16 days in Caribbean Itinerary

16 days in Caribbean Itinerary

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Route & dates

16 days in Caribbean Itinerary

Start: Auckland, New Zealand
Fly:  22 h
1
Nassau, Bahamas
— 2 nights
Fly:  2 h
2
Havana, Cuba
— 5 nights
Fly:  2 h 45 min
3
Santo Domingo, Dominican Republic
— 3 nights
Fly + Bus:  8 h 45 min
4
Ocho Rios, Jamaica
— 1 night
Bus:  1 h 30 min
5
Montego Bay, Jamaica
— 2 nights
Fly:  23 h
End: Auckland, New Zealand

2
nights
Nassau, Bahamas

Nassau ©
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 21st (Sun): meet the residents at Marine Habitat at Atlantis and then enjoy the sand and surf at Cable Beach. Get ready for a full day of sightseeing on the next day: step off the mainland to explore Blue Lagoon Island and then play a few rounds at Ocean Club Golf Course.

To see traveler tips, ratings, and other tourist information, refer to the Nassau trip itinerary builder app .

Auckland, New Zealand to Nassau is an approximately 22-hour flight. Traveling from Auckland to Nassau, you'll gain 17 hours due to the time zone difference. When traveling from Auckland in June, plan for warmer days and a bit warmer nights in Nassau: temperatures range from 37°C by day to 28°C at night. Finish your sightseeing early on the 22nd (Mon) so you can travel to Havana.

Things to do in Nassau

Parks Outdoors Zoos & Aquariums

Side Trip

Paradise Island
Highlights from your plan
Cable Beach ©
Cable Beach
Marine Habitat at Atlantis ©
Marine Habitat at Atlantis
Blue Lagoon Island ©
Blue Lagoon Island

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.
Explore the numerous day-trip ideas around Havana: Cayo Largo (Playa Mal Tiempo & Sirena Beach). The adventure continues: appreciate the extensive heritage of Malecón of Havana, take an in-depth tour of Museum of the Revolution (Museo de la Revolucion), take a stroll through Callejon de Hamel, and make a trip to Paseo del Prado.

To find traveler tips, other places to visit, photos, and other tourist information, read our Havana route planner.

Fly from Nassau to Havana in 2 hours. In June, daily temperatures in Havana can reach 36°C, while at night they dip to 26°C. Finish your sightseeing early on the 27th (Sat) so you can travel to Santo Domingo.

Things to do in Havana

Historic Sites Outdoors Beaches

Side Trips

Cayo Largo, Espiritu Santo Church (Iglesia Del Espiritu Santo)
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Plaza de la Catedral ©
Plaza de la Catedral

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.
Santo Domingo is known for historic sites, nature, and shopping. Your plan includes some of its best attractions: steep yourself in history at Alcazar de Colon, don't miss a visit to Zona Colonial, explore the fascinating underground world of Los Tres Ojos, and observe the fascinating underwater world at National Aquarium.

To see photos, where to stay, reviews, and other tourist information, you can read our Santo Domingo sightseeing planner.

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. Finish your sightseeing early on the 30th (Tue) to allow enough time to travel to Ocho Rios.

Things to do in Santo Domingo

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

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.
Start off your visit on the 1st (Wed): Head underground at Green Grotto Caves. Here are some ideas for day two: take in the dramatic scenery at Dunn's River Falls and Park, trek along Fern Gully, and then admire the sheer force of Blue Hole.

To find photos, maps, traveler tips, and more tourist information, read Ocho Rios journey builder tool .

Getting from Santo Domingo to Ocho Rios by combination of flight and bus takes about 9 hours. The time zone difference moving from Atlantic Standard Time to Eastern Standard Time is minus 1 hour. In July in Ocho Rios, expect temperatures between 38°C during the day and 30°C at night. Wrap up your sightseeing on the 2nd (Thu) early enough to take a bus to Montego Bay.

Things to do in Ocho Rios

Parks Nature Trails

Side Trip

Green Grotto Caves
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Green Grotto Caves ©
Green Grotto Caves
Fern Gully ©
Fern Gully

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.
Kick off your visit on the 3rd (Fri): play a few rounds at Half Moon Golf, Tennis & Beach Club, then steep yourself in history at Rose Hall Great House, and then get a taste of the local shopping with White Witch Golf Course.

Plan my trip to Montego Bay with suggested itineraries provided by Inspirock.

Traveling by bus from Ocho Rios to Montego Bay takes 1.5 hours. Alternatively, you can drive. In July, daily temperatures in Montego Bay can reach 39°C, while at night they dip to 29°C. Finish up your sightseeing early on the 4th (Sat) so you can travel back home.

Things to do in Montego Bay

Outdoors Golf Shopping
Highlights from your plan
White Witch Golf Course ©
White Witch Golf Course
Rose Hall Great House ©
Rose Hall Great House

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