52 days in Caribbean Itinerary

52 days in Caribbean Itinerary

Created using Inspirock Caribbean trip itinerary planner
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1
Southampton Parish, Bermuda
— 1 night
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2
Providenciales, Turks and Caicos
— 4 nights
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3
Punta Cana, Dominican Republic
— 5 nights
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4
Willemstad, Curacao
— 5 nights
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5
Palm - Eagle Beach, Aruba
— 3 nights
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6
Bridgetown, Barbados
— 4 nights
Fly to Beef Island, Ferry to Virgin Gorda
7
Virgin Gorda, British Virgin Islands
— 5 nights
Ferry
8
Cruz Bay, U.S. Virgin Islands
— 5 nights
Ferry
9
Culebra, Puerto Rico
— 3 nights
Fly
10
West End Village, Anguilla
— 4 nights
Taxi to Anguilla, Ferry to Simpson Bay
11
Simpson Bay, St. Maarten-St. Martin
— 5 nights
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12
Ocho Rios, Jamaica
— 2 nights
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13
George Town, Cayman Islands
— 5 nights
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Southampton Parish, Bermuda — 1 night

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.
On the 9th (Thu), don't miss a visit to The Unfinished Church, then explore the fascinating underground world of Crystal & Fantasy Caves, and then kick back and relax at Horseshoe Bay Beach. Here are some ideas for day two: kick back and relax at Elbow Beach and then admire nature's wide array of creatures at Bermuda Aquarium, Natural History Museum & Zoo.

To find reviews, traveler tips, photos, and more tourist information, read Southampton Parish itinerary planner.

Toronto, Canada to Southampton Parish is an approximately 6-hour flight. The time zone difference moving from Eastern Standard Time to Atlantic Standard Time is 1 hour. Expect a bit warmer temperatures when traveling from Toronto in June; daily highs in Southampton Parish reach 32°C and lows reach 26°C. Wrap up your sightseeing on the 10th (Fri) early enough to fly to Providenciales.
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Parks · Beaches · Outdoors · Nature
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Find places to stay Jun 9 — 10:

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.
Providenciales is known for beaches, wildlife, and sightseeing. Your trip includes some of its best attractions: stroll through Grace Bay Beach, take in the dramatic natural features at Smith's Reef, explore the gorgeous colors at Coral Gardens Reef, and trot along with a tour on horseback.

Plan a trip to Providenciales easily and quickly by telling Inspirock to suggest an itinerary.

Traveling by flight from Southampton Parish to Providenciales takes 9 hours. Traveling from Southampton Parish to Providenciales, you'll gain 1 hour due to the time zone difference. Plan for somewhat warmer temperatures traveling from Southampton Parish in June, with highs in Providenciales at 37°C and lows at 31°C. Wrap up your sightseeing on the 14th (Tue) early enough to fly to Punta Cana.
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Find places to stay Jun 10 — 14:

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.
When in Punta Cana, make a side trip to see Altos de Chavon in La Romana, approximately La Romana away. Spend a day of island exploring on the 17th (Fri) at Saona Island. Spend the 19th (Sun) spotting exotic species with a safari tour. There's still lots to do: kick your exploration up a notch at some of the top local zipline courses and adventure parks, indulge in some personalized pampering at Flavio Acuna Spa Natural Center, kick back and relax at Bavaro Beach, and stop by La Perla Dominicana.

For maps, where to stay, other places to visit, and more tourist information, read Punta Cana trip itinerary builder app.

Getting from Providenciales to Punta Cana by flight takes about 5 hours. The time zone changes from Eastern Standard Time to Atlantic Standard Time, which is usually a 1 hour difference. In June, plan for daily highs up to 36°C, and evening lows to 28°C. Finish your sightseeing early on the 19th (Sun) so you can fly to Willemstad.
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Find places to stay Jun 14 — 19:

Willemstad, Curacao — 5 nights

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. Willemstad is known for sightseeing, wildlife, and adventure. Your trip includes some of its best attractions: kick back and relax at Playa PortoMari, snap pictures at Queen Emma Pontoon Bridge, take a leisurely stroll along Handelskade, and wander the streets of Riffort Village.

To find other places to visit, ratings, traveler tips, and other tourist information, refer to the Willemstad attractions planner.

Traveling by flight from Punta Cana to Willemstad takes 4.5 hours. In June in Willemstad, expect temperatures between 37°C during the day and 31°C at night. Cap off your sightseeing on the 24th (Fri) early enough to catch the flight to Palm - Eagle Beach.
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Find places to stay Jun 19 — 24:

Palm - Eagle Beach, Aruba — 3 nights

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. The adventure continues: kick back and relax at Eagle Beach, tour the pleasant surroundings at Palm Beach, and enjoy the sea views from California Lighthouse and Sasariwichi Dunes.

To see photos, where to stay, traveler tips, and tourist information, read our Palm - Eagle Beach trip planning website.

You can fly from Willemstad to Palm - Eagle Beach in 4 hours. In June, daily temperatures in Palm - Eagle Beach can reach 38°C, while at night they dip to 31°C. Wrap up your sightseeing by early afternoon on the 27th (Mon) to allow enough time to fly to Bridgetown.
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Find places to stay Jun 24 — 27:

Bridgetown, Barbados — 4 nights

Bridgetown is the capital and largest city of Barbados. You'll find plenty of places to visit near Bridgetown: Saint Peter Parish (Barbados Wildlife Reserve & St. Nicholas Abbey) and Bottom Bay (in Saint Philip Parish). There's lots more to do: Head underground at Harrison's Cave., take in nature's colorful creations at Welchman Hall Gully, stroll through Carlisle Bay, and brush up on your knowledge of spirits at Mount Gay Visitor Centre.

To find other places to visit, photos, and tourist information, refer to the Bridgetown trip itinerary builder website.

Traveling by flight from Palm - Eagle Beach to Bridgetown takes 9.5 hours. In June, daily temperatures in Bridgetown can reach 35°C, while at night they dip to 30°C. Finish your sightseeing early on the 1st (Fri) so you can travel to Virgin Gorda.
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Parks · Outdoors · Breweries & Distilleries · Beaches
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Find places to stay Jun 27 — Jul 1:

Virgin Gorda, British Virgin Islands — 5 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.
Virgin Gorda is known for nature, wildlife, and beaches. Your trip includes some of its best attractions: get interesting insight from Sunchaser Scuba Ltd., explore and take pictures at Saba Rock, kick back and relax at Spring Bay, and head outdoors with Fusion BVI.

To find traveler tips, maps, other places to visit, and more tourist information, you can read our Virgin Gorda tour itinerary planning app.

Getting from Bridgetown to Virgin Gorda by combination of flight and ferry takes about 6 hours. In July, plan for daily highs up to 37°C, and evening lows to 31°C. Finish your sightseeing early on the 6th (Wed) so you can ride a ferry to Cruz Bay.
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Find places to stay Jul 1 — 6:

Cruz Bay, U.S. Virgin Islands — 5 nights

The gateway to the island of Saint John, Cruz Bay represents the island's largest town, port, and commercial center.
Explore the numerous day-trip ideas around Cruz Bay: Magens Bay (in Magens Bay) and Coral World Ocean Park (in Smith Bay). There's much more to do: enjoy the sand and surf at Trunk Bay Beach, stop by Bamboo Studio, relax and rejuvenate at Coastal Retreat Studios & Wellness, and explore the activities along Hawksnest Beach.

To see ratings, where to stay, reviews, and tourist information, go to the Cruz Bay route builder app.

Traveling by ferry from Virgin Gorda to Cruz Bay takes 2.5 hours. Alternatively, you can do a combination of flight and ferry. In July, plan for daily highs up to 38°C, and evening lows to 31°C. Wrap up your sightseeing on the 11th (Mon) early enough to ride a ferry to Culebra.
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Find places to stay Jul 6 — 11:

Culebra, Puerto Rico — 3 nights

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Culebra is known for beaches, wildlife, and outdoors. Your trip includes some of its best attractions: enjoy the sand and surf at Flamenco Beach, head off the coast to Culebrita, get a new perspective on things with Boat Tours & Water Sports, and stroll through Playa Zoni.

For maps, ratings, reviews, and more tourist information, read Culebra day trip planner.

Traveling by ferry from Cruz Bay to Culebra takes 2.5 hours. In July, daytime highs in Culebra are 38°C, while nighttime lows are 31°C. Cap off your sightseeing on the 14th (Thu) early enough to catch the flight to West End Village.
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Find places to stay Jul 11 — 14:

West End Village, Anguilla — 4 nights

A pleasant coastal town giving access to some of Anguilla's most pristine and picturesque beaches, West End Village attracts visitors looking for a beach resort holiday.
West End Village is known for nature, wildlife, and golf. Your trip includes some of its best attractions: kick back and relax at Shoal Bay, tour the pleasant surroundings at Little Bay, step off the mainland to explore Sandy Island, and explore the activities along Maundays Bay.

Inspirock's itinerary builder makes planning a West End Village trip simple and quick.

You can fly from Culebra to West End Village in 6.5 hours. In July in West End Village, expect temperatures between 36°C during the day and 30°C at night. Finish your sightseeing early on the 18th (Mon) so you can travel to Simpson Bay.
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Find places to stay Jul 14 — 18:

Simpson Bay, St. Maarten-St. Martin — 5 nights

Simpson Bay offers luxury resort living and good access to the main areas of the island.
Simpson Bay is known for wildlife, adventure, and nightlife. Your trip includes some of its best attractions: try to win big at Casino Royale, kick back and relax at Orient Bay Beach, get a new perspective on things with Boat Tours & Water Sports, and explore the activities along Mullet Bay Beach.

To find ratings, maps, other places to visit, and more tourist information, read our Simpson Bay sightseeing planner.

Getting from West End Village to Simpson Bay by combination of taxi and ferry takes about 1.5 hours. Other options: fly. In July, plan for daily highs up to 36°C, and evening lows to 30°C. Wrap up your sightseeing on the 23rd (Sat) early enough to fly to Ocho Rios.
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Find places to stay Jul 18 — 23:

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.
Start off your visit on the 24th (Sun): trek along Fern Gully and then fulfill a lifelong dream with a swim-with-the-dolphins experience. Keep things going the next day: admire the sheer force of Blue Hole and then admire the sheer force of Dunn's River Falls and Park.

For more things to do, photos, where to stay, and other tourist information, refer to the Ocho Rios trip itinerary builder app.

Getting from Simpson Bay to Ocho Rios by flight takes about 5.5 hours. The time zone changes from Atlantic Standard Time to Eastern Standard Time, which is usually a -1 hour difference. In July in Ocho Rios, expect temperatures between 38°C during the day and 30°C at night. Finish your sightseeing early on the 25th (Mon) so you can fly to George Town.
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Parks · Nature · Outdoors · Trails
Find places to stay Jul 23 — 25:

George Town, Cayman Islands — 5 nights

George Town is a city situated on Grand Cayman island of the Cayman Islands. George Town is known for wildlife, adventure, and breweries & distilleries. Your trip includes some of its best attractions: tour the pleasant surroundings at Stingray City Grand Cayman, kick back and relax at Rum Point, browse the exhibits of Cayman Islands National Museum, and look for all kinds of wild species at Wildlife Areas.

For traveler tips, reviews, photos, and tourist information, use the George Town tour planning site.

You can fly from Ocho Rios to George Town in 5 hours. In July, daily temperatures in George Town can reach 38°C, while at night they dip to 30°C. Wrap up your sightseeing on the 30th (Sat) to allow time to fly back home.
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Parks · Outdoors · Wildlife · Beaches
Side Trip
Find places to stay Jul 25 — 30: