14 days in Santo Domingo, Puerto Rico & Punta Cana Itinerary

14 days in Santo Domingo, Puerto Rico & Punta Cana Itinerary

Created using Inspirock Caribbean tour itinerary builder

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1
Santo Domingo, Dominican Republic
— 2 nights
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2
San Juan, Puerto Rico
— 3 nights
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3
Isla de Vieques, Puerto Rico
— 2 nights
Taxi to Vieques, Fly to Culebra
4
Culebra, Puerto Rico
— 3 nights
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5
Punta Cana, Dominican Republic
— 2 nights
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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 29th (Fri), pause for some serene contemplation at Basilica Cathedral of Santa Maria la Menor and then don't miss a visit to Zona Colonial.

For more things to do, where to stay, maps, and tourist information, refer to the Santo Domingo trip itinerary builder site.

Guayaquil, Ecuador to Santo Domingo is an approximately 17-hour flight. Traveling from Guayaquil to Santo Domingo, you'll lose 1 hour due to the time zone difference. Finish up your sightseeing early on the 30th (Sat) so you can travel to San Juan.

Things to do in Santo Domingo

Historic Sites
Find places to stay Apr 28 — 30:

San Juan, Puerto Rico

— 3 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.
San Juan is known for historic sites, adventure, and nightlife. Your plan includes some of its best attractions: get to know the fascinating history of Old San Juan, admire the masterpieces at Museo de Arte de Puerto Rico, let your taste buds guide you at a local gastronomic tour, and skim along the rocks with a canyoning and rapelling tour.

To see photos, maps, reviews, and more tourist information, use the San Juan holiday planner.

Traveling by flight from Santo Domingo to San Juan takes 3 hours. Alternatively, you can ride a ferry. April in San Juan sees daily highs of 36°C and lows of 28°C at night. Wrap up your sightseeing on the 3rd (Tue) to allow time to travel to Isla de Vieques.

Things to do in San Juan

Outdoors · Parks · Beaches · Historic Sites

Side Trip

Find places to stay Apr 30 — May 3:

Isla de Vieques, Puerto Rico

— 2 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.
Start off your visit on the 4th (Wed): take in the waterfront at Mosquito Pier and then enjoy the sand and surf at Sun Bay Beach. On the 5th (Thu), you'll have a packed day of sightseeing: enjoy the sand and surf at Caracas Beach, then stroll through La Chiva, and then add some adventure to your tour with a kayaking and canoeing tour.

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

You can fly from San Juan to Isla de Vieques in 2 hours. Other options are to do a combination of car and ferry; or do a combination of shuttle and ferry. In May, daytime highs in Isla de Vieques are 34°C, while nighttime lows are 28°C. Finish your sightseeing early on the 5th (Thu) to allow enough time to travel to Culebra.

Things to do in Isla de Vieques

Outdoors · Beaches · Parks · Tours
Find places to stay May 3 — 5:

Culebra, Puerto Rico

— 3 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 nature. Your plan includes some of its best attractions: stroll through Flamenco Beach, head off the coast to Culebrita Island, get a new perspective on things with Boat Tours & Water Sports, and kick back and relax at Playa Punta Soldado Beach.

For more things to do, maps, and other tourist information, refer to the Culebra attractions app.

Getting from Isla de Vieques to Culebra by combination of taxi and flight takes about 3 hours. Other options: do a combination of ferry, car, and flight; or ride a ferry. In May in Culebra, expect temperatures between 36°C during the day and 29°C at night. Finish your sightseeing early on the 8th (Sun) to allow enough time to travel to Punta Cana.

Things to do in Culebra

Outdoors · Parks · Beaches · Nature
Find places to stay May 5 — 8:

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 9th (Mon): stop by Nino's Liquors, kick your exploration up a notch at some of the top local zipline courses and adventure parks, and then relax and rejuvenate at Flavio Acuna Spa Natural Center. Get ready for a full day of sightseeing on the 10th (Tue): tour the pleasant surroundings at Macao Beach and then kick back and relax at Bavaro Beach.

For photos, ratings, other places to visit, and tourist information, you can read our Punta Cana travel tool.

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. May in Punta Cana sees daily highs of 35°C and lows of 28°C at night. Finish your sightseeing early on the 10th (Tue) so you can travel back home.

Things to do in Punta Cana

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

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.