55 days in Caribbean Itinerary

55 days in Caribbean Itinerary

Created using Inspirock Caribbean route planner

Make it your trip
Drive to Luis Munoz Marin International Airport, Fly to JAGS McCartney International Airport
1
Cockburn Town, Turks and Caicos
— 5 nights
Fly
2
Providenciales, Turks and Caicos
— 8 nights
Fly
3
Santiago de Cuba, Cuba
— 4 nights
Fly
4
Kingston, Jamaica
— 5 nights
Drive
5
Ocho Rios, Jamaica
— 3 nights
Drive
6
Montego Bay, Jamaica
— 5 nights
Unknown
7
Little Cayman, Cayman Islands
— 5 nights
Fly
8
Seven Mile Beach, Cayman Islands
— 6 nights
Fly to Havana, Drive to Cienfuegos
9
Cienfuegos, Cuba
— 5 nights
Drive
10
Vinales, Cuba
— 2 nights
Drive
11
Havana, Cuba
— 5 nights
Fly

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Cockburn Town, Turks and Caicos

— 5 nights
Cockburn Town is the capital city of the Turks and Caicos Islands.GeographyCockburn Town is located on the largest island in the Turks Islands archipelago, Grand Turk Island. Salt Cay has been added to your itinerary. The adventure continues: get engrossed in the history at Turks & Caicos National Museum, explore the gorgeous colors at SunRay Beach, kick back and relax at Governor's Beach, and head off the coast to Gibbs Cay.

For maps, reviews, and tourist information, read Cockburn Town trip itinerary website.

Ponce, Puerto Rico to Cockburn Town is an approximately 12-hour combination of car and flight. The time zone difference moving from Atlantic Standard Time to Eastern Standard Time is minus 1 hour. On the 25th (Fri), you're off to Providenciales.

Things to do in Cockburn Town

Parks · Wildlife · Nature · Outdoors

Side Trips

Providenciales, Turks and Caicos

— 8 nights
The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
Your day by day itinerary now includes Princess Alexandra National Park as well as Chalk Sound. And it doesn't end there: enjoy the sand and surf at Grace Bay Beach, discover the deep blue sea with a scuba or snorkeling tour, step off the mainland to explore Little Water Cay, and don't miss a visit to Our Lady of Divine Providence.

To see traveler tips, photos, ratings, and tourist information, refer to the Providenciales trip planner.

You can fly from Cockburn Town to Providenciales in 2.5 hours. In November in Providenciales, expect temperatures between 34°C during the day and 29°C at night. On the 3rd (Sat), you'll travel to Santiago de Cuba.

Things to do in Providenciales

Parks · Nature · Wildlife · Outdoors

Side Trip

Santiago de Cuba, Cuba

— 4 nights
Santiago de Cuba has taken almost as much influence from Haiti and the Dominican Republic as it has from Havana, distilling a concoction of cultures to create a city with a distinct identity.
When in Santiago de Cuba, make a side trip to see El Cobre Basilica in El Cobre, approximately El Cobre away. Next up on the itinerary: steep yourself in history at Moncada Barracks, explore the historical opulence of Castillo de San Pedro de la Roca, make a trip to Antonio Maceo Revolution Square, and take in the spiritual surroundings of Cathedral of Our Lady of the Assumption.

To find traveler tips, maps, and tourist information, read our Santiago de Cuba trip itinerary planning app.

Traveling by flight from Providenciales to Santiago de Cuba takes 8.5 hours. In December in Santiago de Cuba, expect temperatures between 34°C during the day and 25°C at night. On the 7th (Wed), you're off to Kingston.

Things to do in Santiago de Cuba

Historic Sites

Side Trip

Kingston, Jamaica

— 5 nights
The country's capital, Kingston offers all the excitement of a lively and storied city, while also housing the services and facilities travelers need to get around and see the rest of the island.
You've now added Reach Falls to your itinerary. Next up on the itinerary: take in the awesome beauty at Blue Mountains, appreciate the history behind Devon House, contemplate the long history of Bob Marley Museum, and stop by Chocolate Dreams.

To find where to stay, traveler tips, photos, and other tourist information, read Kingston travel route planning app.

Fly from Santiago de Cuba to Kingston in 6 hours. December in Kingston sees daily highs of 36°C and lows of 28°C at night. You will leave for Ocho Rios on the 12th (Mon).

Things to do in Kingston

Parks · Nature · Historic Sites · Museums

Side Trip

Ocho Rios, Jamaica

— 3 nights
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
You've now added Island Village to your itinerary. Next up on the itinerary: admire the sheer force of Dunn's River Falls and Park, get close to the beloved marine mammals with a swim-with-the-dolphins experience, and tour the pleasant surroundings at Ocho Rios Bay Beach.

For traveler tips, reviews, and more tourist information, use the Ocho Rios sightseeing planner.

You can drive from Kingston to Ocho Rios in 1.5 hours. Alternatively, you can take a bus. In December in Ocho Rios, expect temperatures between 36°C during the day and 28°C at night. On the 15th (Thu), you're off to Montego Bay.

Things to do in Ocho Rios

Parks · Outdoors · Nature · Wildlife

Montego Bay, Jamaica

— 5 nights
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.
Your day by day itinerary now includes Rick's Cafe as well as YS Falls. Take a break from Montego Bay with a short trip to Seven Mile Beach in Negril, about 1h 25 min away. There's still lots to do: contemplate the long history of Rose Hall Great House, explore the activities along Martha Brae Rafting Village, and tour the pleasant surroundings at Doctor's Cave Beach.

For ratings, maps, reviews, and other tourist information, read our Montego Bay trip planner.

You can drive from Ocho Rios to Montego Bay in 2 hours. Alternatively, you can take a bus. December in Montego Bay sees daily highs of 36°C and lows of 27°C at night. You will leave for Little Cayman on the 20th (Tue).

Things to do in Montego Bay

Parks · Nature · Outdoors · Beaches

Side Trips

Little Cayman, Cayman Islands

— 5 nights
The smallest and undeniably quietest of the Cayman Islands, Little Cayman is truly little in terms of its population, with fewer than 200 permanent residents, almost all of whom work in the tourism industry.
Little Cayman is known for wildlife, nature, and museums. Your plan includes some of its best attractions: tour the pleasant surroundings at Bloody Bay Wall and identify plant and animal life at Point of Sand.

To see where to stay, ratings, traveler tips, and tourist information, use the Little Cayman online trip planner.

The Route module can help you plan travel from Montego Bay to Little Cayman. December in Little Cayman sees daily highs of 34°C and lows of 29°C at night. On the 25th (Sun), you're off to Seven Mile Beach.

Things to do in Little Cayman

Wildlife · Parks · Outdoors · Beaches
Highlights from your trip

Seven Mile Beach, Cayman Islands

— 6 nights
Seven Mile Beach is a long crescent of coral-sand beach on the western end of Grand Cayman island. Your day by day itinerary now includes Queen Elizabeth II Botanic Park as well as Devil's Grotto. And it doesn't end there: stroll through Stingray City Grand Cayman, try out the rides at Cayman Turtle Centre: Island Wildlife Encounter, enjoy the sand and surf at Seven Mile Beach, and sample the fine beverages at Cayman Spirits Co. Distillery.

To see traveler tips, more things to do, where to stay, and other tourist information, read our Seven Mile Beach travel itinerary planner.

You can fly from Little Cayman to Seven Mile Beach in 3 hours. In December, daytime highs in Seven Mile Beach are 34°C, while nighttime lows are 28°C. On the 31st (Sat), you're off to Cienfuegos.

Things to do in Seven Mile Beach

Parks · Wildlife · Theme Parks · Nature

Side Trips

Cienfuegos, Cuba

— 5 nights

Pearl of the South

The city of Cienfuegos sits in a scenic natural bay, attracting visitors from across the country and further afield since its establishment in the early 19th century.
You'll find plenty of places to visit near Cienfuegos: Santa Clara (Che Guevara Mausoleum & Statue of Che Guevara Holding a Child). There's still lots to do: don't miss a visit to Parque Jose Marti, visit Punta Gorda, and admire the sheer force of El Nicho Waterfalls.

To find other places to visit, more things to do, where to stay, and tourist information, read Cienfuegos trip planner.

Do a combination of flight and car from Seven Mile Beach to Cienfuegos in 8 hours. Traveling from Seven Mile Beach in December, plan for slightly colder nights in Cienfuegos, with lows around 22°C. On the 5th (Thu), you'll travel to Vinales.

Things to do in Cienfuegos

Neighborhoods · Parks · Nature

Side Trip

Vinales, Cuba

— 2 nights
Offering a taste of authentic rural life, Vinales remains a small agricultural town, dominated by surrounding low mountain ranges.
To find other places to visit, ratings, and more tourist information, refer to the Vinales trip itinerary maker site.

Drive from Cienfuegos to Vinales in 5.5 hours. Alternatively, you can take a shuttle; or take a bus. In January, plan for daily highs up to 31°C, and evening lows to 20°C. You'll set off for Havana on the 7th (Sat).

Things to do in Vinales

Parks · Nature

Havana, Cuba

— 5 nights

Rome of the Caribbean

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, nightlife, and museums. Your plan includes some of its best attractions: make a trip to Malecón of Havana, steep yourself in history at Fortaleza de San Carlos de la Cabana, get to know the fascinating history of Old Havana, and get engrossed in the history at Museum of the Revolution (Museo de la Revolucion).

For other places to visit, where to stay, traveler tips, and tourist information, go to the Havana travel tool.

Drive from Vinales to Havana in 2.5 hours. Alternatively, you can take a shuttle; or take a bus. In January, plan for daily highs up to 30°C, and evening lows to 19°C. On the 12th (Thu), you're off to home.

Things to do in Havana

Historic Sites · Museums

Turks and Caicos travel guide

4.5
Beaches · Scuba & Snorkeling · Landmarks
Known as the location of one of the longest coral reefs in the world, Turks and Caicos offer scenic white-sand beaches, calm waters, and warm, sunny weather. Apart from the upscale resorts in Providenciales, which is known for its award-winning beach, the rest of the scenery remains mostly pristine and uncrowded. On a trip to Turks and Caicos, you can spend days lazing on a deserted beach, go island hopping, and enjoy a range of fun activities, from world-class snorkeling and diving, to hiking, sailing, deep-sea fishing, and bird-watching.

Cuba travel guide

4.4
Beaches · Historic Walking Areas · Landmarks
The largest island in the Caribbean, Cuba lies just 140 km (90 mi) south of Florida and captivates a growing number of Western visitors with its tropical landscapes and cultural attractions. Sightseeing in Cuba inevitably begins in Havana, a city of photogenic architecture, lively nightlife, and a passion for baseball. The country's smaller colonial towns usually feature central squares, ideal places to meet the locals under wrought-iron street lamps. Savvy visitors escape the cities during their Cuba holidays, devoting plenty of time to the country's charming countryside, where you can get the feel for this diverse land by conversing with friendly tobacco farmers and small-scale fruit producers.

Jamaica travel guide

4.1
Waterfalls · Beaches · Nightlife
The third most populous English-speaking country in the Americas, Jamaica remains a member of the Commonwealth of Nations, with the British monarch its official head of state. Jamaica tourism thrives thanks to the island nation's reputation for natural beauty, outstanding cuisine, and lively music scene. The country's landscape is as diverse as its population, its tropical climate supporting varied ecosystems that include everything from savannahs to rugged mountain slopes. For most visitors, a holiday in Jamaica is a largely outdoor affair, with hiking, fishing, golfing, camping, snorkeling, horseback riding, and kite surfing among the most popular things to do.

Cayman Islands travel guide

4.1
Scuba & Snorkeling · Beaches · Nature & Parks
Known to some as an offshore financial haven, for pleasure seekers Cayman Islands remain one of the world's top vacation destinations, offering developed beaches and pristine reefs. Water-based activities remain among top things to do on Cayman Islands, with dolphin spotting, swimming with stingrays, and scuba diving favored by visitors of all ages. With world-class accommodations and a low crime rate, the islands ensure an ideal setting for relaxing family vacations. A holiday on Cayman Islands also provides a good chance to explore a cosmopolitan culinary scene, with a range of restaurants serving everything from Indian to Italian specialties.