35 days in West Indies Itinerary

35 days in West Indies Itinerary

Created using Inspirock West Indies trip itinerary planner

Make it your trip
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1
Little Cayman, Cayman Islands
— 2 nights
Fly
2
Seven Mile Beach, Cayman Islands
— 5 nights
Fly
3
Montego Bay, Jamaica
— 4 nights
Drive
4
Ocho Rios, Jamaica
— 5 nights
Fly
5
Bridgetown, Barbados
— 4 nights
Fly
6
Roseau, Dominica
— 5 nights
Fly
7
English Harbour, Antigua and Barbuda
— 4 nights
Fly
8
Providenciales, Turks and Caicos
— 5 nights
Fly

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Little Cayman, Cayman Islands

— 2 nights
The smallest and undeniably quietest of the Cayman Islands, Little Cayman is truly little in terms of its population, with fewer than 200 permanent residents, almost all of whom work in the tourism industry.
Little Cayman is known for wildlife, nature, and museums. Your plan includes some of its best attractions: tour the pleasant surroundings at Bloody Bay Wall, see some colorful creatures with Little Cayman Divers, explore the activities along Nancy's Cup of Tea, and head off the coast to Owen Island.

For reviews, photos, ratings, and other tourist information, read our Little Cayman trip itinerary planning tool.

Miami, USA to Little Cayman is an approximately 58-hour travel. Traveling from Miami in November, Little Cayman is a bit warmer at night with lows of 78°F. Finish your sightseeing early on the 4th (Wed) to allow enough time to travel to Seven Mile Beach.

Things to do in Little Cayman

Parks · Wildlife · Nature · Tours
Highlights from your trip

Seven Mile Beach, Cayman Islands

— 5 nights
Seven Mile Beach is a long crescent of coral-sand beach on the western end of Grand Cayman island. Take a break from Seven Mile Beach with a short trip to Davinoff's Concrete Sculpture Garden in North Side, about 40 minutes away. And it doesn't end there: tour the pleasant surroundings at Stingray City Grand Cayman, sample the fine beverages at Cayman Spirits Co. Distillery, see the vivid underwater world at Cemetery Beach and Reef, and kick back and relax at Seven Mile Beach.

To see ratings, other places to visit, traveler tips, and more tourist information, you can read our Seven Mile Beach online tour itinerary planner.

Getting from Little Cayman to Seven Mile Beach by flight takes about 3 hours. Expect a daytime high around 85°F in November, and nighttime lows around 77°F. Wrap up your sightseeing by early afternoon on the 9th (Mon) to allow time for travel to Montego Bay.

Things to do in Seven Mile Beach

Parks · Wildlife · Outdoors · Beaches

Side Trips

Montego Bay, Jamaica

— 4 nights
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.
Get out of town with these interesting Montego Bay side-trips: Negril (Bloody Bay & Seven Mile Beach), Original Mayfield Falls (in Pennycooke) and Tryall Golf Course (in Sandy Bay). Spend the 12th (Thu) wandering through the wild on a nature and wildlife tour. There's lots more to do: contemplate the long history of Rose Hall Great House, play a few rounds at Cinnamon Hill Golf Course, and get engrossed in the history at Greenwood Great House.

For where to stay, traveler tips, photos, and other tourist information, read our Montego Bay online trip itinerary maker.

You can fly from Seven Mile Beach to Montego Bay in 8.5 hours. Expect a daytime high around 88°F in November, and nighttime lows around 76°F. Finish up your sightseeing early on the 13th (Fri) so you can go by car to Ocho Rios.

Things to do in Montego Bay

Outdoors · Tours · Wildlife · Parks

Side Trips

Ocho Rios, Jamaica

— 5 nights
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
When in Ocho Rios, make a side trip to see Blue Mountain Peak in Blue Mountains National Park, approximately Blue Mountains National Park away. There's still lots to do: take in the dramatic scenery at Dunn's River Falls and Park, stroll through Ocho Rios Bay Beach, stop by Jewels & Time Duty Free Jewelers, and head outdoors with Rocketman Jamaica.

To see photos and tourist information, read Ocho Rios trip planner.

You can drive from Montego Bay to Ocho Rios in 2 hours. Another option is to take a bus. In November, plan for daily highs up to 89°F, and evening lows to 76°F. You will have some time to spend on the 18th (Wed) before leaving for Bridgetown.

Things to do in Ocho Rios

Outdoors · Parks · Nature · Trails

Side Trips

Bridgetown, Barbados

— 4 nights
Bridgetown is the capital and largest city of Barbados. When in Bridgetown, make a side trip to see Bottom Bay in Saint Philip Parish, approximately Saint Philip Parish away. The adventure continues: take a tour by water with Boat Tours & Water Sports, sample the fine beverages at Mount Gay Visitor Centre, stroll through Bathsheba Beach, and take in nature's colorful creations at Andromeda Botanic Gardens.

To find photos, traveler tips, reviews, and other tourist information, you can read our Bridgetown trip planner.

Getting from Ocho Rios to Bridgetown by flight takes about 11 hours. The time zone difference moving from Eastern Standard Time to Atlantic Standard Time is 1 hour. In November in Bridgetown, expect temperatures between 86°F during the day and 77°F at night. Cap off your sightseeing on the 22nd (Sun) early enough to travel to Roseau.

Things to do in Bridgetown

Parks · Outdoors · Beaches · Breweries & Distilleries

Side Trips

Roseau, Dominica

— 5 nights
The capital city, Roseau maintains a small scale, but possesses a convincing Caribbean charm in its architecture, cuisine, and culture.
You'll find plenty of places to visit near Roseau: Morne Trois Pitons National Park (Boiling Lake, Jacko Falls, &more). And it doesn't end there: take in the dramatic scenery at Trafalgar Falls, see some colorful creatures with a scuba or snorkeling tour, explore the activities along Breakfast River, and boost your wellbeing at Bongo Baths.

For reviews, maps, other places to visit, and tourist information, read our Roseau day trip planning app.

You can fly from Bridgetown to Roseau in 5 hours. Finish up your sightseeing early on the 27th (Fri) so you can travel to English Harbour.

Things to do in Roseau

Nature · Parks · Wildlife · Outdoors

Side Trips

English Harbour, Antigua and Barbuda

— 4 nights
When in English Harbour, make a side trip to see Devil's Bridge in Willikies, approximately Willikies away. Spend the 28th (Sat) exploring nature at Nelson's Dockyard.

To find more things to do, photos, other places to visit, and tourist information, use the English Harbour trip itinerary planning website.

Getting from Roseau to English Harbour by flight takes about 4.5 hours. Expect a daytime high around 85°F in November, and nighttime lows around 75°F. Finish up your sightseeing early on the 1st (Tue) so you can travel to Providenciales.

Things to do in English Harbour

Parks · Outdoors · Nature · Beaches

Side Trips

Providenciales, Turks and Caicos

— 5 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 plan includes some of its best attractions: kick back and relax at Grace Bay Beach, discover the deep blue sea with a scuba or snorkeling tour, stroll through Taylor Bay Beach, and trot along with a tour on horseback.

To see ratings, maps, photos, and other tourist information, read Providenciales vacation planning site.

Traveling by flight from English Harbour to Providenciales takes 6 hours. The time zone changes from Atlantic Standard Time to Eastern Standard Time, which is usually a -1 hour difference. Expect a daytime high around 83°F in December, and nighttime lows around 75°F. Wrap up your sightseeing on the 6th (Sun) early enough to travel back home.

Things to do in Providenciales

Outdoors · Parks · Beaches · Wildlife

Side Trip