14 days in Caribbean Itinerary

14 days in Caribbean Itinerary

Created using Inspirock Caribbean itinerary builder

Make it your trip
Fly
1
Ocho Rios, Jamaica
— 1 night
Drive
2
Montego Bay, Jamaica
— 2 nights
Fly
3
Varadero, Cuba
— 1 night
Drive
4
Havana, Cuba
— 2 nights
Fly
5
Nassau, Bahamas
— 2 nights
Fly
6
Port-au-Prince, Haiti
— 1 night
Fly
7
Santo Domingo, Dominican Republic
— 2 nights
Shuttle
8
Punta Cana, Dominican Republic
— 2 nights
Fly

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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.
On the 19th (Wed), take in the dramatic scenery at Dunn's River Falls and Park, then hike along Fern Gully, and then admire the sheer force of Blue Hole.

To see other places to visit, traveler tips, maps, and more tourist information, use the Ocho Rios trip planner.

Toronto, Canada to Ocho Rios is an approximately 9-hour flight. In August, Ocho Rios is a bit warmer than Toronto - with highs of 38°C and lows of 30°C. Finish your sightseeing early on the 19th (Wed) to allow enough time to drive to Montego Bay.

Things to do in Ocho Rios

Parks · Nature · Trails · Outdoors

Montego Bay, Jamaica

— 2 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.
Start off your visit on the 20th (Thu): play a few rounds at Tryall Golf Course and then kick back and relax at Doctor's Cave Beach. Keep things going the next day: steep yourself in history at Rose Hall Great House and then identify plant and animal life at Wildlife Areas.

To find reviews, where to stay, traveler tips, and more tourist information, you can read our Montego Bay trip maker website.

Traveling by car from Ocho Rios to Montego Bay takes 2 hours. Alternatively, you can take a bus. In August, daily temperatures in Montego Bay can reach 39°C, while at night they dip to 29°C. Cap off your sightseeing on the 21st (Fri) early enough to travel to Varadero.

Things to do in Montego Bay

Outdoors · Tours · Wildlife · Parks

Side Trip

Varadero, Cuba

— 1 night
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.
Start off your visit on the 22nd (Sat): view the masterpieces at Artecru, tour the pleasant surroundings at Varadero Beach, then contemplate in the serene atmosphere at Iglesia Santa Elvira, and finally walk around Josone Park.

Start your trip to Varadero by creating a personalized itinerary on Inspirock.

Fly from Montego Bay to Varadero in 6 hours. Plan for slightly colder nights when traveling from Montego Bay in August since evenings lows in Varadero dip to 26°C. Finish up your sightseeing early on the 22nd (Sat) so you can go by car to Havana.

Things to do in Varadero

Parks · Outdoors · Beaches · Shopping

Havana, Cuba

— 2 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.
Start off your visit on the 23rd (Sun): contemplate the long history of El Morro, contemplate the long history of Fortaleza de San Carlos de la Cabana, then appreciate the extensive heritage of Malecón of Havana, and finally don't miss a visit to El Capitolio. Get ready for a full day of sightseeing on the 24th (Mon): see the interesting displays at Wifredo Lam Center, don't miss a visit to Old Square (Plaza Vieja), don't miss a visit to Plaza de Armas, then make a trip to Plaza de la Catedral, then admire the striking features of Havana Cathedral, and finally don't miss a visit to Paseo del Prado.

To see more things to do, reviews, maps, and tourist information, you can read our Havana visit planner.

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. In August, daily temperatures in Havana can reach 38°C, while at night they dip to 26°C. Finish your sightseeing early on the 24th (Mon) so you can travel to Nassau.

Things to do in Havana

Historic Sites · Museums

Nassau, Bahamas

— 2 nights
On a trip to Nassau you can immerse yourself in a dynamic city atmosphere or spend your days lazing on the soft golden sands.
Kick off your visit on the 25th (Tue): get up close and personal with brilliant marine life at Marine Habitat at Atlantis and then enjoy the sand and surf at Cable Beach. On the next day, make a trip to The Cloister, tee off at Ocean Club Golf Course, and then enjoy the sand and surf at Cabbage Beach.

For more things to do, photos, other places to visit, and other tourist information, you can read our Nassau trip itinerary planner.

You can fly from Havana to Nassau in 4.5 hours. Expect a bit warmer evenings in Nassau when traveling from Havana in August, with lows around 30°C. Finish your sightseeing early on the 26th (Wed) so you can travel to Port-au-Prince.

Things to do in Nassau

Parks · Outdoors · Beaches · Zoos & Aquariums

Side Trip

Port-au-Prince, Haiti

— 1 night
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.
Start off your visit on the 27th (Thu): sample the tasty concoctions at Barbancourt Rum Distillery, then see the interesting displays at The Bureau of Ethnology, then see the interesting displays at Musee du Pantheon National Haitien, and finally admire all the interesting features of Marche de Fer.

For traveler tips, more things to do, ratings, and more tourist information, you can read our Port-au-Prince trip planner.

You can fly from Nassau to Port-au-Prince in 4 hours. Expect a daytime high around 40°C in August, and nighttime lows around 32°C. Wrap up your sightseeing on the 27th (Thu) to allow time to travel to Santo Domingo.

Things to do in Port-au-Prince

Museums · Shopping · Breweries & Distilleries

Santo Domingo, Dominican Republic

— 2 nights
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Kick off your visit on the 28th (Fri): delve into the distant past at Monasterio de San Francisco, then don't miss a visit to Zona Colonial, and then explore the world behind art at Amber Museum. Keep things going the next day: steep yourself in history at Fortaleza Ozama, then step into the grandiose world of Alcazar de Colon, then browse the exhibits of Columbus Lighthouse (Faro A Colon), and finally walk around Parque Duarte.

For other places to visit, ratings, reviews, and other tourist information, you can read our Santo Domingo planner.

Traveling by flight from Port-au-Prince to Santo Domingo takes 3.5 hours. Alternatively, you can drive; or take a bus. Traveling from Port-au-Prince to Santo Domingo, you'll lose 1 hour due to the time zone difference. Finish your sightseeing early on the 29th (Sat) to allow enough time to take a shuttle to Punta Cana.

Things to do in Santo Domingo

Historic Sites · Museums · Parks · Shopping

Punta Cana, Dominican Republic

— 2 nights
In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.
On the 30th (Sun), stop by HARRISON'S Fine Caribbean Jewelers and then head off the coast to Saona Island. Here are some ideas for day two: stroll through Bavaro Beach.

For other places to visit, more things to do, where to stay, and more tourist information, use the Punta Cana road trip site.

Traveling by shuttle from Santo Domingo to Punta Cana takes 2 hours. Alternatively, you can drive; or fly. In August, daytime highs in Punta Cana are 37°C, while nighttime lows are 29°C. Finish your sightseeing early on the 31st (Mon) to allow enough time to travel back home.

Things to do in Punta Cana

Parks · Nature · Outdoors · Beaches

Side Trip

Jamaica travel guide

4
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.

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.

Bahamas travel guide

3.6
Beaches · Islands · Water & Amusement Parks
Part of an archipelago encompassing hundreds of islets and cays, Bahamas boast many pink beaches, which get their vibrant color from fractured seashells mixed with ordinary sand. For most pleasure seekers an ideal holiday in Bahamas consists of various sea activities, occasionally interrupted by tours of several cities, offering an eclectic music scene dominated by calypso, soca, and junkanoo genres. Romantic enough to attract newlyweds from around the globe, the islands are also a major center of eco-tourism, with visits to national parks and diving tours in colorful reefs among the most popular things to do in Bahamas.

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.