29 days in Caribbean Itinerary

29 days in Caribbean Itinerary

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Route & dates

29 days in Caribbean Itinerary

Start: Brisbane, Australia
Fly:  28​h
1
Kingston, Jamaica
— 4 nights
Fly:  2​h 45​min
2
Montego Bay, Jamaica
— 5 nights
Fly:  11​h 30​min
3
Saint Francois, Guadeloupe
— 3 nights
Fly:  2​h 30​min
4
Fort-de-France, Martinique
— 5 nights
Fly:  5​h 15​min
5
Havana, Cuba
— 8 nights
Fly:  26​h
End: Brisbane, Australia

4
nights
Kingston, Jamaica

Kingston ©
The country's capital, Kingston offers all the excitement of a lively and storied city, while also housing the services and facilities travelers need to get around and see the rest of the island.
Venture out of the city with trips to Ocho Rios (Dunn's River Falls and Park & Blue Hole), Reach Falls (in Port Antonio) and Blue Mountain Peak (in Blue Mountains National Park). There's still lots to do: stroll the grounds of Bob Marley Museum, look for gifts at Chocolate Dreams, browse the different shops at Morgans Creek Ltd, and make a trip to Patwa Apparel.

To find reviews, photos, where to stay, and more tourist information, you can read our Kingston trip planner .

Brisbane, Australia to Kingston is an approximately 28-hour flight. You can also do a combination of flight and bus; or do a combination of bus and flight. You'll gain 15 hours traveling from Brisbane to Kingston due to the time zone difference. Traveling from Brisbane in December, things will get somewhat warmer in Kingston: highs are around 36°C and lows about 28°C. Finish your sightseeing early on the 5th (Sat) to allow enough time to travel to Montego Bay.

Things to do in Kingston

Nature Parks Historic Sites

Side Trips

Ocho Rios, Blue Mountain Peak, Bob Marley Museum, Reach Falls, Patwa Apparel
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Blue Mountain Peak ©
Blue Mountain Peak
Reach Falls ©
Reach Falls

5
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.
Explore the numerous day-trip ideas around Montego Bay: Mayfield Falls Jamaica (Original) (in Pennycooke), Seven Mile Beach (in Negril) and Tryall Golf Course (in Sandy Bay). There's much more to do: admire the sheer force of YS Falls, play a few rounds at Cinnamon Hill Golf Course, stroll through Doctor's Cave Beach, and contemplate the long history of Rose Hall Great House.

To find photos, ratings, more things to do, and tourist information, use the Montego Bay day trip app .

Fly from Kingston to Montego Bay in 3 hours. Alternatively, you can drive; or take a bus. In December, plan for daily highs up to 36°C, and evening lows to 27°C. Cap off your sightseeing on the 10th (Thu) early enough to travel to Saint Francois.

Things to do in Montego Bay

Outdoors Parks Wildlife

Side Trips

YS Falls, Tryall Golf Course, Mayfield Falls Jamaica (Original), Seven Mile Beach, Rocklands Bird Sanctuary (Near Montego Bay)
Highlights from your plan
Nature & Wildlife Tours
YS Falls ©
YS Falls
Seven Mile Beach ©
Seven Mile Beach

3
nights
Saint Francois, Guadeloupe

Saint Francois ©
A modern seaside resort town, Saint Francois attracts visitors with its well-preserved landscape and coastline, along with its large number of luxury hotels.
Venture out of the city with trips to La Soufriere Volcano (in Saint-Claude), Parc des Mamelles, le Zoo de Guadeloupe (in Bouillante) and Deshaies (Plage de Grande Anse & Jardin Botanique de Deshaies). Next up on the itinerary: appreciate the extensive heritage of Pointe des Chateaux, look for gifts at Boutique Ti Lolo La - Vegetables peyi s Exotic fruits, Vanilla, Spices., explore the striking landscape at Porte d'Enfer, and head outdoors with Location Voilier Guadeloupe.

For more things to do, other places to visit, maps, and other tourist information, refer to the Saint Francois tour planner .

You can fly from Montego Bay to Saint Francois in 11.5 hours. The time zone changes from Eastern Standard Time to Atlantic Standard Time, which is usually a 1 hour difference. In December, daytime highs in Saint Francois are 34°C, while nighttime lows are 26°C. Cap off your sightseeing on the 14th (Mon) early enough to travel to Fort-de-France.

Things to do in Saint Francois

Parks Historic Sites Outdoors

Side Trips

Deshaies, Parc des Mamelles, le Zoo de Guadeloupe, La Soufriere Volcano, Porte d'Enfer
Highlights from your plan
La Soufriere Volcano ©
La Soufriere Volcano
Pointe des Chateaux ©
Pointe des Chateaux
Plage de Grande Anse ©
Plage de Grande Anse

5
nights
Fort-de-France, Martinique

Fort-de-France ©
The political capital of Martinique, Fort-de-France has a thriving commercial center and a number of historic sites.
Venture out of the city with trips to La Savane des Esclaves (in Trois-Ilets), Plage des Salines (in Sainte-Anne) and Zoo de Martinique - Habitation Latouche (in Le Carbet). There's still lots to do: contemplate the geological forces at Montagne Pelee, kick back and relax at Pointe du Bout, stroll through Presqu'ile de la Caravelle, and take your sightseeing to a higher altitude at Pitons du Carbet.

To find other places to visit, more things to do, where to stay, and more tourist information, go to the Fort-de-France route tool .

Traveling by flight from Saint Francois to Fort-de-France takes 2.5 hours. Alternatively, you can ride a ferry. In December, plan for daily highs up to 34°C, and evening lows to 27°C. Finish up your sightseeing early on the 19th (Sat) so you can travel to Havana.

Things to do in Fort-de-France

Parks Outdoors Nature

Side Trips

Arrondissement of Saint-Pierre, Les Anses d'Arlet, Martinique, Trois-Ilets, Presqu'ile de la Caravelle
Highlights from your plan
Montagne Pelee ©
Montagne Pelee
Jardin de Balata ©
Jardin de Balata
La Savane des Esclaves ©
La Savane des Esclaves

8
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 out of town with these interesting Havana side-trips: Cayo Largo (Playa Paraiso & Sea Turtle Hatchery). There's lots more to do: get to know the fascinating history of Malecón of Havana, take in the local highlights with Walking tours, make a trip to Old Havana, and admire the masterpieces at Museu Nacional de Belas Artes de Cuba.

To find photos, ratings, where to stay, and more tourist information, read Havana visit planner .

Fly from Fort-de-France to Havana in 5.5 hours. Alternatively, you can do a combination of ferry and flight; or do a combination of ferry, bus, and flight. You'll gain 1 hour traveling from Fort-de-France to Havana due to the time zone difference. Traveling from Fort-de-France in December, plan for slightly colder nights in Havana, with lows around 20°C. Wrap up your sightseeing on the 27th (Sun) to allow time to travel back home.

Things to do in Havana

Historic Sites Tours Parks

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

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