50 days in Caribbean Itinerary

50 days in Caribbean Itinerary

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Route & dates

50 days in Caribbean Itinerary

Start: Tampa, United States
Fly:  7​h 30​min
1
Charlotte Amalie, U.S. Virgin Islands
— 10 nights
Fly:  1​h 30​min
2
Philipsburg, St. Maarten-St. Martin
— 11 nights
Fly:  3​h 15​min
3
Trois-Ilets, Martinique
— 4 nights
Fly + bus:  2​h 15​min
4
Bridgetown, Barbados
— 7 nights
Fly:  8​h 45​min
5
Willemstad, Curacao
— 5 nights
Fly:  4​h 45​min
6
Santo Domingo, Dominican Republic
— 6 nights
+3
Fly + taxi + train + bus:  12​h 15​min
7
Trinidad, Cuba
— 3 nights
+3
train + taxi + Fly + bus:  15​h
End: Tampa, United States

10
nights
Charlotte Amalie, U.S. Virgin Islands

Charlotte Amalie ©
One of the most visited cruise ship destinations in the Caribbean, the town of Charlotte Amalie is known around the world for its duty-free jewelry, perfume, and liquor shops.
Discover out-of-the-way places like Morningstar Beach and Lindqvist Beach. Museum-lovers will appreciate Mystic Valley VI and Mitchell Larsen Studio. The adventure continues: look for gifts at Diamonds International, take in the spiritual surroundings of Beracha Veshalom Vegimulth Hasidim Synagogue, enjoy the sand and surf at Secret Harbour, and stroll through Bluebeard's Beach.

To find ratings, other places to visit, maps, and other tourist information, you can read our Charlotte Amalie holiday builder tool .

Tampa, USA to Charlotte Amalie is an approximately 7.5-hour flight. You can also do a combination of bus and flight. The time zone difference moving from Eastern Standard Time (EST) to Atlantic Standard Time (AST) is 1 hour. Prepare for somewhat warmer weather when traveling from Tampa in November: high temperatures in Charlotte Amalie hover around 86°F and lows are around 76°F. Finish your sightseeing early on the 28th (Thu) so you can travel to Philipsburg.

Things to do in Charlotte Amalie

Outdoors Parks Beaches

Side Trips

St. Thomas, East End, South Coast
Find places to stay Nov 18 — 28:
Highlights from your plan
Lindqvist Beach ©
Lindqvist Beach
Morningstar Beach ©
Morningstar Beach
Honeymoon Beach ©
Honeymoon Beach

11
nights
Philipsburg, St. Maarten-St. Martin

Philipsburg ©
Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Relax by the water at Great Bay Beach and Le Galion Beach. Step off the beaten path and head to Yoda Guy Movie Exhibit and Little Bay Beach. Explore Philipsburg's surroundings by going to Grand Case (Spas & Wellness, WAKE N' GLISSE, & more). There's much more to do: stroll through Baie Rouge, enjoy the sand and surf at Tintamarre Island, identify plant and animal life at The Butterfly Farm (La Ferme des Papillons), and view the masterpieces at Minguet Art Gallery.

Quickly create a custom-made itinerary for Philipsburg using our trip planner.

Traveling by flight from Charlotte Amalie to Philipsburg takes 1.5 hours. Alternatively, you can do a combination of flight and ferry. November in Philipsburg sees daily highs of 86°F and lows of 78°F at night. Finish your sightseeing early on the 9th (Mon) so you can travel to Trois-Ilets.

Things to do in Philipsburg

Parks Outdoors Beaches

Side Trips

Saint-Martin, Grand Case, Simpson Bay, Sint Maarten, Oyster Pond
Find places to stay Nov 28 — Dec 9:
Highlights from your plan
Yoda Guy Movie Exhibit ©
Yoda Guy Movie Exhibit
Le Galion Beach ©
Le Galion Beach
Baie Rouge ©
Baie Rouge

4
nights
Trois-Ilets, Martinique

Trois-Ilets
Named after three nearby islands, Trois-Ilets remains a small town few casual travelers ever get to explore.
Step off the beaten path and head to Anse Dufour and St-Thomas Church of Diamant. Do your shopping at Galerie de Sophen and Aux Couleurs Locales. Change things up with these side-trips from Trois-Ilets: Jardin de Balata (in Fort-de-France) and Habitation Clement (in Le Francois). There's lots more to do: stroll through Petit Anse, see some colorful creatures with a scuba or snorkeling tour, steep yourself in history at La Savane des Esclaves, and pause for some serene contemplation at St. Henry Catholic Church.

To see ratings and other tourist information, read our Trois-Ilets online driving holiday planner .

Fly from Philipsburg to Trois-Ilets in 3.5 hours. Alternatively, you can do a combination of ferry and flight. In December in Trois-Ilets, expect temperatures between 85°F during the day and 74°F at night. Finish up your sightseeing early on the 13th (Fri) so you can travel to Bridgetown.

Things to do in Trois-Ilets

Outdoors Parks Beaches

Side Trips

Les Anses d'Arlet, Fort-de-France, St-Thomas Church of Diamant, Habitation Clement, Les Salines Beach
Find places to stay Dec 9 — 13:
Highlights from your plan
Anse Dufour
Anse Dufour
Petit Anse ©
Petit Anse

7
nights
Bridgetown, Barbados

Bridgetown ©
Bridgetown is the capital and largest city of Barbados. Step off the beaten path and head to Crane Beach and George Washington House. Your inner history buff will appreciate Foursquare Distillery and St Mary's Church. Venture out of the city with trips to Bottom Bay (Harrismith Beach & Cave Bay). There's still lots to do: stroll through Rockley Beach, contemplate the long history of Stavronikita, head outdoors with The Boatyard, and enjoy the sand and surf at Pebbles Beach.

To see photos, more things to do, other places to visit, and more tourist information, read Bridgetown itinerary website .

Traveling by combination of flight and bus from Trois-Ilets to Bridgetown takes 2.5 hours. Alternatively, you can do a combination of ferry and flight. In December, daytime highs in Bridgetown are 85°F, while nighttime lows are 76°F. Finish your sightseeing early on the 20th (Fri) to allow enough time to travel to Willemstad.

Things to do in Bridgetown

Outdoors Parks Beaches

Side Trips

Saint Philip Parish, Gun Hill Signal Station, Paradise Beach, George Washington House, Barbados Concorde Experience
Find places to stay Dec 13 — 20:
Highlights from your plan
Pebbles Beach ©
Pebbles Beach
George Washington House ©
George Washington House
Rockley Beach ©
Rockley Beach

5
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. Museum-lovers will appreciate Kura Hulanda Museum and Evelien Sipkes Studio. Your inner history buff will appreciate Landhuis Ascension and Landhuis Bloemhof. Change things up with these side-trips from Willemstad: Museo di Ka'i Orgel (in Barber) and Sabana Westpunt (Kleine Knip & Playa Piscado/Playa Grandi). Spend the 23rd (Mon) exploring nature at Shete Boka National Park. Next up on the itinerary: tour the pleasant surroundings at Playa Lagun, explore the activities along Kenepa Beach, snap pictures at Queen Juliana Bridge, and relax and rejuvenate at some of the top local wellness centers.

To see ratings, where to stay, and tourist information, refer to the Willemstad itinerary builder site .

Fly from Bridgetown to Willemstad in 9 hours. In December, daily temperatures in Willemstad can reach 86°F, while at night they dip to 77°F. Finish up your sightseeing early on the 26th (Thu) so you can travel to Santo Domingo.

Things to do in Willemstad

Parks Outdoors Beaches

Side Trips

Barber, Sabana Westpunt, Playa Lagun
Find places to stay Dec 20 — 26:
Highlights from your plan
Kleine Knip ©
Kleine Knip
Kleine Knip ©
Kleine Knip
Playa Piscado/Playa Grandi ©
Playa Piscado/Playa Grandi

6
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.
Calle de Las Damas and Palacio de Bellas Artes will appeal to history buffs. Give yourself a bit of retail therapy at Agora Mall and Galeria 360. There's much more to do: contemplate the long history of Parque Colon, view the masterpieces at Amber Museum, take an in-depth tour of Museo Casa Duarte, and step into the grandiose world of Alcazar de Colon.

To find other places to visit, photos, and more tourist information, read our Santo Domingo trip website .

Fly from Willemstad to Santo Domingo in 5 hours. Finish up your sightseeing early on the 1st (Wed) so you can travel to Trinidad.

Things to do in Santo Domingo

Historic Sites Shopping Parks
Find places to stay Dec 26 — Jan 1:
Highlights from your plan
Parque Colon ©
Parque Colon
Calle de Las Damas ©
Calle de Las Damas
Agora Mall ©
Agora Mall

3
nights
Trinidad, Cuba

Trinidad ©
Built on sugar and seemingly preserved in molasses, the town of Trinidad attracts visitors with its well-aged 19th century architecture and rustic charm, showcasing the sounds, scents, and sights of days gone by.
Museum-lovers will get to explore Colonial Architecture Museum and Yudit Vidal Faife. Step off the beaten path and head to Parque Jose Marti and Convento de San Francisco de Asis. Explore the numerous day-trip ideas around Trinidad: Cienfuegos (Poco Bonito, La Fernandina, & more). And it doesn't end there: take a pleasant ride with a tour on horseback, view the masterpieces at Basso Art & Souvenir Gallery, see the interesting displays at Museo Nacional de la Lucha Contra Bandidos, and shop like a local with Galerie D'Art Calleyro.

To see reviews, where to stay, traveler tips, and other tourist information, go to the Trinidad road trip planner.

Traveling by combination of flight and bus from Santo Domingo to Trinidad takes 12.5 hours. Alternatively, you can do a combination of flight, train, and bus; or do a combination of shuttle, flight, and bus. You'll gain 1 hour traveling from Santo Domingo to Trinidad due to the time zone difference. In January in Trinidad, expect temperatures between 81°F during the day and 81°F at night. Finish your sightseeing early on the 5th (Sun) so you can travel back home.

Things to do in Trinidad

Outdoors Museums Shopping

Side Trips

Cienfuegos, Museo Nacional de la Lucha Contra Bandidos, Playa Maria Aguilar
Find places to stay Jan 2 — 5:
Highlights from your plan
Convento de San Francisco de Asis ©
Convento de San Francisco de Asis
Museo de Arqueologia ©
Museo de Arqueologia
Horseback Riding Tours

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