26 days in Caribbean Itinerary

26 days in Caribbean Itinerary

Created using Inspirock Caribbean trip itinerary planner

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Route & dates

26 days in Caribbean Itinerary

Start: London, United Kingdom
Fly:  12​h 15​min
1
Montego Bay, Jamaica
— 3 nights
Fly:  5​h 15​min
2
George Town, Cayman Islands
— 3 nights
Fly:  1​h 30​min
3
Havana, Cuba
— 3 nights
Fly:  4​h
4
Nassau, Bahamas
— 3 nights
Fly:  4​h 45​min
5
Providenciales, Turks and Caicos
— 2 nights
Fly:  1​h 30​min
6
Middle Caicos, Turks and Caicos
— 1 night
Fly:  1​h 45​min
7
Cockburn Town, Turks and Caicos
— 2 nights
Fly:  7​h 15​min
8
Virgin Gorda, British Virgin Islands
— 1 night
Drive:  1​h 30​min
9
West End, British Virgin Islands
— 1 night
Drive + Fly:  8​h 30​min
10
Punta Cana, Dominican Republic
— 5 nights
Fly:  13​h
End: London, United Kingdom

3
nights
Montego Bay, Jamaica

The second largest city in Jamaica, Montego Bay boasts an international airport and a major cruise-line terminal, so it regularly receives a big influx of visitors to the island.
You'll get in some beach time at Seven Mile Beach and Doctor's Cave Beach. Spend the 3rd (Wed) wandering through the wild on a nature and wildlife tour.

To see where to stay, other places to visit, reviews, and tourist information, go to the Montego Bay online driving holiday planner .

London, UK to Montego Bay is an approximately 12.5-hour flight. You can also do a combination of flight and bus. You'll gain 5 hours traveling from London to Montego Bay due to the time zone difference. When traveling from London in July, plan for somewhat warmer days in Montego Bay, with highs around 39°C, while nights are much warmer with lows around 29°C. You will leave for George Town on the 4th (Thu).

Things to do in Montego Bay

Outdoors Tours Wildlife

Side Trip

Seven Mile Beach
Highlights from your plan
Nature & Wildlife Tours
Seven Mile Beach ©
Seven Mile Beach
Doctor's Cave Beach ©
Doctor's Cave Beach

3
nights
George Town, Cayman Islands

George Town ©
George Town is a city situated on Grand Cayman island of the Cayman Islands. On the 5th (Fri), enjoy the sand and surf at Seven Mile Beach and then cool off at Rum Point. On the 6th (Sat), you'll have a packed day of sightseeing: cool off at Cayman Turtle Centre: Island Wildlife Encounter and then get a new perspective on things with Boat Tours & Water Sports.

For ratings, reviews, more things to do, and tourist information, go to the George Town trip itinerary builder app .

You can fly from Montego Bay to George Town in 5.5 hours. Alternatively, you can do a combination of bus and flight. July in George Town sees daily highs of 38°C and lows of 30°C at night. Finish up your sightseeing early on the 7th (Sun) so you can travel to Havana.

Things to do in George Town

Parks Outdoors Wildlife

Side Trips

Seven Mile Beach, Cayman Turtle Centre: Island Wildlife Encounter, Rum Point
Highlights from your plan
Seven Mile Beach ©
Seven Mile Beach
Scuba & Snorkeling

3
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Step out of the city life by going to Playa de Jibacoa and Santa Maria del Mar (Santa Maria Beach). There's still lots to do: get to know the fascinating history of El Malecon, make a trip to Plaza de la Catedral, and kick back and relax at Playas de Este.

To find where to stay, photos, and other tourist information, refer to the Havana trip planner .

Getting from George Town to Havana by flight takes about 1.5 hours. Traveling from George Town in July, expect slightly colder with lows of 26°C in Havana. Cap off your sightseeing on the 10th (Wed) early enough to travel to Nassau.

Things to do in Havana

Outdoors Beaches Parks

Side Trip

Playa de Jibacoa
Highlights from your plan
Playa de Jibacoa ©
Playa de Jibacoa
Santa Maria del Mar ©
Santa Maria del Mar
Malecón of Havana ©
Malecón of Havana

3
nights
Nassau, Bahamas

Nassau ©
On a trip to Nassau you can immerse yourself in a dynamic city atmosphere or spend your days lazing on the soft golden sands.
Visiting Cable Beach and Cabbage Beach will get you outdoors.

Inspirock's itinerary builder makes planning a Nassau trip simple and quick.

You can fly from Havana to Nassau in 4 hours. Traveling from Havana in July, plan for a bit warmer nights in Nassau, with lows around 30°C. Finish up your sightseeing early on the 13th (Sat) so you can travel to Providenciales.

Things to do in Nassau

Outdoors Beaches Parks
Highlights from your plan
Cable Beach ©
Cable Beach
Cabbage Beach ©
Cabbage Beach

2
nights
Providenciales, Turks and Caicos

Providenciales ©
The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
Kick off your visit on the 13th (Sat): see the vivid underwater world at Bight Reef, kick back and relax at Grace Bay, and then see the vivid underwater world at Little Water Cay. Get ready for a full day of sightseeing on the 14th (Sun): kick back and relax at Taylor Bay Beach.

To find traveler tips, maps, photos, and other tourist information, you can read our Providenciales road trip planner .

You can fly from Nassau to Providenciales in 5 hours. In July, daytime highs in Providenciales are 37°C, while nighttime lows are 31°C. Finish your sightseeing early on the 15th (Mon) to allow enough time to travel to Middle Caicos.

Things to do in Providenciales

Parks Outdoors Beaches
Highlights from your plan
Grace Bay Beach ©
Grace Bay Beach
Little Water Cay ©
Little Water Cay
Coral Gardens Reef ©
Coral Gardens Reef

1
night
Middle Caicos, Turks and Caicos

Middle Caicos ©
The largest of the islands, Middle Caicos (also known as Grand Caicos) offers plenty of natural and cultural attractions.
Kick off your visit on the 15th (Mon): enjoy the sand and surf at Bambara Beach and then enjoy the sand and surf at Mudjin Harbor.

To see other places to visit, maps, traveler tips, and more tourist information, refer to the Middle Caicos day trip planner .

You can fly from Providenciales to Middle Caicos in 1.5 hours. In July in Middle Caicos, expect temperatures between 37°C during the day and 31°C at night. Wrap up your sightseeing on the 16th (Tue) to allow time to fly to Cockburn Town.

Things to do in Middle Caicos

Outdoors Beaches Parks
Highlights from your plan
Mudjin Harbor ©
Mudjin Harbor

2
nights
Cockburn Town, Turks and Caicos

Cockburn Town ©
Cockburn Town is the capital city of the Turks and Caicos Islands.GeographyCockburn Town is located on the largest island in the Turks Islands archipelago, Grand Turk Island. On the 16th (Tue), enjoy the sand and surf at Gibbs Cay. On the 17th (Wed), you'll have a packed day of sightseeing: discover the deep blue sea with a scuba or snorkeling tour and then see the vivid underwater world at SunRay Beach.

To find other places to visit, where to stay, and other tourist information, refer to the Cockburn Town sightseeing planning site .

Fly from Middle Caicos to Cockburn Town in 2 hours. Finish up your sightseeing early on the 18th (Thu) so you can travel to West End.

Things to do in Cockburn Town

Outdoors Wildlife Beaches

Side Trip

Grand Turk
Highlights from your plan
Gibbs Cay ©
Gibbs Cay
Scuba & Snorkeling
SunRay Beach ©
SunRay Beach

1
night
Virgin Gorda, British Virgin Islands

Virgin Gorda ©
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.
On the 18th (Thu), enjoy the sand and surf at Savannah Bay, tour the pleasant surroundings at Spring Bay, and then explore the striking landscape at The Baths. Get ready for a full day of sightseeing on the next day: explore the wealth of natural beauty at Devil's Bay National Park.

To plan Virgin Gorda vacation without wasting time, ask Inspirock to design an itinerary.

You can do a combination of flight and ferry from Cockburn Town to Virgin Gorda in 7.5 hours. Another option is to do a combination of flight, car, and ferry. The time zone difference moving from Atlantic Standard Time (AST) to Atlantic Standard Time (AST) is 1 hour. Expect a daytime high around 37°C in July, and nighttime lows around 31°C. Cap off your sightseeing on the 19th (Fri) early enough to travel to West End.

Things to do in Virgin Gorda

Parks Nature Outdoors
Highlights from your plan
Spring Bay ©
Spring Bay
The Baths ©
The Baths
Devil's Bay National Park ©
Devil's Bay National Park

1
night
West End, British Virgin Islands

West End ©
For more things to do, photos, maps, and other tourist information, read West End route planner.

Use the Route module to find suitable travel options from Cockburn Town to West End. Due to the time zone difference, you'll lose 1 hour traveling from Cockburn Town to West End. Expect a daytime high around 37°C in July, and nighttime lows around 31°C. Finish your sightseeing early on the 20th (Sat) to allow enough time to travel to Virgin Gorda.

Things to do in West End

Outdoors Beaches Parks

Side Trip

Long Bay Beach
Highlights from your plan
Long Bay Beach ©
Long Bay Beach

5
nights
Punta Cana, Dominican Republic

Punta Cana ©
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.
You'll enjoy a bit of beach vacationing at Bavaro Beach and Macao Beach. Get in touch with nature at Swim with Dolphins and Safaris. Step out of Punta Cana with an excursion to Scuba & Snorkeling in Bayahibe--about 1h 10 min away. There's more to do: explore the activities along Hoyo Azul and stop by Smile Dominicana.

To find traveler tips, more things to do, and other tourist information, you can read our Punta Cana online tour planner .

You can do a combination of ferry, car, and flight from Virgin Gorda to Punta Cana in 7.5 hours. Other options are to do a combination of ferry and flight; or do a combination of ferry, flight, and shuttle. July in Punta Cana sees daily highs of 36°C and lows of 29°C at night. Finish your sightseeing early on the 27th (Sat) to allow enough time to travel back home.

Things to do in Punta Cana

Outdoors Tours Wildlife

Side Trip

Scuba & Snorkeling
Highlights from your plan
Bavaro Beach ©
Bavaro Beach
Swim with Dolphins
Safaris

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