18 days in Cuba, Dominican Republic & Puerto Rico Itinerary

18 days in Cuba, Dominican Republic & Puerto Rico Itinerary

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Route & dates

18 days in Cuba, Dominican Republic & Puerto Rico Itinerary

Start: Columbus, United States
Fly:  7 h 45 min
1
Havana, Cuba
— 2 nights
Fly:  2 h 45 min
2
Santo Domingo, Dominican Republic
— 3 nights
Shuttle:  2 h
3
Punta Cana, Dominican Republic
— 2 nights
Fly:  2 h 30 min
4
Isla de Vieques, Puerto Rico
— 3 nights
Drive + Fly:  2 h 15 min
5
Culebra, Puerto Rico
— 2 nights
Fly:  30 min
6
San Juan, Puerto Rico
— 5 nights
Fly:  8 h 45 min
End: Columbus, United States

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. Get ready for a full day of sightseeing on the 14th (Fri): tour the pleasant surroundings at CicloCuba, get to know the fascinating history of Malecón of Havana, then don't miss a visit to Plaza de Armas, and finally surround yourself with nature on a nature and wildlife tour.

To find other places to visit, maps, more things to do, and more tourist information, go to the Havana trip planner.

Columbus, USA to Havana is an approximately 8-hour flight. Plan for somewhat warmer temperatures traveling from Columbus in May, with highs in Havana at 87°F and lows at 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.
Satisfy your inner culture vulture at Alcazar de Colon and Zona Colonial. Next up on the itinerary: contemplate in the serene atmosphere at Catedral Primada de America, delve into the distant past at Monasterio de San Francisco, contemplate the long history of Palacio Consistorial, and view the masterpieces at Amber Museum.

For photos, more things to do, other places to visit, and other tourist information, refer to the Santo Domingo trip builder website.

You can fly from Havana to Santo Domingo in 3 hours. You'll lose 1 hour traveling from Havana to Santo Domingo due to the time zone difference. Finish your sightseeing early on the 18th (Tue) to allow enough time to take a shuttle to Punta Cana.

Things to do in Santo Domingo

Historic Sites Museums Zoos & Aquariums
Find places to stay May 15 — 18:
Highlights from your plan
Alcazar de Colon ©
Alcazar de Colon
Zona Colonial ©
Zona Colonial
Catedral Primada de America
Catedral Primada de America

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.
Kick off your visit on the 19th (Wed): look for gifts at HARRISON'S Fine Caribbean Jewelers, then kick back and relax at Macao Beach, and then tour the pleasant surroundings at Bavaro Beach. Get ready for a full day of sightseeing on the next day: tee off at Punta Espada Golf Course and then fulfill a lifelong dream with a swim-with-the-dolphins experience.

To find ratings, more things to do, traveler tips, and tourist information, use the Punta Cana trip maker website.

Traveling by shuttle from Santo Domingo to Punta Cana takes 2 hours. Alternatively, you can drive; or take a bus. In May in Punta Cana, expect temperatures between 86°F during the day and 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.
Take a break from the city and head to Sun Bay Beach and Media Luna Beach. Your cultural itinerary includes sights like Puerto Ferro Lighthouse and El Hombre de Puerto Ferro. And it doesn't end there: enjoy the sand and surf at La Chiva, stroll through Caracas Beach, take in the waterfront at Malecon, and see some colorful creatures with a scuba or snorkeling tour.

To see maps, ratings, traveler tips, and tourist information, read our Isla de Vieques tour itinerary planning tool.

Traveling by flight from Punta Cana to Isla de Vieques takes 2.5 hours. Alternatively, you can do a combination of bus, ferry, and taxi; or do a combination of bus, ferry, and shuttle. Expect a daytime high around 85°F in May, and nighttime lows around 76°F. Finish your sightseeing early on the 23rd (Sun) so you can 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.
Kick off your visit on the 24th (Mon): step off the mainland to explore Culebrita Island, then visit a coastal fixture at Culebrita Lighthouse, and then tour the pleasant surroundings at Zoni Beach. On the next day, tour the pleasant surroundings at Playa Punta Soldado Beach and then tour the pleasant surroundings at Flamenco Beach.

To see other places to visit, photos, traveler tips, and tourist information, use the Culebra online travel planner.

Do a combination of car and flight from Isla de Vieques to Culebra in 2.5 hours. Alternatively, you can ride a ferry. May in Culebra sees daily highs of 87°F and lows of 77°F at night. Finish your sightseeing early on the 25th (Tue) so you can fly to San Juan.

Things to do in Culebra

Parks Outdoors Beaches
Find places to stay May 23 — 25:
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach
Playa Punta Soldado Beach ©
Playa Punta Soldado Beach

5
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Get a sense of the local culture at Old San Juan and El Portal Tropical Forest Center. You'll enjoy a bit of beach vacationing at Luquillo Beach and Condado Beach. Change things up with these side-trips from San Juan: Zipline (in Luquillo) and El Yunque Rain Forest (in El Yunque National Forest). And it doesn't end there: steep yourself in history at Sitio Histórico de San Juan, savor the flavors at Food & Drink, appreciate the history behind Plaza de Colon, and get some thrills out on the water with a waterskiing or jet-skiing adventure.

To see traveler tips, maps, ratings, and more tourist information, read San Juan itinerary maker app.

San Juan is just a stone's throw from Culebra. 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

Outdoors Parks Tours

Side Trips

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

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