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
— 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:  3 h 30 min
5
Bayahibe, Dominican Republic
— 2 nights
Shuttle:  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), explore the world behind art at Museu Nacional de Belas Artes de Cuba, contemplate the long history of Plaza de San Francisco, then appreciate the extensive heritage of Malecón of Havana, and finally wander the streets of Fusterlandia. On the 14th (Fri), you'll have a packed day of sightseeing: take a stroll through Christopher Columbus Cemetery (Cemetario de Colon), then contemplate the long history of El Morro, and then get to know the fascinating history of Old Havana.

To see other places to visit, more things to do, photos, and tourist information, go to the Havana driving holiday tool.

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. Finish your sightseeing early on the 14th (Fri) so you can travel to Santo Domingo.

Things to do in Havana

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

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.
Start off your visit on the 15th (Sat): contemplate in the serene atmosphere at Catedral Primada de America and then don't miss a visit to Palacio Consistorial. On the 16th (Sun), you'll have a packed day of sightseeing: browse the eclectic array of goods at Mercado Modelo, then explore the historical opulence of Alcazar de Colon, then pause for some photo ops at Columbus Lighthouse (Faro A Colon), and finally contemplate the long history of Fortaleza Ozama.

For ratings, reviews, where to stay, and more tourist information, you can read our Santo Domingo online tour itinerary planner.

Getting from Havana to Santo Domingo by flight takes about 3 hours. The time zone difference when traveling from Havana to Santo Domingo is 1 hour. Cap off your sightseeing on the 16th (Sun) early enough 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
Alcazar de Colon ©
Alcazar de Colon
Catedral Primada de America
Catedral Primada de America
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.
Take a break from the city and head to Flamenco Beach and Culebrita Island. You'll discover tucked-away gems like Tamarindo Beach and Carlos Rosario Beach. There's lots more to do: stroll through Zoni Beach, enjoy the sand and surf at Playa Punta Soldado Beach, stop by Zinkowski Art Studio, and enjoy the sea views from Culebrita Lighthouse.

To find where to stay, photos, and tourist information, use the Culebra road trip site.

You can fly from Santo Domingo to Culebra in 3.5 hours. Other options are to do a combination of shuttle and flight; or do a combination of ferry and taxi. In May, daily temperatures in Culebra can reach 87°F, while at night they dip to 77°F. Wrap up your sightseeing on the 19th (Wed) to allow time to travel to Isla de Vieques.

Things to do in Culebra

Parks Outdoors Beaches
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.
Explore hidden gems such as Scuba & Snorkeling and Sun Bay Beach. Popular historic sites such as Isabel Segunda and Puerto Ferro Lighthouse are in your itinerary. The adventure continues: stroll through Caracas Beach, take in the waterfront at Malecon, look for gifts at Isla Vida, and enjoy the sand and surf at La Chiva.

To see other places to visit, where to stay, and tourist information, you can read our Isla de Vieques road trip planning site.

Traveling by combination of flight and car from Culebra to Isla de Vieques takes 2.5 hours. Alternatively, you can ride a ferry. In May, plan for daily highs up to 85°F, and evening lows to 76°F. Finish up your sightseeing early on the 22nd (Sat) so you can travel to Bayahibe.

Things to do in Isla de Vieques

Outdoors Parks Beaches
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): make a trip to Altos de Chavon, explore the world behind art at Conquista Park, and then stroll through Public Beach Playa Dominicus. On the 24th (Mon), you'll have a packed day of sightseeing: see some colorful creatures with a scuba or snorkeling tour, surround yourself with nature on a nature and wildlife tour, and then stop by Museo y Fabrica de Puras.

To find where to stay, other places to visit, reviews, and more tourist information, read Bayahibe trip planner.

Traveling by flight 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, plan for daily highs up to 87°F, and evening lows to 74°F. Finish your sightseeing early on the 24th (Mon) so you can take a shuttle to Punta Cana.

Things to do in Bayahibe

Outdoors Wildlife Tours

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.
Step out of the city life by going to Scuba & Snorkeling and Juanillo Beach. Get a sense of the local culture at Basilica Catedral Nuestra Senora de la Altagracia and Museo de La Altagracia. Step out of Punta Cana to go to Higuey and see Parroquia de San Dionisio, which is approximately 36 minutes away. There's more to do: examine the collection at ChocoMuseo Punta Cana and look for gifts at Nino's Liquors.

For where to stay, other places to visit, traveler tips, and tourist information, go to the Punta Cana visit planner.

Traveling by shuttle from Bayahibe to Punta Cana takes 2.5 hours. 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 Wildlife

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 next day, take in the architecture and atmosphere at Catedral San Pedro Apostol and then enjoy the sand and surf at Juan Dolio Beach.

For other places to visit, reviews, and other tourist information, go to the Juan Dolio trip planner.

You can drive from Punta Cana to Juan Dolio in 1.5 hours. Other options are to take a shuttle; or take a bus. In May, daytime highs in Juan Dolio are 87°F, while nighttime lows are 74°F. On the 29th (Sat), you're off to home.

Things to do in Juan Dolio

Outdoors Parks Beaches

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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