39 days in Caribbean Itinerary

39 days in Caribbean Itinerary

Created using Inspirock Caribbean route planner

Make it your trip
+2
Train to London Kings Cross, Train to London Gatwick, Fly to Montego Bay
1
Montego Bay, Jamaica
— 4 nights
Drive
2
Ocho Rios, Jamaica
— 5 nights
Fly
3
Oranjestad, Aruba
— 6 nights
Fly
4
Basseterre, St. Kitts and Nevis
— 4 nights
Fly
5
Virgin Gorda, British Virgin Islands
— 4 nights
Ferry
6
Road Town, British Virgin Islands
— 3 nights
Taxi to Beef Island, Fly to Dominica
7
Roseau, Dominica
— 3 nights
Fly
8
Castries, St. Lucia
— 2 nights
Drive
9
Soufriere, St. Lucia
— 3 nights
Fly
10
St. George's, Grenada
— 3 nights
Fly

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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 in touch with nature at Blue Hole Mineral Spring and Seven Mile Beach. Satisfy your inner culture vulture at Rose Hall Great House and The Cage. Venture out of the city with trips to Original Mayfield Falls (in Pennycooke) and Negril (Irie Art & Bloody Bay). There's still lots to do: take an exotic tour of Rastasafari Experience, tour the pleasant surroundings at Rocklands Bird Sanctuary, and discover the deep blue sea with a scuba or snorkeling tour.

Find out how to plan Montego Bay trip without stress by asking Inspirock to help create an itinerary.

Newcastle upon Tyne, UK to Montego Bay is an approximately 17.5-hour combination of train and flight. You can also do a combination of train and flight; or fly. The time zone difference when traveling from Newcastle upon Tyne to Montego Bay is minus 5 hours. Prepare for warmer weather when traveling from Newcastle upon Tyne in June: high temperatures in Montego Bay hover around 38°C and lows are around 29°C. Wrap up your sightseeing on the 1st (Thu) early enough to drive to Ocho Rios.

Things to do in Montego Bay

Parks · Outdoors · Nature · Wildlife

Side Trips

Find places to stay Jun 27 — Jul 1:

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.
Your cultural itinerary includes sights like Coyaba River Garden and Museum and Our Lady of Fatima Catholic Church. You'll discover tucked-away gems like Nature & Wildlife Tours and Green Grotto Caves. Step out of Ocho Rios with an excursion to Scuba & Snorkeling in Runaway Bay--about 32 minutes away. There's lots more to do: take in the dramatic scenery at Dunn's River Falls and Park, walk around Konoko Falls, get outside with Outdoor Activities, and contemplate the waterfront views at White River.

Plan a Ocho Rios trip in moments using our itinerary builder.

Traveling by car from Montego Bay to Ocho Rios takes 2 hours. Alternatively, you can take a bus. July in Ocho Rios sees daily highs of 38°C and lows of 30°C at night. On the 6th (Tue), you'll have the morning to explore before heading off to Oranjestad.

Things to do in Ocho Rios

Parks · Outdoors · Tours · Nature

Side Trip

Find places to stay Jul 1 — 6:

Oranjestad, Aruba

— 6 nights
When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
Discover out-of-the-way places like Aruba Bob Snorkeling and Off-Road Tours. Escape the urban bustle at Arikok National Park and Hooiberg. Go for a jaunt from Oranjestad to San Nicolas to see Baby Beach about 32 minutes away. There's much more to do: kick back and relax at Malmok Beach, explore the striking landscape at Seroe Colorado, head off the coast to Renaissance Island, and steep yourself in history at Bushiribana Gold Mill Ruins.

For more things to do, maps, photos, and tourist information, refer to the Oranjestad tour itinerary maker website.

Traveling by flight from Ocho Rios to Oranjestad takes 11.5 hours. The time zone difference moving from Eastern Standard Time (EST) to Atlantic Standard Time (AST) is 1 hour. Expect a daytime high around 38°C in July, and nighttime lows around 31°C. You'll have a few hours on the 12th (Mon) to wrap things up before traveling to Basseterre.

Things to do in Oranjestad

Parks · Outdoors · Nature · Tours

Side Trips

Find places to stay Jul 6 — 12:

Basseterre, St. Kitts and Nevis

— 4 nights
Step out of the city life by going to Greg's Safaris and St.Kitts Water Sports. Eschew the tourist crowds and head to Off-Road Tours and Mount Liamuiga.

To find reviews, other places to visit, where to stay, and tourist information, go to the Basseterre travel website.

You can fly from Oranjestad to Basseterre in 9.5 hours. In July, plan for daily highs up to 36°C, and evening lows to 30°C. Finish your sightseeing early on the 16th (Fri) to allow enough time to travel to Virgin Gorda.

Things to do in Basseterre

Parks · Outdoors · Tours · Nature

Side Trip

Find places to stay Jul 12 — 16:

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.
You'll explore the less-touristy side of things at Devil's Bay National Park and Honeymoon Beach. Take a break from the city and head to Sunchaser Scuba Ltd. and Virgin Gorda Peak. Next up on the itinerary: enjoy the sand and surf at Spring Bay, head outdoors with Fusion BVI, make a trip to Wreck of the Chikuzen, and tour the pleasant surroundings at The Baths.

To see traveler tips, reviews, where to stay, and tourist information, refer to the Virgin Gorda day trip planning app.

Traveling by flight from Basseterre to Virgin Gorda takes 5.5 hours. In July, daytime highs in Virgin Gorda are 37°C, while nighttime lows are 31°C. Finish your sightseeing early on the 20th (Tue) so you can ride a ferry to Road Town.

Things to do in Virgin Gorda

Parks · Outdoors · Nature · Beaches
Find places to stay Jul 16 — 20:

Road Town, British Virgin Islands

— 3 nights
Road Town, located on Tortola, is the capital of the British Virgin Islands. You'll discover tucked-away gems like Smuggler's Cove and Stand-Up Paddleboarding. Get outdoors at Cane Garden Bay and Brewers Bay. There's much more to do: go for a stroll along the water at Rhone National Marine Park, explore the wealth of natural beauty at Sage Mountain National Park, and whizz through the canopy at some of the top local zipline courses and adventure parks.

To see more things to do, other places to visit, photos, and more tourist information, read Road Town online tour itinerary planner.

You can ride a ferry from Virgin Gorda to Road Town in 2 hours. Another option is to do a combination of flight and taxi. In July, plan for daily highs up to 37°C, and evening lows to 31°C. Cap off your sightseeing on the 23rd (Fri) early enough to travel to Roseau.

Things to do in Road Town

Parks · Outdoors · Nature · Beaches

Side Trips

Find places to stay Jul 20 — 23:

Roseau, Dominica

— 3 nights
The capital city, Roseau maintains a small scale, but possesses a convincing Caribbean charm in its architecture, cuisine, and culture.
Step out of the city life by going to Titou Gorge and Boiling Lake. You'll explore the less-touristy side of things at Scuba & Snorkeling and Trafalgar Falls. Explore Roseau's surroundings by going to Morne Trois Pitons National Park (Morne Nichols & Emerald Pool Nature Trail). Next up on the itinerary: get a dose of the wild on a nature and wildlife tour.

Discover how to plan a Roseau trip in just a few steps with Inspirock's itinerary builder.

You can do a combination of taxi and flight from Road Town to Roseau in 5 hours. Finish up your sightseeing early on the 26th (Mon) so you can travel to Castries.

Things to do in Roseau

Nature · Parks · Outdoors · Wildlife

Side Trip

Find places to stay Jul 23 — 26:

Castries, St. Lucia

— 2 nights
The capital and largest city in Saint Lucia, Castries has a number of cultural sites to explore, and recreational areas to enjoy.
Start off your visit on the 27th (Tue): make a trip to Holy Trinity Anglican Church, push the limits with Treetop Adventure Park, and then contemplate the waterfront views at Marigot Bay. Get ready for a full day of sightseeing on the next day: browse the exhibits of Sierra's Souvenir & Gift Shop, then explore the striking landscape of Pigeon Island National Park, and then get outside with Outdoor Activities.

To see maps, ratings, photos, and tourist information, go to the Castries trip builder app.

Traveling by flight from Roseau to Castries takes 4.5 hours. Alternatively, you can ride a ferry. July in Castries sees daily highs of 36°C and lows of 29°C at night. Finish up your sightseeing early on the 28th (Wed) so you can go by car to Soufriere.

Things to do in Castries

Nature · Parks · Outdoors · Tours

Side Trips

Find places to stay Jul 26 — 28:

Soufriere, St. Lucia

— 3 nights
Home to some of Saint Lucia's landmark buildings and natural features, Soufriere provides travelers with an engaging and direct route into the center of island life.
Get outdoors at Tet Paul Nature Trail and Morne Coubaril HIstorical Adventure Park. Discover out-of-the-way places like Scuba & Snorkeling and Nature & Wildlife Tours. There's still lots to do: get outside with ATV Paradise Tours, take in the natural beauty of Sulphur Springs, explore the activities along Anse Mamin, and admire the natural beauty at Diamond Falls Botanical Gardens.

To see ratings, traveler tips, and other tourist information, use the Soufriere trip planner.

Traveling by car from Castries to Soufriere takes 1.5 hours. Alternatively, you can take a bus. In July, plan for daily highs up to 36°C, and evening lows to 30°C. Cap off your sightseeing on the 31st (Sat) early enough to travel to St. George's.

Things to do in Soufriere

Outdoors · Parks · Tours · Nature

Side Trip

Find places to stay Jul 28 — 31:

St. George's, Grenada

— 3 nights
The capital of the Island of Spice, St.
Satisfy your inner culture vulture at Underwater Sculptures and Grenada National Museum. You'll discover tucked-away gems like Scuba & Snorkeling and Soothing Touch Massage Clinic. The adventure continues: kick back and relax at Grand Anse Beach, make a trip to Market Square, examine the collection at House of Chocolate, and admire the sheer force of Seven Sisters Falls.

For more things to do, where to stay, other places to visit, and other tourist information, use the St. George's trip itinerary planner.

Getting from Soufriere to St. George's by flight takes about 4.5 hours. Expect a daytime high around 35°C in July, and nighttime lows around 29°C. Finish up your sightseeing early on the 3rd (Tue) so you can travel back home.

Things to do in St. George's

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay Jul 31 — Aug 3:

Jamaica travel guide

4
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.

Aruba travel guide

4.2
Beaches · Scuba & Snorkeling · Gift & Specialty Shops
Happy Island
A Dutch outpost in the Caribbean, sun-drenched Aruba provides a mix of modern seaside resorts and quiet coastal areas ideal for those wishing to escape the crowds. Vacations in Aruba, known affectionately as the "Happy Island," generally combine water-based activities with tours of the untamed backcountry, where you can discover unusual rock formations, historic churches, ostrich farms, and animal sanctuaries. Island capital Oranjestad offers some of the finest shopping and cultural sightseeing in Aruba, with an eco-friendly electric streetcar providing quick access to all of the city's major attractions, including numerous shops, restaurants, and hotels.

St. Kitts and Nevis travel guide

4
Beaches · Gift & Specialty Shops · Scuba & Snorkeling
A trip to St. Kitts and Nevis takes you to the smallest country in the Americas. Although diminutive in size, the two Caribbean islands offer a distinct tropical experience to visitors. Rich in history, the islands feature forested hills, tranquil beaches, charming villages, and restored sugar plantations. On a tour of St. Kitts and Nevis you can visit historic forts and quaint colonial towns, lounge on picturesque stretches of sand, or enjoy hiking the dormant Mount Liamuiga, the islands' highest peak.

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.

Dominica travel guide

4.2
Waterfalls · Beaches · Scuba & Snorkeling
Nature Isle of the Caribbean
The volcanic island nation of Dominica represents the youngest island in the Lesser Antilles. Such is evidenced in the geothermal action of the island's many hot springs, with relaxing dips in the hot sulfur spring water among the most popular things to do in Dominica. The unspoiled appearance of much of the nation provides a natural backdrop for a wealth of ecotourism adventures, including swimming, hiking, and snorkeling. The main urban areas showcase the ethnic diversity of the land once contested by the British and the French, with a number of local eateries serving West Indian and Creole dishes, and a whole lot of dancing and music to be enjoyed.

St. Lucia travel guide

4.2
Hot Springs · Volcanos · Bodies of Water
The island of St. Lucia is hailed for its scenic landscape of tall mountains, forested hills, and fertile valleys sprinkled with banana plantations. The island's dramatic scenery is most renowned for the Pitons, two volcanic spires that rise from the ocean floor. Whether you're visiting the island as part of a cruise, a romantic honeymoon, or looking for adventure, a St. Lucia vacation offers something for everyone. Discover the island's hidden beaches and coves, go climbing or hiking, and enjoy the picturesque views and tropical weather.

Grenada travel guide

4
Beaches · Scuba & Snorkeling · Historic Sites
Island of Spice
The fertile and lively island nation of Grenada allows for itineraries both adventurous and serene. The main island and six smaller ones offer unspoiled interior landscapes of lush vegetation, impressive waterfalls, and winding rivers, explorable on a number of ecotourism experiences, such as rafting, hiking, and climbing. The coastal areas provide long stretches of golden sand, backed by large and popular resorts, while the humble urban areas have become particularly well-known for their atmospheric eateries, serving local cuisine using produce from the Island of Spice. One of the main things to do in Grenada has to be marine exploration, with dive sites offshore representing some of the most abundant in the region, with impressive coral formations providing home for a schools of tropical fish.