32 days in Caribbean Itinerary

32 days in Caribbean Itinerary

Created using Inspirock Caribbean trip itinerary builder

Make it your trip
Fly to L.F. Wade International International Airport, Drive to St. George
1
St. George, Bermuda
— 2 nights
+2
Drive to L.F. Wade International International Airport, Fly to Owen Roberts International Airport, Drive to Seven Mile Beach
2
Seven Mile Beach, Cayman Islands
— 2 nights
Fly
3
Ocho Rios, Jamaica
— 2 nights
Fly
4
Providenciales, Turks and Caicos
— 4 nights
Fly
5
Santo Domingo, Dominican Republic
— 2 nights
Shuttle
6
Punta Cana, Dominican Republic
— 4 nights
Fly
7
Culebra, Puerto Rico
— 3 nights
Fly
8
Shoal Bay Village, Anguilla
— 3 nights
Ferry
9
Simpson Bay, St. Maarten-St. Martin
— 3 nights
Fly
10
Palm - Eagle Beach, Aruba
— 3 nights
Fly
11
Bridgetown, Barbados
— 3 nights
Fly

S M T W T F S
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21

St. George, Bermuda

— 2 nights
Start off your visit on the 19th (Mon): take an in-depth tour of World Heritage Centre - St. George, contemplate the long history of Fort St. Catherine, then kick back and relax at Tobacco Bay, and finally see the interesting displays at Bermuda National Trust Museum. On your second day here, stroll around Blue Hole Park and then Head underground at Crystal & Fantasy Caves.

To see photos, reviews, traveler tips, and tourist information, you can read our St. George trip builder site.

Lisbon, Portugal to St. George is an approximately 14.5-hour combination of flight and car. You'll gain 4 hours traveling from Lisbon to St. George due to the time zone difference. Plan for somewhat warmer nights when traveling from Lisbon in July since evenings lows in St. George dip to 29°C. Wrap up your sightseeing on the 20th (Tue) to allow time to travel to Seven Mile Beach.

Things to do in St. George

Parks · Museums · Outdoors · Beaches

Side Trips

Seven Mile Beach, Cayman Islands

— 2 nights
Seven Mile Beach is a long crescent of coral-sand beach on the western end of Grand Cayman island. On the 21st (Wed), stroll through Cayman Turtle Centre: Island Wildlife Encounter and then head outdoors with Outdoor Activities. Get ready for a full day of sightseeing on the 22nd (Thu): kick back and relax at Seven Mile Beach, stroll through Stingray City Grand Cayman, and then admire the natural beauty at Queen Elizabeth II Botanic Park.

To find reviews, more things to do, ratings, and tourist information, read Seven Mile Beach online travel route planner.

Explore your travel options from St. George to Seven Mile Beach with the Route module. Due to the time zone difference, you'll gain 1 hour traveling from St. George to Seven Mile Beach. In July, plan for daily highs up to 38°C, and evening lows to 30°C. Cap off your sightseeing on the 22nd (Thu) early enough to catch the flight to Ocho Rios.

Things to do in Seven Mile Beach

Parks · Wildlife · Outdoors · Theme Parks

Side Trips

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 23rd (Fri): admire the sheer force of Blue Hole and then kick back and relax at Ocho Rios Bay Beach. On the 24th (Sat), you'll have a packed day of sightseeing: admire the sheer force of Dunn's River Falls and Park and then walk around Konoko Falls.

To see traveler tips, other places to visit, and other tourist information, use the Ocho Rios tour planning site.

Traveling by flight from Seven Mile Beach to Ocho Rios takes 4.5 hours. In July, daytime highs in Ocho Rios are 38°C, while nighttime lows are 30°C. Cap off your sightseeing on the 24th (Sat) early enough to catch the flight to Providenciales.

Things to do in Ocho Rios

Parks · Nature · Outdoors · Beaches

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 nature. Your trip includes some of its best attractions: enjoy the sand and surf at Grace Bay Beach, contemplate the waterfront views at Chalk Sound, relax and rejuvenate at Glow Fitness TCI, and steep yourself in history at Cheshire Hall Plantation.

To see more things to do and more tourist information, read Providenciales driving holiday planner.

Getting from Ocho Rios to Providenciales by flight takes about 5 hours. July in Providenciales sees daily highs of 37°C and lows of 31°C at night. Finish your sightseeing early on the 28th (Wed) so you can fly to Santo Domingo.

Things to do in Providenciales

Parks · Outdoors · Wildlife · Beaches

Side Trip

Santo Domingo, Dominican Republic

— 2 nights
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
On the 29th (Thu), steep yourself in history at Fortaleza Ozama, then appreciate the history behind Columbus Lighthouse (Faro A Colon), then contemplate the long history of Alcazar de Colon, and finally explore the ancient world of Monasterio de San Francisco. Get ready for a full day of sightseeing on the next day: don't miss a visit to Zona Colonial and then take in the architecture and atmosphere at Basilica Cathedral of Santa Maria la Menor.

For ratings, other places to visit, and tourist information, refer to the Santo Domingo trip planner.

Traveling by flight from Providenciales to Santo Domingo takes 5 hours. You'll lose 1 hour traveling from Providenciales to Santo Domingo due to the time zone difference. Wrap up your sightseeing on the 30th (Fri) to allow time to take a shuttle to Punta Cana.

Things to do in Santo Domingo

Historic Sites · Museums

Punta Cana, Dominican Republic

— 4 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.
Spend a day of island exploring on the 1st (Sun) at Saona Island. The adventure continues: get close to the beloved marine mammals with a swim-with-the-dolphins experience, stop by La Perla Dominicana, kick back and relax at Bavaro Beach, and whizz through the canopy at some of the top local zipline courses and adventure parks.

To find photos, traveler tips, and tourist information, use the Punta Cana road trip site.

Getting from Santo Domingo to Punta Cana by shuttle takes about 2 hours. Other options: drive; or fly. In July in Punta Cana, expect temperatures between 36°C during the day and 29°C at night. Finish your sightseeing early on the 3rd (Tue) to allow enough time to fly to Culebra.

Things to do in Punta Cana

Outdoors · Parks · Tours · Nature

Side Trip

Culebra, Puerto Rico

— 3 nights

Little Island

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: stroll through Flamenco Beach, enjoy the sand and surf at Playa Tamarindo, and step off the mainland to explore Culebrita.

For where to stay, reviews, maps, and other tourist information, read Culebra itinerary builder website.

Getting from Punta Cana to Culebra by flight takes about 7.5 hours. Other options: do a combination of bus, ferry, and taxi; or do a combination of bus, ferry, shuttle, and taxi. August in Culebra sees daily highs of 37°C and lows of 31°C at night. Wrap up your sightseeing by early afternoon on the 6th (Fri) to allow enough time to fly to Shoal Bay Village.

Things to do in Culebra

Parks · Outdoors · Beaches · Nature

Shoal Bay Village, Anguilla

— 3 nights
Explore the numerous day-trip ideas around Shoal Bay Village: West End Village (Maundays Bay & Scuba & Snorkeling).

To see traveler tips, other places to visit, where to stay, and other tourist information, read Shoal Bay Village online trip itinerary planner.

Traveling by flight from Culebra to Shoal Bay Village takes 7.5 hours. In August, daytime highs in Shoal Bay Village are 37°C, while nighttime lows are 30°C. Finish your sightseeing early on the 9th (Mon) to allow enough time to ride a ferry to Simpson Bay.

Things to do in Shoal Bay Village

Parks · Outdoors · Beaches · Nature

Side Trips

Simpson Bay, St. Maarten-St. Martin

— 3 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: tour the pleasant surroundings at Maho Beach, race across the water with a speed boat tour, try your luck at Casino Royale, and kick back and relax at Cupecoy Bay Beach.

For reviews, ratings, maps, and more tourist information, you can read our Simpson Bay holiday planner.

You can ride a ferry from Shoal Bay Village to Simpson Bay in 1.5 hours. Alternatively, you can fly. In August, daytime highs in Simpson Bay are 36°C, while nighttime lows are 31°C. Cap off your sightseeing on the 12th (Thu) early enough to catch the flight to Palm - Eagle Beach.

Things to do in Simpson Bay

Outdoors · Beaches · Parks · Tours

Side Trips

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. And it doesn't end there: kick back and relax at Eagle Beach, stroll through Hadicurari Beach, and visit a coastal fixture at California Lighthouse.

For reviews, other places to visit, more things to do, and more tourist information, use the Palm - Eagle Beach trip planner.

Traveling by flight from Simpson Bay to Palm - Eagle Beach takes 7.5 hours. In August, plan for daily highs up to 39°C, and evening lows to 32°C. Wrap up your sightseeing by early afternoon on the 15th (Sun) to allow time for the flight to Bridgetown.

Things to do in Palm - Eagle Beach

Outdoors · Beaches · Parks · Wildlife

Side Trips

Bridgetown, Barbados

— 3 nights
Bridgetown is the capital and largest city of Barbados. On the 16th (Mon), kick back and relax at Bottom Bay, then contemplate the long history of Andromeda Botanic Gardens, and then Head underground at Animal Flower Cave. On your second day here, admire all the interesting features of Gun Hill Signal Station, take in nature's colorful creations at Hunte's Gardens, then Head underground at Harrison's Cave., then take in nature's colorful creations at Welchman Hall Gully, and finally get outside with Outdoor Activities.

For maps, photos, where to stay, and other tourist information, read Bridgetown road trip tool.

Traveling by flight from Palm - Eagle Beach to Bridgetown takes 9.5 hours. Traveling from Palm - Eagle Beach in August, you will find days in Bridgetown are a bit cooler (35°C), and nights are about the same (30°C). Finish your sightseeing early on the 18th (Wed) to allow enough time to fly back home.

Things to do in Bridgetown

Parks · Outdoors · Historic Sites · Nature

Side Trips