Top Caribbean Sailing Tours - page 15

This is not your average boat charter—Sail Bermuda offers a luxury private sailing experience that’s entirely your own. Whether you want to snorkel offshore reefs and shipwrecks, paddle around a secluded island, or jump from cliffs into turquoise waters, we’ll shape the day around you. With over 20 years of experience, we’ve been perfecting the art of bespoke charters—knowing when and where to go, how to avoid the crowds, and how to make every moment seamless. From hand-picked anchorages to onboard catering served with care, every detail is handled so you can relax. You won’t find rigid itineraries or crowded decks here—just space, comfort, and the freedom to explore Bermuda at your own pace, with a knowledgeable local crew by your side. Please note that you may bring up to 15 passengers in total, including yourself. All of our charters are private, so it will be just you and your group on board.

At Sail Bermuda, a sunset charter isn’t just a sail—it’s your own private escape, curated with care. You’ll glide across calm waters aboard the luxury catamaran Elusive, with no crowds and no preset script. Sip wine, enjoy a hand-selected meal, and take in the shifting sky from the best seat in Bermuda. As night falls, your captain can point out constellations overhead—adding a quiet magic that few ever experience. This is sunset, the Sail Bermuda way: personal, peaceful, unforgettable. Please note that you may bring up to 15 passengers in total, including yourself. All of our charters are private, so it will be just you and your group on board.

Escape to a Private Paradise Begin your day with a personalised welcome at our secluded pier, where refreshing cold towels and dedicated concierge service await. Private Snorkeling Sanctuary Indulge in an exclusive 3-hour snorkeling adventure within the crystal-clear waters of the Caribbean Sea. Our expert guides provide top-quality gear. Tailored Underwater Exploration Discover vibrant coral reefs and marine life at your own pace, guided by specialists attuned to your interests. Secluded Coastal Cruise Unwind on your private boat as it glides along Montego Bay's stunning coastline, offering breathtaking views of golden beaches, lush landscapes, and azure waters. Exclusive Luxury Experience Savour the intimacy of this personalised journey, tailored to provide: - Unparalleled privacy and seclusion - Expert guidance and personalised attention - Uninterrupted relaxation and leisure Create cherished memories, rejuvenate your senses, and experience the ultimate Caribbean luxury.

Discover the serene beauty of Marigot Bay while indulging in a variety of watersports during your stop at Port Castries. Hop on a Hobie Cat for a sailing adventure, challenge your skills on a paddle board, or kayak through the lush mangroves. With snorkel gear provided, explore the vibrant marine life in the calm waters or simply unwind on a beach chair at the water's edge. Perfect for solo travelers or families looking to soak in the Caribbean sun, this activity promises a refreshing escape into paradise.

Set sail on a private charter aboard the luxurious 41 ft Metta sailing catamaran, perfect for a customizable adventure in the stunning waters of the islands. Enjoy a range of options from half-day cruises to sunset sails, all designed to fit your preferences. Whether you want to snorkel, relax on a secluded beach, or indulge in a delicious French picnic, this experience is tailored just for you. - Choose from half-day, full-day, or sunset cruise options - Includes drinks and a selection of gourmet food on board - Family-friendly with free access for infants and tailored activities for all ages - Explore famous local spots like the iguana sanctuary and coral reefs

Gather your friends or family members or even coworkers and set sail on a PRIVATE scenic sunset cruise along Saint Lucia's stunning west coast. This 5-hour adventure begins at your nearest port and leads you to the pristine waters of Sugar Beach for an exhilarating snorkeling experience. After exploring the vibrant underwater life, indulge in delicious local cuisine and refreshing drinks, all while enjoying lively music. As the sun dips below the horizon, keep your eyes peeled for the enchanting green flash—an unforgettable moment during your evening on the water. Ideal for travelers seeking relaxation and captivating views, this cruise offers a perfect blend of leisure and culinary delights. - Snorkeling adventure at the beautiful Sugar Beach (OPTIONAL) - Savor fine foods and refreshing drinks on board - Watch for the magical green flash at sunset -A MINIMUM OF 8 TRAVELERS IS REQUIRED TO CONFIRM THIS TOUR. WE CAN ACCOMMODATE UP TO 85 TRAVELERS IN THIS PRIVATE TOUR.

From the moment you step aboard, we promise an experience filled with excitement. You'll be greeted with a welcome drink as our captain outlines the safety protocols, setting the stage for our sailing journey. As we leave the harbor, we’ll catch the breeze and set sail along the stunning Bonaire coastline. We’ll dock at one of the pristine moorings between Bonaire and Klein Bonaire within the protected Marine Park. Dive into a world of vibrant marine life with our top-quality snorkel gear, complete with detailed instructions and assistance from our expert team. Choose to join a guided exploration or drift through the colorful reef on your own terms.Back on board, as we sail once more, lounge under the sun and let the ocean's rhythm soothe your soul. We’ll treat you with snacks and refreshing beverages.Our trip concludes with a gentle return to the pier, where you’ll have ample time to wander through the streets of Kralendijk, rich with culture.Join us for this exceptional journey!

Where golden skies meet calm seas sunset cruising along the south side of St. Maarten on our luxury sailing catamaran, Don't Worry.

Pirates grab your Rum...!! Our start is bright and early as we head to the heart of Jamaica, travel through the towns as we head toward the Birthplace of the Lion himself BOB MARLEY. Then it's off to Port Royal Kingston, to board the ONLY PIRATE SHIP IN JAMAICA, the music starts, and Jamaica's Castle Black Rum is poured, We stop for swimming and snorkeling at the beautiful island LIME CAY, crystal waters and white sands. get to spend some time taking in the Island Vibes at the heart if Jamaica... after then we sail to the Kingston Harbor where the real Pirates would dock and sell their goods .. Maybe you will catch a glimpse of Jack Sparrow ... or will you see the Ghost of Blackbeard himself or listen to a siren on the ocean. Ahoy, Me Hearties all hands-on Deck, Savvy ...! After the cruise ends, there's some time to enjoy a bite to eat and a last drink before we board the buses back to your resorts...

Where golden skies meet calm seas — sunset cruising along the south side of St. Maarten on our luxury sailing catamaran, Be Happy.

The water in Jamaica's luminous lagoon is full of millions of dinoflagellates which are a type of algae or marine plankton. At nighttime, these microscopic organisms start to glow when they are disturbed. This outlines objects moving in the water such as boats, fish, and yes even people.

Enjoy coastline views from the deck of a sailboat during this sailing cruise from Punta Cana. Step on board to meet your captain and crew, who will offer you a welcome cocktail and regale you with the history of sailing in the Caribbean while you travel. Bring your camera for amazing photo ops of the area while you sip drinks from the open bar.

What makes our Saona Island tour different is the perfect balance between relaxation, adventure, and authentic Dominican charm. Unlike standard excursions, we combine speedboat and catamaran so you experience both the thrill of a fast ride and the fun atmosphere of music and entertainment on the way back. Our tour includes a delicious Dominican buffet right on the beach, plenty of free time to enjoy the island at your own pace, and a stop at the famous Natural Pool, one of the Caribbean’s most iconic spots. With personalized attention, comfort, and a lively atmosphere, we make sure your day in Saona is not just a trip, but an unforgettable experience worth sharing.

Why Guests Love This Experience Flexible booking
 Full refund if canceled due to weather
Friendly, energetic crew
 Safe, fun, and highly recommended by travelers Book Now!
After your reservation, we’ll share contact details to coordinate everything easily via WhatsApp. Come party in paradise and create unforgettable memories in Punta Cana!

Board a comfortable bus for a relaxing ride to the dock, where a spacious catamaran awaits. Sail along Punta Cana's stunning coastline, soaking up the Caribbean sun and enjoying refreshing drinks from the friendly crew. Dive into crystal-clear waters for snorkeling among vibrant coral reefs and colorful tropical fish with provided gear and a guided activity . Then, unwind in a serene natural pool with waist-deep turquoise waters or at a private beach ideal for children to play.

On board Catamaran Maxim we will take you on an unforgettable day. We will sail along the south coast of Bonaire. This pristine island has a stunning scenery and tranquility that everyone is looking for. During this trip we will make several stops, where you can dive into the beautiful underwater landscape of Bonaire. These sites are ideal for beginning snorkelers: Anemones, soft coral, sponges and numerous fish species can be seen. Whether you love to snorkel or would like to enjoy the basics of sailing, with our personal touch we will make your day unforgettable! All you have to do is sit back, relax and enjoy cruising along the crystal clear waters!

Discover paradise at sea with our catamaran tour in Punta Cana! Embark on a unique adventure over the turquoise waters of the Caribbean and enjoy an exclusive experience aboard a luxury catamaran. Sail along the coast of Punta Cana, where the sea meets the sky in a spectacle of stunning colors. During this tour, you will have the opportunity to snorkel on coral reefs full of marine life, discover secret beaches only accessible by sea, and relax on a private island with crystal clear waters that invite you to swim. All while enjoying tropical cocktails and refreshments on board, with the sea breeze caressing your face!

What sets your Saona tour apart is the perfect balance of exclusivity, comfort, and authentic Caribbean vibes. Departing from Bayahibe, we offer smaller groups, personalized service, and a premium atmosphere. Guests enjoy longer stops at the Natural Pool of Palmilla and pristine beaches of Isla Saona, avoiding crowded areas. Your professional crew, quality drinks, fresh food, and curated music create a unique onboard experience. It’s not just a tour it’s a luxury escape where every detail is designed to deliver unforgettable moments in paradise.

Yur main objective is to provide quality service, punctuality, with no long time waiting for transport to arrive, from the moment you take your luggage, the driver will be waiting with a name plate .Your transportation offers Wi-Fi service until reaching the hotel, because we want your passengers to have the best experience in Punta Cana.

The buffet lunch in front of the sea, the smiles of the team and the good vibe will make this day in your heart. Come and enjoy a day of relaxation, fun and natural beauty, on the magical Catalina Island!

Spend 4 hours on a share boat cruise with this excursion from Punta Cana. Relax in comfortable transportation as you make your way from your resort to a private dock. Climb aboard your boat and head to the open waters, where you will see stunning beaches and the incredible coastline of the Dominican Republic. A totally relaxing boat cruise with high volume personalized music with professional and personal guide, then spend time snorkelling on natural coral reefs among tropical fish and stunning underwater landscapes. Enjoy tropical drinks while the island’s music plays in the background. Float past Dolphin Island and the stingray and shark tank before stopping at a natural pool where the Caribbean Sea and Atlantic Ocean meet. Your trip concludes with transportation back to your hote

Join a vibrant 3-hour catamaran booze cruise in Punta Cana, perfect for celebrating Spring Break 2026. Set sail aboard a lively party boat equipped with unlimited premium drinks, including rum, beer, and tropical cocktails. Snorkel in the crystal-clear waters to explore vibrant coral reefs, then relax at a natural pool with a floating bar. This shared experience is ideal for friends and families, creating an unforgettable atmosphere filled with music and fun under the sun. Roundtrip transportation from your hotel is included, making it convenient to enjoy this adventure in paradise. - Duration: 3 hours with hotel pick-up and drop-off included. - Open bar with unlimited premium drinks and snacks provided. - Snorkeling equipment and activities at a natural pool with a floating bar. - Perfect for solo travelers, couples, and small groups looking for a fun-filled day.

Why choose between relaxation, adventure, and nightlife when you can experience all three in one unforgettable day? This unique excursion combines three of Jamaica's most popular experiences into one seamless package. Start by unwinding on a peaceful bamboo raft with a soothing limestone foot massage, then switch gears and enjoy the energy of a catamaran party cruise along Negril's breathtaking coastline. Top it all off at the iconic Rick's Cafe, famous for its cliff divers, lively atmosphere, and world-class sunsets. With round-trip transportation from Montego Bay hotels and Airbnbs included, there's no need to worry about planning, driving, or coordinating multiple tours. It's the perfect way to see more of Jamaica in a single day while creating memories you'll be talking about long after your vacation ends. Relax. Party. Explore. One amazing Jamaican experience.

Looking for a relaxed way to end the day or your trip on Bonaire? Our Sunset Aperitivo is a 3-hour sail along the west coast with drinks, food, and good company. Just sailing, sunset, and the kind of evening you remember. You board at 4:30 PM with our signature drink Limone Spritz (our take on the classic Aperol Spritz) and sail past the Plaza coastline and Klein Bonaire while the sun drops toward the horizon. Throughout the trip we serve three delicious bites including an individually portioned charcuterie board plus an open bar with Prosecco, Aperol, wine, and beer. We dock again at 7:30 PM, in plenty of time for dinner if you want to keep the evening going. Who this is for: Couples and friends who want a sunset experience without it feeling like a party boat Divers and snorkelers who've had their underwater fix and want a relaxed final evening Travelers on their last night who want to send the trip off properly