37 days in Caribbean Itinerary

37 days in Caribbean Itinerary

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Route & dates

37 days in Caribbean Itinerary

Start: Wellington, New Zealand
Fly:  29​h
1
Ocho Rios, Jamaica
— 7 nights
+3
bus + foot + bus + Fly:  5​h 15​min
2
George Town, Cayman Islands
— 4 nights
Fly + shuttle:  6​h 45​min
3
Bayahibe, Dominican Republic
— 1 day
shuttle + Fly:  5​h
4
Bouillante, Guadeloupe
— 3 nights
+2
bus + Drive + Fly:  1​h 45​min
5
Fort-de-France, Martinique
— 6 nights
Fly + bus:  2​h
6
Bridgetown, Barbados
— 4 nights
Fly:  8​h 45​min
7
Willemstad, Curacao
— 6 nights
Fly:  34​h
End: Wellington, New Zealand

7
nights
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.
Explore hidden gems such as Zipline and Spas. Explore Ocho Rios' surroundings by going to Greenwood Great House (in Montego Bay), Scuba & Snorkeling (in Runaway Bay) and Columbus Park (in Discovery Bay). Pack the 16th (Sun) with family-friendly diversions at Rainforest Adventures. The adventure continues: take in the dramatic scenery at Dunn's River Falls and Park, steep yourself in history at Good Hope Plantation, take a pleasant ride with a tour on horseback, and relax and float downstream with a rafting and tubing tour.

For traveler tips, ratings, reviews, and more tourist information, use the Ocho Rios online trip builder .

Wellington, New Zealand to Ocho Rios is an approximately 29-hour flight. You'll gain 17 hours traveling from Wellington to Ocho Rios due to the time zone difference. Traveling from Wellington in February, expect Ocho Rios to be somewhat warmer, temps between 36°C and 26°C. Finish your sightseeing early on the 18th (Tue) to allow enough time to travel to George Town.

Things to do in Ocho Rios

Outdoors Tours Parks

Side Trips

Bob Marley's Mausoleum, Greenwood Great House, Columbus Park, Scuba & Snorkeling, Good Hope Plantation
Find places to stay Feb 11 — 18:
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Shaw Park Gardens & Waterfalls ©
Shaw Park Gardens & Waterfalls
Zipline

4
nights
George Town, Cayman Islands

George Town ©
George Town is a city situated on Grand Cayman island of the Cayman Islands. Explore hidden gems such as Cayman Spirits Co. Distillery and Submarine Tours. Venture out of the city with trips to Mission House (in Bodden Town) and Davinoff's Concrete Sculpture Garden (in North Side). The adventure continues: identify plant and animal life at Stingray City, tour the pleasant surroundings at Rum Point, enjoy the sand and surf at Seven Mile Beach, and stop by Rocky's Diamonds.

For ratings, more things to do, other places to visit, and more tourist information, refer to the George Town online tour itinerary planner .

Getting from Ocho Rios to George Town by combination of bus and flight takes about 5.5 hours. In February, plan for daily highs up to 34°C, and evening lows to 27°C. Finish your sightseeing early on the 23rd (Sun) to allow enough time to travel to Bayahibe.

Things to do in George Town

Parks Wildlife Outdoors

Side Trips

Grand Cayman, Seven Mile Beach, Cayman Turtle Centre: Island Wildlife Encounter, Mission House, Davinoff's Concrete Sculpture Garden
Find places to stay Feb 18 — 23:
Highlights from your plan
Stingray City ©
Stingray City
Seven Mile Beach ©
Seven Mile Beach
Food Tours

1
day
Bayahibe, Dominican Republic

Bayahibe ©
Located on the shore of the Caribbean Sea, the town of Bayahibe has grown from a fishing village into a bona fide tourist destination, with visitors mainly drawn to the many dive sites just off the coast.
On the 24th (Mon), explore the wealth of natural beauty at National Park of the East.

For more things to do, ratings, photos, and tourist information, go to the Bayahibe trip itinerary planner.

You can do a combination of flight and shuttle from George Town to Bayahibe in 7 hours. Traveling from George Town to Bayahibe, you'll lose 1 hour due to the time zone difference. Traveling from George Town in February, Bayahibe is little chillier at night with lows of 22°C. Finish your sightseeing early on the 24th (Mon) so you can travel to Bouillante.

Things to do in Bayahibe

Nature Parks
Find places to stay Feb 23 — 24:
Highlights from your plan
National Park of the East ©
National Park of the East

3
nights
Bouillante, Guadeloupe

Bouillante is a commune in the French overseas region and department of Guadeloupe, in the Lesser Antilles.HistoryBouillante was founded about 1635 with the arrival of some of Guadeloupe's first colonists. Eschew the tourist crowds and head to Scuba & Snorkeling and Reve de Sable. Explore the numerous day-trip ideas around Bouillante: Anse du Souffleur (in Port-Louis) and Deshaies (Jardin Botanique de Deshaies & Plage de Grande Anse). And it doesn't end there: take a memorable tour with Tours, stop by Cap Créole, and admire nature's wide array of creatures at Parc des Mamelles, le Zoo de Guadeloupe.

To see maps, more things to do, and tourist information, refer to the Bouillante trip itinerary tool .

You can do a combination of shuttle and flight from Bayahibe to Bouillante in 5 hours. In February in Bouillante, expect temperatures between 34°C during the day and 24°C at night. Finish your sightseeing early on the 27th (Thu) to allow enough time to travel to Fort-de-France.

Things to do in Bouillante

Outdoors Parks Tours

Side Trips

Deshaies, Anse du Souffleur, Reve de Sable
Find places to stay Feb 24 — 27:
Highlights from your plan
Scuba & Snorkeling
Kayaking & Canoeing
Anse du Souffleur ©
Anse du Souffleur

6
nights
Fort-de-France, Martinique

The political capital of Martinique, Fort-de-France has a thriving commercial center and a number of historic sites.
Eschew the tourist crowds and head to Anse Dufour and Dolphin & Whale Watching. Change things up with these side-trips from Fort-de-France: La Savane des Esclaves (in Trois-Ilets), Sainte-Anne (Etang des Salines & Savane Des Petrifications) and Les Anses d'Arlet (Stand-Up Paddleboarding & St. Henry Catholic Church). Spend the 4th (Wed) exploring nature at Parc Naturel Regional de la Martinique. There's much more to do: take in nature's colorful creations at Jardin de Balata, take in the spiritual surroundings of St. Louis Cathedral, get some thrills out on the water with a waterskiing or jet-skiing adventure, and browse the collection at Schoelcher Library.

For reviews, other places to visit, photos, and other tourist information, use the Fort-de-France trip itinerary builder site .

You can do a combination of car and flight from Bouillante to Fort-de-France in 2 hours. Another option is to ride a ferry. In February, daily temperatures in Fort-de-France can reach 34°C, while at night they dip to 26°C. Finish up your sightseeing early on the 4th (Wed) so you can travel to Bridgetown.

Things to do in Fort-de-France

Outdoors Parks Tours

Side Trips

Trois-Ilets, Les Anses d'Arlet, Sainte-Anne, Habitation Clement, Le Morne Gommier
Find places to stay Feb 27 — Mar 4:
Highlights from your plan
Dolphin & Whale Watching
Anse Dufour
Anse Dufour
Jardin de Balata ©
Jardin de Balata

4
nights
Bridgetown, Barbados

Bridgetown ©
Bridgetown is the capital and largest city of Barbados. You'll explore the less-touristy side of things at Bottom Bay and Pebbles Beach. Venture out of the city with trips to Sunbury Plantation House (in Saint Philip Parish) and Bathsheba (Bathsheba Beach & Andromeda Botanic Gardens). The adventure continues: enjoy the sand and surf at Carlisle Bay, view the masterpieces at Best of Barbados Gift Shop, steep yourself in history at Parliament Buildings, and take in panoramic vistas at Gun Hill Signal Station.

To see other places to visit, maps, where to stay, and tourist information, read our Bridgetown attractions planning app .

Getting from Fort-de-France to Bridgetown by combination of flight and bus takes about 2 hours. Other options: do a combination of ferry and flight. In March in Bridgetown, expect temperatures between 34°C during the day and 28°C at night. Finish up your sightseeing early on the 8th (Sun) so you can travel to Willemstad.

Things to do in Bridgetown

Outdoors Parks Beaches

Side Trips

Bathsheba, Saint Philip Parish, Gun Hill Signal Station, Best of Barbados Gift Shop, Worthing Beach
Find places to stay Mar 4 — 8:
Highlights from your plan
Worthing Beach ©
Worthing Beach
Nidhe Israel Synagogue and Museum ©
Nidhe Israel Synagogue and Museum
Pebbles Beach ©
Pebbles Beach

6
nights
Willemstad, Curacao

Willemstad is the capital city of Curaçao, an island in the southern Caribbean Sea that forms a constituent country of the Kingdom of the Netherlands. You'll explore the less-touristy side of things at Klein (Little) Curacao and Adrenaline & Extreme Tours. Take a break from Willemstad with a short trip to Church of Sint Willibrordus in Sint Willibrordus, about 54 minutes away. There's lots more to do: snap pictures at Queen Emma Pontoon Bridge, take in the waterfront at Handelskade, enjoy the sand and surf at Playa Lagun, and admire the masterpieces at Kura Hulanda Museum.

To see where to stay, photos, traveler tips, and more tourist information, you can read our Willemstad visit planner.

Traveling by flight from Bridgetown to Willemstad takes 9 hours. In March in Willemstad, expect temperatures between 36°C during the day and 29°C at night. Wrap up your sightseeing on the 15th (Sun) early enough to travel back home.

Things to do in Willemstad

Outdoors Parks Beaches

Side Trips

Curacao, Church of Sint Willibrordus
Find places to stay Mar 8 — 15:
Highlights from your plan
Adrenaline & Extreme Tours
Queen Emma Pontoon Bridge ©
Queen Emma Pontoon Bridge
Queen Juliana Bridge ©
Queen Juliana Bridge

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