45 days in Caribbean Itinerary
Created using Inspirock trip itinerary maker
Start: Newark, United States
Fly to L.F. Wade International International Airport, Drive to Southampton Parish
1
Southampton Parish, Bermuda
— 4 nights
Unknown
2
Eleuthera, Bahamas
— 3 nights
Unknown
3
Providenciales, Turks and Caicos
— 4 nights
Fly
4
George Town, Cayman Islands
— 3 nights
Fly
5
Kingston, Jamaica
— 3 nights
Fly
6
Punta Cana, Dominican Republic
— 2 nights
Fly to Luis Munoz Marin International Airport, Drive to Isabela
7
Isabela, Puerto Rico
— 1 night
Drive
8
Rincon, Puerto Rico
— 4 nights
+2
Drive to Luis Munoz Marin International Airport, Fly to Cyril E. King Airport, Drive to Virgin Islands National Park
9
Virgin Islands National Park, U.S. Virgin Islands
— 2 nights
Taxi to Cruz Bay, St John, Ferry to Virgin Gorda
10
Virgin Gorda, British Virgin Islands
— 3 nights
Fly to St Maarten, Ferry to Shoal Bay Village
11
Shoal Bay Village, Anguilla
— 3 nights
Fly
12
Soufriere, St. Lucia
— 4 nights
Fly
13
Bridgetown, Barbados
— 5 nights
Fly
End: Newark, United States
Wed, Feb 1 - Fri, Mar 17
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View full calendar
Southampton Parish, Bermuda — 4 nights
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The area's beaches remain the primary reason to holiday in Southampton Parish, with their number and variety providing entertainments and sights to suit a range of tastes.Your cultural itinerary includes sights like Bermuda Aquarium, Natural History Museum & Zoo and The Unfinished Church. Escape the urban bustle at Horseshoe Bay Beach and Warwick Long Bay Beach. Change things up with a short trip to Crystal & Fantasy Caves in Hamilton Parish (about 30 minutes away). There's lots more to do: steep yourself in history at National Museum of Bermuda, play a few rounds at Port Royal Golf Course, Bermuda, enjoy the sand and surf at Church Bay Beach, and enjoy the sea views from Gibb's Hill Lighthouse.
To find traveler tips, more things to do, other places to visit, and more tourist information, read Southampton Parish trip itinerary builder website.
Newark, USA to Southampton Parish is an approximately 6.5-hour combination of flight and car. Due to the time zone difference, you'll lose 1 hour traveling from Newark to Southampton Parish. In February, Southampton Parish is much hotter than Newark - with highs of 69°F and lows of 61°F. Wrap up your sightseeing on the 5th (Sun) to allow time to fly to Eleuthera.
Side Trips
Hamilton, National Museum of Bermuda, Warwick Long Bay Beach, Crystal & Fantasy Caves, The Unfinished Church
Find places to stay Feb 1 — 5:
Highlights from your trip
Eleuthera, Bahamas — 3 nights
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The long, thin island of Eleuthera has plenty of coast, built up in places and left wild and rural in others.Start off your visit on the 6th (Mon): explore the wealth of natural beauty at Leon Levy Native Plant Preserve, enjoy the sand and surf at French Leave Beach, and then kick back and relax at Ten Bay Beach. On the 7th (Tue), you'll have a packed day of sightseeing: pick up some local products at Eleuthera Island Farm, cool off at Tarpum Bay, and then get interesting insight from Tours.
To find ratings and more tourist information, refer to the Eleuthera attractions planning website.
Explore your travel options from Southampton Parish to Eleuthera with the Route module. The time zone difference moving from Atlantic Standard Time (AST) to Eastern Standard Time (EST) is minus 1 hour. On the 8th (Wed), you'll travel to Providenciales.
Find places to stay Feb 5 — 8:
Highlights from your trip
Providenciales, Turks and Caicos — 4 nights
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The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.Take a break from the city and head to Grace Bay Beach and Sapodilla Bay Beach. Do some cultural sightseeing at Cheshire Hall Plantation and Brilliant Studios. There's lots more to do: play a few rounds at Royal Turks and Caicos Golf Club, take in the pleasant sights at Turks and Caicos Map Mural, take in the exciting artwork at Orion Creations handmade in T.C.I located at Serene By Mel, and soothe aching muscles at Glow Fitness TCI.
For maps, other places to visit, more things to do, and other tourist information, read Providenciales trip itinerary planner.
The Route module can help you plan travel from Eleuthera to Providenciales. In February, plan for daily highs up to 82°F, and evening lows to 74°F. Wrap up your sightseeing by early afternoon on the 12th (Sun) to allow enough time to fly to George Town.
Find places to stay Feb 8 — 12:
Highlights from your trip
George Town, Cayman Islands — 3 nights
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George Town is a city situated on Grand Cayman island of the Cayman Islands. You'll get in some beach time at Rum Point and Smith's Barcadere. Get outdoors at Mastic Trail and Scuba & Snorkeling. When in George Town, make a side trip to see Davinoff's Concrete Sculptures in Old Man Bay, approximately Old Man Bay away. The adventure continues: explore the historical opulence of Pedro St. James National Historic Site, brush up on your knowledge of spirits at Cayman Spirits Co. Distillery, kick back and relax at Starfish Point, and explore the galleries of Cayman Islands National Museum.
For where to stay, other places to visit, more things to do, and tourist information, use the George Town tour planner.
Traveling by flight from Providenciales to George Town takes 9.5 hours. In February, daytime highs in George Town are 84°F, while nighttime lows are 74°F. Finish up your sightseeing early on the 15th (Wed) so you can catch the flight to Kingston.
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For where to stay, other places to visit, more things to do, and tourist information, use the George Town tour planner.
Traveling by flight from Providenciales to George Town takes 9.5 hours. In February, daytime highs in George Town are 84°F, while nighttime lows are 74°F. Finish up your sightseeing early on the 15th (Wed) so you can catch the flight to Kingston.
Side Trips
Find places to stay Feb 12 — 15:
Highlights from your trip
Kingston, Jamaica — 3 nights
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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.Get some cultural insight at Bob Marley Museum and Jamaica National Gallery. Next up on the itinerary: take in the awesome beauty at Blue Mountains, make a trip to Two Sisters Cave, admire all the interesting features of Devon House, and contemplate the long history of Port Royal.
For where to stay, ratings, reviews, and other tourist information, go to the Kingston vacation maker website.
You can fly from George Town to Kingston in 5 hours. February in Kingston sees daily highs of 87°F and lows of 73°F at night. Finish your sightseeing early on the 19th (Sun) so you can fly to Punta Cana.
Side Trip
Find places to stay Feb 15 — 19:
Highlights from your trip
Punta Cana, Dominican Republic — 2 nights
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In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.Visiting Destiny Caribbean Tours and Punta Espada Golf Course will get you outdoors. Altos de Chavon and Aromas Museum are good opportunities to explore the local culture. There's still lots to do: stroll through Bavaro Beach and don't miss a visit to Jesus Maestro Parish.
For more things to do, ratings, other places to visit, and more tourist information, read Punta Cana day trip app.
Traveling by flight from Kingston to Punta Cana takes 5 hours. Due to the time zone difference, you'll lose 1 hour traveling from Kingston to Punta Cana. Expect a daytime high around 83°F in February, and nighttime lows around 71°F. Finish your sightseeing early on the 21st (Tue) so you can travel to Isabela.
Side Trip
Find places to stay Feb 19 — 21:
Highlights from your trip
Isabela, Puerto Rico — 1 night
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Isabela is a municipality of Puerto Rico (U.S.) located in the north-western region of the island, north of San Sebastián; west of Quebradillas; and east of Aguadilla and Moca. Start off your visit on the 22nd (Wed): delve into the lush surroundings at Bosque Estatal De Guajataca, stroll through La Poza De Las Golondrinas, and then enjoy the sand and surf at Jobos Beach. Get ready for a full day of sightseeing on the 23rd (Thu): make a trip to Monumento al Cacique Mabodamaca, enjoy the sand and surf at Playa Crashboat, and then see some colorful creatures with a scuba or snorkeling tour.
For more things to do, photos, traveler tips, and more tourist information, read Isabela tour planner.
The Route module can help you plan travel from Punta Cana to Isabela. In February, daytime highs in Isabela are 82°F, while nighttime lows are 69°F. Finish up your sightseeing early on the 23rd (Thu) so you can go by car to Rincon.
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For more things to do, photos, traveler tips, and more tourist information, read Isabela tour planner.
The Route module can help you plan travel from Punta Cana to Isabela. In February, daytime highs in Isabela are 82°F, while nighttime lows are 69°F. Finish up your sightseeing early on the 23rd (Thu) so you can go by car to Rincon.
Side Trip
Find places to stay Feb 21 — 23:
Highlights from your trip
Rincon, Puerto Rico — 4 nights
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Corner
A seaside playground in the Caribbean, Rincon was a small agricultural and fishing town until it hosted the 1968 World Surfing Championship.Get in touch with nature at Spotin tours and Sandy Beach. Satisfy your inner culture vulture at Faro Los Morrillos and Faro de Punta Higuera. Change things up with a short trip to Playa Sucia in Cabo Rojo (about 1h 25 min away). There's still lots to do: take a memorable tour with Tours, visit a coastal fixture at Punta Higuera Light House, and stop by Ocean State of Mind.
Use Inspirock's suggestions to plan your Rincon trip and find the best activities and attractions for your vacation.
Getting from Isabela to Rincon by car takes about an hour. Plan for a bit warmer nights when traveling from Isabela in February since evenings lows in Rincon dip to 76°F. Finish your sightseeing early on the 27th (Mon) to allow enough time to travel to Virgin Islands National Park.
Side Trips
Find places to stay Feb 23 — 27:
Highlights from your trip
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The hills, valleys, and tropical rainforest of Virgin Islands National Park tell only half the story, with just as much (if not more) to be found under the sea.Your cultural itinerary includes sights like Annaberg Sugar Plantation and Cinnamon Bay Archeology Museum & Lab. Take a break from the city and head to Trunk Bay Beach and Ram Head Trail. There's still lots to do: explore the activities along Salt Pond Bay, discover the deep blue sea with a scuba or snorkeling tour, enjoy the sand and surf at Cinnamon Bay Beach, and stop by TuTu Much.
To find where to stay, maps, ratings, and tourist information, you can read our Virgin Islands National Park holiday builder.
Use the Route module to find suitable travel options from Rincon to Virgin Islands National Park. In February, plan for daily highs up to 84°F, and evening lows to 73°F. Cap off your sightseeing on the 1st (Wed) early enough to travel to Virgin Gorda.
Side Trips
Find places to stay Feb 27 — Mar 1:
Highlights from your trip
Virgin Gorda, British Virgin Islands — 3 nights
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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.You'll get in some beach time at The Baths and Savannah Bay. Step out of the city life by going to Spring Bay and Honeymoon Beach. There's much more to do: discover the deep blue sea with Sunchaser Scuba Ltd., tour the pleasant surroundings at Virgin Gorda Peak, make a trip to Wreck of the Chikuzen, and soothe aching muscles at some of the top local wellness centers.
To see maps, where to stay, ratings, and more tourist information, you can read our Virgin Gorda holiday maker tool.
Getting from Virgin Islands National Park to Virgin Gorda by combination of taxi and ferry takes about 2.5 hours. Other options: do a combination of ferry and flight. In March in Virgin Gorda, expect temperatures between 84°F during the day and 75°F at night. Wrap up your sightseeing on the 4th (Sat) early enough to travel to Shoal Bay Village.
Find places to stay Mar 1 — 4:
Highlights from your trip
Shoal Bay Village, Anguilla — 3 nights
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On the 5th (Sun), kick back and relax at Rendezvous Bay Beach and then tour the pleasant surroundings at Shoal Bay. Get ready for a full day of sightseeing on the next day: step off the mainland to explore Sandy Island, then enjoy the sand and surf at Meads Bay, then get close to the beloved marine mammals with Dolphin Discovery Anguilla, and finally shop like a local with Limin' Boutique.
To see reviews, ratings, other places to visit, and other tourist information, use the Shoal Bay Village road trip site.
Traveling by combination of flight and ferry from Virgin Gorda to Shoal Bay Village takes 4.5 hours. Alternatively, you can do a combination of flight, ferry, and taxi; or fly. Expect a daytime high around 84°F in March, and nighttime lows around 73°F. Cap off your sightseeing on the 7th (Tue) early enough to catch the flight to Soufriere.
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To see reviews, ratings, other places to visit, and other tourist information, use the Shoal Bay Village road trip site.
Traveling by combination of flight and ferry from Virgin Gorda to Shoal Bay Village takes 4.5 hours. Alternatively, you can do a combination of flight, ferry, and taxi; or fly. Expect a daytime high around 84°F in March, and nighttime lows around 73°F. Cap off your sightseeing on the 7th (Tue) early enough to catch the flight to Soufriere.
Side Trips
Find places to stay Mar 4 — 7:
Highlights from your trip
Soufriere, St. Lucia — 4 nights
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.Escape the urban bustle at Dolphin & Whale Watching and Reduit Beach. Step out of Soufriere with an excursion to Anse Cochon Beach in Anse La Raye--about 44 minutes away. There's still lots to do: get impressive views of Pitons, take in nature's colorful creations at Diamond Falls Botanical Gardens, admire the sheer force of Piton Falls, and relax in the rural setting at Fond Doux Eco Resort's Heritage Tours.
For more things to do, other places to visit, reviews, and more tourist information, you can read our Soufriere journey planner.
Traveling by flight from Shoal Bay Village to Soufriere takes 9 hours. In March, daily temperatures in Soufriere can reach 85°F, while at night they dip to 76°F. Finish your sightseeing early on the 11th (Sat) to allow enough time to fly to Bridgetown.
Side Trips
Find places to stay Mar 7 — 11:
Highlights from your trip
Bridgetown, Barbados — 5 nights
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Bridgetown is the capital and largest city of Barbados. Your cultural itinerary includes sights like Carlisle Bay and Mount Gay Visitor Centre. Get in touch with nature at Harrison's Cave. and Dover Beach. You'll find plenty of places to visit near Bridgetown: Crane Beach (in Union Hall), Bottom Bay (in Saint Philip Parish) and Barbados Wildlife Reserve (in Saint Peter Parish). And it doesn't end there: get a new perspective on things with Boat Tours & Water Sports, Head underground at Animal Flower Cave, take in nature's colorful creations at Hunte's Gardens, and enjoy the sand and surf at Bathsheba Beach.
For maps, more things to do, ratings, and tourist information, read Bridgetown trip app.
Traveling by flight from Soufriere to Bridgetown takes 3 hours. In March, daytime highs in Bridgetown are 85°F, while nighttime lows are 75°F. Finish up your sightseeing early on the 16th (Thu) so you can travel back home.
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For maps, more things to do, ratings, and tourist information, read Bridgetown trip app.
Traveling by flight from Soufriere to Bridgetown takes 3 hours. In March, daytime highs in Bridgetown are 85°F, while nighttime lows are 75°F. Finish up your sightseeing early on the 16th (Thu) so you can travel back home.
Side Trips
Find places to stay Mar 11 — 16:
Highlights from your trip
Jamaica travel guide
The third most populous English-speaking country in the Americas, Jamaica remains a member of the Commonwealth of Nations, with the British monarch its official head of state. Jamaica tourism thrives thanks to the island nation's reputation for natural beauty, outstanding cuisine, and lively music scene. The country's landscape is as diverse as its population, its tropical climate supporting varied ecosystems that include everything from savannahs to rugged mountain slopes. For most visitors, a holiday in Jamaica is a largely outdoor affair, with hiking, fishing, golfing, camping, snorkeling, horseback riding, and kite surfing among the most popular things to do.
St. John travel guide
With two thirds of St. John designated as a national park, the smallest of the U.S. Virgin Islands is also the least developed, lacking an airport and cruise ship docks. Although well connected to its more commercialized neighbor, St. Thomas, St. John makes it easy to get away from crowds and enjoy pristine white-sand beaches. On a trip to St. John you can spend your days snorkeling or kayaking, explore the verdant hills of the national park, or head to Cruz Bay, the islands largest town, for excellent dining and shopping.
St. Lucia travel guide
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.
