17 days in Jamaica, Cuba & Dominican Republic Itinerary

17 days in Jamaica, Cuba & Dominican Republic Itinerary

Created using Inspirock Caribbean trip planner

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Route & dates

Start: London, United Kingdom
+2
Train + Fly + Bus:  15 h 15 min
1
Ocho Rios, Jamaica
— 1 night
Bus:  1 h 30 min
2
Montego Bay, Jamaica
— 2 nights
Bus + Fly:  5 h
3
Varadero, Cuba
— 1 night
Drive:  2 h
4
Havana, Cuba
— 5 nights
Fly:  2 h 45 min
5
Santo Domingo, Dominican Republic
— 3 nights
Taxi + Fly:  2 h
6
Punta Cana, Dominican Republic
— 4 nights
Fly + Train:  11 h 45 min
End: London, United Kingdom

1
night
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.
Kick off your visit on the 27th (Fri): take in the dramatic scenery at Dunn's River Falls and Park, trek along Fern Gully, and then take in the dramatic scenery at Blue Hole.

For maps, ratings, other places to visit, and other tourist information, use the Ocho Rios travel planning website.

London, UK to Ocho Rios is an approximately 15.5- hour combination of train, flight, and bus. You can also do a combination of train, flight, and bus; or do a combination of train and flight. The time zone difference moving from Greenwich Mean Time to Eastern Standard Time is minus 5 hours. Plan for much hotter temperatures traveling from London in March, with highs in Ocho Rios at 36°C and lows at 27°C. Wrap up your sightseeing on the 27th (Fri) early enough to take a bus to Montego Bay.

Things to do in Ocho Rios

Parks Nature Trails
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Fern Gully ©
Fern Gully

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 28th (Sat): surround yourself with nature on a nature and wildlife tour, then contemplate the long history of Rose Hall Great House, and then get some thrills out on the water with a waterskiing or jet-skiing adventure. On the next day, shop like a local with Cinnamon Hill Golf Course and then kick back and relax at Doctor's Cave Beach.

Planning Montego Bay trip won't be overwheling when you use's Insprock itinerary maker.

Take a bus from Ocho Rios to Montego Bay in 1.5 hours. Alternatively, you can drive. In March, plan for daily highs up to 36°C, and evening lows to 26°C. Wrap up your sightseeing on the 29th (Sun) to allow time to travel to Varadero.

Things to do in Montego Bay

Outdoors Wildlife Tours
Highlights from your plan
Nature & Wildlife Tours
Rose Hall Great House ©
Rose Hall Great House
Doctor's Cave Beach ©
Doctor's Cave Beach

1
night
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.
On the 30th (Mon), kick back and relax at Varadero Beach, explore the fascinating underground world of Cueva de Saturno, and then surround yourself with nature on a nature and wildlife tour.

To see maps, reviews, ratings, and more tourist information, read our Varadero day trip app.

Do a combination of bus and flight from Montego Bay to Varadero in 5 hours. Alternatively, you can do a combination of bus, flight, and train. Plan for little chillier temperatures traveling from Montego Bay in March, with highs in Varadero at 32°C and lows at 19°C. Finish your sightseeing early on the 30th (Mon) to allow enough time to drive to Havana.

Things to do in Varadero

Outdoors Wildlife Tours
Highlights from your plan
Varadero Beach ©
Varadero Beach
Cueva de Saturno ©
Cueva de Saturno

5
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Visit Old Havana and Old Square (Plaza Vieja) for their historical value. Do some cultural sightseeing at Malecón of Havana and Fortaleza de San Carlos de la Cabana. Get out of town with these interesting Havana side-trips: Cayo Largo (Playa Paraiso, Punta Mal Tiempo, &more). And it doesn't end there: surround yourself with nature on a nature and wildlife tour, pause for some photo ops at Neptune Statue, steep yourself in history at Castillo de la Real Fuerza, and take a stroll through Iglesias de San Francisco de Paula.

To see ratings, traveler tips, and more tourist information, read Havana road trip planning site.

Traveling by car from Varadero to Havana takes 2 hours. Alternatively, you can take a shuttle; or do a combination of taxi and train. Expect a daytime high around 32°C in March, and nighttime lows around 19°C. Cap off your sightseeing on the 4th (Sat) early enough to travel to Santo Domingo.

Things to do in Havana

Outdoors Historic Sites Parks

Side Trip

Cayo Largo
Highlights from your plan
Old Havana ©
Old Havana
Playa Paraiso ©
Playa Paraiso
Malecón of Havana ©
Malecón of Havana

3
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.
Get a sense of the local culture at Alcazar de Colon and Fortaleza Ozama. Visit Catedral Primada de America and Monasterio de San Francisco for their historical value. Next up on the itinerary: make a trip to Zona Colonial, take in the architecture and atmosphere at Basilica Cathedral of Santa Maria la Menor, admire the striking features of La Casa de Los Jesuitas, and examine the collection at Museo De Las Casas Reales.

To see ratings, maps, reviews, and tourist information, use the Santo Domingo day trip website.

You can fly from Havana to Santo Domingo in 3 hours. Due to the time zone difference, you'll lose 1 hour traveling from Havana to Santo Domingo. Cap off your sightseeing on the 7th (Tue) early enough to travel to Punta Cana.

Things to do in Santo Domingo

Historic Sites Museums Parks
Highlights from your plan
Catedral Primada de America
Catedral Primada de America
Alcazar de Colon ©
Alcazar de Colon
Zona Colonial ©
Zona Colonial

4
nights
Punta Cana, Dominican Republic

Punta Cana ©
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.
Take a break from the city and head to Bavaro Beach and Safaris. You'll enjoy a bit of beach vacationing at Playa La Vacama and Macao Beach. Next up on the itinerary: get close to the beloved marine mammals with a swim-with-the-dolphins experience, stop by Smile Dominicana, and explore the fascinating underground world of Cave Oleg Bat House.

Plan my trip to Punta Cana with suggested itineraries provided by Inspirock.

Traveling by combination of taxi and flight from Santo Domingo to Punta Cana takes 1.5 hours. Alternatively, you can take a shuttle; or drive. In April, daytime highs in Punta Cana are 35°C, while nighttime lows are 27°C. Cap off your sightseeing on the 11th (Sat) early enough to travel back home.

Things to do in Punta Cana

Outdoors Parks Wildlife
Highlights from your plan
Bavaro Beach ©
Bavaro Beach
Swim with Dolphins
Safaris

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