42 days in Caribbean Itinerary

42 days in Caribbean Itinerary

Created using Inspirock Caribbean trip itinerary maker
Make it your trip
Fly
1
Punta Cana, Dominican Republic
— 5 nights
Shuttle
2
Santo Domingo, Dominican Republic
— 3 nights
Fly
3
Montego Bay, Jamaica
— 4 nights
Drive
4
Ocho Rios, Jamaica
— 3 nights
Fly
5
Cul de Sac, St. Maarten-St. Martin
— 3 nights
Drive to St. Martin, Ferry to Shoal Bay Village
6
Shoal Bay Village, Anguilla
— 2 nights
Ferry to Sint Maarten, Fly to Port of Spain
7
Port of Spain, Trinidad and Tobago
— 3 nights
Fly
8
Bridgetown, Barbados
— 4 nights
Fly
9
Soufriere, St. Lucia
— 3 nights
Fly
10
St. George's, Grenada
— 4 nights
Fly
11
St. John's, Antigua and Barbuda
— 6 nights
Fly

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Punta Cana, Dominican Republic — 5 nights

In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.
Get out of town with these interesting Punta Cana side-trips: La Romana (Altos de Chavon & Teeth Of The Dog). Spend a day of island exploring on the 12th (Thu) at Saona Island. And it doesn't end there: enjoy the sand and surf at Bavaro Beach, indulge in some personalized pampering at Flavio Acuna Spa Natural Center, play a few rounds at Punta Espada Golf Course, and stop by La Perla Dominicana.

To see more things to do, reviews, traveler tips, and tourist information, you can read our Punta Cana road trip website.

New Delhi, India to Punta Cana is an approximately 23-hour flight. The time zone changes from India Standard Time to Atlantic Standard Time, which is usually a -9.5 hour difference. Traveling from New Delhi in January, you will find days in Punta Cana are somewhat warmer (33°C), and nights are warmer (25°C). Wrap up your sightseeing on the 15th (Sun) early enough to take a shuttle to Santo Domingo.
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Outdoors · Parks · Tours · Golf
Side Trips
Find places to stay Jan 10 — 15:

Santo Domingo, Dominican Republic — 3 nights

Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Santo Domingo is known for historic sites, sightseeing, and nature. Your trip includes some of its best attractions: take in the architecture and atmosphere at Basilica Cathedral of Santa Maria la Menor, appreciate the history behind Columbus Lighthouse (Faro A Colon), contemplate the long history of Alcazar de Colon, and get up close and personal with brilliant marine life at National Aquarium.

To find photos, other places to visit, where to stay, and other tourist information, go to the Santo Domingo online visit planner.

Getting from Punta Cana to Santo Domingo by shuttle takes about 2 hours. Other options: drive; or fly. Finish your sightseeing early on the 18th (Wed) to allow enough time to fly to Montego Bay.
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Historic Sites · Museums · Zoos & Aquariums · Parks
Find places to stay Jan 15 — 18:

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.
Explore Montego Bay's surroundings by going to Seven Mile Beach (in Negril), Original Mayfield Falls Jamaica (in Pennycooke) and Tryall Golf Course (in Sandy Bay). The adventure continues: tee off at White Witch Golf Course, contemplate the long history of Rose Hall Great House, stroll through Doctor's Cave Beach, and look for gifts at Cinnamon Hill Golf Course.

For maps, reviews, where to stay, and more tourist information, read our Montego Bay day trip planning app.

You can fly from Santo Domingo to Montego Bay in 8.5 hours. The time zone difference moving from Atlantic Standard Time to Eastern Standard Time is minus 1 hour. In January, plan for daily highs up to 35°C, and evening lows to 26°C. Wrap up your sightseeing on the 22nd (Sun) to allow time to drive to Ocho Rios.
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Outdoors · Golf · Parks · Beaches
Side Trips
Find places to stay Jan 18 — 22:

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.
Step out of Ocho Rios to go to Runaway Bay and see Green Grotto Caves, which is approximately 38 minutes away. The adventure continues: admire the sheer force of Dunn's River Falls and Park, stroll through Fern Gully, stroll around Konoko Falls, and fulfill a lifelong dream with a swim-with-the-dolphins experience.

To find ratings, traveler tips, reviews, and tourist information, you can read our Ocho Rios trip app.

Getting from Montego Bay to Ocho Rios by car takes about 2 hours. Other options: take a bus. In January, plan for daily highs up to 36°C, and evening lows to 27°C. Wrap up your sightseeing on the 25th (Wed) early enough to fly to Cul de Sac.
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Parks · Nature · Outdoors · Trails
Side Trip
Find places to stay Jan 22 — 25:

Cul de Sac, St. Maarten-St. Martin — 3 nights

Cul de Sac is known for adventure, shopping, and outdoors. Your trip includes some of its best attractions: kick back and relax at Orient Bay Beach, see some colorful creatures with a scuba or snorkeling tour, stroll through Parotte Ville Bird Sanctuary, and view the masterpieces at Tropismes Gallery.

For traveler tips, photos, other places to visit, and more tourist information, read Cul de Sac road trip planning app.

Fly from Ocho Rios to Cul de Sac in 5.5 hours. You'll lose 1 hour traveling from Ocho Rios to Cul de Sac due to the time zone difference. January in Cul de Sac sees daily highs of 33°C and lows of 26°C at night. Finish your sightseeing early on the 28th (Sat) to allow enough time to travel to Shoal Bay Village.
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Parks · Outdoors · Beaches · Wildlife
Side Trips
Find places to stay Jan 25 — 28:

Shoal Bay Village, Anguilla — 2 nights

Start off your visit on the 29th (Sun): kick back and relax at Rendezvous Bay Beach, then contemplate the waterfront views at Maundays Bay, and then see Anguilla Watersports. On the 30th (Mon), you'll have a packed day of sightseeing: stroll through Shoal Bay and then enjoy the sand and surf at Little Bay.

To find more things to do, traveler tips, and other tourist information, read our Shoal Bay Village trip app.

Getting from Cul de Sac to Shoal Bay Village by combination of car and ferry takes about 1.5 hours. Other options: do a combination of shuttle and ferry; or fly. In January, daily temperatures in Shoal Bay Village can reach 33°C, while at night they dip to 26°C. Wrap up your sightseeing on the 30th (Mon) to allow time to travel to Port of Spain.
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Parks · Outdoors · Beaches · Nature
Side Trips
Find places to stay Jan 28 — 30:

Port of Spain, Trinidad and Tobago — 3 nights

Port of Spain, the country's capital, sits between the sea and a scenic green mountain range, and acts as a gateway for eclectic adventures on land and sea.
Take a break from Port of Spain with a short trip to Yerette in Maracas Bay, about 30 minutes away. The adventure continues: tour the pleasant surroundings at Asa Wright Nature Centre, enjoy the sand and surf at Maracas Beach, surround yourself with nature on a nature and wildlife tour, and walk around Queen's Park Savannah.

To find other places to visit, more things to do, reviews, and more tourist information, go to the Port of Spain vacation builder.

Getting from Shoal Bay Village to Port of Spain by combination of ferry and flight takes about 6 hours. Other options: fly. January in Port of Spain sees daily highs of 36°C and lows of 26°C at night. Finish up your sightseeing early on the 2nd (Thu) so you can catch the flight to Bridgetown.
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Parks · Wildlife · Outdoors · Beaches
Side Trips
Find places to stay Jan 30 — Feb 2:

Bridgetown, Barbados — 4 nights

Bridgetown is the capital and largest city of Barbados. You'll find plenty of places to visit near Bridgetown: Saint Philip Parish (Bottom Bay & Foul Bay) and St. Nicholas Abbey (in Saint Peter Parish). There's lots more to do: Head underground at Harrison's Cave., tour the pleasant surroundings at Bathsheba Beach, enjoy the sand and surf at Soup Bowl, and explore and take pictures at Andromeda Botanic Gardens.

To see traveler tips, maps, where to stay, and other tourist information, you can read our Bridgetown trip itinerary builder site.

Traveling by flight from Port of Spain to Bridgetown takes 3 hours. Expect a daytime high around 34°C in February, and nighttime lows around 27°C. Finish your sightseeing early on the 6th (Mon) so you can fly to Soufriere.
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Parks · Outdoors · Beaches · Historic Sites
Side Trips
Find places to stay Feb 2 — 6:

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.
You'll find plenty of places to visit near Soufriere: Anse Cochon Beach (in Anse La Raye) and Castries (Meme Bete & Rodney Bay). There's still lots to do: contemplate the waterfront views at Marigot Bay, admire the sheer force of Piton Falls, see majestic marine mammals with a dolphin and whale watching tour, and take in nature's colorful creations at Diamond Falls Botanical Gardens.

To see maps, other places to visit, and more tourist information, use the Soufriere day trip planning site.

Traveling by flight from Bridgetown to Soufriere takes 3 hours. Expect a daytime high around 34°C in February, and nighttime lows around 28°C. Wrap up your sightseeing on the 9th (Thu) to allow time to fly to St. George's.
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Parks · Outdoors · Nature · Beaches
Side Trips
Find places to stay Feb 6 — 9:

St. George's, Grenada — 4 nights

The capital of the Island of Spice, St.
St. George's is known for historic sites, museums, and wildlife. Your trip includes some of its best attractions: stroll through Grand Anse Beach, brush up on your knowledge of spirits at River Antoine Estate Rum Distillery, take in the dramatic scenery at Annandale Falls, and don't miss a visit to Market Square.

For photos, ratings, more things to do, and more tourist information, read St. George's trip itinerary builder app.

Fly from Soufriere to St. George's in 4.5 hours. In February, daytime highs in St. George's are 34°C, while nighttime lows are 27°C. Finish up your sightseeing early on the 13th (Mon) so you can catch the flight to St. John's.
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Parks · Outdoors · Nature · Beaches
Side Trips
Find places to stay Feb 9 — 13:

St. John's, Antigua and Barbuda — 6 nights

The capital and largest city of Antigua and Barbuda, St John's represents the commercial and touristic center of the twin-island country.
Get out of town with these interesting St. John's side-trips: Half Moon Bay (in Saint Philip Parish), Devil's Bridge (in Willikies) and English Harbour (Nelson's Dockyard & Shirley Heights). There's much more to do: explore the activities along Dickenson Bay, kick back and relax at Valley Church Beach, tour the pleasant surroundings at Galley Bay Beach, and discover the deep blue sea with Stingray City.

To find ratings, reviews, photos, and other tourist information, read our St. John's journey planner.

Traveling by flight from St. George's to St. John's takes 4.5 hours. In February, daily temperatures in St. John's can reach 32°C, while at night they dip to 26°C. On the 19th (Sun), you'll travel back home.
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Parks · Outdoors · Beaches · Nature
Side Trips
Find places to stay Feb 13 — 19:

Dominican Republic travel guide

4.1
Beaches · Islands · Zipline
Sharing the island of Hispaniola with Haiti, friendly Dominican Republic offers two distinct coastlines, one bathed by the Caribbean Sea and the other by the Atlantic Ocean. Nearly 1,600 km (1,000 mi) of palm-shaded beaches figure highly on most Dominican Republic itineraries, allowing visitors to design their vacation around a range of water-based activities. The sun-kissed country benefits from pleasant temperatures throughout the year, so it's no surprise that holidays in Dominican Republic remain a popular choice for visitors from distant and colder corners of the world. A big producer of coffee, cocoa, rum, sugarcane, and tobacco, the country provides a vibrant cultural experience in multicultural cities and quaint countryside.
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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.
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Saint-Martin travel guide

4.1
Beaches · Islands · Nature & Parks
While the charming Saint-Martin shares its small island with the similarly named Dutch constituency, it offers a distinct, more European atmosphere than its counterpart. Noticeably devoid of casinos and less developed than its neighbor, Saint-Martin boasts rocky cliffs, scenic beaches, trendy restaurants, and a leisurely, carefree atmosphere. The island has practically no border control, so you'll easily travel between the two sides to make the most of your Saint-Martin holiday.
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Anguilla travel guide

4.1
Nature & Parks · Islands · Swim with Dolphins
A peaceful set of islands with a pristine, bespoke tourism infrastructure, Anguilla offers a restful vacation for beach-lovers, honeymooners, and diving enthusiasts. A scattering of historic attractions in Anguilla stand as testament to the native and colonial histories of the set of paradisal islands, but the focus here lies much more on coastlines rather than timelines. The beaches of Anguilla remain relatively untouched, allowing the scenery to speak for itself. However, this is no back-to-basics place, with whatever tourist developments there are being made to luxury standards, and priced accordingly.
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Trinidad and Tobago travel guide

4.1
Beaches · Nature & Parks · Waterfalls
With its two landmasses offering different, but complementary Caribbean flavors, the dual island nation of Trinidad and Tobago attracts visitors looking for relaxation and adventure. Cities and bustling market towns set the pace of cosmopolitan Trinidad, by far the larger of the two Caribbean sisters. Holidays in Tobago tend to be more chilled out affairs, with island offering some of the nation's finest resorts and best kept beaches, along with a wealth of protected areas boasting diverse and abundant wildlife. Both have become famous for their Creole culture and traditions, with holidays in Trinidad and Tobago offering plenty of culinary and musical highlights, including red hot curries and spicy calypso music.
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Barbados travel guide

4.4
Beaches · Scuba & Snorkeling · Gardens
Little England
Plan a vacation on the small Caribbean island of Barbados and experience its rich history and vibrant culture. Affectionately called "Little England," the island retains a noticeable British influence in its lively culture, visible especially in sport, religion, and the charming British style buildings with a Caribbean flair. On a tour of Barbados you can lounge on sandy beaches, participate in world-class surfing, roam the World Heritage-listed capital, or explore the lush island interior. When on the island, don't forget to sample its world-famous rum and the signature local dish, the flying fish.
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St. Lucia travel guide

4.1
Hot Springs · Bodies of Water · Landmarks
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.
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Grenada travel guide

4
Beaches · Museums · Scuba & Snorkeling
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.
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Antigua and Barbuda travel guide

4.2
Scuba & Snorkeling · Beaches · Lookouts
Escape civilization with a holiday in Antigua and Barbuda, a beachgoer's paradise. The shorelines of the two islands are dotted with many beaches, from long stretches of sand to tiny coves and picturesque lagoons. While the larger Antigua houses its fair share of high-end resorts and contains the country capital of St. John's, Barbuda is remarkably undeveloped, boasting swathes of pink sand where you can go for hours without seeing a single person.
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