36 days in West Indies Itinerary

36 days in West Indies Itinerary

Created using Inspirock West Indies vacation planner

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Route & dates

36 days in West Indies Itinerary

Start: Dar es Salaam, Tanzania
Fly:  30​h
1
St. John's, Antigua and Barbuda
— 4 nights
Fly + Drive:  3​h 30​min
2
Roseau, Dominica
— 5 nights
Fly:  4​h 45​min
3
Bridgetown, Barbados
— 7 nights
Fly:  7​h
4
Scarborough, Trinidad and Tobago
— 3 nights
Fly:  9​h 45​min
5
George Town, Cayman Islands
— 7 nights
Fly:  5​h 30​min
6
Montego Bay, Jamaica
— 3 nights
Fly:  30​h
End: Dar es Salaam, Tanzania

4
nights
St. John's, Antigua and Barbuda

St. John's ©
The capital and largest city of Antigua and Barbuda, St John's represents the commercial and touristic center of the twin-island country.
Step out of the city life by going to Nelson's Dockyard and Half Moon Bay. Get a sense of the local culture at Shirley Heights and Zemi Art Gallery. And it doesn't end there: buy something for everyone on your list at Heritage Quay, stroll through Valley Church Beach, get engrossed in the history at Betty's Hope, and enjoy the sand and surf at Dickenson Bay.

To see other places to visit, where to stay, ratings, and other tourist information, read St. John's online tour itinerary planner .

Dar es Salaam, Tanzania to St. John's is an approximately 30-hour flight. The time zone difference when traveling from Dar es Salaam to St. John's is minus 7 hours. Traveling from Dar es Salaam in August, plan for a bit warmer nights in St. John's, with lows around 30°C. Wrap up your sightseeing on the 20th (Tue) early enough to travel to Roseau.

Things to do in St. John's

Parks Outdoors Beaches

Side Trips

Jolly Harbour, English Harbour, Dickenson Bay, Gilly Gobinet Art, Half Moon Bay
Find places to stay Aug 16 — 20:
Highlights from your plan
Nelson's Dockyard ©
Nelson's Dockyard
Half Moon Bay ©
Half Moon Bay
Shirley Heights ©
Shirley Heights

5
nights
Roseau, Dominica

Roseau ©
The capital city, Roseau maintains a small scale, but possesses a convincing Caribbean charm in its architecture, cuisine, and culture.
Take a break from the city and head to Boiling Lake and Trafalgar Falls. Satisfy your inner culture vulture at Fort Shirley and St. Patrick's Roman Catholic Cathedral. Explore Roseau's surroundings by going to Scott's Head Pinnacles (in Scotts Head) and Morne Trois Pitons National Park (Emerald Pool Nature Trail, Morne Nichols, & more). There's more to do: explore the activities along Breakfast River and examine the collection at Roseau Museum.

For ratings, photos, more things to do, and other tourist information, read Roseau route maker website .

Do a combination of flight and car from St. John's to Roseau in 3.5 hours. Finish your sightseeing early on the 25th (Sun) to allow enough time to travel to Bridgetown.

Things to do in Roseau

Nature Parks Wildlife

Side Trips

Morne Trois Pitons National Park, Scott's Head Pinnacles, Fort Shirley
Find places to stay Aug 20 — 25:
Highlights from your plan
Boiling Lake ©
Boiling Lake
Emerald Pool Nature Trail ©
Emerald Pool Nature Trail
Trafalgar Falls ©
Trafalgar Falls

7
nights
Bridgetown, Barbados

Bridgetown is the capital and largest city of Barbados. Get some historical perspective at Andromeda Botanic Gardens and George Washington House. Step out of the city life by going to Scuba & Snorkeling and Jammin Catamaran Cruises. Venture out of the city with trips to Saint Philip Parish (Foursquare Distillery, Sunbury Plantation House, & more), Crane Beach (in Union Hall) and Bathsheba Beach (in Bathsheba). There's much more to do: enjoy the sand and surf at Carlisle Bay, steep yourself in history at Garrison Savannah, look for gifts at Jenanya's, and sample the fine beverages at Mount Gay Visitor Centre.

To find where to stay, photos, ratings, and more tourist information, refer to the Bridgetown day trip site .

You can fly from Roseau to Bridgetown in 5 hours. Another option is to do a combination of ferry and flight. In August, daytime highs in Bridgetown are 35°C, while nighttime lows are 30°C. Wrap up your sightseeing on the 1st (Sun) early enough to travel to Scarborough.

Things to do in Bridgetown

Outdoors Parks Beaches

Side Trips

Saint Philip Parish, Bathsheba, Earthworks Pottery, Best of Barbados Gift Shop, Gun Hill Signal Station
Find places to stay Aug 25 — Sep 1:
Highlights from your plan
Scuba & Snorkeling
Bottom Bay ©
Bottom Bay
Carlisle Bay ©
Carlisle Bay

3
nights
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. Relax by the water at Pigeon Point Beach and Pirate's Bay. Head to Genesis Nature Park & Art Gallery and Hummingbird Galleryfor plenty of shopping. Change things up with a short trip to Little Tobago in Northeast Coast (about 1 hour away). There's much more to do: take in the history at Fort King George, take an in-depth tour of Tobago Historical Museum, see the vivid underwater world at Buccoo Reef, and kick back and relax at Stonehaven Bay.

To find photos, traveler tips, reviews, and other tourist information, go to the Scarborough tour itinerary maker website .

Getting from Bridgetown to Scarborough by flight takes about 7 hours. Other options: do a combination of flight and ferry. Cap off your sightseeing on the 5th (Thu) early enough to travel to George Town.

Things to do in Scarborough

Parks Beaches Outdoors

Side Trips

Tobago, Northeast Coast, Hummingbird Gallery
Find places to stay Sep 1 — 5:
Highlights from your plan
Pigeon Point Beach ©
Pigeon Point Beach
Store Bay ©
Store Bay
Buccoo Reef ©
Buccoo Reef

7
nights
George Town, Cayman Islands

George Town is a city situated on Grand Cayman island of the Cayman Islands. Escape the urban bustle at Cayman Turtle Centre: Island Wildlife Encounter and Seven Mile Beach. Museum-lovers will appreciate Pedro St. James National Historic Site and Davinoff's Concrete Sculpture Garden. Take a break from George Town with a short trip to Mission House in Bodden Town, about 36 minutes away. There's lots more to do: look for all kinds of wild species at Wildlife Areas, admire the natural beauty at Queen Elizabeth II Botanic Park, brush up on your knowledge of spirits at Cayman Spirits Co. Distillery, and get close to the beloved marine mammals with a swim-with-the-dolphins experience.

To find more things to do, photos, other places to visit, and other tourist information, use the George Town trip itinerary builder site .

Traveling by flight from Scarborough to George Town takes 10 hours. Alternatively, you can do a combination of ferry and flight. You'll gain 1 hour traveling from Scarborough to George Town due to the time zone difference. In September, plan for daily highs up to 37°C, and evening lows to 30°C. Finish your sightseeing early on the 13th (Fri) so you can travel to Montego Bay.

Things to do in George Town

Parks Outdoors Wildlife

Side Trips

Grand Cayman, Seven Mile Beach, West Bay, Mission House, Davinoff's Concrete Sculpture Garden
Find places to stay Sep 5 — 13:
Highlights from your plan
Scuba & Snorkeling
Seven Mile Beach ©
Seven Mile Beach
Stingray City ©
Stingray City

3
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.
For shopping fun, head to White Witch Golf Course or Ahhh...Ras Natango Gallery and Garden. Your inner history buff will appreciate Rose Hall Great House and Bob Marley's Mausoleum. Explore Montego Bay's surroundings by going to Seven Mile Beach (in Negril) and Original Mayfield Falls Jamaica (in Pennycooke). There's still lots to do: enjoy the sand and surf at Doctor's Cave Beach, pause for some serene contemplation at Blessed Sacrament Cathedral, and make a trip to The Cage.

For traveler tips, maps, photos, and other tourist information, refer to the Montego Bay trip itinerary planning site .

You can fly from George Town to Montego Bay in 5.5 hours. Another option is to do a combination of flight and bus. In September, plan for daily highs up to 38°C, and evening lows to 29°C. Wrap up your sightseeing by early afternoon on the 17th (Tue) to allow enough time to travel back home.

Things to do in Montego Bay

Parks Outdoors Beaches

Side Trips

Bob Marley's Mausoleum, Seven Mile Beach, Original Mayfield Falls Jamaica
Find places to stay Sep 13 — 17:
Highlights from your plan
Rose Hall Great House ©
Rose Hall Great House
Seven Mile Beach ©
Seven Mile Beach
Doctor's Cave Beach ©
Doctor's Cave Beach