52 days in Caribbean Itinerary

52 days in Caribbean Itinerary

Created using Inspirock Caribbean trip planner
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1
Southampton Parish, Bermuda
— 1 night
Fly
2
Providenciales, Turks and Caicos
— 4 nights
Fly
3
Punta Cana, Dominican Republic
— 5 nights
Fly
4
Willemstad, Curacao
— 5 nights
Fly
5
Palm - Eagle Beach, Aruba
— 3 nights
Fly
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
Fly
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 12th (Sun), make a trip to The Unfinished Church, then explore the fascinating underground world of Crystal & Fantasy Caves, and then tour the pleasant surroundings at Horseshoe Bay Beach. On your second day here, stroll through Elbow Beach and then observe the fascinating underwater world at Bermuda Aquarium, Natural History Museum & Zoo.

To see where to stay, more things to do, ratings, and other tourist information, use the Southampton Parish day trip site.

Toronto, Canada to Southampton Parish is an approximately 6-hour flight. Due to the time zone difference, you'll lose 1 hour traveling from Toronto to Southampton Parish. Prepare for somewhat warmer weather when traveling from Toronto in June: high temperatures in Southampton Parish hover around 32°C and lows are around 26°C. Finish your sightseeing early on the 13th (Mon) so you can fly to Providenciales.
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Parks · Beaches · Outdoors · Zoos & Aquariums
Side Trips
Find places to stay Jun 12 — 13:

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: kick back and relax at Grace Bay Beach, make a trip to Leeward Beach, tour the pleasant surroundings at Smith's Reef, and explore the gorgeous colors at Coral Gardens Reef.

To see reviews, other places to visit, more things to do, and other tourist information, go to the Providenciales trip itinerary maker site.

Getting from Southampton Parish to Providenciales by flight takes about 9 hours. Due to the time zone difference, you'll gain 1 hour traveling from Southampton Parish to Providenciales. Traveling from Southampton Parish in June, expect Providenciales to be somewhat warmer, temps between 37°C and 31°C. Cap off your sightseeing on the 17th (Fri) early enough to catch the flight to Punta Cana.
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Outdoors · Parks · Wildlife · Tours
Side Trip
Find places to stay Jun 13 — 17:

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.
Take a break from Punta Cana with a short trip to Altos de Chavon in La Romana, about 1h 20 min away. Spend a day of island exploring on the 20th (Mon) at Saona Island. Spend the 22nd (Wed) spotting exotic species with a safari tour. There's lots more to do: kick your exploration up a notch at some of the top local zipline courses and adventure parks, kick back and relax at Bavaro Beach, stop by La Perla Dominicana, and indulge in some personalized pampering at Flavio Acuna Spa Natural Center.

To find where to stay, ratings, more things to do, and tourist information, use the Punta Cana journey tool.

You can fly from Providenciales to Punta Cana in 5 hours. The time zone difference when traveling from Providenciales to Punta Cana is 1 hour. In June, daily temperatures in Punta Cana can reach 36°C, while at night they dip to 28°C. Finish up your sightseeing early on the 22nd (Wed) so you can catch the flight to Willemstad.
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Outdoors · Tours · Wildlife · Parks
Side Trips
Find places to stay Jun 17 — 22:

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: enjoy the sand and surf at Playa PortoMari, visit Riffort Village, head off the coast to Klein (Little) Curacao, and tour the pleasant surroundings at Mambo Beach.

To see reviews, more things to do, other places to visit, and other tourist information, read Willemstad trip itinerary maker website.

You can fly from Punta Cana to Willemstad in 4.5 hours. In June, daily temperatures in Willemstad can reach 37°C, while at night they dip to 31°C. Wrap up your sightseeing on the 27th (Mon) early enough to fly to Palm - Eagle Beach.
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Parks · Outdoors · Beaches · Nature
Side Trip
Find places to stay Jun 22 — 27:

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.
Take a break from Palm - Eagle Beach with a short trip to Baby Beach in San Nicolas, about 48 minutes away. There's much more to do: stroll through Eagle Beach, enjoy the sea views from California Lighthouse and Sasariwichi Dunes, and enjoy the sand and surf at Palm Beach.

To see photos, ratings, more things to do, and other tourist information, refer to the Palm - Eagle Beach trip planning site.

Traveling by flight from Willemstad to Palm - Eagle Beach takes 4 hours. In June, plan for daily highs up to 38°C, and evening lows to 31°C. Wrap up your sightseeing by early afternoon on the 30th (Thu) to allow enough time to fly to Bridgetown.
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Beaches · Parks · Outdoors · Wildlife
Side Trips
Find places to stay Jun 27 — 30:

Bridgetown, Barbados — 4 nights

Bridgetown is the capital and largest city of Barbados. Explore the numerous day-trip ideas around Bridgetown: Bottom Bay (in Saint Philip Parish) and Saint Peter Parish (Barbados Wildlife Reserve & St. Nicholas Abbey). And it doesn't end there: explore the fascinating underground world of Harrison's Cave., kick back and relax at Carlisle Bay, take in nature's colorful creations at Hunte's Gardens, and steep yourself in history at Andromeda Botanic Gardens.

For other places to visit, reviews, photos, and other tourist information, you can read our Bridgetown trip itinerary site.

You can fly from Palm - Eagle Beach to Bridgetown in 9.5 hours. In June, plan for daily highs up to 35°C, and evening lows to 30°C. Finish your sightseeing early on the 4th (Mon) so you can travel to Virgin Gorda.
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Parks · Outdoors · Breweries & Distilleries · Beaches
Side Trips
Find places to stay Jun 30 — Jul 4:

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 a new perspective on things with Sunchaser Scuba Ltd., go deep underground at Copper Mine Point, contemplate the waterfront views at Savannah Bay, and admire all the interesting features of Wreck of the Chikuzen.

For maps, where to stay, photos, and other tourist information, you can read our Virgin Gorda online day trip planner.

You can do a combination of flight and ferry from Bridgetown to Virgin Gorda in 6 hours. In July, daytime highs in Virgin Gorda are 37°C, while nighttime lows are 31°C. Wrap up your sightseeing on the 9th (Sat) to allow time to ride a ferry to Cruz Bay.
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Outdoors · Beaches · Parks · Wildlife
Find places to stay Jul 4 — 9:

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.
Change things up with these side-trips from Cruz Bay: Magens Bay (in Magens Bay) and Coral World Ocean Park (in Smith Bay). And it doesn't end there: stroll through Trunk Bay Beach, enjoy the sand and surf at Cinnamon Bay Beach, don't miss a visit to Annaberg Sugar Plantation, and look for gifts at Bamboo Studio.

To find traveler tips, maps, other places to visit, and more tourist information, use the Cruz Bay trip planning tool.

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. Finish up your sightseeing early on the 14th (Thu) so you can catch the ferry to Culebra.
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Parks · Outdoors · Beaches · Nature
Side Trips
Find places to stay Jul 9 — 14:

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: kick back and relax at Flamenco Beach, tour the pleasant surroundings at Playa Zoni, take a tour by water with Boat Tours & Water Sports, and step off the mainland to explore Culebrita.

To find maps, ratings, where to stay, and other tourist information, use the Culebra road trip planner.

You can ride a ferry from Cruz Bay to Culebra in 2.5 hours. July in Culebra sees daily highs of 38°C and lows of 31°C at night. Wrap up your sightseeing on the 17th (Sun) early enough to fly to West End Village.
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Parks · Outdoors · Beaches · Nature
Find places to stay Jul 14 — 17:

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 Barnes Bay Beach, step off the mainland to explore Sandy Island, and get a taste of the local shopping with Limin' Boutique.

To see photos, ratings, maps, and more tourist information, go to the West End Village road trip planning tool.

Traveling by flight from Culebra to West End Village takes 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 21st (Thu) to allow enough time to travel to Simpson Bay.
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Parks · Outdoors · Beaches · Nature
Side Trips
Find places to stay Jul 17 — 21:

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 Cupecoy Bay Beach, tour the pleasant surroundings at Maho Beach, and surround yourself with nature on a nature and wildlife tour.

For photos, traveler tips, where to stay, and other tourist information, read our Simpson Bay road trip tool.

Traveling by combination of taxi and ferry from West End Village to Simpson Bay takes 1.5 hours. Alternatively, you can fly. In July, daily temperatures in Simpson Bay can reach 36°C, while at night they dip to 30°C. Wrap up your sightseeing on the 26th (Tue) early enough to fly to Ocho Rios.
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Outdoors · Parks · Beaches · Wildlife
Side Trips
Find places to stay Jul 21 — 26:

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.
Kick off your visit on the 27th (Wed): hike along Fern Gully and then get close to the beloved marine mammals with a swim-with-the-dolphins experience. Get ready for a full day of sightseeing on the next day: admire the sheer force of Blue Hole and then take in the dramatic scenery at Dunn's River Falls and Park.

To see maps, more things to do, ratings, and tourist information, you can read our Ocho Rios trip itinerary builder app.

You can fly from Simpson Bay to Ocho Rios in 5.5 hours. The time zone changes from Atlantic Standard Time (AST) to Eastern Standard Time (EST), which is usually a -1 hour difference. In July, daytime highs in Ocho Rios are 38°C, while nighttime lows are 30°C. Finish your sightseeing early on the 28th (Thu) so you can fly to George Town.
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Parks · Nature · Outdoors · Trails
Find places to stay Jul 26 — 28:

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: stroll through Stingray City Grand Cayman, see majestic marine mammals with a dolphin and whale watching tour, brush up on your knowledge of spirits at Cayman Spirits Co. Distillery, and Head underground at Cayman Crystal Caves.

To see reviews, where to stay, more things to do, and more tourist information, you can read our George Town travel route tool.

Fly from Ocho Rios to George Town in 5 hours. In July, plan for daily highs up to 38°C, and evening lows to 30°C. Wrap up your sightseeing on the 2nd (Tue) early enough to fly back home.
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Parks · Outdoors · Beaches · Wildlife
Side Trip
Find places to stay Jul 28 — Aug 2: