50 days in Caribbean Itinerary

50 days in Caribbean Itinerary

Created using Inspirock Caribbean trip itinerary planner

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Route & dates

50 days in Caribbean Itinerary

Start: London, United Kingdom
Fly:  12​h 45​min
1
Palm - Eagle Beach, Aruba
— 4 nights
Fly:  4​h
2
Simpson Bay, St. Maarten-St. Martin
— 6 nights
Fly:  2​h 45​min
3
Isla de Vieques, Puerto Rico
— 9 nights
Fly:  2​h
4
San Juan, Puerto Rico
— 9 nights
Fly:  30​min
5
Culebra, Puerto Rico
— 5 nights
Fly:  7​h 15​min
6
George Town, Cayman Islands
— 5 nights
Fly:  1​h 30​min
7
Havana, Cuba
— 6 nights
Fly + bus:  7​h 15​min
8
Ocho Rios, Jamaica
— 2 nights
bus + Fly:  15​h
End: London, United Kingdom

4
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.
Step out of Palm - Eagle Beach with an excursion to Baby Beach in San Nicolas--about 48 minutes away. The adventure continues: tour the pleasant surroundings at Eagle Beach, explore the striking landscape at Ayo and Casibari Rock Formations, look for all kinds of wild species at Donkey Sanctuary Aruba, and take a tour by water with Boat Tours & Water Sports.

To find where to stay, ratings, more things to do, and tourist information, use the Palm - Eagle Beach holiday maker site .

London, UK to Palm - Eagle Beach is an approximately 13-hour flight. You can also do a combination of train and flight; or do a combination of train and flight. Traveling from London to Palm - Eagle Beach, you'll gain 4 hours due to the time zone difference. Traveling from London in May, expect Palm - Eagle Beach to be much hotter, temps between 38°C and 31°C. Finish up your sightseeing early on the 6th (Mon) so you can travel to Simpson Bay.

Things to do in Palm - Eagle Beach

Parks Outdoors Beaches

Side Trips

Oranjestad, Noord, Santa Cruz, Ayo and Casibari Rock Formations, Baby Beach
Find places to stay May 2 — 6:
Highlights from your plan
Eagle Beach ©
Eagle Beach
Palm Beach ©
Palm Beach
Arikok National Park ©
Arikok National Park

6
nights
Simpson Bay, St. Maarten-St. Martin

Simpson Bay offers luxury resort living and good access to the main areas of the island.
On the 8th (Wed), spend a thrilling day on the water with a speed boat tour. There's much more to do: enjoy the sand and surf at Maho Beach, stroll through Cupecoy Bay Beach, make a trip to Frontstreet, and hike along Paradise Peak.

To find where to stay, more things to do, maps, and more tourist information, use the Simpson Bay trip itinerary maker .

Traveling by flight from Palm - Eagle Beach to Simpson Bay takes 4 hours. Traveling from Palm - Eagle Beach in May, expect nights in Simpson Bay to be about the same, around 29°C, while days are slightly colder, around 34°C. Finish up your sightseeing early on the 12th (Sun) so you can travel to Isla de Vieques.

Things to do in Simpson Bay

Outdoors Parks Beaches

Side Trips

Philipsburg, Maho, Sint Maarten, Cupecoy Bay Beach, Topper's Rhum Distillery Tours
Find places to stay May 6 — 12:
Highlights from your plan
Speed Boats Tours
Maho Beach ©
Maho Beach
Dawn Beach ©
Dawn Beach

9
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: explore the activities along Sun Bay, kick back and relax at La Chiva, tour the pleasant surroundings at Caracas Beach, and find your balance on the water with some of the best stand-up paddleboarding in the area.

To see other places to visit, ratings, traveler tips, and tourist information, read Isla de Vieques tour itinerary maker site .

Fly from Simpson Bay to Isla de Vieques in 3 hours. In May, plan for daily highs up to 34°C, and evening lows to 28°C. Wrap up your sightseeing on the 21st (Tue) to allow time to travel to San Juan.

Things to do in Isla de Vieques

Outdoors Parks Beaches
Find places to stay May 12 — 21:
Highlights from your plan
Sun Bay ©
Sun Bay
Vieques National Wildlife Refuge ©
Vieques National Wildlife Refuge
La Chiva ©
La Chiva

9
nights
San Juan, Puerto Rico

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), Museo de Arte de Ponce (in Ponce) and El Yunque Rain Forest (in El Yunque National Forest). And it doesn't end there: get to know the fascinating history of Old San Juan, take a memorable tour with Tours, steep yourself in history at San Juan National Historic Site, and enjoy the sand and surf at Carolina Beach.

Planning San Juan trip won't be overwheling when you use's Insprock itinerary maker.

Traveling by flight from Isla de Vieques to San Juan takes 2 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and shuttle. Expect a daytime high around 36°C in May, and nighttime lows around 28°C. Finish up your sightseeing early on the 30th (Thu) so you can catch the flight to Culebra.

Things to do in San Juan

Outdoors Parks Beaches

Side Trips

Carolina, Museo de Arte de Ponce, Horseback Riding Tours, El Yunque Rain Forest, Luquillo Beach
Find places to stay May 21 — 30:
Highlights from your plan
Canyoning & Rappelling Tours
El Yunque Rain Forest ©
El Yunque Rain Forest
Old San Juan ©
Old San Juan

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: kick back and relax at Flamenco Beach, tour the pleasant surroundings at Tamarindo Beach, step off the mainland to explore Culebrita Island, and browse the collection at Culebra Public Library.

For reviews, maps, ratings, and tourist information, you can read our Culebra attractions planning website .

Culebra is just a short distance from San Juan. In May, plan for daily highs up to 36°C, and evening lows to 29°C. Finish your sightseeing early on the 4th (Tue) so you can fly to George Town.

Things to do in Culebra

Parks Outdoors Beaches
Find places to stay May 30 — Jun 4:
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Culebrita Island ©
Culebrita Island
Zoni Beach ©
Zoni Beach

5
nights
George Town, Cayman Islands

George Town is a city situated on Grand Cayman island of the Cayman Islands. George Town is known for wildlife, adventure, breweries & distilleries, shopping, and fun & games. Your plan includes some of its best attractions: look for all kinds of wild species at Stingray City, kick back and relax at Rum Point, laugh and play at Cayman Turtle Centre: Island Wildlife Encounter, and don't miss a visit to Pedro St. James National Historic Site.

To find ratings, where to stay, more things to do, and tourist information, read George Town route planner.

Fly from Culebra to George Town in 7.5 hours. Alternatively, you can do a combination of ferry, shuttle, and flight. The time zone changes from Atlantic Standard Time (AST) to Eastern Standard Time (EST), which is usually a -1 hour difference. In June, daytime highs in George Town are 36°C, while nighttime lows are 30°C. Finish your sightseeing early on the 10th (Mon) so you can travel to Havana.

Things to do in George Town

Parks Outdoors Wildlife

Side Trips

Grand Cayman, Seven Mile Beach, Cayman Turtle Centre: Island Wildlife Encounter
Find places to stay Jun 4 — 10:
Highlights from your plan
Scuba & Snorkeling
Stingray City Grand Cayman ©
Stingray City Grand Cayman
Seven Mile Beach ©
Seven Mile Beach

6
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Havana is known for historic sites, museums, nightlife, beaches, and parks. Your plan includes some of its best attractions: make a trip to El Malecon, get to know the fascinating history of Old Havana, contemplate the long history of Fortaleza de San Carlos de la Cabana, and get engrossed in the history at Museum of the Revolution (Museo de la Revolucion).

To find other places to visit, ratings, reviews, and tourist information, you can read our Havana planning site .

Fly from George Town to Havana in 1.5 hours. Plan for little chillier nights when traveling from George Town in June since evenings lows in Havana dip to 26°C. Finish up your sightseeing early on the 16th (Sun) so you can travel to Ocho Rios.

Things to do in Havana

Historic Sites Museums Tours

Side Trip

Espiritu Santo Church (Iglesia Del Espiritu Santo)
Find places to stay Jun 10 — 16:
Highlights from your plan
Old Havana ©
Old Havana
El Malecon ©
El Malecon
Plaza de la Catedral ©
Plaza de la Catedral

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.
You'll find plenty of places to visit near Ocho Rios: Green Grotto Caves (in Runaway Bay) and Bob Marley's Mausoleum (in St. Ann's Bay). There's still lots to do: take in the dramatic scenery at Dunn's River Falls and Park, kick back and relax at Bamboo Beach Club, hike along Fern Gully, and take a peaceful walk through Cranbrook Flower Forest.

For ratings, reviews, more things to do, and tourist information, read our Ocho Rios trip planning app .

Traveling by combination of flight and bus from Havana to Ocho Rios takes 7.5 hours. Traveling from Havana in June, Ocho Rios is somewhat warmer at night with lows of 30°C. Cap off your sightseeing on the 19th (Wed) early enough to travel back home.

Things to do in Ocho Rios

Parks Nature Outdoors

Side Trips

Cranbrook Flower Forest, Green Grotto Caves, Bob Marley's Mausoleum
Find places to stay Jun 16 — 19:
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Green Grotto Caves ©
Green Grotto Caves
Bob Marley's Mausoleum ©
Bob Marley's Mausoleum

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