20 days in Caribbean Itinerary

20 days in Caribbean Itinerary

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Route & dates

20 days in Caribbean Itinerary

Start: George Town, Cayman Islands
Fly:  7​h 15​min
1
Culebra, Puerto Rico
— 4 nights
Fly:  2​h 15​min
2
Charlotte Amalie, U.S. Virgin Islands
— 4 nights
Fly:  7​h 30​min
3
Palm - Eagle Beach, Aruba
— 2 nights
+2
Drive + Fly + Drive:  13​h 30​min
4
Port Antonio, Jamaica
— 1 night
Drive:  2​h
5
Ocho Rios, Jamaica
— 2 nights
Bus:  1​h 30​min
6
Montego Bay, Jamaica
— 3 nights
Fly:  5​h 30​min
End: George Town, Cayman Islands

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: kick back and relax at Flamenco Beach, tour the pleasant surroundings at Playa Punta Soldado Beach, get lost in a book at Culebra Public Library, and head off the coast to Culebrita Island.

To find other places to visit, traveler tips, photos, and tourist information, use the Culebra trip planner.

Fly from Seven Mile Beach to Culebra in 8 hours. Alternatively, you can do a combination of flight, shuttle, and ferry. The time zone difference when traveling from Seven Mile Beach to Culebra is 1 hour. Expect a daytime high around 34°C in December, and nighttime lows around 28°C. Finish up your sightseeing early on the 22nd (Tue) so you can travel to Charlotte Amalie.

Things to do in Culebra

Parks Outdoors Beaches
Find places to stay Nov 24 — 29:
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Culebrita Island ©
Culebrita Island
Zoni Beach ©
Zoni Beach

4
nights
Charlotte Amalie, U.S. Virgin Islands

One of the most visited cruise ship destinations in the Caribbean, the town of Charlotte Amalie is known around the world for its duty-free jewelry, perfume, and liquor shops.
You've now added Cruise Ship Excursions to your itinerary. You'll find plenty of places to visit near Charlotte Amalie: Virgin Islands National Park (Trunk Bay, Annaberg Sugar Plantation, & more) and Maho Beach (in Cruz Bay). There's lots more to do: enjoy the sand and surf at Magens Bay, stop by Diamonds International, tour the pleasant surroundings at Coki Point Beach, and make a trip to Main Street.

For maps, photos, ratings, and more tourist information, go to the Charlotte Amalie trip itinerary maker site .

Getting from Culebra to Charlotte Amalie by flight takes about 2.5 hours. In November, plan for daily highs up to 35°C, and evening lows to 28°C. Finish up your sightseeing early on the 3rd (Thu) so you can travel to Palm - Eagle Beach.

Things to do in Charlotte Amalie

Outdoors Parks Beaches

Side Trips

East End, Virgin Islands National Park, St. Thomas, Magens Bay, Maho Beach
Find places to stay Nov 29 — Dec 3:
Highlights from your plan
Scuba & Snorkeling
Magens Bay ©
Magens Bay
Trunk Bay ©
Trunk Bay

2
nights
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.
Take a break from Palm - Eagle Beach with a short trip to Baby Beach in San Nicolas, about 48 minutes away. And it doesn't end there: enjoy the sand and surf at Eagle Beach, tour the pleasant surroundings at Palm Beach, visit a coastal fixture at California Lighthouse, and take in the dramatic natural features at Ayo and Casibari Rock Formations.

For maps, other places to visit, more things to do, and more tourist information, read Palm - Eagle Beach road trip tool .

Fly from Charlotte Amalie to Palm - Eagle Beach in 7.5 hours. Alternatively, you can do a combination of ferry and flight. In December in Palm - Eagle Beach, expect temperatures between 36°C during the day and 30°C at night. Finish your sightseeing early on the 6th (Sun) to allow enough time to travel to Port Antonio.

Things to do in Palm - Eagle Beach

Parks Outdoors Beaches

Side Trips

Arikok National Park, Baby Beach, California Lighthouse, Ayo and Casibari Rock Formations
Find places to stay Dec 3 — 6:
Highlights from your plan
Palm Beach ©
Palm Beach
Eagle Beach ©
Eagle Beach
Baby Beach ©
Baby Beach

1
night
Port Antonio, Jamaica

Port Antonio ©
A coastal getaway from coastal getaways, Port Antonio offers a break from the more touristy retreats in the west of the island.
On the 7th (Mon), enjoy the sand and surf at Winifred Beach, explore the activities along Blue Lagoon, and then enjoy the sand and surf at Frenchman's Cove. On the next day, pick up some local products at Boston Jerk Centre and then tour the pleasant surroundings at Boston Beach.

To see where to stay, traveler tips, and other tourist information, read Port Antonio itinerary website .

Use the Route module to find suitable travel options from Palm - Eagle Beach to Port Antonio. The time zone difference moving from Atlantic Standard Time (AST) to Eastern Standard Time (EST) is minus 1 hour. In December in Port Antonio, expect temperatures between 36°C during the day and 28°C at night. Finish up your sightseeing early on the 8th (Tue) so you can go by car to Ocho Rios.

Things to do in Port Antonio

Parks Outdoors Beaches
Find places to stay Dec 7 — 8:
Highlights from your plan
Blue Lagoon ©
Blue Lagoon
Boston Beach ©
Boston Beach
Frenchman's Cove ©
Frenchman's Cove

2
nights
Ocho Rios, Jamaica

Ocho Rios ©
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
Kick off your visit on the 9th (Wed): take in the dramatic scenery at Blue Hole, then discover the deep blue sea with a scuba or snorkeling tour, and then trot along with a tour on horseback. On the 10th (Thu), you'll have a packed day of sightseeing: take in the dramatic scenery at Dunn's River Falls and Park and then stroll through Bamboo Beach Club.

To find photos, maps, where to stay, and other tourist information, refer to the Ocho Rios trip planner .

Getting from Port Antonio to Ocho Rios by car takes about 2 hours. Other options: take a bus. December in Ocho Rios sees daily highs of 36°C and lows of 28°C at night. Wrap up your sightseeing on the 10th (Thu) to allow time to take a bus to Montego Bay.

Things to do in Ocho Rios

Outdoors Parks Nature

Side Trip

Scuba & Snorkeling
Find places to stay Dec 8 — 10:
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Horseback Riding Tours
Scuba & Snorkeling

3
nights
Montego Bay, Jamaica

Montego Bay ©
The second largest city in Jamaica, Montego Bay boasts an international airport and a major cruise-line terminal, so it regularly receives a big influx of visitors to the island.
Kick off your visit on the 11th (Fri): take in the dramatic scenery at Mayfield Falls Jamaica (Original) and then tour the pleasant surroundings at Seven Mile Beach. Here are some ideas for day two: identify plant and animal life at Wildlife Areas, steep yourself in history at Rose Hall Great House, and then browse the different shops at Whitter Village Shopping Mall.

To find more things to do, ratings, maps, and other tourist information, you can read our Montego Bay sightseeing planner.

You can take a bus from Ocho Rios to Montego Bay in 1.5 hours. Another option is to drive. In December, daily temperatures in Montego Bay can reach 36°C, while at night they dip to 27°C. Wrap up your sightseeing by early afternoon on the 13th (Sun) to allow time for travel back home.

Things to do in Montego Bay

Outdoors Wildlife Tours

Side Trips

Mayfield Falls Jamaica (Original), Seven Mile Beach
Find places to stay Dec 10 — 13:
Highlights from your plan
Seven Mile Beach ©
Seven Mile Beach
Rose Hall Great House ©
Rose Hall Great House
Nature & Wildlife Tours

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