43 days in Caribbean Itinerary

43 days in Caribbean Itinerary

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Route & dates

43 days in Caribbean Itinerary

Start: Cairo, Egypt
Fly + Drive:  20​h 30​min
1
Saint Joseph Parish, Barbados
— 2 nights
Bus + Fly:  5​h 15​min
2
Philipsburg, St. Maarten-St. Martin
— 5 nights
Fly:  3​h 45​min
3
Providenciales, Turks and Caicos
— 4 nights
Fly:  5​h 30​min
4
Havana, Cuba
— 5 nights
Fly:  2​h
5
Seven Mile Beach, Cayman Islands
— 3 nights
Fly:  8​h 15​min
6
Isla de Vieques, Puerto Rico
— 8 nights
Drive + Fly:  2​h 15​min
7
Culebra, Puerto Rico
— 5 nights
Fly:  30​min
8
San Juan, Puerto Rico
— 8 nights
Fly:  18​h 15​min
End: Cairo, Egypt

2
nights
Saint Joseph Parish, Barbados

Saint Joseph Parish ©
Lush Saint Joseph Parish has a particularly rugged aspect to it down by the sea, so much so that it has gained the nickname 'Scotland District'.
Start off your visit on the 6th (Fri): kick back and relax at Bottom Bay, see the interesting displays at Sunbury Plantation House, steep yourself in history at Andromeda Botanic Gardens, then admire the natural beauty at Hunte's Gardens, and finally explore the fascinating underground world of Harrison's Cave.. Keep things going the next day: take in nature's colorful creations at Welchman Hall Gully, then tour the pleasant surroundings at Soup Bowl, then take in panoramic vistas at Gun Hill Signal Station, and finally enjoy the sand and surf at Carlisle Bay.

For photos, traveler tips, more things to do, and tourist information, read our Saint Joseph Parish trip planner .

Cairo, Egypt to Saint Joseph Parish is an approximately 20.5-hour combination of flight and car. Traveling from Cairo to Saint Joseph Parish, you'll gain 6 hours due to the time zone difference. Traveling from Cairo in December, you will find days in Saint Joseph Parish are a bit warmer (34°C), and nights are much warmer (28°C). Cap off your sightseeing on the 7th (Sat) early enough to travel to Philipsburg.

Things to do in Saint Joseph Parish

Parks Outdoors Beaches

Side Trips

Saint Philip Parish, Saint Thomas Parish, Gun Hill Signal Station, Carlisle Bay
Find places to stay Dec 5 — 7:
Highlights from your plan
Hunte's Gardens ©
Hunte's Gardens
Harrison's Cave. ©
Harrison's Cave.
Bottom Bay ©
Bottom Bay

5
nights
Philipsburg, St. Maarten-St. Martin

Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Step out of Philipsburg with an excursion to Cupecoy Bay Beach in Cupecoy Bay--about 30 minutes away. And it doesn't end there: enjoy the sand and surf at Maho Beach, make a trip to Frontstreet, get some thrills on the water with a speed boat tour, and stroll through Dawn Beach.

To see ratings, other places to visit, where to stay, and more tourist information, refer to the Philipsburg tour website .

You can do a combination of bus and flight from Saint Joseph Parish to Philipsburg in 5.5 hours. In December, plan for daily highs up to 34°C, and evening lows to 28°C. Finish your sightseeing early on the 12th (Thu) so you can travel to Providenciales.

Things to do in Philipsburg

Outdoors Parks Beaches

Side Trips

Sint Maarten, Maho, WAKE N' GLISSE, Brown Pelicans, Friar's Bay
Find places to stay Dec 7 — 12:
Highlights from your plan
Speed Boats Tours
Orient Bay Beach ©
Orient Bay Beach
Mullet Bay Beach ©
Mullet Bay Beach

4
nights
Providenciales, Turks and Caicos

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, adventure, nature, and spas. Your plan includes some of its best attractions: enjoy the sand and surf at Grace Bay Beach, make a trip to Leeward Beach, stop by Flowers by EA, and tour the pleasant surroundings at Half Moon Bay.

To see photos, maps, reviews, and more tourist information, use the Providenciales trip itinerary builder website .

You can fly from Philipsburg to Providenciales in 4 hours. Due to the time zone difference, you'll gain 1 hour traveling from Philipsburg to Providenciales. In December, daily temperatures in Providenciales can reach 33°C, while at night they dip to 28°C. Wrap up your sightseeing on the 16th (Mon) early enough to travel to Havana.

Things to do in Providenciales

Outdoors Parks Beaches

Side Trip

Smith's Reef
Find places to stay Dec 12 — 16:
Highlights from your plan
Shark Diving
Provo Golf Club ©
Provo Golf Club
Little Water Cay ©
Little Water Cay

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. There's still lots to do: appreciate the extensive heritage of Malecón of Havana, get the lay of the land with Walking tours, admire the masterpieces at Museu Nacional de Belas Artes de Cuba, and steep yourself in history at Fortaleza de San Carlos de la Cabana.

For photos, maps, more things to do, and tourist information, you can read our Havana online trip builder .

Traveling by flight from Providenciales to Havana takes 5.5 hours. Traveling from Providenciales in December, you can expect nighttime temperatures to be a bit cooler in Havana, with lows of 20°C. Cap off your sightseeing on the 21st (Sat) early enough to travel to Seven Mile Beach.

Things to do in Havana

Historic Sites Tours Museums

Side Trip

Playa Paraiso
Find places to stay Dec 16 — 21:
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Plaza de la Catedral ©
Plaza de la Catedral

3
nights
Seven Mile Beach, Cayman Islands

When in Seven Mile Beach, make a side trip to see Davinoff's Concrete Sculpture Garden in North Side, approximately 40 minutes away.

To see more things to do, photos, and tourist information, refer to the Seven Mile Beach trip planner .

Fly from Havana to Seven Mile Beach in 2 hours. Plan for a bit warmer nights when traveling from Havana in December since evenings lows in Seven Mile Beach dip to 28°C. Wrap up your sightseeing on the 24th (Tue) to allow time to travel to Isla de Vieques.

Things to do in Seven Mile Beach

Parks Wildlife Outdoors

Side Trips

Grand Cayman, George Town, Davinoff's Concrete Sculpture Garden, Cayman Turtle Centre: Island Wildlife Encounter
Find places to stay Dec 21 — 24:
Highlights from your plan
Scuba & Snorkeling
Seven Mile Beach ©
Seven Mile Beach

8
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, adventure, wildlife, and nightlife. Your plan includes some of its best attractions: contemplate the waterfront views at Sun Bay Beach, kick back and relax at Media Luna Beach, enjoy some diversion at Vieques Gun Club & Sporting Clays, and stroll through La Chiva.

To see reviews, traveler tips, photos, and more tourist information, read Isla de Vieques online day trip planner .

You can fly from Seven Mile Beach to Isla de Vieques in 8.5 hours. Due to the time zone difference, you'll lose 1 hour traveling from Seven Mile Beach to Isla de Vieques. In December, daytime highs in Isla de Vieques are 34°C, while nighttime lows are 28°C. Wrap up your sightseeing on the 2nd (Thu) early enough to travel to Culebra.

Things to do in Isla de Vieques

Outdoors Parks Beaches
Find places to stay Dec 24 — Jan 2:
Highlights from your plan
Sun Bay Beach ©
Sun Bay Beach
Vieques National Wildlife Refuge ©
Vieques National Wildlife Refuge
Media Luna Beach ©
Media Luna Beach

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, nature, outdoors, and adventure. Your plan includes some of its best attractions: enjoy the sand and surf at Flamenco Beach, tour the pleasant surroundings at Culebra National Wildlife Refuge, browse the collection at Culebra Public Library, and discover the deep blue sea with a scuba or snorkeling tour.

To see other places to visit, reviews, ratings, and tourist information, read Culebra trip planner .

Traveling by combination of car and flight from Isla de Vieques to Culebra takes 2.5 hours. Alternatively, you can ride a ferry. January in Culebra sees daily highs of 34°C and lows of 26°C at night. Finish your sightseeing early on the 7th (Tue) so you can fly to San Juan.

Things to do in Culebra

Parks Outdoors Beaches
Find places to stay Jan 2 — 7:
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Culebrita Island ©
Culebrita Island
Zoni Beach ©
Zoni Beach

8
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Change things up with these side-trips from San Juan: Luquillo Beach (in Luquillo), Parque Nacional de las Cavernas del Rio Camuy (in Camuy) and El Yunque Rain Forest (in El Yunque National Forest). There's much more to do: get to know the fascinating history of Old San Juan, play a few rounds at Costa Caribe Golf & Country Club, enjoy the sand and surf at Condado Beach, and contemplate the long history of Sitio Histórico de San Juan.

To see ratings, more things to do, and other tourist information, read our San Juan trip itinerary planner .

San Juan is just a short distance from Culebra. In January in San Juan, expect temperatures between 34°C during the day and 26°C at night. Wrap up your sightseeing on the 15th (Wed) to allow time to travel back home.

Things to do in San Juan

Outdoors Parks Nature

Side Trips

Puerto Rico, Ponce, El Yunque Rain Forest, Parque Nacional de las Cavernas del Rio Camuy, Luquillo Beach
Find places to stay Jan 7 — 15:
Highlights from your plan
Old San Juan ©
Old San Juan
El Yunque Rain Forest ©
El Yunque Rain Forest
Sitio Histórico de San Juan ©
Sitio Histórico de San Juan

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