20 days in Caribbean Itinerary

20 days in Caribbean Itinerary

Created using Inspirock Caribbean trip maker

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Route & dates

20 days in Caribbean Itinerary

Start: London, United Kingdom
Fly:  13​h
1
Havana, Cuba
— 4 nights
Fly:  2​h
2
Seven Mile Beach, Cayman Islands
— 2 nights
Fly:  6​h 15​min
3
Palm - Eagle Beach, Aruba
— 1 night
Fly:  2​h 15​min
4
Santo Domingo, Dominican Republic
— 3 nights
Fly:  4​h 30​min
5
Culebra, Puerto Rico
— 4 nights
Fly:  3​h 45​min
6
Punta Cana, Dominican Republic
— 4 nights
Fly:  12​h 45​min
End: London, United Kingdom

4
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Step out of Havana with an excursion to Playa Paraiso in Cayo Largo--about 2 hours away. There's still lots to do: get to know the fascinating history of El Malecon, steep yourself in history at Castillo de la Real Fuerza, make a trip to Paseo del Prado, and capture your vacation like a pro with an inspiring photography tour.

To see where to stay, more things to do, maps, and more tourist information, you can read our Havana online trip itinerary maker .

London, UK to Havana is an approximately 13-hour flight. The time zone difference when traveling from London to Havana is minus 5 hours. Traveling from London in October, expect Havana to be much hotter, temps between 35°C and 24°C. Wrap up your sightseeing on the 10th (Thu) early enough to travel to Seven Mile Beach.

Things to do in Havana

Historic Sites Tours Outdoors

Side Trip

Playa Paraiso
Find places to stay Oct 6 — 10:
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Plaza de la Catedral ©
Plaza de la Catedral

2
nights
Seven Mile Beach, Cayman Islands

Kick off your visit on the 11th (Fri): kick back and relax at Seven Mile Beach, brush up on your knowledge of spirits at Cayman Spirits Co. Distillery, and then identify plant and animal life at Stingray City Grand Cayman. Get ready for a full day of sightseeing on the next day: get a new perspective on things with Boat Tours & Water Sports, then identify plant and animal life at Cayman Turtle Centre: Island Wildlife Encounter, and then don't miss a visit to Hell Gift Store.

To see ratings, reviews, photos, and tourist information, use the Seven Mile Beach trip planner.

Getting from Havana to Seven Mile Beach by flight takes about 2 hours. Traveling from Havana in October, expect somewhat warmer with lows of 30°C in Seven Mile Beach. Wrap up your sightseeing on the 12th (Sat) to allow time to travel to Palm - Eagle Beach.

Things to do in Seven Mile Beach

Parks Wildlife Outdoors

Side Trips

Grand Cayman, Cayman Spirits Co. Distillery, Cayman Turtle Centre: Island Wildlife Encounter
Find places to stay Oct 10 — 12:
Highlights from your plan
Scuba & Snorkeling
Stingray City Grand Cayman ©
Stingray City Grand Cayman
Seven Mile Beach ©
Seven Mile Beach

1
night
Palm - Eagle Beach, Aruba

Palm - Eagle Beach ©
A long stretch of powdery white sand and aquamarine waters, Palm - Eagle Beach remains one of Aruba's most visited vacation spots.
Kick off your visit on the 13th (Sun): enjoy the sand and surf at Eagle Beach. On the 14th (Mon), you'll have a packed day of sightseeing: enjoy the sand and surf at Palm Beach and then visit a coastal fixture at California Lighthouse.

To see photos, where to stay, maps, and other tourist information, use the Palm - Eagle Beach road trip tool .

Traveling by flight from Seven Mile Beach to Palm - Eagle Beach takes 6.5 hours. The time zone difference moving from Eastern Standard Time to Atlantic Standard Time is 1 hour. In October, daily temperatures in Palm - Eagle Beach can reach 38°C, while at night they dip to 32°C. Finish your sightseeing early on the 14th (Mon) so you can travel to Santo Domingo.

Things to do in Palm - Eagle Beach

Outdoors Beaches Parks

Side Trip

California Lighthouse
Find places to stay Oct 12 — 14:
Highlights from your plan
Eagle Beach ©
Eagle Beach
Palm Beach ©
Palm Beach
California Lighthouse ©
California Lighthouse

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.
Santo Domingo is known for historic sites, nature, shopping, museums, and beaches. Your plan includes some of its best attractions: make a trip to Zona Colonial, delve into the distant past at Monasterio de San Francisco, pause for some serene contemplation at Basilica Cathedral of Santa Maria la Menor, and explore the historical opulence of Alcazar de Colon.

To find ratings, reviews, where to stay, and other tourist information, use the Santo Domingo trip itinerary app .

Getting from Palm - Eagle Beach to Santo Domingo by flight takes about 2.5 hours. Cap off your sightseeing on the 17th (Thu) early enough to travel to Culebra.

Things to do in Santo Domingo

Historic Sites Parks Museums

Side Trip

Los Tres Ojos
Find places to stay Oct 14 — 17:
Highlights from your plan
Alcazar de Colon ©
Alcazar de Colon
Zona Colonial ©
Zona Colonial
Catedral Primada de America
Catedral Primada de America

4
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.
Culebra is known for beaches, wildlife, nature, outdoors, and adventure. Your plan includes some of its best attractions: stroll through Flamenco Beach, get lost in a book at Culebra Public Library, enjoy the sand and surf at Melones Beach, and glide peacefully along the water with some of the best stand-up paddleboarding in the area.

For photos, other places to visit, more things to do, and tourist information, refer to the Culebra itinerary planning app .

You can fly from Santo Domingo to Culebra in 4.5 hours. Alternatively, you can do a combination of flight, shuttle, and ferry; or ride a ferry. In October in Culebra, expect temperatures between 36°C during the day and 30°C at night. Finish your sightseeing early on the 21st (Mon) to allow enough time to travel to Punta Cana.

Things to do in Culebra

Parks Outdoors Beaches
Find places to stay Oct 17 — 21:
Highlights from your plan
Culebrita Island ©
Culebrita Island
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach

4
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.
Take a break from Punta Cana with a short trip to Altos de Chavon in La Romana, about 1h 20 min away. The adventure continues: get close to the beloved marine mammals with a swim-with-the-dolphins experience, step off the mainland to explore Saona Island, enjoy the sand and surf at Macao Beach, and stroll through Bavaro Beach.

For more things to do, traveler tips, and tourist information, refer to the Punta Cana trip itinerary builder tool .

Traveling by flight from Culebra to Punta Cana takes 4 hours. Alternatively, you can do a combination of flight and shuttle; or do a combination of ferry, shuttle, and flight. Expect a daytime high around 36°C in October, and nighttime lows around 28°C. Cap off your sightseeing on the 25th (Fri) early enough to travel back home.

Things to do in Punta Cana

Parks Outdoors Beaches

Side Trip

Altos de Chavon
Find places to stay Oct 21 — 25:
Highlights from your plan
Bavaro Beach ©
Bavaro Beach
Swim with Dolphins
Saona Island ©
Saona Island

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