17 days in Caribbean Itinerary

17 days in Caribbean Itinerary

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Route & dates

17 days in Caribbean Itinerary

Start: Ocho Rios, Jamaica
bus:  1​h 45​min
1
Montego Bay, Jamaica
— 2 nights
Fly:  9​h
2
San Juan, Puerto Rico
— 5 nights
Fly:  4​h 45​min
3
Santo Domingo, Dominican Republic
— 3 nights
Fly:  4​h 15​min
4
Havana, Cuba
— 4 nights
+2
Fly + foot + bus:  2​h 15​min
5
West Bay, Cayman Islands
— 2 nights
+3
bus + foot + Fly + bus:  7​h 15​min
End: Ocho Rios, Jamaica

2
nights
Montego Bay, Jamaica

Montego Bay ©
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 7th (Wed), stop by Tropicana Jewelers, steep yourself in history at Rose Hall Great House, and then kick back and relax at Doctor's Cave Beach. Get ready for a full day of sightseeing on the 8th (Thu): tee off at Tryall Golf Course and then make a splash at Aquasol Beach Park.

To see where to stay, ratings, reviews, and other tourist information, read our Montego Bay trip maker .

Ocho Rios to Montego Bay is an approximately 2-hour bus ride. You can also drive. In March, daytime highs in Montego Bay are 34°C, while nighttime lows are 26°C. Cap off your sightseeing on the 9th (Fri) early enough to travel to San Juan.

Things to do in Montego Bay

#Outdoors, #Theme Parks, #Golf

Side Trip

Tryall Golf Course
Find places to stay Mar 7 — 9:
Highlights from your plan
Aquasol Beach Park ©
Aquasol Beach Park
Rose Hall Great House ©
Rose Hall Great House
Doctor's Cave Beach ©
Doctor's Cave Beach

5
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Old San Juan and San Juan National Historic Site are good opportunities to explore the local culture. Get out of town with these interesting San Juan side-trips: El Yunque Rain Forest (in El Yunque National Forest) and Museo de Arte de Ponce (in Ponce). There's much more to do: admire the masterpieces at Museo de Arte de Puerto Rico, shake up your sightseeing with a climbing tour, get engrossed in the history at Cathedral of San Juan Bautista, and stroll through Parque de las Palomas.

For maps, more things to do, photos, and tourist information, read San Juan vacation planner.

You can fly from Montego Bay to San Juan in 9 hours. Another option is to do a combination of bus and flight. Traveling from Montego Bay to San Juan, you'll lose 1 hour due to the time zone difference. March in San Juan sees daily highs of 34°C and lows of 26°C at night. Finish your sightseeing early on the 14th (Wed) so you can travel to Santo Domingo.

Things to do in San Juan

#Parks, #Outdoors, #Wildlife

Side Trips

Pine Grove Beach, El Yunque Rain Forest, Museo de Arte de Ponce
Find places to stay Mar 9 — 14:
Highlights from your plan
Old San Juan ©
Old San Juan
San Juan National Historic Site ©
San Juan National Historic Site
El Yunque Rain Forest ©
El Yunque Rain Forest

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.
Catedral Primada de America and Fort Ozama are good opportunities to explore the local culture. Visit Alcazar de Colon and Monasterio de San Francisco for their historical value. Next up on the itinerary: don't miss a visit to Zona Colonial, examine the collection at Bosque Jurasico 3D, ponder the world of politics at National Palace, and steep yourself in history at Ruinas del Hospital San Nicolás de Bari.

To see photos, more things to do, maps, and tourist information, use the Santo Domingo trip itinerary maker app .

Traveling by flight from San Juan to Santo Domingo takes 5 hours. Alternatively, you can do a combination of flight and bus; or ride a ferry. Wrap up your sightseeing on the 17th (Sat) to allow time to travel to Havana.

Things to do in Santo Domingo

#Historic Sites, #Museums
Find places to stay Mar 14 — 17:
Highlights from your plan
Catedral Primada de America
Catedral Primada de America
Alcazar de Colon ©
Alcazar de Colon
Fort Ozama ©
Fort Ozama

4
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Get some cultural insight at Old Havana and El Malecon. Popular historic sites such as El Morro and Old Square (Plaza Vieja) are in your itinerary. There's lots more to do: don't miss a visit to Plaza de la Catedral, admire the landmark architecture of Casa de la Amistad, wander the streets of Callejon de Hamel, and steep yourself in history at Castillo de San Carlos de la Cabana.

To find where to stay, reviews, maps, and other tourist information, read our Havana sightseeing app .

Getting from Santo Domingo to Havana by flight takes about 4.5 hours. You'll gain 1 hour traveling from Santo Domingo to Havana due to the time zone difference. March in Havana sees daily highs of 32°C and lows of 19°C at night. Cap off your sightseeing on the 21st (Wed) early enough to travel to West Bay.

Things to do in Havana

#Historic Sites, #Neighborhoods, #Museums
Find places to stay Mar 17 — 21:
Highlights from your plan
Old Havana ©
Old Havana
El Morro ©
El Morro
Old Square (Plaza Vieja) ©
Old Square (Plaza Vieja)

2
nights
West Bay, Cayman Islands

West Bay ©
West Bay is known for theme parks, adventure, wildlife, nature, and water activities. Your plan includes some of its best attractions: identify plant and animal life at Stingray City, brush up on your knowledge of spirits at Cayman Spirits Co. Distillery, see some colorful creatures with a scuba or snorkeling tour, and make a splash at Cayman Turtle Centre: Island Wildlife Encounter.

For ratings, reviews, other places to visit, and tourist information, go to the West Bay travel route builder app .

Traveling by combination of flight and bus from Havana to West Bay takes 2.5 hours. Traveling from Havana in March, West Bay is a bit warmer at night with lows of 27°C. Wrap up your sightseeing on the 23rd (Fri) to allow time to travel back home.

Things to do in West Bay

#Wildlife, #Parks, #Outdoors

Side Trips

Grand Cayman, Seven Mile Beach, Cayman Spirits Co. Distillery
Find places to stay Mar 21 — 23:
Highlights from your plan
Stingray City ©
Stingray City
Scuba & Snorkeling

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