18 days in Cuba, Dominican Republic & Puerto Rico Itinerary

18 days in Cuba, Dominican Republic & Puerto Rico Itinerary

Created using Inspirock Caribbean trip itinerary maker

Plan created by another user. Make it yours

Route & dates

1
Havana, Cuba
— 2 nights
2
Santo Domingo, Dominican Republic
— 3 nights
3
Punta Cana, Dominican Republic
— 2 nights
4
Isla de Vieques, Puerto Rico
— 3 nights
5
Culebra, Puerto Rico
— 2 nights
6
San Juan, Puerto Rico
— 5 nights

2
nights
Havana, Cuba

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
On the 13th (Thu), contemplate the long history of Revolution Plaza Havana. Get ready for a full day of sightseeing on the 14th (Fri): explore the landscape on two wheels at CicloCuba, then appreciate the extensive heritage of Malecón of Havana, then don't miss a visit to Plaza de Armas, and finally get a dose of the wild on a nature and wildlife tour.

For more things to do, maps, and more tourist information, go to the Havana road trip planning site.

Columbus, USA to Havana is an approximately 8-hour flight. Traveling from Columbus in May, expect Havana to be a bit warmer, temps between 87°F and 69°F. Wrap up your sightseeing on the 15th (Sat) to allow time to travel to Santo Domingo.

Things to do in Havana

Outdoors · Parks · Wildlife
Find places to stay May 13 — 15:
Highlights from your plan
Nature & Wildlife Tours
Malecón of Havana ©
Malecón of Havana
Plaza de la Catedral ©
Plaza de la Catedral

3
nights
Santo Domingo, Dominican Republic

Santo Domingo ©
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Get a sense of the local culture at Zona Colonial and Columbus Lighthouse (Faro A Colon). There's lots more to do: explore the historical opulence of Alcazar de Colon, admire the landmark architecture of La Casa de Los Jesuitas, take some stellar pictures from Santo Domingo Skyline, and explore the ancient world of Monasterio de San Francisco.

To find photos, other places to visit, reviews, and more tourist information, use the Santo Domingo trip planning tool.

Traveling by flight from Havana to Santo Domingo takes 5.5 hours. You'll lose 1 hour traveling from Havana to Santo Domingo due to the time zone difference. Wrap up your sightseeing on the 18th (Tue) to allow time to take a shuttle to Punta Cana.

Things to do in Santo Domingo

Museums · Historic Sites · Parks
Find places to stay May 15 — 18:
Highlights from your plan
Columbus Lighthouse (Faro A Colon) ©
Columbus Lighthouse (Faro A Colon)
Alcazar de Colon ©
Alcazar de Colon
Zona Colonial ©
Zona Colonial

2
nights
Punta Cana, Dominican Republic

Punta Cana ©
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.
On the 19th (Wed), stop by HARRISON'S Fine Caribbean Jewelers, then enjoy the sand and surf at Macao Beach, and then enjoy the sand and surf at Bavaro Beach. Get ready for a full day of sightseeing on the next day: play a few rounds at Punta Espada Golf Course and then take a tour by water with Boat Tours & Water Sports.

To see where to stay, photos, traveler tips, and other tourist information, use the Punta Cana trip itinerary planner.

You can take a shuttle from Santo Domingo to Punta Cana in 2 hours. Alternatively, you can drive; or fly. May in Punta Cana sees daily highs of 86°F and lows of 75°F at night. Wrap up your sightseeing on the 20th (Thu) to allow time to travel to Isla de Vieques.

Things to do in Punta Cana

Outdoors · Parks · Beaches
Find places to stay May 18 — 20:
Highlights from your plan
Bavaro Beach ©
Bavaro Beach
Swim with Dolphins
Macao Beach ©
Macao Beach

3
nights
Isla de Vieques, Puerto Rico

Isla de Vieques ©
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.
You'll get in some beach time at Sun Bay Beach and Media Luna Beach. Visiting Stand-Up Paddleboarding and La Chiva will get you outdoors. And it doesn't end there: enjoy the sand and surf at Caracas Beach, take a leisurely stroll along Malecon, make a trip to Puerto Ferro Lighthouse, and explore the ancient world of El Hombre de Puerto Ferro.

To see reviews, photos, other places to visit, and tourist information, read our Isla de Vieques holiday app.

You can fly from Punta Cana to Isla de Vieques in 5 hours. Other options are to do a combination of bus, ferry, and taxi; or do a combination of shuttle, ferry, and taxi. May in Isla de Vieques sees daily highs of 85°F and lows of 76°F at night. Wrap up your sightseeing on the 23rd (Sun) to allow time to travel to Culebra.

Things to do in Isla de Vieques

Outdoors · Parks · Beaches
Find places to stay May 20 — 23:
Highlights from your plan
Sun Bay Beach ©
Sun Bay Beach
Media Luna Beach ©
Media Luna Beach
La Chiva ©
La Chiva

2
nights
Culebra, Puerto Rico

Culebra ©
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 24th (Mon): head off the coast to Culebrita Island, enjoy the sea views from Culebrita Lighthouse, and then stroll through Zoni Beach. Keep things going the next day: kick back and relax at Playa Punta Soldado Beach and then enjoy the sand and surf at Flamenco Beach.

To see traveler tips, ratings, and more tourist information, read Culebra tour builder site.

Do a combination of car and flight from Isla de Vieques to Culebra in 4 hours. Alternatively, you can ride a ferry. Expect a daytime high around 87°F in May, and nighttime lows around 77°F. Finish your sightseeing early on the 25th (Tue) to allow enough time to travel to San Juan.

Things to do in Culebra

Parks · Beaches · Outdoors
Find places to stay May 23 — 25:
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach
Culebrita Island ©
Culebrita Island

5
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Get some cultural insight at Old San Juan and Sitio Histórico de San Juan. We've included these beaches for you: Condado Beach and Luquillo Beach. Change things up with these side-trips from San Juan: El Yunque National Forest (El Yunque Rain Forest & El Portal Tropical Forest Center) and Zipline (in Luquillo). Next up on the itinerary: skim along the rocks with a canyoning and rapelling tour, appreciate the history behind Plaza de Colon, savor the flavors at Food & Drink, and get some thrills out on the water with a waterskiing or jet-skiing adventure.

For ratings, other places to visit, where to stay, and tourist information, read San Juan journey maker website.

You can fly from Culebra to San Juan in 2 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and shuttle. In May, plan for daily highs up to 88°F, and evening lows to 76°F. Wrap up your sightseeing by early afternoon on the 30th (Sun) to allow enough time to travel back home.

Things to do in San Juan

Parks · Outdoors · Tours

Side Trips

El Yunque National Forest, Luquillo
Find places to stay May 25 — 30:
Highlights from your plan
Old San Juan ©
Old San Juan
El Yunque Rain Forest ©
El Yunque Rain Forest
Condado Beach ©
Condado Beach

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