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Caribbean Sailing

Sailing in the Caribbean

Do you want more from your holiday than lying on a beach and drinking fancy cocktails? Sure that sounds enticing however imagine you can enjoy those cocktails whilst taking in the sun on a sailing boat? 

Become a captain of the Caribbean Sea and get that feeling of freedom and liberty that only be experienced on a mass of open water. We have assembled some of the best hotels in the Caribbean where you do have the possibilty to rent a boat or get some sailing lessons, so what are you waiting for? Further holiday options include Dive SchoolGolfWaterskiing Included.

Browse by Caribbean destination

Browse by Caribbean destination

Antigua Sailing Holidays

Blue Waters

Blue Waters

Flight & Hotel

7 nights from £1199

Blue Waters, on the northern shore of Antigua, is a privately owned resort ideal for honeymoons and weddings because of its intimate and secluded atmosphere but also gladly accommodates families.

7 nights from £1199

  • 3 Swimming Pools
  • Watersports
  • 6 Restaurants & Bars
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7 nights from £1199

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The Verandah Resort & Spa

The Verandah Resort & Spa

Flight & Hotel

7 nights from £1141

Located next to a National Park, The Verandah Resort & Spa by Elite proves that ‘eco-friendly’ and ‘luxury’ aren't mutually exclusive. Amenities are plentiful and include tennis courts, a spa and watersports.

7 nights from £1141

  • Watersports
  • 2 Beaches
  • Local Cooking Classes
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Flight & Hotel

7 nights from £1141

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Carlisle Bay

Carlisle Bay

Flight & Hotel

7 nights from £1736

Situated on a stunning bay in Antigua’s capital, the Carlisle Bay resort is an idyllic piece of haven with high-end spa facilities where you can relax as well as take advantage of the water activities which are aplenty.

7 nights from £1736

  • Secluded Hotel
  • 9 Tennis Courts
  • Cinema Room
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7 nights from £1736

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Curtain Bluff

Curtain Bluff

Flight & Hotel

7 nights from £2499

Curtain Bluff is a 5-star luxury resort offering an all-inclusive service which is outstanding. Amenities include tennis, yoga and a vast array of water sports as well as a 5,000 feet spa with outdoor treatments.

7 nights from £2499

  • Free Scuba Diving
  • Kids' Activities
  • 3 Restaurants
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7 nights from £2499

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Galley Bay Resort & Spa

Galley Bay Resort & Spa

Flight & Hotel

7 nights from £1727

Set on Antigua’s west coast, the Galley Bay is an all-inclusive, adults only resort known for its white beaches and tropical, lush gardens. You’ll encounter and endless list of activities including a fantastic spa.

7 nights from £1727

  • Romantic Hotel
  • Bike Rentals
  • Kayaking
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Flight & Hotel

7 nights from £1727

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Nonsuch Bay Resort

Nonsuch Bay Resort

Flight & Hotel

7 nights from £1219

Located on an idyllic, secluded bay in the south east of Antigua, Nonsuch Bay is the perfect resort for those seeking a tranquil haven of serenity, relaxing spa treatments and renowned sailing spots.

7 nights from £1219

  • All inclusive
  • Sailing
  • Free Private Transfers
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7 nights from £1219

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Hawksbill by rex resorts

Hawksbill by rex resorts

Flight & Hotel

7 nights from £857

The Hawksbill by rex resorts in the northwest of Antigua accommodates everyone whether you’re looking for a romantic getaway, a family-friendly resort or wedding packages.

7 nights from £857

  • All Inclusive Hotel
  • Tennis Courts
  • 4 Secluded Beaches
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Flight & Hotel

7 nights from £857

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Pineapple Beach Club Antigua

Pineapple Beach Club Antigua

Flight & Hotel

7 nights from £1089

If you’re looking for an affordable resort with an informal atmosphere the Pineapple Beach Club Antigua is just the ticket. The friendly staff put on great shows every night.

7 nights from £1089

  • Watersports
  • Nightly Entertainment
  • 8 Restaurants & Bars
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Flight & Hotel

7 nights from £1089

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St James’s Club & Villas

St James’s Club & Villas

Flight & Hotel

7 nights from £1156

St James’s Club & Villas is a popular resort all year round due to its extensive catalogue of watersports such as catamaran tours, snorkelling and surfing as well as a fun kids club.

7 nights from £1156

  • 6 Swimming Pools
  • 5 Restaurants & Bars
  • 2 Beaches
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Flight & Hotel

7 nights from £1156

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Halcyon Cove by rex resorts

Halcyon Cove by rex resorts

Flight & Hotel

7 nights from £865

The Halcyon Cove by Rex Resorts is a delightful and affordable hotel that is widely known for its kids club, offering a vast array of fun activities for young travellers and leaving the parents plenty of time to relax.

7 nights from £865

  • All Inclusive Hotel
  • Kids Club
  • Sunfish Sailing Boats
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Flight & Hotel

7 nights from £865

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Sandals Grande Antigua Resort & Spa

Sandals Grande Antigua Resort & Spa

Flight & Hotel

7 nights from £1566

Sandals Grande Antigua Resort & Spa is an award-winning retreat, famous for its weddings and honeymoons, with a great variety of accommodations and dining outlets.

7 nights from £1566

  • Free Scuba Diving
  • Couples Only
  • 6 Swimming Pools
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7 nights from £1566

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Anguilla Sailing Holidays

CuisinArt Resort & Spa

CuisinArt Resort & Spa

Flight & Hotel

10 nights from £3467

The CuisinArt Golf Resort and Spa not only offers a fantastic golf course as well as luscious spa treatments but also uses fresh produce in their eateries that they grow themselves in their organic garden.

10 nights from £3467

  • BBQ
  • Beach Bar
  • Cooking Classes
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10 nights from £3467

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Four Seasons Anguilla

Four Seasons Anguilla

Flight & Hotel

10 nights from £3217

Suited for honeymoons and family holidays alike, Four Seasons Anguilla is constituted of stylishly designed villas as well as suites and is as exclusive as it gets when it comes to 5-star accommodation.

10 nights from £3217

  • Family Friendly
  • Kids Club
  • Tennis Courts
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Flight & Hotel

10 nights from £3217

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Aruba Sailing Holidays

Hyatt Regency Aruba Resort & Casino

Hyatt Regency Aruba Resort & Casino

Flight & Hotel

7 nights from £1179

The Hyatt Regency Aruba Resort & Casino is the perfect retreat if you're looking for stunning rooms and exclusive amenities like adventurous watersports, a glamorous casino and a luxury spa.

7 nights from £1179

  • Casino On Site
  • Luxury Hotel
  • 12 Restaurants & Bars
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7 nights from £1179

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Bahamas Sailing Holidays

Atlantis Paradise Island

Atlantis Paradise Island

Flight & Hotel

7 nights from £1194

When it comes to luxury and exclusivity Atlantis Paradise Island is unrivaled. A Nobu Restaurant, golf course and dolphin habitat are just a fraction of the attractions.

7 nights from £1194

  • 20 Swimming Pools
  • Water Park
  • Dolphin Interaction
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7 nights from £1194

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Atlantis Harbourside Resort

Atlantis Harbourside Resort

Flight & Hotel

7 nights from £1473

The best spot to bring the kids to in the Bahamas: 141 acre sized water park, seven acres of salt-water lagoons and tonnes of watersports and water based activities on offer.

7 nights from £1473

  • Full Kitchen
  • Water Park
  • Suites & Villas
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7 nights from £1473

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Atlantis The Cove

Atlantis The Cove

Flight & Hotel

7 nights from £1868

A top spot for younger couples, honeymooners and groups of friends, The Cove Atlantis Resort offers extraordinary amenities, including its own beach club, casino, golf course and spa.

7 nights from £1868

  • Family Friendly
  • Water Park
  • Luxury Hotel
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Flight & Hotel

7 nights from £1868

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Atlantis The Reef

Atlantis The Reef

Flight & Hotel

7 nights from £1655

Located in a truly spectacular setting in the Bahamas, the Atlantis Reef is a luxury resort destination offering all the comfort and privacy that Paradise Island has to offer.

7 nights from £1655

  • Kids' Activities
  • Watersports
  • Dolphin Interaction
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Flight & Hotel

7 nights from £1655

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Tiamo, Andros

Tiamo, Andros

Flight & Hotel

7 nights from £2833

A collection of beachfront luxury villas, Tiamo Resort combine luxury living with responsible environmental design.

7 nights from £2833

  • Padi Dive School
  • Beachfront Hotel
  • Private Beach
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Flight & Hotel

7 nights from £2833

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Bermuda Sailing Holidays

Rosewood Tucker's Point

Rosewood Tucker's Point

Flight & Hotel

7 nights from £1745

This stunning resort guarantees you a luxury holiday in Bermuda like no other. A spa, 3 restaurants and a huge range of activities ensure that you'll have the holiday of your dreams.

7 nights from £1745

  • Golf nearby
  • Poolside Dining
  • Pink sand beach
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Flight & Hotel

7 nights from £1745

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Grotto Bay Beach Resort

Grotto Bay Beach Resort

Flight & Hotel

7 nights from £1158

Perfectly situated for diving in Bermuda's most beautiful underwater world. Many recreational activities available, from sunset boat cruises to golf courses.

7 nights from £1158

  • Tennis Courts
  • Watersports
  • Cottages
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Flight & Hotel

7 nights from £1158

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British Virgin Islands Sailing Holidays

Bitter End Yacht Club

Bitter End Yacht Club

Flight & Hotel

7 nights from £2318

Imitating a typical Caribbean beachfront village in style and lifestyle, this resort offers guests unforgettable sailing experiences. Its own sailing school will teach you how.

7 nights from £2318

  • Secluded Hotel
  • Fresh Water Pool
  • Sunset Cruises
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Flight & Hotel

7 nights from £2318

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Peter Island Resort & Spa

Peter Island Resort & Spa

Flight & Hotel

7 nights from £2082

This luxury beachfront resort is unsurpassed in the British Virgin Islands in terms of romance it offers. Perfect to visit with the one you love.

7 nights from £2082

  • Eco Friendly Hotel
  • Private Island
  • Family Owned
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Flight & Hotel

7 nights from £2082

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Guana Island

Guana Island

Flight & Hotel

7 nights from £3031

This stunning private island retreat is flanked by incredible waters and boasts seven gorgeous beaches that invite guests to relax and explore in equal measure.

7 nights from £3031

  • Private Island
  • Breathtaking Location
  • 7 Private Beaches
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Flight & Hotel

7 nights from £3031

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Dominican Republic Sailing Holidays

Now Larimar Punta Cana

Now Larimar Punta Cana

Flight & Hotel

7 nights from £1040

Sophisticated amenities, deluxe pools, outdoor cinema on the beach - all this and more awaits you at this stylish all-inclusive resort.

7 nights from £1040

  • Kids Club
  • Luxury Spa
  • Unlimited-Luxury®
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Flight & Hotel

7 nights from £1040

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Breathless Punta Cana Resort & Spa

Breathless Punta Cana Resort & Spa

Flight & Hotel

7 nights from £1190

With an all inclusive package that promises Unlimited-Luxury®, and a Club Level that will simply amaze you, Breathless Punta Cana Resort & Spa is an adults only beachfront resort to be reckoned with.

7 nights from £1190

  • 8 Swimming Pools
  • 16 Restaurants & Bars
  • Unlimited Connectivity
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Flight & Hotel

7 nights from £1190

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Casa de Campo

Casa de Campo

Flight & Hotel

7 nights from £1157

Practically an oceanfront town in its own right, multi-award-winning Casa de Campo is a 7,000-acre dream, featuring top golf courses, an equestrian centre, beach and incredible spa.

7 nights from £1157

  • Golf Course in Resort
  • Watersports
  • Luxury Retreat
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7 nights from £1157

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Dreams La Romana

Dreams La Romana

Flight & Hotel

7 nights from £1058

Set on the southeast coast of the Dominican Republic, Dreams La Romana is the perfect resort for singles, couples and families. Enjoy their Unlimited-Luxury package, where nearly everything is included.

7 nights from £1058

  • Watersports
  • 20 Restaurants & Bars
  • Unlimited Connectivity
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Flight & Hotel

7 nights from £1058

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Dreams Palm Beach

Dreams Palm Beach

Flight & Hotel

7 nights from £1045

Great for those who want an out-of-the-ordinary Caribbean retreat. Modern spa, delicious Caribbean cuisine, and an 18-hole golf course are among the resort's special features.

7 nights from £1045

  • Swim Up Bar
  • Luxury Spa
  • Unlimited Connectivity
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Flight & Hotel

7 nights from £1045

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Dreams Punta Cana Resort & Spa

Dreams Punta Cana Resort & Spa

Flight & Hotel

7 nights from £1065

Unlimited luxury. Everything included. No rush. No stress. Just you, and your perfect Caribbean holiday on the soft white sands of the Dominican Republic.

7 nights from £1065

  • All Inclusive Hotel
  • 17 Restaurants & Bars
  • Unlimited Connectivity
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7 nights from £1065

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Secrets Royal Beach

Secrets Royal Beach

Flight & Hotel

7 nights from £1272

Your ideal all inclusive holiday of relaxation, perfect for couples or families. No matter what the occasion, there's plenty enough to keep everyone happy.

7 nights from £1272

  • Golf Course in Resort
  • 5 Bars
  • Wine Cellar
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Flight & Hotel

7 nights from £1272

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Melia Caribe Tropical

Melia Caribe Tropical

Flight & Hotel

7 nights from £1096

This family-friendly, all-inclusive resort features two spas, numerous Jacuzzis, and a golf course with stunningly beautiful natural views.

7 nights from £1096

  • 10 Swimming Pools
  • Free Golf
  • All Inclusive Hotel
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Flight & Hotel

7 nights from £1096

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St Lucia Sailing Holidays

Calabash Cove Resort & Spa

Calabash Cove Resort & Spa

Flight & Hotel

7 nights from £1336

Five star boutique resort and spa with spectacular villas and suites on offer. A really lovely luxury resort that caters for romantic adult-only escapades.

7 nights from £1336

  • Boutique Hotel
  • Swim Up Bar
  • All Suite Hotel
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Flight & Hotel

7 nights from £1336

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The Landings Resort and Spa by Elegant Hotels

The Landings Resort and Spa by Elegant Hotels

Flight & Hotel

7 nights from £1287

Family friendly The Landings Resort and Spa by Elegant Hotels features a private harbour, and combines some of the island's best luxury suites with superb service and a full range of leisure activities.

7 nights from £1287

  • Spa Facilities
  • 3 Swimming Pools
  • Family Luxury
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Flight & Hotel

7 nights from £1287

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Anse Chastanet Resort

Anse Chastanet Resort

Flight & Hotel

7 nights from £1284

This resort's local natural beauty is some of the best that you will find in the Caribbean; boasting a mountainous backdrop, perfect white sand and an idyllic azure ocean.

7 nights from £1284

  • Luxury Hotel
  • Pitons view
  • Cooking Classes
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Flight & Hotel

7 nights from £1284

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St Vincent & Grenadines Sailing Holidays

Petit St Vincent

Petit St Vincent

After undergoing a complete refurbishment, this private island of 22 luxury holiday cottages makes Petit St. Vincent in St. Vincent and the Grenadines a unique Caribbean experience.

  • Private Beach
  • Snorkelling
  • Romantic Hotel
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Young Island

Young Island

The one and only Young Island is for everyone who was young, is young, and will forever be young in heart. Let go of your daily struggles and troubles, come and enjoy life at its best, at Young Island.

  • Beachfront Hotel
  • Snorkelling
  • Cottages
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Tobago Sailing Holidays

Magdalena Grand Beach Resort

Magdalena Grand Beach Resort

Flight & Hotel

7 nights from £897

Magdalena Grand Beach Resort is a gorgeous community of private villas and bungalows perched on the Tobago Plantations Estate, sprawled over acres of beautiful land.

7 nights from £897

  • Family Friendly
  • Entertainment
  • 3 Swimming Pools
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Flight & Hotel

7 nights from £897

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Turtle Beach by Rex Resorts

Turtle Beach by Rex Resorts

Flight & Hotel

7 nights from £963

Ideal for a family holiday the Turtle Beach by Rex Resorts is a beautiful secluded hotel located on its own private beach in Tobago.

7 nights from £963

  • Beachfront Location
  • Kids Club
  • All Inclusive Option
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Flight & Hotel

7 nights from £963

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Turks & Caicos Sailing Holidays

The Sands at Grace Bay

The Sands at Grace Bay

Flight & Hotel

7 nights from £1009

The luxury resort is set on the jewel of the archipelago, Providenciales, and enjoys sweeping views of Grace Bay, a munificence of natural beauty. With a golf course, casino and spa, you’ll live the high life.

7 nights from £1009

  • Kitchenette
  • Snorkelling
  • All Suite Hotel
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Flight & Hotel

7 nights from £1009

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Beaches Turks & Caicos Resort

Beaches Turks & Caicos Resort

Flight & Hotel

7 nights from £2162

The award winning Beaches Turks & Caicos Resort Villages & Spa offers lots of family fun in the Caribbean. With a kids club, nursery, water-park and Xbox360 garage, you'll soon see why.

7 nights from £2162

  • Water Park
  • Sesame Street®
  • 20 Restaurants
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7 nights from £2162

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