60 days in Caribbean Itinerary

60 days in Caribbean Itinerary

Created using Inspirock Caribbean trip planner

Plan created by another user. Make it yours
1
Havana, Cuba
— 15 nights
2
Trinidad, Cuba
— 4 nights
3
Camaguey, Cuba
— 3 nights
4
Santiago de Cuba, Cuba
— 3 nights
5
Port-au-Prince, Haiti
— 9 nights
6
Cap-Haitien, Haiti
— 2 nights
7
Santo Domingo, Dominican Republic
— 9 nights
8
El Yunque National Forest, Puerto Rico
— 2 nights
9
San Juan, Puerto Rico
— 6 nights
10
Negril, Jamaica
— 2 nights
11
Kingston, Jamaica
— 4 nights

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15
nights
Havana, Cuba

Havana ©

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 Museo Napoleonico. Visit Malecón of Havana and Fort San Salvador (Castillo De San Salvador De La Punta) for their historical value. There's still lots to do: make a trip to Old Havana, steep yourself in history at Old Square (Plaza Vieja), 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

Find places to stay Jan 1 — 16:
Highlights from your plan
Palacio De Los Capitanes Generales ©
Palacio De Los Capitanes Generales
Malecón of Havana ©
Malecón of Havana
Church and Convent of St. Francis of Asisi ©

4
nights
Trinidad, Cuba

Trinidad ©
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 Gio's Cuba Photo Tours. 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. There's lots more to do: make a trip to Ruinas de Ingenio San Isidro de los Destiladeros, take in the architecture and atmosphere at Church of the Holy Trinity, see the interesting displays at Colonial Architecture Museum, and head outdoors with Parque Guanayara.

To find traveler tips, more things to do, photos, and other tourist information, you can read our Trinidad trip itinerary planning site.

Getting from Havana to Trinidad by car takes about 4 hours. Other options: take a shuttle; or take a bus. Expect somewhat warmer evenings in Trinidad when traveling from Havana in January, with lows around 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

Find places to stay Jan 16 — 20:
Highlights from your plan
Convento de San Francisco de Asis ©
Convento de San Francisco de Asis
Trinidad Sightseeing ©
Trinidad Sightseeing
Topes de Collantes ©
Topes de Collantes

3
nights
Camaguey, Cuba

Camaguey ©
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 Martha Jimenez's Studio Workshop. Popular historic sites such as Plaza San Juan de Dios and Iglesia Nuestra Senora del Carmen are in your itinerary. There's lots more to do: appreciate the extensive heritage of Camaguey Centro, view the masterpieces at Estudio Galeria Magdiel, stroll around Casino Campestre, and get a taste of the local shopping with Casa de Arte Jover.

For ratings, maps, and tourist information, read Camaguey trip 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, Camaguey is slightly colder at night with lows of 65°F. Finish up your sightseeing early on the 23rd (Sat) so you can go by car to Santiago de Cuba.

Things to do in Camaguey

Historic Sites · Parks · Shopping · Museums
Find places to stay Jan 20 — 23:
Highlights from your plan
Plaza San Juan de Dios ©
Plaza San Juan de Dios
Plaza del Carmen ©
Plaza del Carmen
Camaguey Centro ©
Camaguey Centro

3
nights
Santiago de Cuba, Cuba

Santiago de Cuba ©
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 Cementerio Santa Ifigenia. 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. And it doesn't end there: take in the spiritual surroundings of Cathedral of Our Lady of the Assumption, 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, maps, and other tourist information, refer to the Santiago de Cuba travel site.

You can drive from Camaguey to Santiago de Cuba in 5.5 hours. Other options are to take a bus; or take a train. In January, daily temperatures in Santiago de Cuba can reach 83°F, while at night they dip to 69°F. Finish up your sightseeing early on the 26th (Tue) so you can travel to Port-au-Prince.

Things to do in Santiago de Cuba

Historic Sites · Parks · Nature · Museums

Side Trips

Find places to stay Jan 23 — 26:
Highlights from your plan
Cementerio Santa Ifigenia ©
Cementerio Santa Ifigenia
Castillo de San Pedro de la Roca ©
Castillo de San Pedro de la Roca
Cathedral of Our Lady of the Assumption ©
Cathedral of Our Lady of the Assumption

9
nights
Port-au-Prince, Haiti

Port-au-Prince ©
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 Notre Dame Cathedral Ruins. Get in touch with nature at Kay Piat and Kokoye Beach. You'll find plenty of places to visit near Port-au-Prince: Village Artistique de Noailles (in Croix-des-Bouquets), Place Saint-Pierre (in Petionville) and Montrouis (Haiti Discovery & Off Road Haiti). There's lots more to do: examine the collection at Musee du Pantheon National Haitien, take in the spiritual surroundings of Sainte Anne Church, don't miss a visit to Fort Jacques, and admire the natural beauty at Parc de Martissant.

For more things to do, traveler tips, photos, and other tourist information, go to the Port-au-Prince trip itinerary builder website.

Explore your travel options from Santiago de Cuba to Port-au-Prince with the Route module. Traveling from Santiago de Cuba in January, Port-au-Prince is a bit warmer at night with lows of 75°F. On the 4th (Thu), you're off to Cap-Haitien.

Things to do in Port-au-Prince

Outdoors · Museums · Historic Sites · Shopping

Side Trips

Find places to stay Jan 26 — Feb 4:
Highlights from your plan
Haiti Discovery ©
Haiti Discovery
Musee du Pantheon National Haitien ©
Musee du Pantheon National Haitien
Museum Ogier-Fombrun ©
Museum Ogier-Fombrun

2
nights
Cap-Haitien, Haiti

Cap-Haitien ©

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
Find places to stay Feb 4 — 6:
Highlights from your plan
Cathedrale Notre Dame de Cap Haitien ©
Cathedrale Notre Dame de Cap Haitien
Heros de Vertieres ©
Heros de Vertieres

9
nights
Santo Domingo, Dominican Republic

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 Fortaleza Ozama. 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. There's still lots to do: experience rural life at Kahkow Experience, take in the architecture and atmosphere at Santuario Nuestra Senora De La Altagracia, examine the collection at Amber World Museum, and pause for some photo ops at Columbus Lighthouse (Faro A Colon).

To find photos, reviews, more things to do, and other tourist information, use the Santo Domingo trip itinerary tool.

Traveling by car from Cap-Haitien to Santo Domingo takes 5.5 hours. Alternatively, you can do a combination of bus and flight; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Cap-Haitien to Santo Domingo. On the 15th (Mon), wrap the sightseeing up by early afternoon so you can travel to El Yunque National Forest.

Things to do in Santo Domingo

Parks · Historic Sites · Nature · Museums

Side Trips

Find places to stay Feb 6 — 15:
Highlights from your plan
Scuba & Snorkeling
Alcazar de Colon ©
Alcazar de Colon
Cueva de las Maravillas ©
Cueva de las Maravillas

2
nights

El Yunque National Forest ©
Start off your visit on the 16th (Tue): take your sightseeing to a higher altitude at El Yunque, then take a peaceful walk through Bosque Nacional El Yunque, and then stroll through Angelito Trail. Get ready for a full day of sightseeing on the next day: take in the dramatic scenery at Juan Diego Falls, take your sightseeing to a higher altitude at El Toro, and then see the interesting displays at El Portal Tropical Forest Center.

For ratings, maps, where to stay, and more tourist information, you can read our El Yunque National Forest trip itinerary 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. Wrap up your sightseeing on the 17th (Wed) early enough to drive to San Juan.

Things to do in El Yunque National Forest

Parks · Nature · Wildlife · Museums

Side Trip

Find places to stay Feb 15 — 17:
Highlights from your plan
Juan Diego Falls ©
Juan Diego Falls
El Yunque ©
El Yunque
Bosque Nacional El Yunque ©
Bosque Nacional El Yunque

6
nights
San Juan, Puerto Rico

San Juan ©

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Take a break from the city and head to Explora Puerto Rico and Nature & Wildlife Tours. You'll explore the less-touristy side of things at Catedral Metropolitana Basilica de San Juan Bautista and The Poet's Passage. Explore the numerous day-trip ideas around San Juan: Natural Reserve of Humacao (in Humacao) and La Marquesa Forest Park (in Guaynabo). There's lots more to do: appreciate the extensive heritage of Old San Juan, make a trip to Parque de las Palomas, ponder the world of politics at La Fortaleza - Palacio de Santa Catalina, and steep yourself in history at Sitio Histórico de San Juan.

For maps, reviews, where to stay, and other tourist information, use the San Juan trip builder.

Traveling by car from El Yunque National Forest to San Juan takes 1.5 hours. Alternatively, you can take a shuttle. In February in San Juan, expect temperatures between 84°F during the day and 73°F at night. You'll set off for Negril on the 23rd (Tue).

Things to do in San Juan

Side Trips

Find places to stay Feb 17 — 23:
Highlights from your plan
Old San Juan ©
Old San Juan
Natural Reserve of Humacao ©
Natural Reserve of Humacao

2
nights
Negril, Jamaica

Negril ©
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 11.5 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 · Beaches · Wildlife

Side Trip

Find places to stay Feb 23 — 25:
Highlights from your plan
Mary, Gate of Heaven Catholic Church ©
Mary, Gate of Heaven Catholic Church
Seven Mile Beach ©
Seven Mile Beach
Barney's Flower & Hummingbird Garden Jamaica ©

4
nights
Kingston, Jamaica

Kingston ©
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 Blue Hole. Get some historical perspective at Fort Charles and Trench Town. There's much more to do: steep yourself in history at Bob Marley Museum, see the interesting displays at Peter Tosh Museum, explore and take pictures at Port Royal, and get outside with Lime Cay.

To see ratings, other places to visit, reviews, and other tourist information, read Kingston trip maker app.

Getting from Negril to Kingston by car takes about 4 hours. Other options: take a bus. In February, daily temperatures in Kingston can reach 87°F, while at night they dip to 73°F. Finish your sightseeing early on the 1st (Mon) to allow enough time to travel back home.

Things to do in Kingston

Historic Sites · Outdoors · Museums · Parks

Side Trips

Find places to stay Feb 25 — Mar 1:
Highlights from your plan
Sun Valley Plantation ©
Sun Valley Plantation
Fort Charles ©
Fort Charles
Trench Town Culture Yard ©
Trench Town Culture Yard

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