30 days in Caribbean Itinerary

30 days in Caribbean Itinerary

Created using Inspirock Caribbean trip itinerary planner
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1
Providenciales, Turks and Caicos
— 4 nights
Fly
2
Punta Cana, Dominican Republic
— 5 nights
Shuttle to Santo Domingo, Fly to Palm - Eagle Beach
3
Palm - Eagle Beach, Aruba
— 2 nights
Fly
4
Culebra, Puerto Rico
— 4 nights
Fly
5
Charlotte Amalie, U.S. Virgin Islands
— 2 nights
Taxi to St Thomas - Red Hook, Ferry to Virgin Gorda
6
Virgin Gorda, British Virgin Islands
— 3 nights
Fly to St Maarten, Ferry to Shoal Bay Village
7
Shoal Bay Village, Anguilla
— 2 nights
Ferry to Sint Maarten, Fly to St. John's
8
St. John's, Antigua and Barbuda
— 3 nights
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9
Saint James Parish, Barbados
— 2 nights
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10
Ocho Rios, Jamaica
— 2 nights
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Providenciales, Turks and Caicos — 4 nights

The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
Bring the kids along to Grace Bay Beach and Shark Diving. And it doesn't end there: enjoy the sand and surf at Taylor Bay Beach, explore the striking landscape at Smith's Reef, make a trip to Leeward Beach, and stroll through Half Moon Bay.

To find traveler tips, photos, maps, and other tourist information, use the Providenciales online travel planner.

Durham, USA to Providenciales is an approximately 9.5-hour flight. Traveling from Durham in January, things will get much warmer in Providenciales: highs are around 82°F and lows about 74°F. Finish your sightseeing early on the 16th (Mon) so you can fly to Punta Cana.
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Outdoors · Parks · Beaches · Wildlife
Side Trip
Find places to stay Jan 12 — 16:

Punta Cana, Dominican Republic — 5 nights

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.
Family-friendly places like Bavaro Beach and Aqua Track Private Day Trips will thrill your kids. Spend a day of island exploring on the 19th (Thu) at Saona Island. There's much more to do: kick your exploration up a notch at some of the top local zipline courses and adventure parks, look for gifts at La Perla Dominicana, get in on the family fun at Manati Park Bavaro, and play a few rounds at Punta Espada Golf Course.

For photos, where to stay, more things to do, and other tourist information, refer to the Punta Cana tour builder tool.

Getting from Providenciales to Punta Cana by flight takes about 5 hours. Due to the time zone difference, you'll lose 1 hour traveling from Providenciales to Punta Cana. Expect a daytime high around 83°F in January, and nighttime lows around 71°F. Cap off your sightseeing on the 21st (Sat) early enough to travel to Palm - Eagle Beach.
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Side Trip
Find places to stay Jan 16 — 21:

Palm - Eagle Beach, Aruba — 2 nights

A long stretch of powdery white sand and aquamarine waters, Palm - Eagle Beach remains one of Aruba's most visited vacation spots.
Start off your visit on the 22nd (Sun): explore the striking landscape at Ayo Rock Formations and then kick back and relax at Eagle Beach.

For where to stay, photos, ratings, and tourist information, refer to the Palm - Eagle Beach planner.

Do a combination of shuttle and flight from Punta Cana to Palm - Eagle Beach in 8 hours. In January, plan for daily highs up to 86°F, and evening lows to 76°F. Wrap up your sightseeing by early afternoon on the 23rd (Mon) to allow enough time to fly to Culebra.
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Find places to stay Jan 21 — 23:

Culebra, Puerto Rico — 4 nights

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Kids will appreciate attractions like Flamenco Beach and Brava Beach. There's much more to do: step off the mainland to explore Culebrita, enjoy the sea views from Culebrita Lighthouse, enjoy the sand and surf at Playa Zoni, and tour the pleasant surroundings at Culebra National Wildlife Refuge.

For reviews, other places to visit, where to stay, and tourist information, you can read our Culebra trip itinerary planner.

Getting from Palm - Eagle Beach to Culebra by flight takes about 10 hours. In January, daily temperatures in Culebra can reach 84°F, while at night they dip to 73°F. Finish your sightseeing early on the 27th (Fri) so you can fly to Charlotte Amalie.
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Find places to stay Jan 23 — 27:

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

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 28th (Sat): enjoy the sand and surf at Trunk Bay Beach and then make a short side trip with Sailing The Cosmos Charters. Keep things going the next day: learn about wildlife with up-close encounters at Coral World Ocean Park, kick back and relax at Coki Point Beach, and then kick back and relax at Magens Bay.

To see ratings, photos, and other tourist information, refer to the Charlotte Amalie day trip planner.

You can fly from Culebra to Charlotte Amalie in 5.5 hours. In January, daily temperatures in Charlotte Amalie can reach 84°F, while at night they dip to 73°F. Wrap up your sightseeing on the 29th (Sun) early enough to travel to Virgin Gorda.
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Find places to stay Jan 27 — 29:

Virgin Gorda, British Virgin Islands — 3 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.
Kids will enjoy The Baths and Spring Bay. Spend the 1st (Wed) exploring nature at Devil's Bay National Park. There's much more to do: surround yourself with nature on a nature and wildlife tour, hike along Biras Creek Trail, and contemplate the waterfront views at Savannah Bay.

For photos, other places to visit, more things to do, and tourist information, read our Virgin Gorda trip planner.

You can do a combination of taxi and ferry from Charlotte Amalie to Virgin Gorda in 2.5 hours. Other options are to ride a ferry; or fly. In January in Virgin Gorda, expect temperatures between 84°F during the day and 75°F at night. Wrap up your sightseeing on the 1st (Wed) early enough to travel to Shoal Bay Village.
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Parks · Outdoors · Nature · Beaches
Find places to stay Jan 29 — Feb 1:

Shoal Bay Village, Anguilla — 2 nights

Start off your visit on the 2nd (Thu): step off the mainland to explore Sandy Island, see some colorful creatures with Vigilant Divers Anguilla, and then tour the pleasant surroundings at Shoal Bay. Get ready for a full day of sightseeing on the next day: stroll through Meads Bay, explore the activities along Maundays Bay, and then tour the pleasant surroundings at Rendezvous Bay Beach.

To find more things to do, other places to visit, and more tourist information, you can read our Shoal Bay Village trip itinerary app.

You can do a combination of flight and ferry from Virgin Gorda to Shoal Bay Village in 4 hours. Alternatively, you can fly. In February, daytime highs in Shoal Bay Village are 83°F, while nighttime lows are 72°F. Wrap up your sightseeing on the 3rd (Fri) to allow time to travel to St. John's.
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Side Trips
Find places to stay Feb 1 — 3:

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.
Family-friendly places like Dickenson Bay and Galley Bay Beach will thrill your kids. Step out of St. John's with an excursion to Nelson's Dockyard in English Harbour--about 40 minutes away. And it doesn't end there: tour the pleasant surroundings at Valley Church Beach, look for all kinds of wild species at Stingray City, and look for gifts at Silver Chelles.

For traveler tips, reviews, ratings, and other tourist information, read our St. John's day trip planning tool.

Getting from Shoal Bay Village to St. John's by combination of ferry and flight takes about 4.5 hours. February in St. John's sees daily highs of 82°F and lows of 72°F at night. Finish your sightseeing early on the 6th (Mon) so you can fly to Saint James Parish.
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Side Trips
Find places to stay Feb 3 — 6:

Saint James Parish, Barbados — 2 nights

Saint James Parish, with its white sand coastline and modern coastal developments, has gained a reputation as a favorite haunt of the rich and famous.
Start off your visit on the 7th (Tue): take a tour by water with Boat Tours & Water Sports, then admire the natural beauty at Hunte's Gardens, then admire the natural beauty at Andromeda Botanic Gardens, and finally kick back and relax at Soup Bowl. Here are some ideas for day two: Head underground at Harrison's Cave., take in nature's colorful creations at Welchman Hall Gully, then kick back and relax at Bottom Bay, and finally kick back and relax at Carlisle Bay.

For ratings, traveler tips, photos, and more tourist information, refer to the Saint James Parish visit planning tool.

You can fly from St. John's to Saint James Parish in 4.5 hours. In February, plan for daily highs up to 84°F, and evening lows to 74°F. Finish up your sightseeing early on the 8th (Wed) so you can catch the flight to Ocho Rios.
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Find places to stay Feb 6 — 8:

Ocho Rios, Jamaica — 2 nights

A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
On the 9th (Thu), take in the dramatic scenery at Dunn's River Falls and Park and then tour the pleasant surroundings at Fern Gully. On the next day, take in the dramatic scenery at Blue Hole.

To see traveler tips, maps, ratings, and more tourist information, use the Ocho Rios trip itinerary planning tool.

Traveling by flight from Saint James Parish to Ocho Rios takes 6 hours. Due to the time zone difference, you'll gain 1 hour traveling from Saint James Parish to Ocho Rios. In February, daily temperatures in Ocho Rios can reach 87°F, while at night they dip to 73°F. Wrap up your sightseeing by early afternoon on the 10th (Fri) to allow time for the flight back home.
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Parks · Nature · Outdoors · Trails
Find places to stay Feb 8 — 10: