21 days in Dominican Republic, Puerto Rico & Jamaica Itinerary

21 days in Dominican Republic, Puerto Rico & Jamaica Itinerary

Created using Inspirock Caribbean trip 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

S M T W T F S
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23

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.
Bring the kids along to Bavaro Beach and Nino's Liquors. You'll find plenty of places to visit near Punta Cana: La Romana (Teeth Of The Dog & Altos de Chavon Regional Museum of Archaeology). There's lots more to do: head off the coast to Saona Island, stroll through Macao Beach, and make a trip to Jesus Maestro Parish.

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

Ankara, Turkey to Punta Cana is an approximately 18.5-hour flight. The time zone difference moving from Turkey Time to Atlantic Standard Time is minus 7 hours. While traveling from Ankara, expect warmer days and somewhat warmer nights in Punta Cana, ranging from highs of 36°C to lows of 28°C. Cap off your sightseeing on the 3rd (Sun) early enough to catch the shuttle to Santo Domingo.

Things to do in Punta Cana

Parks · Outdoors · Beaches · Golf

Side Trips

Find places to stay Sep 30 — Oct 3:

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 4th (Mon): explore the historical opulence of Alcazar de Colon, then make a trip to Zona Colonial, and then admire the masterpieces at Amber Museum. On the 5th (Tue), you'll have a packed day of sightseeing: delve into the distant past at Monasterio de San Francisco, then make a trip to Columbus Lighthouse (Faro A Colon), then steep yourself in history at Fortaleza Ozama, and finally make a trip to Santo Domingo Skyline.

For where to stay, more things to do, other places to visit, and other tourist information, you can read our Santo Domingo online visit planner.

Traveling by shuttle from Punta Cana to Santo Domingo takes 2 hours. Alternatively, you can drive; or fly. Cap off your sightseeing on the 5th (Tue) early enough to catch the flight to San Juan.

Things to do in Santo Domingo

Historic Sites · Museums · Shopping
Find places to stay Oct 3 — 5:

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 6th (Wed), let your taste buds guide you at a local gastronomic tour, then get to know the fascinating history of 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.

For reviews, where to stay, traveler tips, and more tourist information, read our San Juan road trip planning site.

You can fly from Santo Domingo to San Juan in 3 hours. Another option is to ride a ferry. In October in San Juan, expect temperatures between 38°C during the day and 30°C at night. Finish up your sightseeing early on the 7th (Thu) so you can catch the flight to Culebra.

Things to do in San Juan

Outdoors · Tours · Neighborhoods · Historic Sites
Find places to stay Oct 5 — 7:

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.
Kids will appreciate attractions like Flamenco Beach and Culebra Public Library. And it doesn't end there: head off the coast to Culebrita, enjoy the sand and surf at Brava Beach, and tour the pleasant surroundings at Playa Punta Soldado Beach.

To find traveler tips, where to stay, more things to do, and other tourist information, read Culebra trip itinerary planning tool.

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 October in Culebra, expect temperatures between 36°C during the day and 30°C at night. Finish up your sightseeing early on the 11th (Mon) so you can catch the flight to Isla de Vieques.

Things to do in Culebra

Parks · Beaches · Outdoors · Nature
Find places to stay Oct 7 — 11:

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.
Attractions like Balneario Sun Bay and Playa Media Luna make great kid-friendly stops. The adventure continues: stroll through Vieques National Wildlife Refuge, take in the waterfront at Malecon, head off the coast to Vieques Island, and expand your understanding of the military at Camp Garcia.

Make your Isla de Vieques itinerary with Inspirock to find out what to see and where to go.

Traveling by flight from Culebra to Isla de Vieques takes 3.5 hours. Alternatively, you can ride a ferry. In October, daily temperatures in Isla de Vieques can reach 36°C, while at night they dip to 28°C. Finish up your sightseeing early on the 16th (Sat) so you can catch the flight to Ocho Rios.

Things to do in Isla de Vieques

Outdoors · Parks · Beaches · Wildlife
Find places to stay Oct 11 — 16:

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 17th (Sun): take in the dramatic scenery at Dunn's River Falls and Park and then take in the dramatic scenery at Blue Hole. Get ready for a full day of sightseeing on the next day: take in the architecture and atmosphere at Our Lady of Fatima Catholic Church, then contemplate the long history of Rose Hall Great House, and then stop by White Witch Golf Course.

To see where to stay, traveler tips, reviews, and other tourist information, refer to the Ocho Rios trip itinerary website.

Traveling by flight from Isla de Vieques to Ocho Rios takes 11 hours. The time zone difference moving from Atlantic Standard Time (AST) to Eastern Standard Time (EST) is minus 1 hour. In October, daily temperatures in Ocho Rios can reach 38°C, while at night they dip to 30°C. Wrap up your sightseeing by early afternoon on the 19th (Tue) to allow enough time to fly back home.

Things to do in Ocho Rios

Parks · Outdoors · Nature · Golf

Side Trip

Find places to stay Oct 16 — 19:

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.