17 days in Haiti, Cuba & Jamaica Itinerary

17 days in Haiti, Cuba & Jamaica Itinerary

Created using Inspirock Caribbean tour itinerary planner

Make it your trip
Fly
1
Santiago de Cuba, Cuba
— 2 nights
Fly
2
Havana, Cuba
— 1 night
Drive
3
Vinales, Cuba
Drive
4
Havana, Cuba
— 1 night
Drive
5
Varadero, Cuba
— 1 day
Drive
6
Havana, Cuba
— 2 nights
Fly
7
Montego Bay, Jamaica
— 1 night
Drive
8
Ocho Rios, Jamaica
— 1 night
Drive
9
Negril, Jamaica
— 1 night
Drive
10
Kingston, Jamaica
— 1 night
Fly
11
Cap-Haitien, Haiti
— 2 nights
Drive
12
Jacmel, Haiti
— 2 nights
Drive to Toussaint Louverture International Airport, Fly to San Jose

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Santiago de Cuba, Cuba

— 2 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.
Start off your visit on the 16th (Sat): take an in-depth tour of Casa de Diego Velazquez, explore the different monuments and memorials at Cementerio Santa Ifigenia, contemplate the long history of Moncada Barracks, then explore the historical opulence of Castillo de San Pedro de la Roca, and finally appreciate the extensive heritage of La Gran Piedra (The Big Rock).

To find ratings, more things to do, where to stay, and other tourist information, you can read our Santiago de Cuba sightseeing planner.

San Jose, Costa Rica to Santiago de Cuba is an approximately 13.5-hour flight. Due to the time zone difference, you'll lose 1 hour traveling from San Jose to Santiago de Cuba. Plan for a bit warmer temperatures traveling from San Jose in October, with highs in Santiago de Cuba at 36°C and lows at 27°C. Finish up your sightseeing early on the 17th (Sun) so you can catch the flight to Havana.

Things to do in Santiago de Cuba

Historic Sites · Outdoors · Scenic Drive · Museums
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Havana, Cuba

— 1 night

Rome of the Caribbean

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Start off your visit on the 17th (Sun): get the lay of the land with Walking tours, make a trip to Plaza de Armas, then appreciate the extensive heritage of Malecón of Havana, and finally appreciate the history behind Neptune Statue.

For maps, reviews, other places to visit, and tourist information, go to the Havana day trip website.

Traveling by flight from Santiago de Cuba to Havana takes 3 hours. Alternatively, you can drive; or take a train. Expect a daytime high around 35°C in October, and nighttime lows around 24°C. Finish your sightseeing early on the 18th (Mon) so you can drive to Vinales.

Things to do in Havana

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Vinales, Cuba

Offering a taste of authentic rural life, Vinales remains a small agricultural town, dominated by surrounding low mountain ranges.
On the 18th (Mon), Head underground at Cuevas de Santo Tomas.

To find ratings, traveler tips, photos, and more tourist information, refer to the Vinales holiday planner.

Getting from Havana to Vinales by car takes about 2.5 hours. Other options: take a shuttle; or take a bus. In October, daytime highs in Vinales are 36°C, while nighttime lows are 26°C. Wrap up your sightseeing by early afternoon on the 18th (Mon) to allow enough time to drive to Havana.

Things to do in Vinales

Nature · Parks
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Highlights from your trip

Havana, Cuba

— 1 night

Rome of the Caribbean

Kick off your visit on the 18th (Mon): make a trip to El Capitolio.

To find reviews, maps, more things to do, and more tourist information, use the Havana road trip tool.

Traveling by car from Vinales to Havana takes 2.5 hours. Alternatively, you can take a shuttle; or take a bus. Finish your sightseeing early on the 19th (Tue) so you can drive to Varadero.
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Highlights from your trip

Varadero, Cuba

— 1 day
One of the largest resort towns in the Caribbean, Varadero boasts a 20 km (12 mi) long stretch of sand, lined with hotels and all-inclusive resorts.
Kick off your visit on the 19th (Tue): kick back and relax at Cayos Blancos, explore the fascinating underground world of Cueva de Saturno, and then stroll through Varadero Beach.

You can plan Varadero trip in no time by asking Inspirock to help create your itinerary.

You can drive from Havana to Varadero in 2 hours. Other options are to take a shuttle; or do a combination of train and taxi. In October, plan for daily highs up to 35°C, and evening lows to 24°C. Finish your sightseeing early on the 19th (Tue) so you can drive to Havana.

Things to do in Varadero

Parks · Beaches · Outdoors · Nature
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Havana, Cuba

— 2 nights

Rome of the Caribbean

Kick off your visit on the 20th (Wed): don't miss a visit to Old Square (Plaza Vieja), don't miss a visit to Plaza de la Catedral, then contemplate the long history of El Morro, and finally steep yourself in history at Revolution Plaza Havana.

To find maps, more things to do, where to stay, and more tourist information, you can read our Havana tour itinerary builder website.

You can drive from Varadero to Havana in 2 hours. Other options are to take a shuttle; or do a combination of taxi and train. Wrap up your sightseeing on the 21st (Thu) early enough to fly to Montego Bay.

Things to do in Havana

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Montego Bay, Jamaica

— 1 night
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 21st (Thu): steep yourself in history at Rose Hall Great House and then surround yourself with nature on a nature and wildlife tour. Get ready for a full day of sightseeing on the 22nd (Fri): identify plant and animal life at Wildlife Areas, kick back and relax at Doctor's Cave Beach, and then buy something for everyone on your list at Whitter Village Shopping Mall.

To find where to stay, more things to do, ratings, and other tourist information, read our Montego Bay trip itinerary maker website.

You can fly from Havana to Montego Bay in 8 hours. Expect a bit warmer evenings in Montego Bay when traveling from Havana in October, with lows around 28°C. Cap off your sightseeing on the 22nd (Fri) early enough to go by car to Ocho Rios.

Things to do in Montego Bay

Outdoors · Tours · Wildlife · Beaches
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Ocho Rios, Jamaica

— 1 night
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 23rd (Sat): let the river carry you with a rafting and tubing tour, then take in the dramatic scenery at Dunn's River Falls and Park, and then admire the sheer force of Blue Hole.

To find reviews, where to stay, traveler tips, and other tourist information, use the Ocho Rios tour builder website.

You can drive from Montego Bay to Ocho Rios in 2 hours. Another option is to take a bus. Expect a daytime high around 38°C in October, and nighttime lows around 30°C. Wrap up your sightseeing on the 23rd (Sat) to allow time to drive to Negril.

Things to do in Ocho Rios

Nature · Parks · Tours · Outdoors
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Negril, Jamaica

— 1 night
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
For where to stay, ratings, other places to visit, and other tourist information, read Negril online holiday builder.

Traveling by car from Ocho Rios to Negril takes 3 hours. Alternatively, you can take a bus. In October, daily temperatures in Negril can reach 38°C, while at night they dip to 28°C. You'll set off for Kingston on the 24th (Sun).

Things to do in Negril

Tours · Outdoors · Wildlife · Transportation
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Kingston, Jamaica

— 1 night
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.
On the 24th (Sun), examine the collection at Bob Marley Museum, then examine the collection at Trench Town Culture Yard, then go for a stroll along the water at Port Royal, and finally don't miss a visit to Two Sisters Cave. Here are some ideas for day two: take in the architecture and design of University Of The West Indies - Mona, then look for gifts at Chocolate Dreams, and then contemplate the long history of Devon House.

To find photos, where to stay, other places to visit, and more tourist information, use the Kingston online trip planner.

You can drive from Negril to Kingston in 3.5 hours. Another option is to take a bus. In October, plan for daily highs up to 38°C, and evening lows to 30°C. Finish up your sightseeing early on the 25th (Mon) so you can travel to Cap-Haitien.

Things to do in Kingston

Historic Sites · Parks · Museums · Shopping

Side Trip

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Cap-Haitien, Haiti

— 2 nights

Cap

Haiti's second city, Cap-Haitien offers an atmosphere at odds with what you'll find in the capital.
Explore Cap-Haitien's surroundings by going to Milot (Cathedrale de Milot, Citadelle Laferrière, &more). The adventure continues: steep yourself in history at National History Park - Citadel, Sans Souci, Ramiers, take in the architecture and atmosphere at Cathedrale Notre Dame de Cap Haitien, and pause for some photo ops at Heros de Vertieres.

To plan Cap-Haitien vacation without wasting time, ask Inspirock to design an itinerary.

Use the Route module to find suitable travel options from Kingston to Cap-Haitien. In October, daily temperatures in Cap-Haitien can reach 35°C, while at night they dip to 30°C. You'll set off for Jacmel on the 28th (Thu).

Things to do in Cap-Haitien

Historic Sites

Side Trips

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Jacmel, Haiti

— 2 nights
Sitting sheltered from the elements in a wide bay, Jacmel has gained a reputation as a welcoming and peaceful coastal town.
Start off your visit on the 29th (Fri): explore the world behind art at Jacmel Arts Center, take in the dramatic scenery at Bassin Bleu, and then hunt for treasures at Marche de Fer. On your second day here, enjoy the sand and surf at Jacmel Beach.

To see photos, where to stay, maps, and other tourist information, you can read our Jacmel route maker tool.

Getting from Cap-Haitien to Jacmel by car takes about 5.5 hours. Other options: do a combination of bus and taxi; or take a bus. In October, daily temperatures in Jacmel can reach 38°C, while at night they dip to 30°C. Wrap up your sightseeing by early afternoon on the 30th (Sat) to allow time for travel back home.

Things to do in Jacmel

Parks · Shopping · Nature · Beaches
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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
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.

Haiti travel guide

3.8
Historic Walking Areas · Historic Sites · Zipline
The culture of Haiti has always been the reason for people to visit, and it will be the reason people visit in larger and larger numbers as the nation heals from the devastating effects of the 2010 earthquake. The interesting tale of colonialism, revolution, and political struggle has left Haiti with a wealth of historical sites and cultural influences. Sightseeing in Haiti offers perspectives on the many stages in the country's history, with colonial forts standing in ruins and monuments memorializing the revolution. The music, the art, the folklore, and the cuisine of Haiti all deserve to be explored in person.