wrap up your sightseeing on the 9th (Sun) early enough to fly to Ocho Rios.

Things to do in Isla de Vieques

Outdoors · Parks · Beaches · Wildlife
Find places to stay Jan 4 — 9:

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.
Start off your visit on the 10th (Mon): take in the dramatic scenery at Dunn's River Falls and Park and then admire the sheer force of Blue Hole. On your second day here, take in the architecture and atmosphere at Our Lady of Fatima Catholic Church, contemplate the long history of Rose Hall Great House, and then look for gifts at White Witch Golf Course.

For other places to visit, maps, and tourist information, refer to the Ocho Rios day trip planning app.

You can fly from Isla de Vieques to Ocho Rios in 11 hours. The time zone changes from Atlantic Standard Time to Eastern Standard Time, which is usually a -1 hour difference. In January, plan for daily highs up to 36°C, and evening lows to 27°C. Wrap up your sightseeing by early afternoon on the 12th (Wed) to allow enough time to fly back home.

Things to do in Ocho Rios

Parks · Outdoors · Nature · Shopping

Side Trip

Find places to stay Jan 9 — 12:

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.