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Top Caribbean Multi-day & Extended Tours

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67 Caribbean Multi-day & Extended Tours

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Did you know?You can reserve your spot today and pay when you're ready.
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Did you know?
You can reserve your spot today and pay when you're ready.Learn more

Overnight Tours

"THREE DAYS COMBO TOURS": Day1- West. Day2- South and Day3- North Coast

"Remember this Tour is design for those who want to see the real Jamaica". Blue Hole is located in Ocho Rios Jamaica. Also known as Secret Falls, the Blue Hole is undoubtedly one of Jamaica's hidden treasures. "It's a must see Falls". Blue Hole Falls is very deep, which make it excellent for divers, swimmers and thrill seekers. Swing on the rope like Tarzan and hike along the river. Explore Cliff Jump, small Caves, divers and much more. Irie Blue Hole is the true definition of paradise in JAMAICA .!! *Very important to all Blue Hole Visitors and Participants you must be able to swim*. "A Language guide will be with you upon Request" Note: A minimum of 2 people are required to book. Includes round trip transportation and tour to locations Lunch, entrance fees, activities fees and language guides are NOT included in cost
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  • 2 days
  • Free Cancellation
From  
US$256,42 
From  
US$256,42 
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  • 2 days
  • Free Cancellation

Jamaica Jump and Slide Two Day Adventure from Ocho RiosOvernight Tours

Jamaica Jump and Slide Two Day Adventure from Ocho Rios

Get ready for an epic adventure on your two day tour package in the beautiful town of Ocho Rios.
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  • 2 days
  • Free Cancellation
From  
US$256,42 
Price varies by group size
From  
US$256,42 
Price varies by group size
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  • 2 days
  • Free Cancellation

Exumas/Nassau 8 days catamaran cruise, inc. foodMulti-day Tours

Exumas/Nassau 8 days catamaran cruise, inc. food

Sail the Exumas islands on a luxury private all-inclusive cruise: the ultimate yacht experience. See the islands in style as you sail from Highborn Cay to Norman’s Cay, on a blissful tour of many of the area’s highlights. Try deep-sea fishing, kayaking, and paddleboarding. Snorkel among tropical fish and vivid coral, meet local iguanas and even swim with the famous swimming pigs. Rest your sea legs as you enjoy drinks at the yacht club, and unwind across heavenly powdered sandy beaches.
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  • 8 days
From  
US$1 667,90 
From  
US$1 667,90 
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  • 8 days

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Blue Mountains, Port Royal and Kingston 2-Day Tour from Ocho RiosNature & Wildlife

Blue Mountains, Port Royal and Kingston 2-Day Tour from Ocho Rios

Leave Ocho Rios behind and see the UNESCO World Heritage panoramic Blue Mountains, visit historic city of Kingston member of the Creative Cities Network Organisation and Port Royal where you can tour a military fort built in the 17th century where pirates of the Caribbean once ruled!
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  • 2 days
  • Free Cancellation
From  
US$1 076,93 
From  
US$1 076,93 
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  • 2 days
  • Free Cancellation

Jamaica's Premier Bachelorette GetawayMulti-day Tours

Jamaica's Premier Bachelorette Getaway

star-5
Get the full VIP treatment with REEL Vacations Bachelorette All-inclusive vacation package.  Experience the best of Jamaica's party scene in Montego Bay, Negril, Ocho Rios and Kingston!  Sunbathe at the most pristine private beaches in Jamaica's north coast!  We handle everything for you – 5 Star Villas, food made to order by private chef, drinks, entrance fees and all transportation.  This is a TRUE All-Inclusive Experience!  Check out our reviews on TripAdvisor to hear from our prior guests.
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  • 5 days
  • Free Cancellation
From  
US$1 742,57 
From  
US$1 742,57 
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  • 5 days
  • Free Cancellation

Jamaica Bob Sled, Blue Hole & Bob Marley Nine Miles, 3 Tours from Ocho RiosMulti-day Tours

Jamaica Bob Sled, Blue Hole & Bob Marley Nine Miles, 3 Tours from Ocho Rios

star-4
Add a hassle free, 3 days adventure tour package to your vacation in the beautiful town of Ocho Rios. Experience Bob Sled at Mystic Mountain, Blue Hole & Bob Marley Mausoleum, three of the top things to do in this super saver combo package in three days. Choose your custom times with private transfers pick up and drop off at your hotel lobby.
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  • 3 days
  • Free Cancellation
From  
US$405,13 
Price varies by group size
From  
US$405,13 
Price varies by group size
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  • 3 days
  • Free Cancellation

5-Day Mini-Vacation Package at Jewel Grande Montego Bay, JamaicaMulti-day Tours

5-Day Mini-Vacation Package at Jewel Grande Montego Bay, Jamaica

Best Vacation Ever! 5 Days/4 Nights All-Inclusive Accommodation at a Montego Bay Family Resort with Family Morning Catamaran Cruise and Snorkeling Experience.
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  • 5 days
From  
US$961,54 
From  
US$961,54 
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  • 5 days

British Virgin Islands 8 days catamaran cruise, inc. foodMulti-day Tours

British Virgin Islands 8 days catamaran cruise, inc. food

Unforgettable sailing in The British Virgin Islands in a private double cabin aboard Ipanema 58 premium catamaran with captain, hostess and food included. Visit the infamous Tortola, Jost van Dyke, Virgin Gorda and Anegada. These and all the small islands in between are a diverse mix, each one with its own personality.  You will be well cared for on your crewed, spacious catamaran. Enjoy white sand beaches, coral reefs, incredible marine life, boutiques and friendly bars. 
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  • 8 days
From  
US$1 547,33 
From  
US$1 547,33 
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  • 8 days

Guadeloupe 8 days catamaran cruise, inc. foodMulti-day Tours

Guadeloupe 8 days catamaran cruise, inc. food

Explore Guadeloupe in private cabins on a week long premium catamaran cruise aboard our Ipanema 58 with captain, hostess and food included. A dream bareboat sailing vacation on the French archipelago of Guadeloupe is the ideal family or romantic getaway. Make sure you don’t miss the beautiful Crayfish waterfall and a swim in it’s refreshing pools. For an even more dramatic sight, head south of Basse Terre and visit the famous 350-foot Carbet Waterfalls. 
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  • 8 days
From  
US$1 469,46 
From  
US$1 469,46 
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  • 8 days

2-Day Adventure Tour of St Thomas and St JohnOvernight Tours

2-Day Adventure Tour of St Thomas and St John

star-4
Immerse yourself in the culture, traditions and history of St John and St Thomas during this 2-day trip. With a local guide, visit sites on both islands like the Virgin Islands National Park and the Annenberg Plantation on St John, as well as Drake's Seat, Skyline Lookout and Mountain Top on St Thomas. Stroll through downtown Charlotte Amelie on St Thomas and take in some sun and surf on St John's Cinnamon Bay Beach. Listen to engaging commentary from your local guide as you travel. Round-trip transportation from St Thomas hotels and lunch on St John is included.
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  • 2 days
From  
US$166,92 
Price varies by group size
From  
US$166,92 
Price varies by group size
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  • 2 days

6-Day Private Tour of Jamaica from KingstonMulti-day Tours

6-Day Private Tour of Jamaica from Kingston

Enjoy a 6-day Jamaican adventure where you will visit Kingston, Ocho Rios and Portland. Enjoy both relaxing days on the beach and days packed with sightseeing and activities. This is a perfectly customized tour that will allow you to enjoy your vacation the old fashioned way.
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  • 6 days
  • Free Cancellation
From  
US$2 800,00 
From  
US$2 800,00 
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  • 6 days
  • Free Cancellation

Portland Nature and Eco TourMulti-day Tours

Portland Nature and Eco Tour

star-5
Explore the quiet peacefulness of the region near Portland on an eco-tour. Over three days and two nights, experience the natural beauty of this part of the Eastern coast of Jamaica. Relax on the beach, paddle a canoe, hike to a waterfall, and raft on the river. This excursion gives you the chance to get away from it all and bask in Mother Nature in the Caribbean.
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  • 3 days
  • Free Cancellation
From  
US$999,00 
Price varies by group size
From  
US$999,00 
Price varies by group size
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  • 3 days
  • Free Cancellation

Jamaica 8-Days Island Tour From Montego BayMulti-day Tours

Jamaica 8-Days Island Tour From Montego Bay

Exploring Jamaica on this 8-day sightseeing vacation tour package which will take you across Jamaica to experience some of the most amazing locations the island has to offer. Our true Jamaican culture will captivate and entertain you. See locations in parishes such St James, Hanover, Westmoreland, Mandeville, Kingston and St Ann. This vacation package can be customized for individuals, families or groups, and your cost includes accommodation, airport transfers, daily transportation, all tour costs and daily breakfast and dinner.
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  • 8 days
  • Free Cancellation
From  
US$2 564,11 
From  
US$2 564,11 
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  • 8 days
  • Free Cancellation

PAP Kenscoff and Jacmel Tour From HaitiMulti-day Tours

PAP Kenscoff and Jacmel Tour From Haiti

This private tour of Port au Prince/Kenscoff and Jacmel sets off with pickup from the airport, your hotel. You will visit a number of sites in these locations including City Tours of Port au Prince and City Tours of Jacmel and sightseeing the Blue waterfall. Five nights accommodation are included and all include such, as well as breakfast each morning in the hotels, dinner, supper and beverages, and a welcome drink upon arrival.
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  • 6 days
From  
US$2 500,00 
From  
US$2 500,00 
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  • 6 days

3-days Jamaica Sightseeing Tour of Treasure Beach and Negril departing from KingstonMulti-day Tours

3-days Jamaica Sightseeing Tour of Treasure Beach and Negril departing from Kingston

Jamaica Discovery 3-days sightseeing tour from Kingston to Treasure Beach and Negril is all things Jamaican with the full cast of Jamaican people – we are “a day in the life vacation” with an emphasis on showcasing the true Jamaica and its rich culture which will captivate and entertain.  Included are Appleton Estate Rum Tour, trip to Pelican Bar, Dolphin Quest & Black River Safari, Rick's Cafe and Negril's seven (7) miles beach and more. "Change the World by sharing ours and we shall never remain unchanged"...
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  • 3 days
From  
US$695,00 
Price varies by group size
From  
US$695,00 
Price varies by group size
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  • 3 days

7-Day Bus Tour Across Jamaica from Montego BayMulti-day Tours

7-Day Bus Tour Across Jamaica from Montego Bay

Get a full picture of Jamaica during this 7-day bus journey departing from Montego Bay. With a local guide, travel through verdant rain forests, along rushing rivers and up mountainsides in the country. Traverse coastal roads along the bright blue Caribbean Sea and learn about the history, people, culture and cuisine of this diverse island nation.
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  • 7 days
  • Free Cancellation
From  
US$2 769,24 
From  
US$2 769,24 
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  • 7 days
  • Free Cancellation

 5-Day Mini-Vacation Package at Holiday Inn Montego Bay, JamaicaMulti-day Tours

5-Day Mini-Vacation Package at Holiday Inn Montego Bay, Jamaica

Best Vacation Ever! 5 Days/4 Nights All-Inclusive Accommodation at a Montego Bay Family Resort with Family Morning Catamaran Cruise and Snorkeling Experience.
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  • 5 days
From  
US$769,24 
From  
US$769,24 
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  • 5 days

8 day All Inclusive Jamaica VacationMulti-day Tours

8 day All Inclusive Jamaica Vacation

Get up and close with nature on this 8 day Tropical Vacation in Jamaica. This trip includes all the must see and do in Jamaica, and best of all it is affordable and all inclusive. Relax on powdery soft white sand beach, visit Bob Marley museum, take a scenic trip to the Blue Mountain coffee farm, eat delicious Jamaican food, relax in a natural mineral spring and so much more. Perfect for the entire family, small groups, couples and solo-travelers!
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  • 8 days
From  
US$3 025,65 
Price varies by group size
From  
US$3 025,65 
Price varies by group size
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  • 8 days

Private 3-Day PAP La Gonave Island, Cotes des Arcadins From HAITIMulti-day Tours

Private 3-Day PAP La Gonave Island, Cotes des Arcadins From HAITI

This private tour of Port au Prince/Cotes des Arcadins, La Gonave Island sets off with pickup from the airport to your hotel. You will visit a number of sites in these locations including City Tours of Port au Prince, Petion Ville,the Observatoire, Cotes des Arcadins , Montrouis, Private Yatch por La Gonave Island, ANse a Galets, Museum Ogier Fombrun. Two night accommodation such, as well as breakfast each morning in the hotels, and beverages, and a welcome drink upon arrival.
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  • 3 days
From  
US$750,00 
From  
US$750,00 
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  • 3 days

Tortola (BVI) 8 days catamaran cruise, inc. foodMulti-day Tours

Tortola (BVI) 8 days catamaran cruise, inc. food

Explore Tortola in private cabins on a week long premium catamaran cruise aboard our Lagoon 620 with captain, hostess and food included. Monkey Point on Guana Island is home to dazzlingly diverse aquatic life. Cane Garden Bay is the perfect place to stroll along the shoreline. Sandy Cay is covered in beautiful trails. All in all, the Tortola Dream Premium cruise is the ultimate treat, and crewed, catered, fully-planned sailing provides a view of the BVI you won’t want to miss. Start from our Nassau base and explore everywhere from Highborn Cay to Norman’s Cay. 
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  • 8 days
From  
US$1 703,07 
From  
US$1 703,07 
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  • 8 days

Bahía de las águilas glamping experience from Santo DomingoOvernight Tours

Bahía de las águilas glamping experience from Santo Domingo

star-5
Bahía de las Aguilas is known as one of the best unique beaches in the whole world, is located far in the south of the island, in this experience you wont stop seeing amazing locations located within the Dominican Republic, we are pretty sure you will come to love this great country and get to know it in ways few people know.
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  • 2 days
  • Free Cancellation
From  
US$502,56 
Price varies by group size
From  
US$502,56 
Price varies by group size
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  • 2 days
  • Free Cancellation

Dominican getawayMulti-day Tours

Dominican getaway

Between the Caribbean Sea and the Atlantic Ocean, the Dominican Republic offers a multitude of exciting discoveries. From the colonial area of the old town of Santo Domingo to the ubiquitous and green nature of the island, through exceptional beaches, all the ingredients are there to spend a dream vacation.
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  • 7 days
  • Free Cancellation
From  
US$592,83 
From  
US$592,83 
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  • 7 days
  • Free Cancellation

Dominican Republic: See & Do it ALL in in 6 Days, 1st Class TravelingMulti-day Tours

Dominican Republic: See & Do it ALL in in 6 Days, 1st Class Traveling

star-4
You absolutely will not find another tour out there as packed with activities and attractions as this one, provided by CharlieTheTraveler. You will also not find another tour out there that offers it all "FIRST CLASS," yet for a relatively low price. We have thousands of travelers taking this specific tour every year-and that's because no competitor can beat us on quality, price and substance. Below are just some examples of what you will see and do on this tour: ► Catamaran Rides to Unspoiled Islands ► Open Bars on Speedboats & on Exotic Beaches ► A Private Tour Guide & Driver in Colonial Santo Domingo ► Visiting an Italianate-Looking Village ► Lunch Buffets & Delicious Food ► Rich Culture And Much, Much More…
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  • 6 days
From  
US$1 496,00 
From  
US$1 496,00 
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  • 6 days

5-Day Mini-Vacation Package at Royal Decameron Montego Bay, JamaicaMulti-day Tours

5-Day Mini-Vacation Package at Royal Decameron Montego Bay, Jamaica

Best Vacation Ever! 5 Days/4 Nights All-Inclusive Accommodation at a Montego Bay Family Resort with Family Morning or Adults Only Afternoon Catamaran Cruise and Snorkeling Experience.
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  • 5 days
From  
US$615,39 
From  
US$615,39 
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  • 5 days


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