57 days in Caribbean Itinerary

57 days in Caribbean Itinerary

Created using Inspirock Caribbean journey builder
Make it your trip
Fly
1
San Juan, Puerto Rico
— 3 nights
Drive
2
Rincon, Puerto Rico
— 2 nights
Drive
3
Ponce, Puerto Rico
— 2 nights
Drive to Ceiba, Puerto Rico, Ferry to Isla de Vieques
4
Isla de Vieques, Puerto Rico
— 2 nights
Fly
5
St. Croix, U.S. Virgin Islands
— 2 nights
Fly
6
Charlotte Amalie, U.S. Virgin Islands
— 2 nights
Taxi to Red Hook, St Thomas, Ferry to Cruz Bay
7
Cruz Bay, U.S. Virgin Islands
— 2 nights
Ferry
8
Virgin Gorda, British Virgin Islands
— 2 nights
Fly
9
Simpson Bay, St. Maarten-St. Martin
— 2 nights
Ferry to Anguilla, Taxi to The Valley
10
The Valley, Anguilla
— 3 nights
Taxi
11
Shoal Bay Village, Anguilla
— 1 day
+2
Ferry to St. Martin, Foot to Marigot, Saint Martin, Ferry to Gustavia
12
Gustavia, St. Barthelemy
— 2 nights
+2
Ferry to Simpson Bay, Drive to St Maarten, Fly to Basseterre
13
Basseterre, St. Kitts and Nevis
— 1 night
Ferry
14
Nevis, St. Kitts and Nevis
— 1 night
+2
Taxi to Oualie Beach, Ferry to Cockleshell Beach Road, Fly to St. John's
15
St. John's, Antigua and Barbuda
— 3 nights
Fly
16
Barbuda, Antigua and Barbuda
— 2 nights
Fly
17
Saint Francois, Guadeloupe
— 2 nights
Fly
18
Roseau, Dominica
— 2 nights
Fly
19
Trois-Ilets, Martinique
— 2 nights
Drive to Fort-de-France, Ferry to Castries
20
Castries, St. Lucia
— 1 night
Fly
21
Kingstown, St. Vincent and the Grenadines
— 2 nights
Ferry
22
Bequia, St. Vincent and the Grenadines
— 2 nights
Ferry to Mustique, Fly to Bridgetown
23
Bridgetown, Barbados
— 2 nights
Fly
24
St. George's, Grenada
— 4 nights
Unknown
25
Charlotteville, Trinidad and Tobago
— 1 night
Drive
26
Scarborough, Trinidad and Tobago
— 1 night
Ferry
27
Port of Spain, Trinidad and Tobago
— 4 nights
Fly

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San Juan, Puerto Rico — 3 nights

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S. jurisdiction and one of the oldest in the Americas.
Your day by day itinerary now includes Condado Beach as well as El Yunque National Forest. Satisfy your inner culture vulture at Old San Juan and The Poet's Passage. Step off the beaten path and head to Catedral Basilica Menor de San Juan Bautista and Fishing Charters & Tours. There's still lots to do: get to know the fascinating history of Paseo de la Princesa, explore the different monuments and memorials at Santa Maria Magdalena de Pazzis Cemetery, steep yourself in history at Holocaust Memorial Monument, and explore the world behind art at Fundacion Casa Cortes.

To see reviews, photos, traveler tips, and more tourist information, use the San Juan road trip planning tool.

New York City, USA to San Juan is an approximately 7-hour flight. The time zone difference moving from Eastern Standard Time (EST) to Atlantic Standard Time (AST) is 1 hour. In November, San Juan is warmer than New York City - with highs of 87°F and lows of 76°F. Wrap up your sightseeing on the 25th (Sat) to allow time to drive to Rincon.
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Find places to stay Nov 22 — 25:

Rincon, Puerto Rico — 2 nights

Corner

A seaside playground in the Caribbean, Rincon was a small agricultural and fishing town until it hosted the 1968 World Surfing Championship.
Your day by day itinerary now includes Parque Nacional de las Cavernas del Rio Camuy as well as Domes Beach. Kick off your visit on the 25th (Sat): stroll through Domes Beach, Head underground at Parque Nacional de las Cavernas del Rio Camuy, then visit a coastal fixture at Faro de Punta Higuera, then enjoy the sea views from Punta Higuera Light House, and finally see majestic marine mammals with Fathom Charters.

To find ratings, reviews, traveler tips, and tourist information, refer to the Rincon tour planning site.

Traveling by car from San Juan to Rincon takes 2 hours. Alternatively, you can fly; or do a combination of shuttle and car. In November, daily temperatures in Rincon can reach 85°F, while at night they dip to 77°F. You will leave for Ponce on the 27th (Mon).
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Find places to stay Nov 25 — 27:

Ponce, Puerto Rico — 2 nights

Ponce is both a city and a municipality in the southern part of Puerto Rico. Your day by day itinerary now includes Playa Sucia as well as Aventura Cueva Ventana. Kick off your visit on the 27th (Mon): explore the fascinating underground world of Aventura Cueva Ventana, then take an in-depth tour of Museo de Arte de Ponce, then discover the deep blue sea with a scuba or snorkeling tour, and finally enjoy the sea views from Cardona Island Light. Get ready for a full day of sightseeing on the next day: take an in-depth tour of Ponce History Museum, admire the striking features of Casa Wiechers-Villaronga, then kick back and relax at Cana Gorda Beach, and finally kick back and relax at Playa Sucia.

Plan my day in Ponce using traveler tips and tourist information provided by Inspirock.

Getting from Rincon to Ponce by car takes about 1.5 hours. Other options: do a combination of taxi, flight, and shuttle. November in Ponce sees daily highs of 82°F and lows of 73°F at night. Wrap up your sightseeing on the 29th (Wed) to allow time to travel to Isla de Vieques.
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Find places to stay Nov 27 — 29:

Isla de Vieques, Puerto Rico — 2 nights

Isla Nena

For sixty years until 2003, most of the Isla de Vieques was closed off to the public, with the US Navy using the island's beaches and surrounding waters for drills and testing of new military machinery, such as bombs.
Your day by day itinerary now includes Vieques Island as well as Playa Caracas. On the 29th (Wed), enjoy the sand and surf at Playa Caracas, step off the mainland to explore Vieques Island, then explore the galleries of Siddhia Hutchinson Fine Art Gallery, then kick back and relax at Playa La Chiva, and finally add some adventure to your tour with a kayaking and canoeing tour.

To see where to stay and tourist information, use the Isla de Vieques travel app.

You can do a combination of car and ferry from Ponce to Isla de Vieques in 3.5 hours. Alternatively, you can do a combination of car, bus, taxi, and ferry; or do a combination of shuttle and flight. Expect a daytime high around 86°F in November, and nighttime lows around 75°F. On the 1st (Fri), you're off to St. Croix.
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Find places to stay Nov 29 — Dec 1:

St. Croix, U.S. Virgin Islands — 2 nights

Twin City

The largest of the U.S. Virgin Islands, St.
Kick off your visit on the 1st (Fri): enjoy the sand and surf at Davis Bay, contemplate the long history of Fort Christiansvaern, and then kick back and relax at Shoy Beach. On your second day here, take in the spiritual surroundings of St. Patrick's Catholic Church, then look for all kinds of wild species at Mermaid Adventures, and then appreciate the extensive heritage of Estate Mount Washington Plantation.

To find traveler tips, maps, more things to do, and tourist information, you can read our St. Croix travel route planner.

Fly from Isla de Vieques to St. Croix in 4 hours. In December in St. Croix, expect temperatures between 85°F during the day and 74°F at night. Finish your sightseeing early on the 3rd (Sun) to allow enough time to fly to Charlotte Amalie.
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Find places to stay Dec 1 — 3:

Charlotte Amalie, U.S. Virgin Islands — 2 nights

Duty-free Capital of the World

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.
Kick off your visit on the 3rd (Sun): get a new perspective on things with Blue Island DIvers, kick back and relax at Bluebeard's Beach, and then kick back and relax at Morningstar Beach. On the next day, contemplate in the serene atmosphere at Frederick Lutheran Church, contemplate in the serene atmosphere at Hebrew Congregation of St. Thomas, don't miss a visit to St. Thomas Synagogue, then stop by Gold Mine Fine Jewelry, and finally take some stellar pictures from Charlotte Amalie Overlook.

Plan trip to Charlotte Amalie with our itinerary maker to find out where to go and what to do.

Traveling by flight from St. Croix to Charlotte Amalie takes 2.5 hours. Alternatively, you can ride a ferry. In December, plan for daily highs up to 85°F, and evening lows to 75°F. Finish your sightseeing early on the 5th (Tue) so you can travel to Cruz Bay.
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Find places to stay Dec 3 — 5:

Cruz Bay, U.S. Virgin Islands — 2 nights

Love City

The gateway to the island of Saint John, Cruz Bay represents the island's largest town, port, and commercial center.
Your day by day itinerary now includes Trunk Bay Beach as well as Maho Bay Beach. Start off your visit on the 5th (Tue): kick back and relax at Maho Bay Beach, kick back and relax at Trunk Bay Beach, enjoy the sand and surf at Oppenheimer Beach, then see the interesting displays at Cinnamon Bay Archeology Museum & Lab, then delve into the distant past at Cinnamon Bay Nature Trail, and finally stop by Just Beach St. John. Get ready for a full day of sightseeing on the 6th (Wed): enjoy the sand and surf at Caneel Bay Beach, then kick back and relax at Salomon Beach, and then trek along Lind Point Trail.

To see where to stay, ratings, photos, and more tourist information, go to the Cruz Bay trip itinerary planning website.

Traveling by combination of taxi and ferry from Charlotte Amalie to Cruz Bay takes 1.5 hours. Alternatively, you can ride a ferry. December in Cruz Bay sees daily highs of 85°F and lows of 75°F at night. Finish your sightseeing early on the 7th (Thu) so you can ride a ferry to Virgin Gorda.
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Find places to stay Dec 5 — 7:

Virgin Gorda, British Virgin Islands — 2 nights

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.
Start off your visit on the 7th (Thu): take in the dramatic natural features at The Baths and then surround yourself with nature on a nature and wildlife tour. Get ready for a full day of sightseeing on the next day: trek along Biras Creek Trail, contemplate the long history of Wreck of the Chikuzen, and then relax and rejuvenate at some of the top local wellness centers.

To find more things to do, photos, and tourist information, use the Virgin Gorda trip planner.

You can ride a ferry from Cruz Bay to Virgin Gorda in 2.5 hours. Another option is to do a combination of ferry and flight. In December, daytime highs in Virgin Gorda are 85°F, while nighttime lows are 76°F. Finish your sightseeing early on the 9th (Sat) so you can fly to Simpson Bay.
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Find places to stay Dec 7 — 9:

Simpson Bay, St. Maarten-St. Martin — 2 nights

Simpson Bay offers luxury resort living and good access to the main areas of the island.
Your day by day itinerary now includes Mullet Bay Beach, Friar's Bay and Little Bay Beach. On the 9th (Sat), stroll through Friar's Bay, contemplate the waterfront views at Mullet Bay Beach, stroll through Little Bay Beach, then get a dose of the wild on a nature and wildlife tour, then examine the collection at Yoda Guy Movie Exhibit, and finally pause for some serene contemplation at Saint Martin of Tours Church. Get ready for a full day of sightseeing on the 10th (Sun): stroll through Maho Beach, then see some colorful creatures with a scuba or snorkeling tour, and then enjoy the sand and surf at Kim Sha Beach.

To see maps, reviews, other places to visit, and other tourist information, read Simpson Bay tour itinerary tool.

Traveling by flight from Virgin Gorda to Simpson Bay takes 4.5 hours. Expect a daytime high around 84°F in December, and nighttime lows around 76°F. Finish your sightseeing early on the 11th (Mon) so you can travel to The Valley.
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Find places to stay Dec 9 — 11:

The Valley, Anguilla — 3 nights

The Valley is the capital of Anguilla, one of its fourteen districts, and the main "town" on the island., it had a population of 1,067.HistoryHistorical landmarksThe Valley has few examples of colonial architecture due to the relocation of Anguilla's administration to St. Satisfy your inner culture vulture at St. Gerard Roman Catholic Church and Old Factory. You'll explore the less-touristy side of things at Meads Bay and Crocus Bay Beach. There's lots more to do: kick back and relax at Little Bay, get a taste of the local shopping with Limin' Boutique, tour the pleasant surroundings at Rendezvous Bay Beach, and discover the deep blue sea with Vigilant Divers Anguilla.

To find other places to visit, photos, reviews, and other tourist information, go to the The Valley trip planner.

You can do a combination of ferry and taxi from Simpson Bay to The Valley in 1.5 hours. Another option is to fly. In December in The Valley, expect temperatures between 85°F during the day and 73°F at night. Cap off your sightseeing on the 14th (Thu) early enough to go by car to Shoal Bay Village.
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Find places to stay Dec 11 — 14:

Shoal Bay Village, Anguilla — 1 day

Kick off your visit on the 14th (Thu): kick back and relax at Shoal Bay and then soothe aching muscles at Malakh Day Spa.

To see maps, more things to do, photos, and more tourist information, read our Shoal Bay Village trip planner.

Shoal Bay Village is just a stone's throw from The Valley. December in Shoal Bay Village sees daily highs of 85°F and lows of 73°F at night. Finish your sightseeing early on the 14th (Thu) so you can travel to Gustavia.
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Find places to stay Dec 14 — 15:

Gustavia, St. Barthelemy — 2 nights

On the 15th (Fri), examine the collection at Inter Oceans Museum, contemplate the long history of Corossol, then discover the deep blue sea with a scuba or snorkeling tour, then kick back and relax at Shell Beach, and finally browse the exhibits of Kalinas & Tainos. On your second day here, tour the pleasant surroundings at Piscines Naturelles, stroll through Anse de Grande Saline, then enjoy the sand and surf at Lorient, and finally stroll through Toiny Coast.

To see other places to visit, traveler tips, more things to do, and other tourist information, go to the Gustavia trip itinerary builder site.

Ride a ferry from Shoal Bay Village to Gustavia in 3 hours. Alternatively, you can do a combination of flight, car, and ferry; or do a combination of ferry, shuttle, and flight. Wrap up your sightseeing on the 17th (Sun) early enough to travel to Basseterre.
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Find places to stay Dec 14 — 17:

Basseterre, St. Kitts and Nevis — 1 night

Kick off your visit on the 17th (Sun): cruise along Timothy Hill. Get ready for a full day of sightseeing on the 18th (Mon): take in the exciting artwork at Glass Island Designz, take in the architecture and atmosphere at Immaculate Conception Co-Cathedral Catholic Church, then see some colorful creatures with a scuba or snorkeling tour, and finally get engrossed in the history at St. Christopher Heritage Society.

To see traveler tips, photos, other places to visit, and more tourist information, go to the Basseterre trip planner.

Traveling by combination of ferry, car, and flight from Gustavia to Basseterre takes 4.5 hours. Alternatively, you can fly. In December, plan for daily highs up to 85°F, and evening lows to 75°F. Finish up your sightseeing early on the 18th (Mon) so you can catch the ferry to Nevis.
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Side Trip
Find places to stay Dec 17 — 18:

Nevis, St. Kitts and Nevis — 1 night

An old British colony that only gained its independence in the 1980s, Nevis remains one of the world's least-spoiled holiday spots.
Your day by day itinerary now includes New River Estate as well as Newcastle Beach. On the 19th (Tue), enjoy the sand and surf at Newcastle Beach, contemplate the long history of New River Estate, and then trek along Nevis Peak Hike.

To find reviews, traveler tips, and tourist information, read Nevis trip planning website.

Traveling by ferry from Basseterre to Nevis takes an hour. Alternatively, you can fly. In December, daily temperatures in Nevis can reach 85°F, while at night they dip to 76°F. Finish your sightseeing early on the 19th (Tue) to allow enough time to travel to St. John's.
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Find places to stay Dec 18 — 19:

St. John's, Antigua and Barbuda — 3 nights

The capital and largest city of Antigua and Barbuda, St John's represents the commercial and touristic center of the twin-island country.
You've added Prickly Pear Island, Turners Beach, Nelson's Dockyard, and other attractions to your itinerary. Kick off your visit on the 20th (Wed): kick back and relax at Turners Beach, head off the coast to Prickly Pear Island, enjoy the sand and surf at Valley Church Beach, explore the wealth of natural beauty at Nelson's Dockyard, then get to know the resident critters at Wadadli Animal Nature Park, and finally explore the striking landscape at Devil's Bridge. Keep things going the next day: explore the galleries of Zemi Art Gallery, then stop by Silver Chelles, then tour the pleasant surroundings at Galley Bay Beach, and finally kick back and relax at Deep Bay Beach.

To find reviews, maps, other places to visit, and more tourist information, go to the St. John's trip site.

You can do a combination of taxi, ferry, and flight from Nevis to St. John's in 3 hours. In December, daytime highs in St. John's are 83°F, while nighttime lows are 74°F. Wrap up your sightseeing on the 22nd (Fri) early enough to fly to Barbuda.
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Find places to stay Dec 19 — 22:

Barbuda, Antigua and Barbuda — 2 nights

Home to a large population of magnificent frigatebirds, Barbuda has a reputation for excellent bird-watching, along with many other relaxing pursuits.
Your day by day itinerary now includes Pink Sand Beach as well as Princess Diana Beach. Kick off your visit on the 22nd (Fri): tour the pleasant surroundings at 17-Mile Beach, then tour the pleasant surroundings at Princess Diana Beach, then kick back and relax at Pink Sand Beach, and finally browse the exhibits of Artcafe. Keep things going the next day: stroll through Frigate Bird Sanctuary and then contemplate the waterfront views at Low Bay.

To find photos, where to stay, other places to visit, and other tourist information, go to the Barbuda trip planner.

Getting from St. John's to Barbuda by flight takes about 2 hours. In December, plan for daily highs up to 83°F, and evening lows to 74°F. Finish your sightseeing early on the 24th (Sun) to allow enough time to fly to Saint Francois.
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Find places to stay Dec 22 — 24:

Saint Francois, Guadeloupe — 2 nights

A modern seaside resort town, Saint Francois attracts visitors with its well-preserved landscape and coastline, along with its large number of luxury hotels.
You've added Saut de la Lezarde, La Soufriere Volcano, Guadeloupe National Park, and other attractions to your itinerary. Kick off your visit on the 24th (Sun): tour the pleasant surroundings at Plage de Petit-Havre, get impressive views of La Soufriere Volcano, admire the sheer force of Saut de la Lezarde, explore the striking landscape of Guadeloupe National Park, then take an in-depth tour of Musee Costumes et Traditions, and finally enjoy the sand and surf at St. Anne Beach. Get ready for a full day of sightseeing on the 25th (Mon): glide through the air with a parasailing or paragliding tour, explore the different monuments and memorials at Cimetiere de Morne-A-l'Eau, then enjoy the sand and surf at Anse a la Gourde, then take in the exciting artwork at Kreol West Indies, and finally stroll through La Douche.

To find reviews, maps, other places to visit, and tourist information, use the Saint Francois trip builder website.

You can fly from Barbuda to Saint Francois in 3 hours. Another option is to do a combination of flight and bus. December in Saint Francois sees daily highs of 85°F and lows of 72°F at night. Wrap up your sightseeing on the 26th (Tue) to allow time to fly to Roseau.
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Find places to stay Dec 24 — 26:

Roseau, Dominica — 2 nights

The capital city, Roseau maintains a small scale, but possesses a convincing Caribbean charm in its architecture, cuisine, and culture.
Your day by day itinerary now includes Champagne Beach, Fort Shirley, Boiling Lake, and other attractions you added. Kick off your visit on the 26th (Tue): steep yourself in history at Fort Shirley, stroll through Soufriere Bay, witness a stunning natural landmark at Boiling Lake, explore the striking landscape of Cabrits National Park, then take in the dramatic scenery at Jacko Falls, and finally hike along Emerald Pool Nature Trail. Get ready for a full day of sightseeing on the next day: browse the exhibits of Roseau Museum, contemplate in the serene atmosphere at St. Patrick's Roman Catholic Cathedral, then take in the spiritual surroundings of St. George's Anglican Church, and finally kick back and relax at Champagne Beach.

For reviews, traveler tips, other places to visit, and other tourist information, use the Roseau online attractions planner.

Getting from Saint Francois to Roseau by flight takes about 3 hours. Other options: ride a ferry. Cap off your sightseeing on the 28th (Thu) early enough to catch the flight to Trois-Ilets.
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Find places to stay Dec 26 — 28:

Trois-Ilets, Martinique — 2 nights

Named after three nearby islands, Trois-Ilets remains a small town few casual travelers ever get to explore.
Start off your visit on the 28th (Thu): explore the galleries of La Savane des Esclaves, then kick back and relax at Grand Anse d'Arlet, then see some colorful creatures with a scuba or snorkeling tour, and finally take in the architecture and atmosphere at St. Henry Catholic Church. On your second day here, trek along Parcours de sante, then kick back and relax at Anse Mabouya, and then get impressive views of Morne Larcher.

For where to stay, ratings, and other tourist information, you can read our Trois-Ilets sightseeing planning site.

You can fly from Roseau to Trois-Ilets in 4 hours. Alternatively, you can ride a ferry. December in Trois-Ilets sees daily highs of 85°F and lows of 74°F at night. Finish your sightseeing early on the 30th (Sat) so you can travel to Castries.
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Find places to stay Dec 28 — 30:

Castries, St. Lucia — 1 night

The capital and largest city in Saint Lucia, Castries has a number of cultural sites to explore, and recreational areas to enjoy.
You've added Splash Island Water Park Saint Lucia, Pitons, Pigeon Island National Park, and other attractions to your itinerary. Start off your visit on the 30th (Sat): take in the natural beauty of Sulphur Springs, admire the natural beauty at Diamond Falls Botanical Gardens, explore the striking landscape at Pitons, then take in the dramatic scenery at Superman Falls, then explore the wealth of natural beauty at Pigeon Island National Park, and finally try out the rides at Splash Island Water Park Saint Lucia. Get ready for a full day of sightseeing on the 31st (Sun): stop by Diamonds International St. Lucia, kick back and relax at Vigie Beach, and then contemplate in the serene atmosphere at Immaculate Conception Church.

For reviews, photos, maps, and more tourist information, go to the Castries online trip builder.

You can do a combination of car and ferry from Trois-Ilets to Castries in 3 hours. Another option is to fly. Expect a daytime high around 85°F in December, and nighttime lows around 75°F. Cap off your sightseeing on the 31st (Sun) early enough to catch the flight to Kingstown.
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Find places to stay Dec 30 — 31:

Kingstown, St. Vincent and the Grenadines — 2 nights

Kingstown is the capital, chief port, and main commercial centre of Saint Vincent and the Grenadines. Your day by day itinerary now includes Petit Tabac, Fort Duvernette and Falls of Baleine. On the 1st (Mon), take in the dramatic scenery at Falls of Baleine, don't miss a visit to Fort Duvernette, stroll through Petit Tabac, admire the natural beauty at Botanical Gardens, then take an in-depth tour of National Museum, and finally contemplate the long history of Fort Charlotte.

To find more things to do, ratings, and more tourist information, go to the Kingstown trip itinerary planning app.

Traveling by flight from Castries to Kingstown takes 4 hours. In January, plan for daily highs up to 85°F, and evening lows to 75°F. On the 3rd (Wed), you'll travel to Bequia.
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Side Trip
Find places to stay Dec 31 — Jan 3:

Bequia, St. Vincent and the Grenadines — 2 nights

Although it covers just 18 sq km (7 sq mi), Bequia is the largest of over 30 islands making up the Grenadines chain.
Your day by day itinerary now includes Lagoon Beach. Start off your visit on the 3rd (Wed): stroll through Lagoon Beach, see some colorful creatures with a scuba or snorkeling tour, look for gifts at Sargeant Brothers Model Boat Shop, shop like a local with The Oasis Art Gallery & Gift Shop, then learn about all things military at Bequia Maritime Museum, and finally contemplate the long history of Port Elizabeth. On the 4th (Thu), you'll have a packed day of sightseeing: relax and rejuvenate at Serenity Day Spa, then kick back and relax at Princess Margaret Beach, and then enjoy the sand and surf at Lower Bay Beach.

Planning Bequia trip won't be overwhelming when you use Inspirock's itinerary maker.

You can ride a ferry from Kingstown to Bequia in 1.5 hours. Expect a daytime high around 85°F in January, and nighttime lows around 75°F. Cap off your sightseeing on the 5th (Fri) early enough to travel to Bridgetown.
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Side Trip
Find places to stay Jan 3 — 5:

Bridgetown, Barbados — 2 nights

Bridgetown is the capital and largest city of Barbados. Your day by day itinerary now includes Bottom Bay, Hastings Beach and Miami Beach Barbados. On the 5th (Fri), kick back and relax at Bottom Bay, kick back and relax at Miami Beach Barbados, kick back and relax at Hastings Beach, contemplate the long history of St.John's Church, then take in the architecture and atmosphere at St. John's Parish Church, and finally stroll through Soup Bowl. Get ready for a full day of sightseeing on the next day: Head underground at Harrison's Cave., enjoy the sand and surf at Rockley Beach, then take in the exciting artwork at Best of Barbados Gift Shop, and finally kick back and relax at Accra Beach.

To find other places to visit, traveler tips, where to stay, and tourist information, read Bridgetown journey planning app.

Do a combination of ferry and flight from Bequia to Bridgetown in 4.5 hours. In January, plan for daily highs up to 84°F, and evening lows to 74°F. Cap off your sightseeing on the 7th (Sun) early enough to catch the flight to St. George's.
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Find places to stay Jan 5 — 7:

St. George's, Grenada — 4 nights

The capital of the Island of Spice, St.
Your day by day itinerary now includes Bathway Beach, Mount St. Catherine, Annandale Falls, and other attractions you added. Do some cultural sightseeing at Underwater Sculptures and Carenage. Take a break from the city and head to Dolphin & Whale Watching and Magazine Beach. And it doesn't end there: pause for some serene contemplation at The Cathedral of the Immaculate Conception, browse the exhibits of Art and Soul Gallery, and relax and rejuvenate at some of the best spas.

To find other places to visit, reviews, where to stay, and other tourist information, read St. George's road trip app.

Getting from Bridgetown to St. George's by flight takes about 4.5 hours. In January, daily temperatures in St. George's can reach 85°F, while at night they dip to 74°F. On the 11th (Thu), you'll travel to Charlotteville.
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Find places to stay Jan 7 — 11:

Charlotteville, Trinidad and Tobago — 1 night

Charlotteville is a village lying on the northeastern tip of Tobago on Man-o-war Bay.First European settlers to the area arrived in 1633, with more settlers arriving in 1639. Start off your visit on the 12th (Fri): discover the deep blue sea with a scuba or snorkeling tour and then stroll through Pirate's Bay.

To see photos, where to stay, traveler tips, and tourist information, read Charlotteville day trip site.

Explore your travel options from St. George's to Charlotteville with the Route module. Cap off your sightseeing on the 12th (Fri) early enough to go by car to Scarborough.
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Find places to stay Jan 11 — 12:

Scarborough, Trinidad and Tobago — 1 night

Scarborough is the largest city and capital of the Island of Tobago and the fifth-most-populous in Trinidad and Tobago. Start off your visit on the 13th (Sat): contemplate the long history of Fort King George, stroll through Minster Bay, then enjoy the sand and surf at Blue Haven Beach, and finally explore the landscape on two wheels at Eden's Door.

To see photos, ratings, where to stay, and tourist information, use the Scarborough online travel planner.

You can drive from Charlotteville to Scarborough in 1.5 hours. Another option is to take a bus. Finish up your sightseeing early on the 13th (Sat) so you can catch the ferry to Port of Spain.
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Parks · Outdoors · Beaches · Historic Sites
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Highlights from your trip

Port of Spain, Trinidad and Tobago — 4 nights

Port of Spain, the country's capital, sits between the sea and a scenic green mountain range, and acts as a gateway for eclectic adventures on land and sea.
Your day by day itinerary now includes Harry's Water Park, La Brea Pitch Lake, Paria Falls, and other attractions you added. Step out of the city life by going to Caroni Swamp and Maracas Beach. Discover out-of-the-way places like Nature & Wildlife Tours and Green Market. Change things up with a short trip to Tyrico Bay in Maracas Bay (about 36 minutes away). It doesn't end there: explore the wealth of natural beauty at Caroni Lagoon National Park and pause for some serene contemplation at Holy Trinity Cathedral.

For more things to do, other places to visit, maps, and tourist information, go to the Port of Spain vacation app.

You can ride a ferry from Scarborough to Port of Spain in 4.5 hours. In January, plan for daily highs up to 87°F, and evening lows to 72°F. You'll set off for home on the 17th (Wed).
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Parks · Nature · Outdoors · Beaches
Side Trips
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U.S. Virgin Islands travel guide

4.5
Beaches · Gift & Specialty Shops · Scuba & Snorkeling
America's Paradise
Three main and a number of minor islands that make up U.S. Virgin Islands treat visitors to a blend of historical sites and picture-perfect beaches. Though officially American territory--nicknamed "America's Paradise"--these islands boast a mix of cultures that make for culturally enriching vacations. A no-passport-required status makes holidays in U.S. Virgin Islands extremely popular with American tourists, who flock to this tropical heaven to enjoy scenic beaches, outdoor activities, and tasty local food. The islands are also a duty-free shopping destination, which also makes them appealing to shopaholics from across the world.
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British Virgin Islands travel guide

4.4
Geologic Formations · Bodies of Water · Beaches
Escape from civilization and take a trip to British Virgin Islands, a collection of 60 small islands and cays in the Virgin Islands archipelago. Although British territory, the island is not noticeably British, offering a quiet and serene vibe that lives on despite a major tourism boom. With most of its islets uninhabited, British Virgin Islands remain a paradise for sailing, snorkeling, lazing on a deserted beach, and exploring sleepy seaside villages.
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St. Maarten-St. Martin travel guide

4.4
Gift & Specialty Shops · Beaches · Scuba & Snorkeling
A trip to St. Maarten-St. Martin allows you to discover two separate colonies occupying one small island of just 95 sq km (37 sq mi). Divided between France and the Netherlands, this tiny spit of land in the Caribbean treats visitors to a surprisingly diverse blend of native and European cultures. A tour of St. Maarten-St. Martin reveals a landscape of both urban and untamed areas, with sandy beaches and pristine rainforests often appearing as extensions of one another. The French north of the island offers a string of outstanding restaurants and lively beaches popular with a young party-loving crowd. The Dutch southern section lures visitors with its dynamic bar scene and casinos.
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Anguilla travel guide

4.1
Nature & Parks · Islands · Swim with Dolphins
A peaceful set of islands with a pristine, bespoke tourism infrastructure, Anguilla offers a restful vacation for beach-lovers, honeymooners, and diving enthusiasts. A scattering of historic attractions in Anguilla stand as testament to the native and colonial histories of the set of paradisal islands, but the focus here lies much more on coastlines rather than timelines. The beaches of Anguilla remain relatively untouched, allowing the scenery to speak for itself. However, this is no back-to-basics place, with whatever tourist developments there are being made to luxury standards, and priced accordingly.
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St. Barthelemy travel guide

4
Nature & Parks · Scuba & Snorkeling · Shopping
St. Barts
The volcanic island of St. Barthelemy has become a popular holiday destination for the rich and famous. It doesn't take a large leap of the imagination to see why, with the towering mountainous backdrop, green hills, and waters protected by a coral reef. The beaches offer ample room for lazing under the sun, while the calm waters offer rich marine environments, easily accessible on dives or snorkeling trips. A St. Barthelemy vacation can work to a budget more modest than a millionaire's too, with good deal available during off season.
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St. Kitts and Nevis travel guide

4
Beaches · Shopping · Scuba & Snorkeling
A trip to St. Kitts and Nevis takes you to the smallest country in the Americas. Although diminutive in size, the two Caribbean islands offer a distinct tropical experience to visitors. Rich in history, the islands feature forested hills, tranquil beaches, charming villages, and restored sugar plantations. On a tour of St. Kitts and Nevis you can visit historic forts and quaint colonial towns, lounge on picturesque stretches of sand, or enjoy hiking the dormant Mount Liamuiga, the islands' highest peak.
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Antigua travel guide

4.2
Scuba & Snorkeling · Beaches · Lookouts
A true tropical getaway, Antigua attracts travelers from all over the world with its innumerable beaches, coves, and bays. Although an important cruise ship destination with upscale resorts and facilities, Antigua doesn't lack tranquility. With picturesque and secluded stretches of sand and sleepy villages waiting at every corner, a vacation in Antigua is the perfect opportunity to lounge on the waterfront, enjoy swimming and snorkeling, and indulge in delicious seafood.
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Guadeloupe travel guide

4.1
Beaches · Scuba & Snorkeling · Gardens
Butterfly Island
Experience a lively mixture of French and Afro-Caribbean culture on your Guadeloupe vacation. The archipelago consists of two main islands connected by bridges spanning a mangrove swamp, and a number of smaller islands to the south. The island of Grande Terre is mostly flat and arid, offering numerous scenic beaches and lively small towns, while Basse Terre features verdant jungles and mountainous terrain, crowned by a tall volcano. On a tour of Guadeloupe, you can enjoy a variety of beach activities, partake in hiking through a national park, and bask in the vibrant atmosphere of charming towns and villages.
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Dominica travel guide

4.2
Waterfalls · Beaches · Bodies of Water
Nature Isle of the Caribbean
The volcanic island nation of Dominica represents the youngest island in the Lesser Antilles. Such is evidenced in the geothermal action of the island's many hot springs, with relaxing dips in the hot sulfur spring water among the most popular things to do in Dominica. The unspoiled appearance of much of the nation provides a natural backdrop for a wealth of ecotourism adventures, including swimming, hiking, and snorkeling. The main urban areas showcase the ethnic diversity of the land once contested by the British and the French, with a number of local eateries serving West Indian and Creole dishes, and a whole lot of dancing and music to be enjoyed.
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Martinique travel guide

4.4
Beaches · Scuba & Snorkeling · Gardens
The mountainous island of Martinique offers travelers everything from stunning natural landscapes, to vibrant towns and enticing cuisine. The island's varied scenery includes numerous scenic beaches, lush forests, and a majestic volcano that towers over the St. Pierre harbor. A range of activities await you on your Martinique holiday, allowing you to spend your days lounging on the sand and enjoying the azure waters, sampling gastronomic delicacies, or frequenting the shops, clubs, and cafes in the capital city of Fort-de-France.
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St. Lucia travel guide

4.1
Hot Springs · Bodies of Water · Landmarks
The island of St. Lucia is hailed for its scenic landscape of tall mountains, forested hills, and fertile valleys sprinkled with banana plantations. The island's dramatic scenery is most renowned for the Pitons, two volcanic spires that rise from the ocean floor. Whether you're visiting the island as part of a cruise, a romantic honeymoon, or looking for adventure, a St. Lucia vacation offers something for everyone. Discover the island's hidden beaches and coves, go climbing or hiking, and enjoy the picturesque views and tropical weather.
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St. Vincent and the Grenadines travel guide

4.1
Beaches · Historic Sites · Islands
Vacations in St. Vincent and the Grenadines offer eco-adventures and luxury, with the island nation catering to the tastes of mega yacht owners and backpackers alike. The main island's interior volcanic and hilly terrain has been covered in lush tropical rainforest, rich in wildlife, while the coastal areas offer beaches both popular and secluded. Taking a chartered boat tour of the islands represents one of the more popular things to do in St. Vincent and the Grenadines, with island hopping revealing uninhabited paradisal islands, unspoiled by development of any kind.
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Barbados travel guide

4.4
Beaches · Scuba & Snorkeling · Gardens
Little England
Plan a vacation on the small Caribbean island of Barbados and experience its rich history and vibrant culture. Affectionately called "Little England," the island retains a noticeable British influence in its lively culture, visible especially in sport, religion, and the charming British style buildings with a Caribbean flair. On a tour of Barbados you can lounge on sandy beaches, participate in world-class surfing, roam the World Heritage-listed capital, or explore the lush island interior. When on the island, don't forget to sample its world-famous rum and the signature local dish, the flying fish.
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Grenada travel guide

4
Beaches · Scuba & Snorkeling · Specialty Museums
Island of Spice
The fertile and lively island nation of Grenada allows for itineraries both adventurous and serene. The main island and six smaller ones offer unspoiled interior landscapes of lush vegetation, impressive waterfalls, and winding rivers, explorable on a number of ecotourism experiences, such as rafting, hiking, and climbing. The coastal areas provide long stretches of golden sand, backed by large and popular resorts, while the humble urban areas have become particularly well-known for their atmospheric eateries, serving local cuisine using produce from the Island of Spice. One of the main things to do in Grenada has to be marine exploration, with dive sites offshore representing some of the most abundant in the region, with impressive coral formations providing home for a schools of tropical fish.
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Trinidad and Tobago travel guide

4
Beaches · Nature & Parks · Waterfalls
With its two landmasses offering different, but complementary Caribbean flavors, the dual island nation of Trinidad and Tobago attracts visitors looking for relaxation and adventure. Cities and bustling market towns set the pace of cosmopolitan Trinidad, by far the larger of the two Caribbean sisters. Holidays in Tobago tend to be more chilled out affairs, with island offering some of the nation's finest resorts and best kept beaches, along with a wealth of protected areas boasting diverse and abundant wildlife. Both have become famous for their Creole culture and traditions, with holidays in Trinidad and Tobago offering plenty of culinary and musical highlights, including red hot curries and spicy calypso music.
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