16 days in Jamaica, Cuba & Dominican Republic Itinerary

16 days in Jamaica, Cuba & Dominican Republic Itinerary

Created using Inspirock Caribbean tour planner

Make it your trip
Fly
1
Montego Bay, Jamaica
— 3 nights
Fly
2
Havana, Cuba
— 5 nights
Fly
3
Santo Domingo, Dominican Republic
— 4 nights
Shuttle
4
Punta Cana, Dominican Republic
— 2 nights
Fly

S M T W T F S
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21

Montego Bay, Jamaica

— 3 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.
On the 6th (Fri), look for gifts at Tropicana Jewelers. Get ready for a full day of sightseeing on the 7th (Sat): look for gifts at The Craft Market at the Hip Strip and then stroll through Seven Mile Beach.

For traveler tips, more things to do, ratings, and other tourist information, read Montego Bay online tour planner.

Doha, Qatar to Montego Bay is an approximately 22-hour flight. The time zone difference moving from Arabian Standard Time to Eastern Standard Time is minus 8 hours. When traveling from Doha in May, plan for little chillier days in Montego Bay, with highs around 38°C, while nights are about the same with lows around 28°C. Cap off your sightseeing on the 9th (Mon) early enough to catch the flight to Havana.

Things to do in Montego Bay

Parks · Outdoors · Beaches · Shopping

Side Trip

Havana, Cuba

— 5 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.
Your cultural itinerary includes sights like Malecón of Havana and Old Havana. Your inner history buff will appreciate El Morro and Christopher Columbus Cemetery (Cemetario de Colon). Take a break from Havana with a short trip to Pharmaceutical Museum in Matanzas, about 1h 35 min away. There's still lots to do: take an in-depth tour of Museum of the Revolution (Museo de la Revolucion), don't miss a visit to Plaza de Armas, admire the landmark architecture of Bacardi Building, and see the interesting displays at Wifredo Lam Center.

To see more things to do, maps, where to stay, and other tourist information, use the Havana online visit planner.

Traveling by flight from Montego Bay to Havana takes 8 hours. Traveling from Montego Bay in May, Havana is a bit cooler at night with lows of 24°C. Cap off your sightseeing on the 14th (Sat) early enough to catch the flight to Santo Domingo.

Things to do in Havana

Historic Sites · Museums · Neighborhoods

Side Trip

Santo Domingo, Dominican Republic

— 4 nights
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Head to Mercado Modelo and Agora Mallfor some retail therapy. Popular historic sites such as Alcazar de Colon and Fortaleza Ozama are in your itinerary. There's much more to do: make a trip to Columbus Lighthouse (Faro A Colon), steep yourself in history at Ruinas del Hospital San Nicolás de Bari, admire the natural beauty at National Botanical Garden, and examine the collection at Bosque Jurasico 3D.

To see traveler tips, other places to visit, more things to do, and other tourist information, go to the Santo Domingo holiday planning app.

Traveling by flight from Havana to Santo Domingo takes 5.5 hours. Traveling from Havana to Santo Domingo, you'll lose 1 hour due to the time zone difference. Wrap up your sightseeing on the 18th (Wed) to allow time to take a shuttle to Punta Cana.

Things to do in Santo Domingo

Nature · Parks · Shopping · Historic Sites

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.
Do your shopping at Tropical Treasure and Palma Real Shopping Village. Get outdoors at Bavaro Beach and Saona Island. The adventure continues: stop by La Perla Dominicana.

To see traveler tips, more things to do, ratings, and tourist information, refer to the Punta Cana trip maker.

Take a shuttle from Santo Domingo to Punta Cana in 2 hours. Alternatively, you can drive; or fly. In May, daily temperatures in Punta Cana can reach 35°C, while at night they dip to 28°C. Finish up your sightseeing early on the 20th (Fri) so you can catch the flight back home.

Things to do in Punta Cana

Parks · Shopping · Outdoors · Beaches

Side Trip

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.

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.

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.