60 days in Caribbean Itinerary

60 days in Caribbean Itinerary

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Route & dates

60 days in Caribbean Itinerary

Start: Toronto, Canada
Fly:  6​h
1
Palm - Eagle Beach, Aruba
— 4 nights
Fly + bus:  1​h 45​min
2
Willemstad, Curacao
— 6 nights
Fly:  8​h 45​min
3
Bridgetown, Barbados
— 4 nights
bus + Fly:  2​h
4
Fort-de-France, Martinique
— 2 nights
ferry + Drive:  1​h 30​min
5
Soufriere, St. Lucia
— 4 nights
Fly:  4​h 45​min
6
Basseterre, St. Kitts and Nevis
— 2 nights
Fly + ferry:  2​h 15​min
7
Virgin Gorda, British Virgin Islands
— 3 nights
Fly:  4​h 15​min
8
Providenciales, Turks and Caicos
— 6 nights
Fly:  4​h 30​min
9
Montego Bay, Jamaica
— 5 nights
bus:  1​h 45​min
10
Ocho Rios, Jamaica
— 5 nights
+3
bus + foot + bus + Fly:  4​h 30​min
11
George Town, Cayman Islands
— 4 nights
Fly:  1​h 30​min
12
Havana, Cuba
— 6 nights
Fly:  4​h
13
Nassau, Bahamas
— 7 nights
Fly:  7​h
End: Toronto, Canada

4
nights
Palm - Eagle Beach, Aruba

Palm - Eagle Beach ©
A long stretch of powdery white sand and aquamarine waters, Palm - Eagle Beach remains one of Aruba's most visited vacation spots.
Go for a jaunt from Palm - Eagle Beach to San Nicolas to see Baby Beach about 48 minutes away. Next up on the itinerary: stroll through Eagle Beach, stop by Kay's Fine Jewelry, contemplate the long history of Antilla Shipwreck, and enjoy the sand and surf at Palm Beach.

To find more things to do, where to stay, photos, and tourist information, read Palm - Eagle Beach travel route planner.

Toronto, Canada to Palm - Eagle Beach is an approximately 6-hour combination of flight and car. You can also do a combination of bus, flight, and car. The time zone difference when traveling from Toronto to Palm - Eagle Beach is 1 hour. In December, Palm - Eagle Beach is much hotter than Toronto - with highs of 36°C and lows of 30°C. Wrap up your sightseeing on the 5th (Wed) early enough to travel to Willemstad.

Things to do in Palm - Eagle Beach

Parks Outdoors Beaches

Side Trips

Oranjestad, Noord, Santa Cruz, Baby Beach
Find places to stay Dec 1 — 5:
Highlights from your plan
Eagle Beach ©
Eagle Beach
Palm Beach ©
Palm Beach
Arikok National Park ©
Arikok National Park

6
nights
Willemstad, Curacao

Willemstad ©
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. Take a break from Willemstad with a short trip to Church of Sint Willibrordus in Sint Willibrordus, about 54 minutes away. And it doesn't end there: head off the coast to Klein (Little) Curacao, enjoy the sand and surf at Playa Porto Marie, see the interesting displays at Mikve Israel-Emanuel Synagogue, and discover the deep blue sea with a scuba or snorkeling tour.

To see where to stay, reviews, more things to do, and other tourist information, you can read our Willemstad travel itinerary planner.

Traveling by combination of car, flight, and bus from Palm - Eagle Beach to Willemstad takes 2 hours. Expect a daytime high around 35°C in December, and nighttime lows around 29°C. Finish your sightseeing early on the 11th (Tue) so you can travel to Bridgetown.

Things to do in Willemstad

Parks Outdoors Beaches

Side Trips

Curacao, Church of Sint Willibrordus
Find places to stay Dec 5 — 11:
Highlights from your plan
Klein (Little) Curacao ©
Klein (Little) Curacao
Queen Emma Pontoon Bridge ©
Queen Emma Pontoon Bridge
Cas Abao Beach ©
Cas Abao Beach

4
nights
Bridgetown, Barbados

Bridgetown ©
Bridgetown is the capital and largest city of Barbados. You'll find plenty of places to visit near Bridgetown: Animal Flower Cave (in Saint Lucy Parish), Saint Peter Parish (St. Nicholas Abbey & Barbados Wildlife Reserve) and Saint Philip Parish (Sunbury Plantation House, Foul Bay, & more). And it doesn't end there: Head underground at Harrison's Cave, enjoy breathtaking views from Gun Hill Signal Station, take a peaceful walk through Flower Forest, and get a new perspective on things with Jammin Catamaran Cruises.

To see reviews and tourist information, use the Bridgetown day trip app .

Traveling by flight from Willemstad to Bridgetown takes 9 hours. In December in Bridgetown, expect temperatures between 34°C during the day and 28°C at night. Wrap up your sightseeing on the 16th (Sun) early enough to travel to Fort-de-France.

Things to do in Bridgetown

Parks Historic Sites Outdoors

Side Trips

Saint Joseph Parish, Saint Philip Parish, Saint Peter Parish, Saint Thomas Parish, Animal Flower Cave
Find places to stay Dec 11 — 16:
Highlights from your plan
Hunte's Gardens ©
Hunte's Gardens
Harrison's Cave. ©
Harrison's Cave.
Bottom Bay ©
Bottom Bay

2
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.
On the 17th (Mon), stop by Tournicoti Parapluie, then kick back and relax at Pointe du Bout, then take an in-depth tour of La Savane des Esclaves, and finally take in nature's colorful creations at Jardin de Balata. Here are some ideas for day two: browse the collection at Schoelcher Library, contemplate in the serene atmosphere at St. Louis Cathedral, then look for gifts at Grand Marche, and finally stroll through Les Salines Beach.

To find photos, maps, more things to do, and tourist information, use the Fort-de-France day trip planning website .

Traveling by combination of bus and flight from Bridgetown to Fort-de-France takes 2 hours. Alternatively, you can do a combination of flight and ferry. Expect a daytime high around 34°C in December, and nighttime lows around 27°C. Finish your sightseeing early on the 18th (Tue) so you can travel to Soufriere.

Things to do in Fort-de-France

Parks Beaches Outdoors

Side Trips

Trois-Ilets, Martinique
Find places to stay Dec 16 — 18:
Highlights from your plan
Jardin de Balata ©
Jardin de Balata
La Savane des Esclaves ©
La Savane des Esclaves
St. Louis Cathedral ©
St. Louis Cathedral

4
nights
Soufriere, St. Lucia

Soufriere ©
Home to some of Saint Lucia's landmark buildings and natural features, Soufriere provides travelers with an engaging and direct route into the center of island life.
Step out of Soufriere to go to Castries and see Rodney Bay, which is approximately 1h 15 min away. There's lots more to do: get impressive views of Pitons, get some thrills on the water with a speed boat tour, explore the activities along Marigot Bay, and tour the pleasant surroundings at Tet Paul Nature Trail.

For maps, reviews, ratings, and more tourist information, read Soufriere trip itinerary builder site .

You can do a combination of flight and car from Fort-de-France to Soufriere in 1.5 hours. Another option is to do a combination of ferry and bus. Expect a daytime high around 34°C in December, and nighttime lows around 28°C. Wrap up your sightseeing on the 22nd (Sat) early enough to travel to Basseterre.

Things to do in Soufriere

Parks Outdoors Nature

Side Trips

St. Lucia, Rodney Bay
Find places to stay Dec 18 — 22:
Highlights from your plan
Gros Piton ©
Gros Piton
Diamond Falls Botanical Gardens ©
Diamond Falls Botanical Gardens
Marigot Bay ©
Marigot Bay

2
nights
Basseterre, St. Kitts and Nevis

Basseterre ©
Basseterre, estimated population 13,000 in 2011, is the capital of the Federation of Saint Kitts and Nevis in the West Indies. On the 23rd (Sun), tee off at Royal St. Kitts Golf Club, stop by Royal Gems, and then explore the wealth of natural beauty at Brimstone Hill Fortress. On the 24th (Mon), you'll have a packed day of sightseeing: cruise along Timothy Hill, head outdoors with Frigate Bay, and then take in the awesome beauty at Mount Liamuiga.

For more things to do, photos, maps, and tourist information, you can read our Basseterre online trip maker .

Fly from Soufriere to Basseterre in 5 hours. In December, daily temperatures in Basseterre can reach 34°C, while at night they dip to 28°C. Finish your sightseeing early on the 24th (Mon) so you can travel to Virgin Gorda.

Things to do in Basseterre

Nature Parks Outdoors

Side Trips

St. Kitts, Royal St. Kitts Golf Club
Find places to stay Dec 22 — 24:
Highlights from your plan
Brimstone Hill Fortress National Park ©
Frigate Bay ©
Frigate Bay
Royal St. Kitts Golf Club ©
Royal St. Kitts Golf Club

3
nights
Virgin Gorda, British Virgin Islands

Virgin Gorda ©
Thankfully lacking some of the commercialism of other islands nearby, Virgin Gorda offers a relaxing place to holiday, and maintains a feeling of intimacy despite its reputation as an exclusive destination.
Spend the 26th (Wed) exploring nature at Devil's Bay National Park. There's much more to do: take in the dramatic natural features at The Baths, head off the coast to Cooper Island, enjoy the sand and surf at Spring Bay, and explore the activities along Savannah Bay.

For ratings, reviews, more things to do, and tourist information, go to the Virgin Gorda trip itinerary planning website .

Traveling by combination of flight and ferry from Basseterre to Virgin Gorda takes 2.5 hours. Alternatively, you can do a combination of flight, car, and ferry. In December in Virgin Gorda, expect temperatures between 34°C during the day and 28°C at night. Wrap up your sightseeing on the 27th (Thu) early enough to travel to Providenciales.

Things to do in Virgin Gorda

Parks Nature Beaches

Side Trip

Cooper Island
Find places to stay Dec 24 — 27:
Highlights from your plan
Spring Bay ©
Spring Bay
The Baths ©
The Baths
Cooper Island ©
Cooper Island

6
nights
Providenciales, Turks and Caicos

Providenciales ©
The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
Providenciales is known for adventure, beaches, nature, outdoors, and spas. Your plan includes some of its best attractions: kick back and relax at Grace Bay, tour the pleasant surroundings at Mudjin Harbor, explore the gorgeous colors at Smith's Reef, and tee off at Provo Golf Club.

To see ratings, photos, other places to visit, and tourist information, use the Providenciales vacation maker .

Do a combination of ferry and flight from Virgin Gorda to Providenciales in 4.5 hours. Alternatively, you can do a combination of ferry, car, and flight. Traveling from Virgin Gorda to Providenciales, you'll gain 1 hour due to the time zone difference. December in Providenciales sees daily highs of 33°C and lows of 28°C at night. Finish your sightseeing early on the 2nd (Wed) to allow enough time to travel to Montego Bay.

Things to do in Providenciales

Parks Outdoors Beaches

Side Trips

Smith's Reef, Mudjin Harbor
Find places to stay Dec 27 — Jan 2:
Highlights from your plan
Grace Bay Beach ©
Grace Bay Beach
Provo Golf Club ©
Provo Golf Club
Little Water Cay ©
Little Water Cay

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 Montego Bay's surroundings by going to Tryall Golf Course (in Sandy Bay) and Negril (Seven Mile Beach & Mayfield Falls). Spend the 5th (Sat) wandering through the wild on a nature and wildlife tour. The adventure continues: kick back and relax at Doctor's Cave Beach, shop like a local with White Witch Golf Course, steep yourself in history at Rose Hall Great House, and play a few rounds at Cinnamon Hill Golf Course.

For other places to visit, reviews, where to stay, and tourist information, refer to the Montego Bay trip planning tool .

You can fly from Providenciales to Montego Bay in 4.5 hours. Another option is to do a combination of flight and bus. January in Montego Bay sees daily highs of 35°C and lows of 26°C at night. Finish your sightseeing early on the 7th (Mon) to allow enough time to take a bus to Ocho Rios.

Things to do in Montego Bay

Outdoors Shopping Parks

Side Trips

Tryall Golf Course, Original Mayfield Falls Jamaica, Seven Mile Beach
Find places to stay Jan 2 — 7:
Highlights from your plan
Nature & Wildlife Tours
Seven Mile Beach ©
Seven Mile Beach
White Witch Golf Course ©
White Witch Golf Course

5
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.
Change things up with these side-trips from Ocho Rios: Blue Mountain Peak (in Blue Mountains National Park), Green Grotto Caves (in Runaway Bay) and Columbus Park (in Discovery Bay). Next up on the itinerary: take in the dramatic scenery at Dunn's River Falls and Park, take a pleasant ride with a tour on horseback, pause for some serene contemplation at Our Lady of Fatima Catholic Church, and hike along Fern Gully.

For other places to visit, photos, and other tourist information, refer to the Ocho Rios vacation planning tool .

You can take a bus from Montego Bay to Ocho Rios in 2 hours. Alternatively, you can drive. In January in Ocho Rios, expect temperatures between 36°C during the day and 27°C at night. Finish your sightseeing early on the 12th (Sat) to allow enough time to travel to George Town.

Things to do in Ocho Rios

Parks Outdoors Nature

Side Trips

Columbus Park, Blue Mountain Peak, Green Grotto Caves, Firefly
Find places to stay Jan 7 — 12:
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Blue Mountain Peak ©
Blue Mountain Peak
Green Grotto Caves ©
Green Grotto Caves

4
nights
George Town, Cayman Islands

George Town is a city situated on Grand Cayman island of the Cayman Islands. George Town is known for adventure, breweries, shopping, fun & games, and museums. Your plan includes some of its best attractions: identify plant and animal life at Stingray City, hike along Queen Elizabeth II Botanic Park, sample the fine beverages at Cayman Spirits Co. Distillery, and discover the deep blue sea with a scuba or snorkeling tour.

For traveler tips, more things to do, photos, and tourist information, you can read our George Town trip itinerary planning tool .

Traveling by combination of bus and flight from Ocho Rios to George Town takes 4.5 hours. In January, plan for daily highs up to 33°C, and evening lows to 27°C. Wrap up your sightseeing on the 16th (Wed) to allow time to travel to Havana.

Things to do in George Town

Parks Wildlife Outdoors

Side Trips

Grand Cayman, Seven Mile Beach, Cayman Turtle Centre: Island Wildlife Encounter
Find places to stay Jan 12 — 16:
Highlights from your plan
Scuba & Snorkeling
Stingray City Grand Cayman ©
Stingray City Grand Cayman
Seven Mile Beach ©
Seven Mile Beach

6
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Havana is known for historic sites, museums, nightlife, beaches, and parks. Your plan includes some of its best attractions: appreciate the extensive heritage of Old Havana, admire the striking features of Casa de la Amistad, steep yourself in history at Old Square (Plaza Vieja), and get engrossed in the history at Museum of the Revolution (Museo de la Revolucion).

To see ratings, reviews, more things to do, and more tourist information, read our Havana trip itinerary builder .

You can fly from George Town to Havana in 1.5 hours. Plan for a bit cooler nights when traveling from George Town in January since evenings lows in Havana dip to 19°C. Finish up your sightseeing early on the 22nd (Tue) so you can travel to Nassau.

Things to do in Havana

Historic Sites Museums Beaches
Find places to stay Jan 16 — 22:
Highlights from your plan
Old Havana ©
Old Havana
El Malecon ©
El Malecon
Plaza de la Catedral ©
Plaza de la Catedral

7
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.
Change things up with a short trip to Pink Sands Beach in Harbour Island (about 1h 40 min away). Plan for a day of cool, family-friendly fun on the 28th (Mon) at Aquaventure Water Park at Atlantis Paradise Island. There's still lots to do: admire nature's wide array of creatures at Marine Habitat at Atlantis, admire the natural beauty at Versailles Gardens and French Cloister, stroll through Cabbage Beach, and step off the mainland to explore Blue Lagoon Island.

To find photos, traveler tips, ratings, and other tourist information, read Nassau trip planner.

You can fly from Havana to Nassau in 4 hours. January in Nassau sees daily highs of 31°C and lows of 22°C at night. Wrap up your sightseeing on the 29th (Tue) early enough to travel back home.

Things to do in Nassau

Parks Outdoors Beaches

Side Trips

Paradise Island, Pink Sands Beach
Find places to stay Jan 22 — 29:
Highlights from your plan
Marine Habitat at Atlantis ©
Marine Habitat at Atlantis
Cable Beach ©
Cable Beach
Pink Sands Beach ©
Pink Sands Beach

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