15 days in Caribbean Itinerary

15 days in Caribbean Itinerary

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Route & dates

15 days in Caribbean Itinerary

Start: Columbus, United States
Fly:  8​h 30​min
1
San Juan, Puerto Rico
— 3 nights
Fly:  30​min
2
Culebra, Puerto Rico
— 3 nights
Fly + Drive:  2​h 15​min
3
Isla de Vieques, Puerto Rico
— 4 nights
Fly:  7​h 45​min
4
George Town, Cayman Islands
— 2 nights
Fly:  1​h 30​min
5
Havana, Cuba
— 2 nights
Fly:  7​h 30​min
End: Columbus, United States

3
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Step out of San Juan with an excursion to El Yunque Rain Forest in El Yunque National Forest--about 1h 10 min away. There's much more to do: get to know the fascinating history of Old San Juan, don't miss a visit to Plaza de la Catedral, pause for some photo ops at Paseo de los Presidentes, and kick back and relax at Condado Beach.

To see maps, photos, where to stay, and tourist information, read our San Juan online itinerary planner .

Columbus, USA to San Juan is an approximately 8.5-hour flight. You can also do a combination of flight and car. Traveling from Columbus to San Juan, you'll lose 1 hour due to the time zone difference. In June, San Juan is somewhat warmer than Columbus - with highs of 89°F and lows of 78°F. Finish up your sightseeing early on the 16th (Tue) so you can catch the flight to Culebra.

Things to do in San Juan

Outdoors Parks Tours

Side Trip

El Yunque Rain Forest
Highlights from your plan
Old San Juan ©
Old San Juan
El Yunque Rain Forest ©
El Yunque Rain Forest
Canyoning & Rappelling Tours

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.
Culebra is known for beaches, wildlife, nature, outdoors, and adventure. Your plan includes some of its best attractions: kick back and relax at Flamenco Beach, enjoy the sea views from Culebrita Lighthouse, tour the pleasant surroundings at Tamarindo Beach, and browse the collection at Culebra Public Library.

To see maps, traveler tips, more things to do, and more tourist information, refer to the Culebra trip maker website .

Culebra is very close to San Juan. In June, daily temperatures in Culebra can reach 89°F, while at night they dip to 79°F. Finish your sightseeing early on the 19th (Fri) so you can travel to Isla de Vieques.

Things to do in Culebra

Outdoors Parks Beaches
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Culebrita Island ©
Culebrita Island
Zoni Beach ©
Zoni Beach

4
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.
Isla de Vieques is known for nature, beaches, wildlife, adventure, and nightlife. Your plan includes some of its best attractions: contemplate the waterfront views at Sun Bay, enjoy the sand and surf at Media Luna Beach, deepen your knowledge of military history at Camp Garcia, and enjoy some diversion at Vieques Gun Club & Sporting Clays.

To see reviews, maps, and other tourist information, you can read our Isla de Vieques road trip planning tool .

You can do a combination of flight and car from Culebra to Isla de Vieques in 2.5 hours. Alternatively, you can ride a ferry. June in Isla de Vieques sees daily highs of 87°F and lows of 78°F at night. Finish up your sightseeing early on the 23rd (Tue) so you can travel to George Town.

Things to do in Isla de Vieques

Outdoors Parks Beaches
Highlights from your plan
Sun Bay Beach ©
Sun Bay Beach
Vieques National Wildlife Refuge ©
Vieques National Wildlife Refuge
Media Luna Beach ©
Media Luna Beach

2
nights
George Town, Cayman Islands

George Town is a city situated on Grand Cayman island of the Cayman Islands. Start off your visit on the 24th (Wed): identify plant and animal life at Stingray City Grand Cayman, then look for gifts at Cayman Scents, and then kick back and relax at Seven Mile Beach. Keep things going the next day: try out the rides at Cayman Turtle Centre: Island Wildlife Encounter and then see some colorful creatures with a scuba or snorkeling tour.

To find other places to visit, ratings, maps, and other tourist information, refer to the George Town trip planning website .

Traveling by flight from Isla de Vieques to George Town takes 8 hours. Traveling from Isla de Vieques to George Town, you'll gain 1 hour due to the time zone difference. In June, daily temperatures in George Town can reach 88°F, while at night they dip to 79°F. Wrap up your sightseeing on the 25th (Thu) to allow time to travel to Havana.

Things to do in George Town

Wildlife Parks Outdoors

Side Trips

Grand Cayman, Seven Mile Beach, Cayman Turtle Centre: Island Wildlife Encounter
Highlights from your plan
Scuba & Snorkeling
Stingray City Grand Cayman ©
Stingray City Grand Cayman
Seven Mile Beach ©
Seven Mile Beach

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.
Kick off your visit on the 26th (Fri): don't miss a visit to Old Havana, appreciate the extensive heritage of El Malecon, and then don't miss a visit to El Capitolio. Here are some ideas for day two: steep yourself in history at Fortaleza de San Carlos de la Cabana, then make a trip to Plaza de Armas, and then make a trip to Plaza de la Catedral.

For photos, other places to visit, ratings, and other tourist information, refer to the Havana journey maker tool .

Traveling by flight from George Town to Havana takes 1.5 hours. Expect slightly colder evenings in Havana when traveling from George Town in June, with lows around 72°F. Finish your sightseeing early on the 27th (Sat) so you can travel back home.

Things to do in Havana

Historic Sites
Highlights from your plan
Old Havana ©
Old Havana
El Malecon ©
El Malecon
Plaza de la Catedral ©
Plaza de la Catedral

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