18 days in Cuba, Dominican Republic & Puerto Rico Itinerary

18 days in Cuba, Dominican Republic & Puerto Rico Itinerary

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Route & dates

Start: Columbus, United States
Fly:  7 h 45 min
1
Havana, Cuba
— 2 nights
Fly:  2 h 45 min
2
Santo Domingo, Dominican Republic
— 2 nights
Fly:  3 h 15 min
3
Culebra, Puerto Rico
— 3 nights
Fly + Drive:  2 h 15 min
4
Isla de Vieques, Puerto Rico
— 3 nights
Fly + Taxi:  3 h 30 min
5
Bayahibe, Dominican Republic
— 2 nights
Drive:  2 h 15 min
6
Punta Cana, Dominican Republic
— 3 nights
Drive:  1 h 30 min
7
Juan Dolio, Dominican Republic
— 2 nights
Drive + Fly:  10 h
End: Columbus, United States

2
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
On the 13th (Thu), admire the masterpieces at Museu Nacional de Belas Artes de Cuba, steep yourself in history at Plaza de San Francisco, then make a trip to Malecón of Havana, and finally wander the streets of Fusterlandia. Get ready for a full day of sightseeing on the next day: take a stroll through Christopher Columbus Cemetery (Cemetario de Colon), steep yourself in history at El Morro, and then don't miss a visit to Old Havana.

To see ratings, more things to do, other places to visit, and tourist information, you can read our Havana holiday planner.

Columbus, USA to Havana is an approximately 8- hour flight. Traveling from Columbus in May, things will get somewhat warmer in Havana: highs are around 87°F and lows about 69°F. Wrap up your sightseeing on the 14th (Fri) to allow time to travel to Santo Domingo.

Things to do in Havana

Historic Sites Neighborhoods Museums
Find places to stay May 12 — 14:
Highlights from your plan
Fusterlandia ©
Fusterlandia
Malecón of Havana ©
Malecón of Havana
Plaza de San Francisco ©
Plaza de San Francisco

2
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.
Kick off your visit on the 15th (Sat): contemplate in the serene atmosphere at Catedral Primada de America and then steep yourself in history at Palacio Consistorial. On your second day here, browse the eclectic array of goods at Mercado Modelo, explore the historical opulence of Alcazar de Colon, then appreciate the history behind Columbus Lighthouse (Faro A Colon), and finally steep yourself in history at Fortaleza Ozama.

To see other places to visit, where to stay, ratings, and other tourist information, use the Santo Domingo online road trip planner.

Fly from Havana to Santo Domingo in 3 hours. The time zone difference moving from Cuba Standard Time to Atlantic Standard Time is 1 hour. Wrap up your sightseeing on the 16th (Sun) to allow time to travel to Culebra.

Things to do in Santo Domingo

Historic Sites Shopping Museums
Find places to stay May 14 — 16:
Highlights from your plan
Catedral Primada de America
Catedral Primada de America
Alcazar de Colon ©
Alcazar de Colon
Fortaleza Ozama ©
Fortaleza Ozama

3
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.
Get in touch with nature at Flamenco Beach and Culebrita Island. Discover out-of-the-way places like Tamarindo Beach and Zinkowski Art Studio. There's still lots to do: kick back and relax at Zoni Beach, stroll through Carlos Rosario Beach, and visit a coastal fixture at Culebrita Lighthouse.

To find more things to do, other places to visit, photos, and more tourist information, read Culebra day trip planning app.

You can fly from Santo Domingo to Culebra in 3.5 hours. Alternatively, you can do a combination of shuttle and flight; or do a combination of ferry and taxi. In May in Culebra, expect temperatures between 87°F during the day and 77°F at night. Wrap up your sightseeing on the 19th (Wed) to allow time to travel to Isla de Vieques.

Things to do in Culebra

Parks Beaches Outdoors
Find places to stay May 16 — 19:
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Tamarindo Beach ©
Tamarindo Beach
Zoni Beach ©
Zoni 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 Caracas Beach and La Chiva. Get a sense of the local culture at Siddhia Hutchinson Fine Art Gallery and Puerto Ferro Lighthouse. There's much more to do: discover the deep blue sea with a scuba or snorkeling tour, look for gifts at Isla Vida, contemplate the long history of Isabel Segunda, and take in the waterfront at Malecon.

For reviews, ratings, traveler tips, and other tourist information, you can read our Isla de Vieques trip planner.

You can do a combination of flight and car from Culebra to Isla de Vieques in 2.5 hours. Another option is to ride a ferry. May in Isla de Vieques sees daily highs of 85°F and lows of 76°F at night. Finish up your sightseeing early on the 22nd (Sat) so you can travel to Bayahibe.

Things to do in Isla de Vieques

Outdoors Beaches Parks
Find places to stay May 19 — 22:
Highlights from your plan
Caracas Beach ©
Caracas Beach
La Chiva ©
La Chiva
Scuba & Snorkeling

2
nights
Bayahibe, Dominican Republic

Bayahibe ©
Located on the shore of the Caribbean Sea, the town of Bayahibe has grown from a fishing village into a bona fide tourist destination, with visitors mainly drawn to the many dive sites just off the coast.
Start off your visit on the 23rd (Sun): get to know the fascinating history of Altos de Chavon, then admire the masterpieces at Conquista Park, and then enjoy the sand and surf at Public Beach Playa Dominicus. On your second day here, see some colorful creatures with a scuba or snorkeling tour, then get a dose of the wild on a nature and wildlife tour, and then stop by Museo y Fabrica de Puras.

To find other places to visit, traveler tips, and tourist information, read Bayahibe trip planner.

Traveling by combination of flight and taxi from Isla de Vieques to Bayahibe takes 3.5 hours. Alternatively, you can do a combination of flight and shuttle; or do a combination of ferry, taxi, and bus. In May, daily temperatures in Bayahibe can reach 87°F, while at night they dip to 74°F. Finish your sightseeing early on the 24th (Mon) to allow enough time to drive to Punta Cana.

Things to do in Bayahibe

Outdoors Tours Wildlife

Side Trip

Altos de Chavon
Find places to stay May 22 — 24:
Highlights from your plan
Altos de Chavon ©
Altos de Chavon
Nature & Wildlife Tours
Public Beach Playa Dominicus ©
Public Beach Playa Dominicus

3
nights
Punta Cana, Dominican Republic

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.
Museum-lovers will get to explore Museo de La Altagracia and ChocoMuseo Punta Cana. Satisfy your inner culture vulture at Basilica Catedral Nuestra Senora de la Altagracia and Parroquia de San Dionisio. There's lots more to do: look for all kinds of wild species at Wildlife Areas, kick back and relax at Juanillo Beach, and stop by Nino's Liquors.

For maps, more things to do, other places to visit, and other tourist information, read our Punta Cana trip itinerary planning tool.

Getting from Bayahibe to Punta Cana by car takes about an hour. In May, daytime highs in Punta Cana are 86°F, while nighttime lows are 75°F. Wrap up your sightseeing by early afternoon on the 27th (Thu) to allow time for the car ride to Juan Dolio.

Things to do in Punta Cana

Outdoors Museums Tours

Side Trip

Higuey
Find places to stay May 24 — 27:
Highlights from your plan
Scuba & Snorkeling
Juanillo Beach ©
Juanillo Beach

2
nights
Juan Dolio, Dominican Republic

Juan Dolio ©
The beach town of Juan Dolio offers a number of sprawling resorts and more independent businesses than most tourist destinations in the area.
On the 28th (Fri), you'll have a packed day of sightseeing: pause for some serene contemplation at Catedral San Pedro Apostol and then kick back and relax at Juan Dolio Beach.

To see other places to visit, more things to do, photos, and tourist information, read Juan Dolio online day trip planner.

Getting from Punta Cana to Juan Dolio by car takes about 1.5 hours. Other options: take a bus. In May, daytime highs in Juan Dolio are 87°F, while nighttime lows are 74°F. You will leave for home on the 29th (Sat).

Things to do in Juan Dolio

Beaches Outdoors Historic Sites

Side Trip

Catedral San Pedro Apostol
Find places to stay May 27 — 29:
Highlights from your plan
Juan Dolio Beach ©
Juan Dolio Beach
Catedral San Pedro Apostol ©
Catedral San Pedro Apostol

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