20 days in Caribbean Itinerary

20 days in Caribbean Itinerary

Created using Inspirock Caribbean trip planner

Plan created by another user. Make it yours
1
Culebra, Puerto Rico
— 4 nights
2
San Juan, Puerto Rico
— 4 nights
3
Santo Domingo, Dominican Republic
— 4 nights
4
Havana, Cuba
— 4 nights
5
George Town, Cayman Islands
— 3 nights

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4
nights
Culebra, Puerto Rico

Culebra ©

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
You'll visit kid-friendly attractions like Flamenco Beach and Playa Punta Soldado Beach. And it doesn't end there: step off the mainland to explore Culebrita Island, kick back and relax at Zoni Beach, tour the pleasant surroundings at Tamarindo Beach, and enjoy the sea views from Culebrita Lighthouse.

For traveler tips, maps, where to stay, and more tourist information, refer to the Culebra journey planner.

Washington DC, USA to Culebra is an approximately 9-hour flight. Traveling from Washington DC to Culebra, you'll lose 1 hour due to the time zone difference. Traveling from Washington DC in July, expect somewhat warmer with lows of 80°F in Culebra. Finish up your sightseeing early on the 29th (Mon) so you can travel to San Juan.

Things to do in Culebra

Parks · Outdoors · Beaches · Nature
Find places to stay Jul 25 — 29:
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Culebrita Island ©
Culebrita Island
Zoni Beach ©
Zoni Beach

4
nights
San Juan, Puerto Rico

San Juan ©

Walled City

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 Parque de Bombas. Kids will appreciate attractions like Sitio Histórico de San Juan and Catedral Metropolitana Basilica de San Juan Bautista. You'll find plenty of places to visit near San Juan: El Yunque Rain Forest (in El Yunque National Forest), Museo de Arte de Ponce (in Ponce) and Luquillo Beach (in Luquillo). There's more to do: explore the world behind art at Museo de Las Americas.

To find other places to visit, ratings, where to stay, and more tourist information, read our San Juan trip website.

Traveling by flight from Culebra to San Juan takes 2 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and shuttle. In July, daytime highs in San Juan are 89°F, while nighttime lows are 78°F. Cap off your sightseeing on the 2nd (Fri) early enough to travel to Santo Domingo.

Things to do in San Juan

Side Trips

Find places to stay Jul 29 — Aug 2:
Highlights from your plan
El Yunque Rain Forest ©
El Yunque Rain Forest
Old San Juan ©
Old San Juan
Sitio Histórico de San Juan ©
Sitio Histórico de San Juan

4
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 Basilica Cathedral of Santa Maria la Menor and Zona Colonial. You'll visit kid-friendly attractions like Alcazar de Colon and Fortaleza Ozama. Next up on the itinerary: appreciate the history behind Columbus Lighthouse (Faro A Colon), admire nature's wide array of creatures at National Aquarium, view the masterpieces at Amber Museum, and examine the collection at Museo De Las Casas Reales.

To find traveler tips, where to stay, ratings, and tourist information, read Santo Domingo travel itinerary planner.

Traveling by flight from San Juan to Santo Domingo takes 3 hours. Alternatively, you can ride a ferry. Finish your sightseeing early on the 6th (Tue) so you can travel to Havana.

Things to do in Santo Domingo

Historic Sites · Parks · Museums · Nature
Find places to stay Aug 2 — 6:
Highlights from your plan
Basilica Cathedral of Santa Maria la Menor ©
Alcazar de Colon ©
Alcazar de Colon
Zona Colonial ©
Zona Colonial

4
nights
Havana, Cuba

Havana ©

Rome of the Caribbean

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Satisfy your inner culture vulture at Malecón of Havana and Plaza de la Catedral. Kids will enjoy Old Havana and Museum of the Revolution (Museo de la Revolucion). There's much more to do: don't miss a visit to Old Square (Plaza Vieja), examine the collection at Wifredo Lam Center, contemplate the long history of Finca Vigía, and take a stroll through Christopher Columbus Cemetery (Cemetario de Colon).

For ratings, reviews, where to stay, and tourist information, go to the Havana itinerary maker site.

You can fly from Santo Domingo to Havana in 5.5 hours. You'll gain 1 hour traveling from Santo Domingo to Havana due to the time zone difference. August in Havana sees daily highs of 90°F and lows of 72°F at night. Finish your sightseeing early on the 10th (Sat) so you can travel to George Town.

Things to do in Havana

Find places to stay Aug 6 — 10:
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Old Square (Plaza Vieja) ©
Old Square (Plaza Vieja)

3
nights
George Town, Cayman Islands

George Town ©
George Town is a city situated on Grand Cayman island of the Cayman Islands. Pedro St. James National Historic Site and Cayman Islands National Museum are good opportunities to explore the local culture. You'll visit kid-friendly attractions like Stingray City Grand Cayman and Cayman Turtle Centre: Island Wildlife Encounter. Take a break from George Town with a short trip to Davinoff's Concrete Sculpture Garden in North Side, about 38 minutes away. And it doesn't end there: kick back and relax at Seven Mile Beach, brush up on your knowledge of spirits at Cayman Spirits Co. Distillery, and see some colorful creatures with a scuba or snorkeling tour.

To find reviews, more things to do, and other tourist information, read George Town trip itinerary planner.

You can fly from Havana to George Town in 4 hours. Expect a bit warmer evenings in George Town when traveling from Havana in August, with lows around 80°F. Finish your sightseeing early on the 13th (Tue) to allow enough time to travel back home.

Things to do in George Town

Parks · Wildlife · Outdoors · Theme Parks

Side Trips

Find places to stay Aug 10 — 13:
Highlights from your plan
Stingray City Grand Cayman ©
Stingray City Grand Cayman
Seven Mile Beach ©
Seven Mile Beach

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