38 days in Caribbean Itinerary

38 days in Caribbean Itinerary

Created using Inspirock Caribbean trip planner

Plan created by another user. Make it yours

Route & dates

1
Havana, Cuba
— 4 nights
2
Varadero, Cuba
— 3 nights
3
Cayo Largo, Cuba
— 3 nights
4
Trinidad, Cuba
— 2 nights
5
Santiago de Cuba, Cuba
— 1 night
6
Port-au-Prince, Haiti
— 1 night
7
Santo Domingo, Dominican Republic
— 2 nights
8
Puerto Plata, Dominican Republic
— 3 nights
9
Isla de Vieques, Puerto Rico
— 1 night
10
El Yunque National Forest, Puerto Rico
— 2 nights
11
Culebra, Puerto Rico
— 2 nights
12
San Juan, Puerto Rico
— 2 nights
13
Bayahibe, Dominican Republic
— 2 nights
14
Negril, Jamaica
— 2 nights
15
Montego Bay, Jamaica
— 2 nights
16
Ocho Rios, Jamaica
— 2 nights

4
nights
Havana, Cuba

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
You'll discover tucked-away gems like Palacio De Los Capitanes Generales and Nature & Wildlife Tours. Visit Fortaleza de San Carlos de la Cabana and Malecón of Havana for their historical value. And it doesn't end there: make a trip to Old Havana, contemplate the long history of El Morro, examine the collection at Taquechel Pharmacy Museum, and visit Vedado.

To see traveler tips, more things to do, other places to visit, and tourist information, you can read our Havana day trip planning website.

San Francisco, USA to Havana is an approximately 10.5-hour flight. The time zone difference moving from Pacific Standard Time (PST) to Cuba Standard Time (CST) is 3 hours. In October, Havana is somewhat warmer than San Francisco - with highs of °F and lows of °F. Finish your sightseeing early on the 5th (Mon) to allow enough time to drive to Varadero.

Things to do in Havana

Historic Sites Outdoors Wildlife
Highlights from your plan
Nature & Wildlife Tours
Plaza de San Francisco ©
Plaza de San Francisco
Palacio De Los Capitanes Generales ©
Palacio De Los Capitanes Generales

3
nights
Varadero, Cuba

Varadero ©
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.
Explore hidden gems such as Cueva de Saturno and Josone Park. Cueva de Ambrosio and Iglesia Santa Elvira are good opportunities to explore the local culture. Explore Varadero's surroundings by going to Matanzas (Parque de la Libertad, Pharmaceutical Museum, &more). Next up on the itinerary: tour the pleasant surroundings at Cayos Blancos, surround yourself with nature on a nature and wildlife tour, identify plant and animal life at Varahicacos Ecological Reserve, and examine the collection at House of Rum.

To find photos, other places to visit, traveler tips, and other tourist information, read our Varadero day trip site.

Getting from Havana to Varadero by car takes about 2 hours. Other options: take a shuttle; or do a combination of train and taxi. In October, daytime highs in Varadero are °F, while nighttime lows are °F. Finish your sightseeing early on the 8th (Thu) to allow enough time to travel to Cayo Largo.

Things to do in Varadero

Outdoors Parks Wildlife

Side Trip

Matanzas
Highlights from your plan
Varadero Beach ©
Varadero Beach
Cueva de Saturno ©
Cueva de Saturno
Cueva de Ambrosio ©
Cueva de Ambrosio

3
nights
Cayo Largo, Cuba

Cayo Largo ©
The stress of modern life feels a million miles away when you holiday on Cayo Largo, a small and unspoiled resort island off the coast of Cuba.
On the 9th (Fri), identify plant and animal life at Sea Turtle Hatchery and then kick back and relax at Playa Paraiso. On your second day here, kick back and relax at Sirena Beach, thenhead off the coast to Cayo Rico, and then kick back and relax at Punta Mal Tiempo.

Plan a trip to Cayo Largo easily and quickly by telling Inspirock to suggest an itinerary.

Traveling by flight from Varadero to Cayo Largo takes 3.5 hours. Alternatively, you can take a bus. In October, daytime highs in Cayo Largo are °F, while nighttime lows are °F. Finish your sightseeing early on the 11th (Sun) so you can take a bus to Trinidad.

Things to do in Cayo Largo

Parks Outdoors Beaches
Highlights from your plan
Sirena Beach ©
Sirena Beach
Playa Paraiso ©
Playa Paraiso
Sea Turtle Hatchery ©
Sea Turtle Hatchery

2
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.
You'll explore the less-touristy side of things at Plaza Mayor and Topes de Collantes. Do some cultural sightseeing at Convento de San Francisco de Asis and Museo de Historia Municipal. Go for a jaunt from Trinidad to Topes de Collantes to see Vegas Grande Waterfall about 32 minutes away. And it doesn't end there: enjoy breathtaking views from Iznaga Tower, see the interesting displays at Colonial Architecture Museum, take in the exciting artwork at Galerie D'Art Calleyro, and enjoy the sand and surf at Playa Maria Aguilar.

To see where to stay, maps, and tourist information, use the Trinidad day trip planning app.

Traveling by bus from Cayo Largo to Trinidad takes 4.5 hours. October in Trinidad sees daily highs of °F and lows of °F at night. Cap off your sightseeing on the 13th (Tue) early enough to go by car to Santiago de Cuba.

Things to do in Trinidad

Parks Nature Outdoors

Side Trips

Topes de Collantes, Playa Maria Aguilar
Highlights from your plan
Vegas Grande Waterfall ©
Vegas Grande Waterfall
Topes de Collantes ©
Topes de Collantes
Plaza Mayor ©
Plaza Mayor

1
night
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.
Start off your visit on the 14th (Wed): pause for some serene contemplation at Iglesia Sagrada Familia, thenpause for some serene contemplation at Basilica de la Virgen de la Caridad del Cobre, thenstroll the grounds of Cementerio Santa Ifigenia, and finally contemplate the long history of Escalinata de Padre Pico. Get ready for a full day of sightseeing on the 15th (Thu): brush up on your military savvy at Museo de la Lucha Clandestina, look for all kinds of wild species at Comandancia de la plata, visit a coastal fixture at Faro del Morro, step into the grandiose world of Castillo de San Pedro de la Roca, thenget engrossed in the history at Casa de Diego Velazquez, and finally steep yourself in history at Moncada Barracks.

Plan my trip to Santiago de Cuba with suggested itineraries provided by Inspirock.

You can drive from Trinidad to Santiago de Cuba in 9 hours. Alternatively, you can do a combination of bus, train, and flight; or take a bus. In October, daytime highs in Santiago de Cuba are °F, while nighttime lows are °F. Wrap up your sightseeing on the 15th (Thu) to allow time to travel to Port-au-Prince.

Things to do in Santiago de Cuba

Historic Sites Wildlife Museums

Side Trip

Basilica de la Virgen de la Caridad del Cobre
Highlights from your plan
Castillo de San Pedro de la Roca ©
Castillo de San Pedro de la Roca
Cementerio Santa Ifigenia ©
Cementerio Santa Ifigenia

1
night
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.
On the 16th (Fri), take in the architecture and atmosphere at Notre Dame Cathedral Ruins, see the interesting displays at Musee du Pantheon National Haitien, examine the collection at The Bureau of Ethnology, thenstop by Comite Artisanal Haitien, and finally take in the architecture and atmosphere at Sainte Anne Church. On the next day, delve into the mystery of Atis rezistans, thenexplore the world behind art at El-Saieh Gallery, thenexplore the ancient world of Papillon Enterprise, and finally admire the landmark architecture of Marche de Fer.

To see reviews, maps, where to stay, and other tourist information, read Port-au-Prince online trip itinerary maker.

The Route module can help you plan travel from Santiago de Cuba to Port-au-Prince. October in Port-au-Prince sees daily highs of °F and lows of °F at night. Finish your sightseeing early on the 17th (Sat) so you can travel to Santo Domingo.

Things to do in Port-au-Prince

Historic Sites Shopping Museums
Highlights from your plan
Papillon Enterprise ©
Papillon Enterprise
Sainte Anne Church ©
Sainte Anne Church
Notre Dame Cathedral Ruins ©
Notre Dame Cathedral Ruins

2
nights
Santo Domingo, Dominican Republic

Santo Domingo ©
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
On the 18th (Sun), take in the spiritual surroundings of Catedral Primada de America, thencontemplate the long history of Convento de los Dominicos, thensteep yourself in history at Alcazar de Colon, and finally steep yourself in history at Fortaleza Ozama. Here are some ideas for day two: see some colorful creatures with a scuba or snorkeling tour, thenget to know the fascinating history of La Atarazana, thenrelax in the rural setting at Kahkow Experience, and finally admire the landmark architecture of La Casa de Los Jesuitas.

For traveler tips, photos, where to stay, and tourist information, read our Santo Domingo online itinerary planner.

Getting from Port-au-Prince to Santo Domingo by flight takes about 3.5 hours. Other options: drive; or take a bus. The time zone changes from Eastern Standard Time (EST) to Atlantic Standard Time (AST), which is usually a 1 hour difference. Wrap up your sightseeing on the 19th (Mon) early enough to drive to Puerto Plata.

Things to do in Santo Domingo

Historic Sites Outdoors Wildlife

Side Trip

Scuba & Snorkeling
Highlights from your plan
Fortaleza Ozama ©
Fortaleza Ozama
Catedral Primada de America
Catedral Primada de America
Scuba & Snorkeling

3
nights
Puerto Plata, Dominican Republic

Although out of fashion in the past decades, major revitalization efforts have made a trip to Puerto Plata a growingly popular option for the adventurous travelers.
Start off your visit on the 20th (Tue): push the limits with an extreme tour and then take in the dramatic scenery at 27 Charcos. Get ready for a full day of sightseeing on the next day: get interesting insight from Tours, thenbrowse the exhibits of Joyeria Las Americas, thensteep yourself in history at Fortaleza San Felipe, and finally see some colorful creatures with a scuba or snorkeling tour.

To find where to stay, reviews, other places to visit, and tourist information, you can read our Puerto Plata sightseeing planner.

Drive from Santo Domingo to Puerto Plata in 3 hours. Alternatively, you can take a bus. In October, daytime highs in Puerto Plata are °F, while nighttime lows are °F. Finish up your sightseeing early on the 22nd (Thu) so you can travel to Isla de Vieques.

Things to do in Puerto Plata

Outdoors Tours Nature
Highlights from your plan
Adrenaline & Extreme Tours
27 Charcos ©
27 Charcos
Scuba & Snorkeling

1
night
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.
On the 22nd (Thu), view the masterpieces at Siddhia Hutchinson Fine Art Gallery, thenstop by Isla Vida, thentake some stellar pictures from Puerto Ferro Lighthouse, and finally stroll through La Plata Beach. Get ready for a full day of sightseeing on the next day: explore the ancient world of El Hombre de Puerto Ferro and then contemplate the waterfront views at Sun Bay Beach.

To find reviews, other places to visit, where to stay, and tourist information, use the Isla de Vieques journey planning website.

Traveling by flight from Puerto Plata to Isla de Vieques takes 7 hours. Alternatively, you can do a combination of bus, ferry, and taxi; or do a combination of bus, ferry, shuttle, and taxi. October in Isla de Vieques sees daily highs of °F and lows of °F at night. Wrap up your sightseeing on the 23rd (Fri) early enough to travel to El Yunque National Forest.

Things to do in Isla de Vieques

Outdoors Beaches Parks
Highlights from your plan
Sun Bay Beach ©
Sun Bay Beach
El Hombre de Puerto Ferro ©
El Hombre de Puerto Ferro
Puerto Ferro Lighthouse ©
Puerto Ferro Lighthouse

2
nights
El Yunque National Forest, Puerto Rico

El Yunque National Forest ©
Kick off your visit on the 24th (Sat): trek along Big Tree Trail and then take a peaceful walk through El Yunque Rain Forest. On the 25th (Sun), you'll have a packed day of sightseeing: see the interesting displays at El Portal Tropical Forest Center, thenget a sense of history and politics at Monumento Historico Cueva Maria de La Cruz, thenbrowse the exhibits of Estudio de Arte Samuel Lind, and finally admire the sheer force of Juan Diego Falls.

For photos, ratings, maps, and tourist information, refer to the El Yunque National Forest online trip planner.

Do a combination of ferry and car from Isla de Vieques to El Yunque National Forest in 2.5 hours. Alternatively, you can drive; or do a combination of ferry and shuttle. In October, daytime highs in El Yunque National Forest are °F, while nighttime lows are °F. Finish up your sightseeing early on the 25th (Sun) so you can travel to Culebra.

Things to do in El Yunque National Forest

Parks Nature Wildlife

Side Trip

Loiza
Highlights from your plan
Big Tree Trail ©
Big Tree Trail
El Yunque Rain Forest ©
El Yunque Rain Forest
Juan Diego Falls ©
Juan Diego Falls

2
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.
On the 26th (Mon), stroll through Melones Beach, thentour the pleasant surroundings at Playa Punta Soldado Beach, and then stroll through Carlos Rosario Beach. Get ready for a full day of sightseeing on the 27th (Tue): step off the mainland to explore Culebrita Island, visit a coastal fixture at Culebrita Lighthouse, and then examine the collection at Museo Historico de Culebra.

For photos, ratings, maps, and other tourist information, refer to the Culebra sightseeing planner.

You can fly from El Yunque National Forest to Culebra in 2.5 hours. Alternatively, you can do a combination of car and ferry; or do a combination of shuttle and ferry. Expect a daytime high around °F in October, and nighttime lows around °F. Wrap up your sightseeing on the 27th (Tue) early enough to travel to San Juan.

Things to do in Culebra

Parks Outdoors Beaches
Highlights from your plan
Culebrita Island ©
Culebrita Island
Carlos Rosario Beach ©
Carlos Rosario Beach
Melones Beach ©
Melones Beach

2
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Start off your visit on the 28th (Wed): delve into the lush surroundings at La Marquesa Forest Park, explore the world behind art at Museo de Las Americas, and then get to know the fascinating history of La Muralla. Get ready for a full day of sightseeing on the 29th (Thu): steep yourself in history at La Fortaleza - Palacio de Santa Catalina, get to know the fascinating history of Sitio Histórico de San Juan, and then pause for some photo ops at Plaza de Colon.

For reviews, where to stay, maps, and tourist information, go to the San Juan day trip website.

You can fly from Culebra to San Juan in 2 hours. Other options are to do a combination of ferry and car; or do a combination of ferry and shuttle. In October in San Juan, expect temperatures between °F during the day and °F at night. Wrap up your sightseeing on the 29th (Thu) early enough to travel to Bayahibe.

Things to do in San Juan

Historic Sites Nature Wildlife

Side Trip

La Marquesa Forest Park
Highlights from your plan
Sitio Histórico de San Juan ©
Sitio Histórico de San Juan
La Marquesa Forest Park ©
La Marquesa Forest Park
Museo de Las Americas ©
Museo de Las Americas

2
nights
Bayahibe, Dominican Republic

Located on the shore of the Caribbean Sea, the town of Bayahibe has grown from a fishing village into a bona fide tourist destination, with visitors mainly drawn to the many dive sites just off the coast.
Start off your visit on the 30th (Fri): appreciate the extensive heritage of Altos de Chavon, admire the masterpieces at Conquista Park, and then Head underground at Cueva Padre Nuestro. Get ready for a full day of sightseeing on the 31st (Sat): stop by Museo y Fabrica de Puras, thensurround yourself with nature on a nature and wildlife tour, and then identify plant and animal life at Wildlife Areas.

To see reviews, photos, traveler tips, and more tourist information, read our Bayahibe vacation planner.

Getting from San Juan to Bayahibe by flight takes about 3.5 hours. Other options: do a combination of ferry and car; or do a combination of ferry and bus. In October in Bayahibe, expect temperatures between °F during the day and °F at night. Finish up your sightseeing early on the 31st (Sat) so you can travel to Negril.

Things to do in Bayahibe

Outdoors Wildlife Tours

Side Trip

Altos de Chavon
Highlights from your plan
Scuba & Snorkeling
Nature & Wildlife Tours
Altos de Chavon ©
Altos de Chavon

2
nights
Negril, Jamaica

Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
Kick off your visit on the 1st (Sun): take in the dramatic natural features at The Throne Room, thenlearn insider's secrets on a distillery tour, and then stop by Irie Art. Get ready for a full day of sightseeing on the 2nd (Mon): take in the history at St Mary Catholic Church, Revival, Jamaica, take in the architecture and atmosphere at Mary, Gate of Heaven Catholic Church, and then enjoy the sand and surf at Seven Mile Beach.

To find photos, more things to do, reviews, and more tourist information, you can read our Negril driving holiday planner.

Traveling by flight from Bayahibe to Negril takes 6 hours. Due to the time zone difference, you'll gain 1 hour traveling from Bayahibe to Negril. In October, plan for daily highs up to °F, and evening lows to °F. Wrap up your sightseeing on the 2nd (Mon) early enough to drive to Montego Bay.

Things to do in Negril

Outdoors Parks Wildlife
Highlights from your plan
Distillery Tours
Seven Mile Beach ©
Seven Mile Beach
Mary, Gate of Heaven Catholic Church ©
Mary, Gate of Heaven Catholic Church

2
nights
Montego Bay, Jamaica

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 3rd (Tue): buy something for everyone on your list at Whitter Village Shopping Mall, thensteep yourself in history at Rose Hall Great House, thensee what you can catch with a fishing tour, and finally enjoy the sand and surf at Burwood Beach. On the 4th (Wed), you'll have a packed day of sightseeing: get a dose of the wild on a nature and wildlife tour and then kick your exploration up a notch at some of the top local zipline courses and adventure parks.

For ratings, traveler tips, reviews, and more tourist information, read Montego Bay day trip site.

Drive from Negril to Montego Bay in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around °F in November, and nighttime lows around °F. Finish your sightseeing early on the 4th (Wed) so you can drive to Ocho Rios.

Things to do in Montego Bay

Outdoors Tours Wildlife

Side Trip

Falmouth
Highlights from your plan
Nature & Wildlife Tours
Rose Hall Great House ©
Rose Hall Great House
Zipline

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.
On the 5th (Thu), take in the dramatic scenery at Dunn's River Falls and Park, thentake in the dramatic scenery at Blue Hole, and then get engrossed in the history at Coyaba River Garden and Museum. Keep things going the next day: discover the deep blue sea with a scuba or snorkeling tour and then admire the sheer force of Little Dunn's River Falls.

For traveler tips, reviews, where to stay, and more tourist information, use the Ocho Rios online visit planner.

Drive from Montego Bay to Ocho Rios in 2 hours. Alternatively, you can take a bus. In November in Ocho Rios, expect temperatures between °F during the day and °F at night. Cap off your sightseeing on the 6th (Fri) early enough to travel back home.

Things to do in Ocho Rios

Parks Nature Outdoors
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Scuba & Snorkeling

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