60 days in Caribbean Itinerary

60 days in Caribbean Itinerary

Created using Inspirock Caribbean trip planner

Make it your trip
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Havana, Cuba
— 15 nights
Shuttle
2
Trinidad, Cuba
— 4 nights
Drive
3
Camaguey, Cuba
— 3 nights
Drive
4
Santiago de Cuba, Cuba
— 3 nights
Fly
5
Port-au-Prince, Haiti
— 9 nights
Drive
6
Cap-Haitien, Haiti
— 2 nights
Drive
7
Santo Domingo, Dominican Republic
— 9 nights
Fly to Luis Munoz Marin International Airport, Drive to El Yunque National Forest
8
El Yunque National Forest, Puerto Rico
— 2 nights
Drive
9
San Juan, Puerto Rico
— 6 nights
Fly
10
Negril, Jamaica
— 2 nights
Drive
11
Kingston, Jamaica
— 4 nights

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Havana, Cuba

— 15 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.
You've added Espiritu Santo Church (Iglesia Del Espiritu Santo), Jardin Botanico Nacional, Cubas Historiske Arkiv Asger Jorn paintings, and other attractions to your itinerary. You'll discover tucked-away gems like Palacio De Los Capitanes Generales and Fortaleza de San Carlos de la Cabana. Visit Malecón of Havana and Old Square (Plaza Vieja) for their historical value. There's still lots to do: make a trip to Old Havana, steep yourself in history at Fort San Salvador (Castillo De San Salvador De La Punta), see the interesting displays at Taquechel Pharmacy Museum, and wander the streets of Central Havana.

To find where to stay, ratings, photos, and other tourist information, refer to the Havana itinerary planner.

If you are flying in from United States, the closest major aiports are José Martí International Airport, Juan Gualberto Gomez International Airport and Vilo Acuña International Airport. In January, daytime highs in Havana are 79°F, while nighttime lows are 62°F. On the 16th (Sat), you'll travel to Trinidad.

Things to do in Havana

Historic Sites · Museums · Parks · Classes

Side Trips

Trinidad, Cuba

— 4 nights
Built on sugar and seemingly preserved in molasses, the town of Trinidad attracts visitors with its well-aged 19th century architecture and rustic charm, showcasing the sounds, scents, and sights of days gone by.
Get outdoors at Trinidad Sightseeing and Ancon Beach. Convento de San Francisco de Asis and Plaza Mayor are good opportunities to explore the local culture. Step out of Trinidad with an excursion to Vegas Grande Waterfall in Topes de Collantes--about 32 minutes away. Next up on the itinerary: don't miss a visit to Ruinas de Ingenio San Isidro de los Destiladeros, head outdoors with Parque Guanayara, see the interesting displays at Colonial Architecture Museum, and get a taste of the local shopping with YuditVidalFaife.

To see more things to do, maps, photos, and tourist information, read Trinidad travel planner.

You can drive from Havana to Trinidad in 4 hours. Alternatively, you can take a shuttle; or take a bus. Traveling from Havana in January, Trinidad is somewhat warmer at night with lows of 81°F. Wrap up your sightseeing by early afternoon on the 20th (Wed) to allow enough time to drive to Camaguey.

Things to do in Trinidad

Outdoors · Parks · Tours · Wildlife

Side Trips

Camaguey, Cuba

— 3 nights
Camaguey encompasses the central section of Cuba and remains largely agricultural, its economy dependent on small-scale cattle raising and fruit production.
Discover out-of-the-way places like Plaza del Carmen and Plaza San Juan de Dios. Popular historic sites such as Camaguey Centro and Iglecia de san juan de dios are in your itinerary. And it doesn't end there: view the masterpieces at Martha Jimenez's Studio Workshop, shop like a local with Estudio Galeria Magdiel, see the interesting displays at Museo Provincial General Ignacio Agramonte, and make a trip to Plaza de los Trabajadores.

For more things to do, where to stay, ratings, and other tourist information, you can read our Camaguey travel itinerary planner.

Drive from Trinidad to Camaguey in 4 hours. Alternatively, you can take a bus; or do a combination of taxi and train. Traveling from Trinidad in January, you can expect nighttime temperatures to be a bit cooler in Camaguey, with lows of 65°F. Cap off your sightseeing on the 23rd (Sat) early enough to go by car to Santiago de Cuba.

Things to do in Camaguey

Historic Sites · Parks · Museums · Shopping

Santiago de Cuba, Cuba

— 3 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.
Escape the urban bustle at Guayabo Falls and Salto del Guayabo. Satisfy your inner culture vulture at Castillo de San Pedro de la Roca and Cathedral of Our Lady of the Assumption. Step out of Santiago de Cuba to go to El Cobre and see Basilica de la Virgen de la Caridad del Cobre, which is approximately 38 minutes away. The adventure continues: explore the different monuments and memorials at Cementerio Santa Ifigenia, don't miss a visit to La Alameda, contemplate the long history of Moncada Barracks, and learn about all things military at Museo de la Lucha Clandestina.

To see where to stay, traveler tips, more things to do, and tourist information, read Santiago de Cuba trip itinerary builder app.

Getting from Camaguey to Santiago de Cuba by car takes about 5.5 hours. Other options: take a bus; or take a train. Expect a daytime high around 83°F in January, and nighttime lows around 69°F. Wrap up your sightseeing on the 26th (Tue) to allow time to travel to Port-au-Prince.

Things to do in Santiago de Cuba

Historic Sites · Parks · Nature · Museums

Side Trips

Port-au-Prince, Haiti

— 9 nights
Port-au-Prince, the capital of Haiti, gives most visitors their first taste of the country, along with all of its rugged and lively charm.
Your cultural itinerary includes sights like Museum Ogier-Fombrun and Sainte Anne Church. Get in touch with nature at Kay Piat and Kokoye Beach. You'll find plenty of places to visit near Port-au-Prince: Montrouis (Haiti Discovery & Off Road Haiti), Village Artistique de Noailles (in Croix-des-Bouquets) and Place Saint-Pierre (in Petionville). Next up on the itinerary: see the interesting displays at Musee du Pantheon National Haitien, take in the architecture and atmosphere at Notre Dame Cathedral Ruins, indulge your thirst for a good beer at Barbancourt Rum Distillery, and explore the ancient world of Papillon Enterprise.

To see traveler tips, maps, ratings, and other tourist information, read Port-au-Prince trip itinerary planning tool.

Explore your travel options from Santiago de Cuba to Port-au-Prince with the Route module. Traveling from Santiago de Cuba in January, expect somewhat warmer with lows of 75°F in Port-au-Prince. You will leave for Cap-Haitien on the 4th (Thu).

Things to do in Port-au-Prince

Outdoors · Museums · Historic Sites · Shopping

Side Trips

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.
Start off your visit on the 5th (Fri): steep yourself in history at Heros de Vertieres.

Make your Cap-Haitien itinerary with Inspirock to find out what to see and where to go.

Traveling by car from Port-au-Prince to Cap-Haitien takes 4 hours. Alternatively, you can take a bus. Traveling from Port-au-Prince in February, you will find days in Cap-Haitien are little chillier (79°F), and nights are about the same (73°F). Wrap up your sightseeing by early afternoon on the 6th (Sat) to allow time for the car ride to Santo Domingo.

Things to do in Cap-Haitien

Historic Sites

Santo Domingo, Dominican Republic

— 9 nights
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Take a break from the city and head to Cueva de las Maravillas and National Botanical Garden. Get some historical perspective at Alcazar de Colon and Santo Domingo Dominican Republic Temple. Go for a jaunt from Santo Domingo to Boca Chica to see Scuba & Snorkeling about 44 minutes away. Spend the 14th (Sun) among the memorable landscape of The 3 Eyes National Park. And it doesn't end there: experience rural life at Kahkow Experience, make a trip to The Church and Convent of Santo Domingo Regina Angelorum, steep yourself in history at Fortaleza Ozama, and examine the collection at Amber World Museum.

To find traveler tips, where to stay, photos, and more tourist information, use the Santo Domingo travel itinerary planner.

Getting from Cap-Haitien to Santo Domingo by car takes about 5.5 hours. Other options: take a bus; or do a combination of bus and flight. Due to the time zone difference, you'll lose 1 hour traveling from Cap-Haitien to Santo Domingo. Wrap up your sightseeing by early afternoon on the 15th (Mon) to allow enough time to travel to El Yunque National Forest.

Things to do in Santo Domingo

Parks · Historic Sites · Nature · Museums

Side Trips

El Yunque National Forest, Puerto Rico

— 2 nights
Start off your visit on the 16th (Tue): take your sightseeing to a higher altitude at El Yunque and then stroll through Angelito Trail. Here are some ideas for day two: take in the dramatic scenery at Cataratas Juan Diego, then take your sightseeing to a higher altitude at El Toro, and then examine the collection at El Portal Tropical Forest Center.

For reviews, ratings, traveler tips, and tourist information, use the El Yunque National Forest online day trip planner.

Explore your travel options from Santo Domingo to El Yunque National Forest with the Route module. In February in El Yunque National Forest, expect temperatures between 84°F during the day and 73°F at night. Finish your sightseeing early on the 17th (Wed) so you can drive to San Juan.

Things to do in El Yunque National Forest

Parks · Nature · Wildlife · Museums

San Juan, Puerto Rico

— 6 nights

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S. jurisdiction and one of the oldest in the Americas.
Take a break from the city and head to Explora Puerto Rico and Reserva Natural de Humacao. You'll explore the less-touristy side of things at Catedral Basilica Menor de San Juan Bautista and Nature & Wildlife Tours. There's lots more to do: get to know the fascinating history of Old San Juan, stroll through La Marquesa Forest Park, don't miss a visit to La Muralla, and explore the world behind art at Fundacion Casa Cortes.

To see where to stay, other places to visit, reviews, and tourist information, read San Juan trip planning site.

Getting from El Yunque National Forest to San Juan by car takes about 1.5 hours. Other options: drive; or take a shuttle. In February, daily temperatures in San Juan can reach 84°F, while at night they dip to 73°F. You'll set off for Negril on the 23rd (Tue).

Things to do in San Juan

Wildlife · Outdoors · Tours · Historic Sites

Side Trips

Negril, Jamaica

— 2 nights
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
Kick off your visit on the 24th (Wed): trot along with Rhodes Hall Plantation, then soothe aching muscles at some of the top local wellness centers, then stop by Irie Art, and finally take in the architecture and atmosphere at Mary, Gate of Heaven Catholic Church. Here are some ideas for day two: take in nature's colorful creations at Barney's Flower & Hummingbird Garden Jamaica, enjoy the sand and surf at Seven Mile Beach, and then Head underground at The Throne Room.

To see where to stay, traveler tips, other places to visit, and tourist information, you can read our Negril trip itinerary website.

Getting from San Juan to Negril by flight takes about 9 hours. The time zone difference moving from Atlantic Standard Time (AST) to Eastern Standard Time (EST) is minus 1 hour. February in Negril sees daily highs of 86°F and lows of 72°F at night. Cap off your sightseeing on the 25th (Thu) early enough to go by car to Kingston.

Things to do in Negril

Parks · Outdoors · Wildlife · Beaches

Side Trip

Kingston, Jamaica

— 4 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.
Take a break from the city and head to Sun Valley Plantation and Lime Cay. Get some historical perspective at Fort Charles and Trench Town. Step out of Kingston with an excursion to Blue Hole in Ocho Rios--about 1h 30 min away. There's still lots to do: see the interesting displays at Trench Town Culture Yard, take in the waterfront activity at Port Royal, browse the exhibits of Bob Marley Museum, and buy something for everyone on your list at Morgans Creek Ltd.

For ratings, maps, more things to do, and other tourist information, use the Kingston journey planner.

Getting from Negril to Kingston by car takes about 4 hours. Other options: drive; or take a bus. In February, plan for daily highs up to 87°F, and evening lows to 73°F. Finish up your sightseeing early on the 1st (Mon) so you can travel back home.

Things to do in Kingston

Historic Sites · Museums · Outdoors · Parks

Side Trips

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.

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.

Dominican Republic travel guide

4.1
Beaches · Islands · Zipline
Sharing the island of Hispaniola with Haiti, friendly Dominican Republic offers two distinct coastlines, one bathed by the Caribbean Sea and the other by the Atlantic Ocean. Nearly 1,600 km (1,000 mi) of palm-shaded beaches figure highly on most Dominican Republic itineraries, allowing visitors to design their vacation around a range of water-based activities. The sun-kissed country benefits from pleasant temperatures throughout the year, so it's no surprise that holidays in Dominican Republic remain a popular choice for visitors from distant and colder corners of the world. A big producer of coffee, cocoa, rum, sugarcane, and tobacco, the country provides a vibrant cultural experience in multicultural cities and quaint countryside.

Puerto Rico travel guide

4.5
Historic Walking Areas · Beaches · Forests
A U.S. territory encompassing one big island and several smaller ones, Puerto Rico appeals to visitors from around the globe with its rich history, pleasant climate, natural beauty, and renowned local cuisine. Most tourists take a vacation in Puerto Rico for that classic seaside experience, though the island offers much more than just sun and sand. Tours of Puerto Rico usually start in the city of San Juan, which boasts a trendy bar scene and plenty of art museums for visitors looking to add a bit of culture to their vacation. A short drive from the island's urban centers, pristine rainforests serve as peaceful retreats from the city bustle and ensure plenty of chances to spot wildlife and take exhilarating nature walks.

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.