11 days in Barbados, Trinidad and Tobago & Jamaica Itinerary

11 days in Barbados, Trinidad and Tobago & Jamaica Itinerary

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Route & dates

11 days in Barbados, Trinidad and Tobago & Jamaica Itinerary

Start: Cape Town, South Africa
Fly:  27​h
1
Bridgetown, Barbados
— 2 nights
Fly:  7​h
2
Scarborough, Trinidad and Tobago
— 1 night
Fly + bus:  14​h
3
Negril, Jamaica
— 1 night
bus:  1​h 30​min
4
Montego Bay, Jamaica
— 2 nights
Fly:  25​h
End: Cape Town, South Africa

2
nights
Bridgetown, Barbados

Bridgetown ©
Bridgetown is the capital and largest city of Barbados. Relax by the water at Pebbles Beach and Hastings Beach. Explore hidden gems such as Accra Beach and Bottom Bay. There's much more to do: take a tour by water with Jammin Catamaran Cruises, kick back and relax at Enterprise (Miami) Beach, stroll through Allamanda Beach Boardwalk, and steep yourself in history at Parliament Buildings.

To see photos, where to stay, traveler tips, and more tourist information, you can read our Bridgetown trip planner .

Cape Town, South Africa to Bridgetown is an approximately 27-hour flight. The time zone changes from South Africa Standard Time to Atlantic Standard Time, which is usually a -6 hour difference. Traveling from Cape Town in September, you will find days in Bridgetown are somewhat warmer (36°C), and nights are much warmer (30°C). Finish your sightseeing early on the 8th (Sun) to allow enough time to travel to Scarborough.

Things to do in Bridgetown

Outdoors Parks Beaches

Side Trips

Hastings, Enterprise (Miami) Beach, Accra Beach, Bottom Bay
Find places to stay Sep 6 — 8:
Highlights from your plan
Bottom Bay ©
Bottom Bay
Pebbles Beach ©
Pebbles Beach
Enterprise (Miami) Beach ©
Enterprise (Miami) Beach

1
night
Scarborough, Trinidad and Tobago

Scarborough ©
Scarborough is the largest city and capital of the Island of Tobago and the fifth-most-populous in Trinidad and Tobago. Kick off your visit on the 9th (Mon): stroll through Castara Bay, then stroll through Englishman's Bay, and then take in the history at Fort King George. On the 10th (Tue), you'll have a packed day of sightseeing: kick back and relax at Nylon Pool, see some colorful creatures with a scuba or snorkeling tour, and then stroll through Store Bay.

To see more things to do, ratings, other places to visit, and other tourist information, read our Scarborough tour planner.

Do a combination of flight and bus from Bridgetown to Scarborough in 7 hours. Alternatively, you can do a combination of flight and ferry. Finish your sightseeing early on the 10th (Tue) to allow enough time to travel to Negril.

Things to do in Scarborough

Outdoors Parks Beaches

Side Trips

Tobago, Scuba & Snorkeling
Find places to stay Sep 8 — 10:
Highlights from your plan
Castara Bay ©
Castara Bay
Englishman's Bay ©
Englishman's Bay
Store Bay ©
Store Bay

1
night
Negril, Jamaica

Negril ©
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
On the 11th (Wed), look for all kinds of wild species at Barney's Flower & Hummingbird Garden Jamaica, then head off the coast to Booby Cay Island, and then enjoy the sand and surf at Seven Mile Beach. Keep things going the next day: relax and rejuvenate at some of the top local wellness centers, then take a memorable tour with Tours, and then kick back and relax at Half Moon Beach.

To see ratings, traveler tips, other places to visit, and other tourist information, read our Negril trip builder tool .

Getting from Scarborough to Negril by combination of bus and flight takes about 14 hours. Other options: do a combination of ferry, flight, and bus. The time zone changes from Atlantic Standard Time (AST) to Eastern Standard Time (EST), which is usually a -1 hour difference. Expect a daytime high around 38°C in September, and nighttime lows around 29°C. Wrap up your sightseeing on the 12th (Thu) to allow time to drive to Montego Bay.

Things to do in Negril

Parks Outdoors Beaches
Find places to stay Sep 11 — 12:
Highlights from your plan
Seven Mile Beach ©
Seven Mile Beach
Half Moon Beach ©
Half Moon Beach

2
nights
Montego Bay, Jamaica

Montego Bay ©
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.
Kick off your visit on the 13th (Fri): relax in the rural setting at Croydon Plantation, look for all kinds of wild species at Rocklands Bird Sanctuary (Near Montego Bay), and then kick back and relax at Doctor's Cave Beach. Keep things going the next day: kick your exploration up a notch at some of the top local zipline courses and adventure parks and then play a few rounds at Cinnamon Hill Golf Course.

To see more things to do, ratings, other places to visit, and tourist information, read our Montego Bay trip itinerary website .

Getting from Negril to Montego Bay by car takes about 1.5 hours. Other options: take a bus. In September, plan for daily highs up to 38°C, and evening lows to 29°C. Finish your sightseeing early on the 14th (Sat) so you can travel back home.

Things to do in Montego Bay

Outdoors Parks Wildlife

Side Trip

Rocklands Bird Sanctuary (Near Montego Bay)
Find places to stay Sep 12 — 14:
Highlights from your plan
Doctor's Cave Beach ©
Doctor's Cave Beach
Zipline

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