13 days in Caribbean Itinerary

13 days in Caribbean Itinerary

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Route & dates

13 days in Caribbean Itinerary

Start: Fort Lauderdale, United States
Fly:  5​h 45​min
1
San Juan, Puerto Rico
— 3 nights
Fly:  2​h 45​min
2
Santo Domingo, Dominican Republic
— 2 nights
Fly:  7​h 30​min
3
Southampton Parish, Bermuda
— 1 night
Fly:  6​h
4
George Town, Cayman Islands
— 2 nights
Fly:  1​h 30​min
5
Havana, Cuba
— 3 nights
Fly:  4​h 15​min
End: Fort Lauderdale, 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.
Get some historical perspective at Paseo de la Princesa and Sitio Histórico de San Juan. You'll explore the less-touristy side of things at Santa Maria Magdalena de Pazzis Cemetery and San Jose Church. 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, skim along the rocks with a canyoning and rapelling tour, contemplate the long history of 104 Calle La Fortaleza, and take an in-depth tour of Catedral Metropolitana Basilica de San Juan Bautista.

To see traveler tips, maps, photos, and other tourist information, refer to the San Juan online trip builder .

Fort Lauderdale, USA to San Juan is an approximately 6-hour flight. You can also do a combination of bus and flight; or do a combination of flight and car. The time zone difference when traveling from Fort Lauderdale to San Juan is 1 hour. In July, plan for daily highs up to 89°F, and evening lows to 78°F. Cap off your sightseeing on the 29th (Mon) early enough to travel to Santo Domingo.

Things to do in San Juan

Historic Sites Wildlife Parks

Side Trip

El Yunque Rain Forest
Highlights from your plan
Paseo de la Princesa ©
Paseo de la Princesa

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.
On the 30th (Tue), make a trip to Parque Colon, contemplate in the serene atmosphere at Catedral Primada de America, then get to know the fascinating history of Calle de Las Damas, then step into the grandiose world of Alcazar de Colon, and finally contemplate the long history of Palacio Consistorial. Get ready for a full day of sightseeing on the next day: explore the striking landscape at The 3 Eyes National Park, then steep yourself in history at Fortaleza Ozama, and then steep yourself in history at Palacio de Bellas Artes.

To see traveler tips, maps, reviews, and tourist information, use the Santo Domingo online itinerary planner .

You can fly from San Juan to Santo Domingo in 3 hours. Alternatively, you can do a combination of flight and shuttle; or ride a ferry. Wrap up your sightseeing on the 31st (Wed) early enough to travel to Southampton Parish.

Things to do in Santo Domingo

Historic Sites Parks Nature
Highlights from your plan
Catedral Primada de America
Catedral Primada de America
Calle de Las Damas ©
Calle de Las Damas
Parque Colon ©
Parque Colon

1
night
Southampton Parish, Bermuda

Southampton Parish ©
The area's beaches remain the primary reason to holiday in Southampton Parish, with their number and variety providing entertainments and sights to suit a range of tastes.
On the 1st (Thu), enjoy the sea views from Gibb's Hill Lighthouse and then enjoy the sand and surf at Horseshoe Bay Beach. On the next day, steep yourself in history at National Museum of Bermuda, then explore the fascinating underground world of Crystal & Fantasy Caves, then contemplate in the serene atmosphere at St. Peter's Church, and finally contemplate in the serene atmosphere at The Unfinished Church.

To find photos, maps, and other tourist information, go to the Southampton Parish online road trip planner .

Getting from Santo Domingo to Southampton Parish by flight takes about 7.5 hours. In August, daytime highs in Southampton Parish are 85°F, while nighttime lows are 77°F. Finish up your sightseeing early on the 2nd (Fri) so you can travel to George Town.

Things to do in Southampton Parish

Historic Sites Parks Outdoors

Side Trips

St. George, Crystal & Fantasy Caves, National Museum of Bermuda
Highlights from your plan
Gibb's Hill Lighthouse ©
Gibb's Hill Lighthouse
St. Peter's Church ©
St. Peter's Church
National Museum of Bermuda ©
National Museum of Bermuda

2
nights
George Town, Cayman Islands

George Town ©
George Town is a city situated on Grand Cayman island of the Cayman Islands. Kick off your visit on the 3rd (Sat): enjoy the sand and surf at Seven Mile Beach and then identify plant and animal life at Stingray City Grand Cayman. Here are some ideas for day two: cool off at Cayman Turtle Centre: Island Wildlife Encounter and then see some colorful creatures with a scuba or snorkeling tour.

For other places to visit, reviews, photos, and other tourist information, go to the George Town online holiday planner .

Traveling by flight from Southampton Parish to George Town takes 6 hours. The time zone difference moving from Atlantic Standard Time to Eastern Standard Time is minus 1 hour. In August, daily temperatures in George Town can reach 90°F, while at night they dip to 80°F. Wrap up your sightseeing on the 4th (Sun) to allow time to travel to Havana.

Things to do in George Town

Wildlife Parks Outdoors

Side Trips

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

3
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
You'll discover tucked-away gems like Havana Cathedral and Fortaleza de San Carlos de la Cabana. Popular historic sites such as El Malecon and Old Havana are in your itinerary. There's much more to do: steep yourself in history at FINCA VIGÍA, don't miss a visit to Plaza de San Francisco, explore the different monuments and memorials at Christopher Columbus Cemetery (Cemetario de Colon), and admire the striking features of Casa de la Amistad.

To find ratings, reviews, photos, and other tourist information, read our Havana attractions planning tool .

You can fly from George Town to Havana in 1.5 hours. Traveling from George Town in August, expect a bit cooler with lows of 72°F in Havana. Finish your sightseeing early on the 7th (Wed) to allow enough time to travel back home.

Things to do in Havana

Historic Sites Neighborhoods
Highlights from your plan
Old Havana ©
Old Havana
El Malecon ©
El Malecon
Fortaleza de San Carlos de la Cabana ©

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