31 days in Caribbean Itinerary

31 days in Caribbean Itinerary

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Route & dates

31 days in Caribbean Itinerary

Start: Nassau, Bahamas
Fly:  2 h
1
George Town, Cayman Islands
— 2 nights
Fly:  1 h 30 min
2
Havana, Cuba
— 5 nights
Fly:  5 h 15 min
3
Fort-de-France, Martinique
— 3 nights
Fly:  7 h 30 min
4
Isla de Vieques, Puerto Rico
— 6 nights
Drive + Fly:  2 h 15 min
5
Culebra, Puerto Rico
— 5 nights
Fly:  30 min
6
San Juan, Puerto Rico
— 5 nights
Fly:  3 h 30 min
7
Providenciales, Turks and Caicos
— 3 nights
Fly:  5 h
End: Nassau, Bahamas

2
nights
George Town, Cayman Islands

George Town ©
George Town is a city situated on Grand Cayman island of the Cayman Islands. George Town is known for wildlife, adventure, and breweries & distilleries. Your plan includes some of its best attractions: stroll through Stingray City Grand Cayman, stop by TAG Heuer Boutique, take in nature's colorful creations at Queen Elizabeth II Botanic Park, and laugh and play at Wowballs Caribbean.

To see where to stay, ratings, photos, and tourist information, refer to the George Town road trip planning app.

Nassau, Bahamas to George Town is an approximately 2-hour flight. Traveling from Nassau in January, expect a bit warmer with lows of 27°C in George Town. Wrap up your sightseeing on the 3rd (Sun) early enough to travel to Havana.

Things to do in George Town

Parks Wildlife Nature

Side Trip

Grand Cayman
Find places to stay Jan 1 — 3:
Highlights from your plan
Cayman Spirits Co. Distillery ©
Cayman Spirits Co. Distillery
Stingray City Grand Cayman ©
Stingray City Grand Cayman
Mastic Trail ©
Mastic Trail

5
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Go for a jaunt from Havana to Cayo Largo to see Playa Paraiso about 2 hours away. The adventure continues: don't miss a visit to Malecón of Havana, get the lay of the land with Walking tours, take a stroll through Christopher Columbus Cemetery (Cemetario de Colon), and get to know the fascinating history of Old Havana.

To find more things to do, where to stay, ratings, and other tourist information, you can read our Havana online trip builder.

Traveling by flight from George Town to Havana takes 1.5 hours. Traveling from George Town in January, you can expect nighttime temperatures to be slightly colder in Havana, with lows of 19°C. Finish your sightseeing early on the 8th (Fri) so you can travel to Fort-de-France.

Things to do in Havana

Historic Sites Tours Outdoors

Side Trip

Playa Paraiso
Find places to stay Jan 3 — 8:
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Playa Paraiso ©
Playa Paraiso

3
nights
Fort-de-France, Martinique

Fort-de-France ©
The political capital of Martinique, Fort-de-France has a thriving commercial center and a number of historic sites.
Change things up with these side-trips from Fort-de-France: Sainte-Anne (Plage des Salines & Grande Anse des Salines) and La Savane des Esclaves (in Trois-Ilets). There's still lots to do: admire the natural beauty at Jardin de Balata, get lost in a book at Schoelcher Library, contemplate the long history of Habitation Clement, and take in the spiritual surroundings of St. Louis Cathedral.

To find photos, where to stay, traveler tips, and more tourist information, read Fort-de-France attractions planning website.

Traveling by flight from Havana to Fort-de-France takes 5.5 hours. Alternatively, you can do a combination of flight and ferry; or do a combination of flight, bus, and ferry. The time zone changes from Cuba Standard Time (CST) to Atlantic Standard Time (AST), which is usually a 1 hour difference. Traveling from Havana in January, expect a bit warmer with lows of 26°C in Fort-de-France. Finish up your sightseeing early on the 11th (Mon) so you can travel to Isla de Vieques.

Things to do in Fort-de-France

Parks Nature Outdoors

Side Trips

Sainte-Anne, Habitation Clement, La Savane des Esclaves, Montagne Pelee
Find places to stay Jan 8 — 11:
Highlights from your plan
Montagne Pelee ©
Montagne Pelee
Jardin de Balata ©
Jardin de Balata
La Savane des Esclaves ©
La Savane des Esclaves

6
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, and wildlife. Your plan includes some of its best attractions: enjoy the sand and surf at Sun Bay Beach, tour the pleasant surroundings at Caracas Beach, get engrossed in the history at Fortin Conde de Mirasol Museum, and tour in harmony with nature at Eco Tours.

To find ratings, maps, more things to do, and more tourist information, read our Isla de Vieques road trip planner.

You can fly from Fort-de-France to Isla de Vieques in 7.5 hours. Alternatively, you can do a combination of ferry and flight. January in Isla de Vieques sees daily highs of 32°C and lows of 26°C at night. Wrap up your sightseeing on the 18th (Mon) to allow time to travel to Culebra.

Things to do in Isla de Vieques

Parks Outdoors Beaches
Find places to stay Jan 11 — 18:
Highlights from your plan
Sun Bay Beach ©
Sun Bay Beach
Vieques National Wildlife Refuge ©
Vieques National Wildlife Refuge
La Chiva ©
La Chiva

5
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, and nature. Your plan includes some of its best attractions: kick back and relax at Flamenco Beach, stroll through Zoni Beach, browse the collection at Culebra Public Library, and head off the coast to Culebrita Island.

To find other places to visit, maps, where to stay, and other tourist information, use the Culebra online journey planner.

You can do a combination of car and flight from Isla de Vieques to Culebra in 2.5 hours. Another option is to ride a ferry. In January in Culebra, expect temperatures between 34°C during the day and 26°C at night. Wrap up your sightseeing on the 23rd (Sat) to allow time to fly to San Juan.

Things to do in Culebra

Parks Outdoors Beaches
Find places to stay Jan 18 — 23:
Highlights from your plan
Culebrita Island ©
Culebrita Island
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach

5
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Venture out of the city with trips to Ponce (Museo de Arte de Ponce & Casa Wiechers-Villaronga), El Yunque Rain Forest (in El Yunque National Forest) and Luquillo Beach (in Luquillo). Next up on the itinerary: contemplate the long history of Old San Juan, make a trip to Holocaust Memorial Monument, scramble along the landscape with a canyoning and rapelling tour, and tour the pleasant surroundings at Condado Beach.

For other places to visit, traveler tips, where to stay, and other tourist information, read San Juan itinerary builder tool.

San Juan is just a short distance from Culebra. January in San Juan sees daily highs of 34°C and lows of 26°C at night. Wrap up your sightseeing on the 28th (Thu) early enough to travel to Providenciales.

Things to do in San Juan

Parks Outdoors Nature

Side Trips

Ponce, Bosque Nacional El Yunque, Luquillo Beach, El Yunque Rain Forest
Find places to stay Jan 23 — 28:
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

3
nights
Providenciales, Turks and Caicos

Providenciales ©
The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
Providenciales is known for beaches, wildlife, and adventure. Your plan includes some of its best attractions: enjoy the sand and surf at Grace Bay Beach, tour the pleasant surroundings at Taylor Bay Beach, explore the striking landscape at Smith's Reef, and make a trip to Leeward Beach.

To find maps, traveler tips, other places to visit, and tourist information, you can read our Providenciales trip planning site.

Traveling by flight from San Juan to Providenciales takes 3.5 hours. Alternatively, you can do a combination of car and flight. Due to the time zone difference, you'll gain 1 hour traveling from San Juan to Providenciales. In January, plan for daily highs up to 32°C, and evening lows to 27°C. Wrap up your sightseeing on the 31st (Sun) early enough to travel back home.

Things to do in Providenciales

Parks Outdoors Beaches

Side Trip

Smith's Reef
Find places to stay Jan 28 — 31:
Highlights from your plan
Grace Bay Beach ©
Grace Bay Beach
Provo Golf Club ©
Provo Golf Club
Little Water Cay ©
Little Water Cay

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