42 days in Caribbean Itinerary

42 days in Caribbean Itinerary

Created using Inspirock Caribbean holiday planner

Make it your trip
Fly
1
Nassau, Bahamas
— 4 nights
Fly
2
George Town, Bahamas
— 2 nights
Fly
3
Eleuthera, Bahamas
— 3 nights
Fly
4
Grand Bahama Island, Bahamas
— 4 nights
Fly to Charlotte Amalie, Ferry to Cruz Bay
5
Cruz Bay, U.S. Virgin Islands
— 4 nights
Ferry
6
Virgin Gorda, British Virgin Islands
— 4 nights
Ferry
7
Road Town, British Virgin Islands
— 2 nights
Ferry
8
Charlotte Amalie, U.S. Virgin Islands
— 5 nights
Fly
9
St. Croix, U.S. Virgin Islands
— 3 nights
Fly
10
Ocho Rios, Jamaica
— 3 nights
Drive
11
Negril, Jamaica
— 2 nights
Drive
12
Montego Bay, Jamaica
— 5 nights
Fly

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Nassau, Bahamas

— 4 nights
On a trip to Nassau you can immerse yourself in a dynamic city atmosphere or spend your days lazing on the soft golden sands.
Get in touch with nature at Cable Beach and Cabbage Beach. There's lots more to do: take in nature's colorful creations at Ardastra Gardens & Wildlife Conservation Centre, hunt for treasures at Straw Market, step off the mainland to explore Blue Lagoon Island, and discover the deep blue sea with a scuba or snorkeling tour.

For ratings, maps, and tourist information, you can read our Nassau driving holiday planner.

Copenhagen, Denmark to Nassau is an approximately 15.5-hour flight. Due to the time zone difference, you'll gain 6 hours traveling from Copenhagen to Nassau. Plan for much warmer temperatures traveling from Copenhagen in October, with highs in Nassau at 36°C and lows at 28°C. Wrap up your sightseeing on the 24th (Mon) to allow time to fly to George Town.

Things to do in Nassau

Parks · Outdoors · Wildlife · Tours

Side Trip

George Town, Bahamas

— 2 nights
Few island getaways are more idyllic than George Town, a small settlement on the east coast of the Bahamian island of Exuma.
On the 25th (Tue), stroll through Jolly Hall Beach and then kick back and relax at Beaches of Stocking Island. Get ready for a full day of sightseeing on the 26th (Wed): have unforgettable encounters with Aquaquest Escapes and then kick back and relax at Coco Plum Beach.

Plan a trip to George Town easily and quickly by telling Inspirock to suggest an itinerary.

You can fly from Nassau to George Town in 2.5 hours. Another option is to ride a ferry. Finish your sightseeing early on the 26th (Wed) to allow enough time to fly to Eleuthera.

Things to do in George Town

Outdoors · Parks · Beaches · Wildlife

Side Trip

Eleuthera, Bahamas

— 3 nights
The long, thin island of Eleuthera has plenty of coast, built up in places and left wild and rural in others.
Take a break from the city and head to Spanish Wells Fishing and Bahamas Ocean Safaris. Next up on the itinerary: stroll through Lighthouse Beach, relax and rejuvenate at Bodyworks Spanish Wells Bahamas, and explore the wealth of natural beauty at Leon Levy Native Plant Preserve.

To see where to stay, reviews, traveler tips, and other tourist information, read our Eleuthera road trip planner.

Traveling by flight from George Town to Eleuthera takes 4 hours. Alternatively, you can do a combination of ferry and taxi; or ride a ferry. Finish your sightseeing early on the 29th (Sat) to allow enough time to fly to Grand Bahama Island.

Things to do in Eleuthera

Outdoors · Parks · Beaches · Wildlife

Grand Bahama Island, Bahamas

— 4 nights
Despite its name, Grand Bahama Island isn't the biggest island in its archipelago.
Take a break from the city and head to Pat & Diane Snorkeling and Lucayan National Park. The adventure continues: get a dose of the wild on Chad4Nature Tours - Private Tours, kick back and relax at Gold Rock Beach, stroll through Theo's Wreck, and buy something for everyone on your list at Port Lucaya Marketplace.

For where to stay, more things to do, traveler tips, and other tourist information, you can read our Grand Bahama Island tour itinerary builder app.

You can fly from Eleuthera to Grand Bahama Island in 4.5 hours. Other options are to do a combination of car and ferry; or ride a ferry. In October, daily temperatures in Grand Bahama Island can reach 34°C, while at night they dip to 26°C. Wrap up your sightseeing by early afternoon on the 2nd (Wed) to allow time for travel to Cruz Bay.

Things to do in Grand Bahama Island

Wildlife · Parks · Outdoors · Tours

Cruz Bay, U.S. Virgin Islands

— 4 nights

Love City

The gateway to the island of Saint John, Cruz Bay represents the island's largest town, port, and commercial center.
Take a break from the city and head to Kayaking & Canoeing and Trunk Bay Beach. There's still lots to do: stroll through Leinster Bay, steep yourself in history at Cinnamon Bay Nature Trail, kick back and relax at Caneel Bay Beach, and look for all kinds of wild species at Honeymoon Beach.

To find photos, ratings, maps, and other tourist information, use the Cruz Bay tour itinerary maker site.

You can do a combination of flight and ferry from Grand Bahama Island to Cruz Bay in 9.5 hours. Alternatively, you can do a combination of flight and ferry. The time zone difference when traveling from Grand Bahama Island to Cruz Bay is 1 hour. Plan for somewhat warmer temperatures traveling from Grand Bahama Island in November, with highs in Cruz Bay at 35°C and lows at 28°C. Cap off your sightseeing on the 6th (Sun) early enough to catch the ferry to Virgin Gorda.

Things to do in Cruz Bay

Outdoors · Parks · Beaches · Wildlife

Side Trips

Virgin Gorda, British Virgin Islands

— 4 nights
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.
Get outdoors at Sunchaser Scuba Ltd. and Devil's Bay National Park. There's much more to do: explore the striking landscape at The Baths, tour the pleasant surroundings at Spring Bay, explore and take pictures at Wreck of the Chikuzen, and relax and rejuvenate at some of the top local wellness centers.

For other places to visit, photos, reviews, and more tourist information, you can read our Virgin Gorda travel route builder.

You can ride a ferry from Cruz Bay to Virgin Gorda in 2.5 hours. Another option is to do a combination of ferry and flight. November in Virgin Gorda sees daily highs of 35°C and lows of 30°C at night. Finish your sightseeing early on the 10th (Thu) so you can ride a ferry to Road Town.

Things to do in Virgin Gorda

Parks · Outdoors · Nature · Beaches

Road Town, British Virgin Islands

— 2 nights
Road Town, located on Tortola, is the capital of the British Virgin Islands. Kick off your visit on the 11th (Fri): see the vivid underwater world at Smuggler's Cove, then tour the pleasant surroundings at Cane Garden Bay, and then explore the activities along Brewers Bay. Get ready for a full day of sightseeing on the next day: get a new perspective on things with Bad Dog Charters and then explore the wealth of natural beauty at Sage Mountain National Park.

To see maps, other places to visit, traveler tips, and other tourist information, read Road Town online tour planner.

Traveling by ferry from Virgin Gorda to Road Town takes 2 hours. Alternatively, you can ride a ferry; or fly. In November, daily temperatures in Road Town can reach 35°C, while at night they dip to 30°C. Finish your sightseeing early on the 12th (Sat) so you can ride a ferry to Charlotte Amalie.

Things to do in Road Town

Outdoors · Parks · Nature · Beaches

Side Trip

Charlotte Amalie, U.S. Virgin Islands

— 5 nights

Duty-free Capital of the World

One of the most visited cruise ship destinations in the Caribbean, the town of Charlotte Amalie is known around the world for its duty-free jewelry, perfume, and liquor shops.
For shopping fun, head to Imperial Dynasty Jewelers or A.H. Riise Mall. Take a break from the city and head to Magens Bay and Scuba & Snorkeling. Step out of Charlotte Amalie to go to Virgin Islands National Park and see Waterlemon Cay, which is approximately 54 minutes away. There's much more to do: enjoy the sand and surf at Coki Point Beach, tour the pleasant surroundings at The Butterfly Garden, step off the mainland to explore Water Island, and get to know the resident critters at Coral World Ocean Park.

To see traveler tips, ratings, other places to visit, and more tourist information, read Charlotte Amalie trip planning app.

Traveling by ferry from Road Town to Charlotte Amalie takes 2 hours. Alternatively, you can fly. In November, daytime highs in Charlotte Amalie are 35°C, while nighttime lows are 28°C. Cap off your sightseeing on the 17th (Thu) early enough to catch the flight to St. Croix.

Things to do in Charlotte Amalie

Parks · Outdoors · Wildlife · Beaches

Side Trips

St. Croix, U.S. Virgin Islands

— 3 nights

Twin City

The largest of the U.S. Virgin Islands, St.
Take a break from the city and head to Scuba & Snorkeling and Cane Bay. There's much more to do: tour the pleasant surroundings at Buck Island Reef National Monument, stop by Crucian Gold, and try to win big at Divi Carina Bay Casino.

For maps, reviews, traveler tips, and other tourist information, use the St. Croix online trip itinerary maker.

You can fly from Charlotte Amalie to St. Croix in 2.5 hours. Alternatively, you can fly; or ride a ferry. November in St. Croix sees daily highs of 36°C and lows of 28°C at night. Cap off your sightseeing on the 20th (Sun) early enough to catch the flight to Ocho Rios.

Things to do in St. Croix

Parks · Wildlife · Outdoors · Shopping

Ocho Rios, Jamaica

— 3 nights
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
Get in touch with nature at Dunn's River Falls and Park and Green Grotto Caves. There's lots more to do: get a new perspective on things with Boat Tours & Water Sports, trek along Fern Gully, admire the sheer force of Blue Hole, and identify plant and animal life at BJ's Island Tours.

To find other places to visit, traveler tips, more things to do, and tourist information, you can read our Ocho Rios day trip site.

Traveling by flight from St. Croix to Ocho Rios takes 9 hours. Traveling from St. Croix to Ocho Rios, you'll gain 1 hour due to the time zone difference. In November, plan for daily highs up to 37°C, and evening lows to 28°C. Cap off your sightseeing on the 23rd (Wed) early enough to go by car to Negril.

Things to do in Ocho Rios

Parks · Nature · Outdoors · Wildlife

Side Trip

Negril, Jamaica

— 2 nights
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
On the 24th (Thu), contemplate the waterfront views at Bloody Bay, then enjoy the sand and surf at Seven Mile Beach, and then soothe aching muscles at some of the top local wellness centers. Here are some ideas for day two: surround yourself with nature on Kingsley's Take Care Tours - Day Tours and then take in the dramatic natural features at Negril Cliffs.

To see other places to visit, photos, and other tourist information, you can read our Negril day trip website.

You can drive from Ocho Rios to Negril in 3 hours. Alternatively, you can take a bus. In November in Negril, expect temperatures between 36°C during the day and 28°C at night. Cap off your sightseeing on the 25th (Fri) early enough to go by car to Montego Bay.

Things to do in Negril

Parks · Outdoors · Nature · Beaches

Montego Bay, Jamaica

— 5 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.
Visiting White Witch Golf Course and Original Mayfield Falls Jamaica will get you outdoors. Change things up with a short trip to Tryall Golf Course in Sandy Bay (about 44 minutes away). Spend the 26th (Sat) wandering through the wild on a nature and wildlife tour. There's still lots to do: take an exotic tour of Rastasafari Experience, see some colorful creatures with a scuba or snorkeling tour, and enjoy the sand and surf at Doctor's Cave Beach.

For where to stay, more things to do, ratings, and other tourist information, refer to the Montego Bay trip itinerary builder.

You can drive from Negril to Montego Bay in 1.5 hours. Another option is to take a bus. In November, plan for daily highs up to 36°C, and evening lows to 28°C. Finish your sightseeing early on the 30th (Wed) to allow enough time to fly back home.

Things to do in Montego Bay

Outdoors · Wildlife · Tours · Golf

Side Trips

Bahamas travel guide

3.8
Beaches · Islands · Water & Amusement Parks
Part of an archipelago encompassing hundreds of islets and cays, Bahamas boast many pink beaches, which get their vibrant color from fractured seashells mixed with ordinary sand. For most pleasure seekers an ideal holiday in Bahamas consists of various sea activities, occasionally interrupted by tours of several cities, offering an eclectic music scene dominated by calypso, soca, and junkanoo genres. Romantic enough to attract newlyweds from around the globe, the islands are also a major center of eco-tourism, with visits to national parks and diving tours in colorful reefs among the most popular things to do in Bahamas.

U.S. Virgin Islands travel guide

4.5
Beaches · Gift & Specialty Shops · Scuba & Snorkeling
America's Paradise
Three main and a number of minor islands that make up U.S. Virgin Islands treat visitors to a blend of historical sites and picture-perfect beaches. Though officially American territory--nicknamed "America's Paradise"--these islands boast a mix of cultures that make for culturally enriching vacations. A no-passport-required status makes holidays in U.S. Virgin Islands extremely popular with American tourists, who flock to this tropical heaven to enjoy scenic beaches, outdoor activities, and tasty local food. The islands are also a duty-free shopping destination, which also makes them appealing to shopaholics from across the world.

British Virgin Islands travel guide

4.4
Geologic Formations · Bodies of Water · Beaches
Escape from civilization and take a trip to British Virgin Islands, a collection of 60 small islands and cays in the Virgin Islands archipelago. Although British territory, the island is not noticeably British, offering a quiet and serene vibe that lives on despite a major tourism boom. With most of its islets uninhabited, British Virgin Islands remain a paradise for sailing, snorkeling, lazing on a deserted beach, and exploring sleepy seaside villages.

Jamaica travel guide

4.1
Waterfalls · Beaches · Nightlife
The third most populous English-speaking country in the Americas, Jamaica remains a member of the Commonwealth of Nations, with the British monarch its official head of state. Jamaica tourism thrives thanks to the island nation's reputation for natural beauty, outstanding cuisine, and lively music scene. The country's landscape is as diverse as its population, its tropical climate supporting varied ecosystems that include everything from savannahs to rugged mountain slopes. For most visitors, a holiday in Jamaica is a largely outdoor affair, with hiking, fishing, golfing, camping, snorkeling, horseback riding, and kite surfing among the most popular things to do.