The Caribbean

A nautical paradise for you to discover

Sailing Holidays in the Caribbean


The beautiful islands in the Caribbean Sea need little introduction to boating enthusiasts around the world - it’s a nautical paradise! Hop aboard one of Sailo’s Caribbean yacht charters, grab your snorkeling gear and get ready to be amazed. If sailing the Virgin Islands is on your bucket list, make sure you plan for a day trip to Virgin Gorda in the BVI’s, or a shopping jaunt in St Thomas, USVI’s. Choose one of our BVI yacht charters and check out the special attractions by boat we recommend in the area: pristine beaches, best snorkeling spots, and the trendiest bars. A weekend on a Bahamas yacht charter with destination Bimini, fishing around Nassau or cruising the Abacos is the perfect idea for those of you who want to try sport fishing, or enjoy shipwreck diving. The newest addition to our offer of sailing holidays in the Caribbean is Cuba - a boating destination waiting to be discovered. No matter what your destination will be - BVI, USVI, Cuba, or the Bahamas - the amazing turquoise waters, white fine sandy beaches and the laid-back atmosphere will transform your holiday into a fantastic experience. Sailo’s Caribbean catamaran charters and carefully selected BVI yacht charters are docked in all major harbors, so all you need to do is browse, choose, book your dream boat in minutes and start packing!

Our Favorite Sailing Itineraries in the Caribbean


  • 1

    BVI Yacht Charters from Tortola

    An Underwater Action Itinerary
    • Day 1

      Tortola

      Stop 1
      • Tortola

        Starting Location

        Start in Tortola to clear customs and pick up everything you might need for the next week sailing. This itinerary is popular and considered by many one of the best sailing holidays in the Caribbean that you can plan for!

    • Day 1-2

      Norman Island

      Stop 2
      • Norman Island

        8 NM from last stop

        Your first stop is the Norman Island. Sail around until you find the perfect spot to jump in the water and to cool off. Drop anchor and enjoy lunch at one of the restaurants on the beach. Most of our BVI yacht charters are equipped with snorkeling gear, perfect to explore the caves of this rocky island. Once you pick one of our Caribbean yacht charters, make sure to check with your boat representative what gear will be available on board for your trip.

    • Day 2-3

      Cooper Island

      Stop 4
      • Cooper Island

        9 NM from last stop

        Cooper Island is the next destination to test your snorkeling gear and capture unforgettable underwater memories for a lifetime. Sea turtles are also frequent visitors to these waters. Off the southwestern coast of the island is located one of the most popular diving spots in the BVI’s - the “Wreck Alley” - with four sunken ships transformed in amazing marine life habitats.

    • Day 3-4

      Salt Island

      Stop 5
      • Salt Island

        2 NM from last stop

        Your snorkeling and scuba adventure on one of our BVI yacht charters continues at Salt Island. The most notable attraction is a big, complete wreck that you can explore underwater.

    • Day 4-5

      Trellis Bay

      Stop 6
      • Trellis Bay

        6 NM from last stop

        Pull into Trellis Bay - home to popular full-moon parties and other exciting nightlife. Trellis Bay Market on the western side of the island is a good spot for fresh provisions. Go for a stroll to check the local art shops and stop for a drink or a nice lunch at the De Loose Mongoose. For a snorkeling afternoon trip, check out the northern side of the cay.

    • Day 5-6

      The Baths

      Stop 7
      • The Baths

        6 NM from last stop

        The Virgin Gorda Baths are an exquisite and unique natural formation. These huge rocks and the surrounding mini coves are great to explore above and underwater, or even climb. Moor your BVI catamaran charter (or yacht if that’s your choice) at the Devil’s Bay Fort Point and spend a great day in water. The nearby Devil's Bay local restaurant/bar is just a short walk away.

    • Day 6-7

      Tortola

      Stop 8
      • Tortola

        10 NM from last stop

        Your trip loops back around to the origin city of Tortola. Get reacquainted with dry land around the town before heading back home. We hope this itinerary will make one of your best sailing holidays in the Caribbean on one of Sailo’s BVI yacht charters!

    2

    Sailing the Virgin Islands

    9 Days Itinerary from St Thomas, BVIs
    • Day 1

      St. Thomas

      Stop 1
      • St. Thomas

        Starting Port

        Come a few days early (or save time at the end of your trip) to visit the beautiful island of St. Thomas. Gather all your supplies for the next week of sailing on your USVI catamaran charter through the charming Virgin Islands.

    • Day 1-2

      Christmas Cove, Great St. James

      Stop 2
      • Christmas Cove, Great St. James

        6 NM from last port

        The turquoise waters at Christmas Cove are perfect for an afternoon swim and snorkel post short sail from St. Thomas. The calm waters of this protected cove are a National Marine Sanctuary where you will see lots of fish, sea turtles, and friendly stingrays. This location is perfect for overnights on any of our Caribbean yacht charters.

    • Day 2-3

      Caneel Bay, St. Johns

      Stop 3
      • Caneel Bay, St. Johns

        4 NM from last port

        Drop anchor on your USVI catamaran charter and visit the Caneel Bay Resort, which was built on the site of an 18th century sugar plantation. Bring our your inner "foodie" and visit the Beach Terrace for buffet-style offerings. Feel free to walk the grounds of this luxury beach resort while enjoying the sparkling lights of St. Thomas on the distant horizon, before heading back to your private yacht.

    • Day 3-4

      Jost Van Dyke

      Stop 4
      • Jost Van Dyke

        6.5 NM from last port

        Jost Van Dyke is one of the finest among the Caribbean beaches with its lively bars, comfortable hammocks, and strangers that will be your best friend by the day's end! After a day spent on the beach sipping rum cocktails, Foxy's Tamarind Bar and Grill is a favorite of boating enthusiasts enjoying their time on Sailo’s BVI yacht charters. Enjoy their great local food, Friday and Saturday barbecues, flying fish sandwiches, grilled fresh fish, and lobster for dinner.

    • Day 4-5

      Marina Cay

      Stop 5
      • Marina Cay

        16 NM from last port

        Green Cay is an exciting dive and snorkel site which has a series of pinnacles covered with brightly colored sponges and branching hydroid that shelter and abundant marine life. From the stunning coral beach you can walk to a small shipwreck of a more modern-looking boat. Before arriving on one of our BVI yacht charters at Marina Cay for the night, make one last stop at Sandy Cay, a picture-perfect little gem in the ocean, surrounded by white sandy beaches speckled with clusters of rock, green vegetation, and two lonely coconut palms. Tourists from all over the world come here on their Caribbean yacht charters to enjoy sunbathing, excellent snorkeling, and picnics with a view.
        Marina Cay, your stop for the night, is a flower-covered eight-acre island ringed by a powdery white sandy beach and sheltered by a lagoon with calm and warm waters. Enjoy a mellow night on the deck of your USVI catamaran charter with drinks and a dinner on board.

    • Day 5-6

      Spanish Town, Virgin Gorda

      Stop 6
      • Spanish Town, Virgin Gorda

        5 NM from last port

        Moor your boat and explore the famous Baths, with the scenic boulders and the caves open to the sea. Enjoy the day snorkeling or diving the Wreck of the Rhone, famous from the movie "The Deep". Spanish Town is the perfect overnight stop for all sailing holidays in the Caribbean that include Virgin Gorda island, offering plenty of options for shopping and dining around the harbor.

    • Day 6-7

      North Sound, Virgin Gorda

      Stop 7
      • North Sound, Virgin Gorda

        6 NM from last port

        Dog Islands are a small group of islets in the Sir Francis Drake Channel. They are part of BVI’s Marine National Park and Seabird Refuge making them great diving and snorkeling spots. After an activity-packed day, visit The Bitter End Yacht Club and dine at the Clubhouse Steak and Seafood Grille, a casual, yet elegant restaurant located right on the water.

    • Day 7-8

      Norman Island

      Stop 8
      • Norman Island

        20 NM from last port

        On your way to Norman Island stop at Peter Island and explore one of the most beautiful beaches in the Caribbean: Deadman's Bay. It’s a great snorkeling spot and also a good option for a fresh lunch right on the beach. If you're looking for a quiet stretch of sand, take a walk to the secluded Honeymoon Beach at the tip of the peninsula. Once you drop anchor on one of Sailo’s BVI yacht charters at Norman Island (your overnight stop), try snorkeling around the 3 water-level caves at the base of cliffs. At the end of the day you can enjoy a casual dinner and a fun happy hour at the famous floating bar and restaurant Willie T’s.

    • Day 8

      St. Thomas, USVI

      Stop 9
      • St. Thomas, USVI

        19 NM from last port

        Your final destination is the delightful Frenchtown in St. Thomas. Boating enthusiasts sharing memories from their sailing holidays in the Caribbean recommend this small quaint town as home to some really great casual restaurants. Here you will make lots of friends as the bar is always filled with a crowd of very friendly folks. A perfect dining experience to conclude the perfect vacation on a Sailo USVI catamaran charter!

    3

    Sailing Holidays in the Caribbeans - Bahamas

    Abaco Islands Itinerary
    • Day 1

      Hope Town

      Stop 1
      • Hope Town

        Starting Point

        Get on board on one of our Caribbean yacht charters in Hope Town, home to a rare, old lighthouse - one of only three kerosene-powered lights in the world, and all three are in the Bahamas.

    • Day 1-2

      Man-O-War Cay

      Stop 2
      • Man-O-War Cay

        6 NM from last port

        Man-O-War Cay is known to sailors as the boat-building capital of the Bahamas. Although the quiet island is often overlooked by the organized sailing tours, we recommend it as one of the places you can really feel like “the only people in the world”.

    • Day 3

      Green Turtle Cay

      Stop 3
      • Green Turtle Cay

        20 NM from last port

        Green Turtle Cay is one of the most beautiful of the Abaco Islands, known for some of the most beautiful beaches in the Bahamas. It’s also a great starting point for deep-sea fishing, snorkeling or scuba diving adventures.

    • Day 4

      Little Harbour

      Stop 4
      • Little Harbour

        15 NM from last port

        Head south to the end of the Sea of Abaco to stop by at Little Harbor. Once you made it into the small and protected port, moor your boat at Pete’s Pub beach bar and stop by for a fresh lunch and some of the best rum drinks around. If you chose one of our Caribbean yacht charters with a dinghy, now it’s a good moment to use it! Take a ride to the rocks and visit the caves and the old lighthouse ruins.

    • Day 5

      Great Guana Cay

      Stop 5
      • Great Guana Cay

        19 NM from last port

        Great Guana Cay is one of the small island close to main island of Abaco, popular in our sailing community for offering something for every taste: a romantic retreat, a laid-back retreat, or a vacation packed with fun activities for the whole family. Check out the white and pink sand beaches and the calm, crystal clear waters on the Atlantic side.

    • Day 6

      New Plymouth

      Stop 6
      • New Plymouth

        12 NM from last port

        Going back to the Green Turtle Cay, your next stop is New Plymouth - a quaint and brightly colored picturesque village that preserves a typical New England architecture. Enjoy the national drink "Goombay Smash" at Miss Emily's or wander about and explore the area.

    • Day 7

      Treasure Cay

      Stop 7
      • Treasure Cay

        6 NM from last port

        Your last stop on your way back to Hope Town is Treasure Cay, famous for its 3.5 miles of powdery white sand spectacular beach. Relax while taking in the stunning tropical scenery, go paddle boarding or snorkeling the sparkling turquoise waters.

    • Day 7

      Hope Town

      Ending point
      • Hope Town

        20 NM from last port

        After a relax stop at Treasure Kay, set sail in the afternoon for your last 20 NM back to Hope Town.We hope you had a great nautical adventure on one of Sailo’s Caribbean yacht charters. Looking forward to welcoming you soon on one of our boats around the world!

    4

    Island Hopping from Road Town, Tortola

    7 Days Itinerary in the BVIs
    • Day 1

      ROAD TOWN

      Stop 1
      • Tortola

        Starting point

        Choose one of Sailo’s Caribbean yacht charters in Tortola and set sail for fun and relaxed trip, hitting all the prime spots in the British Virgin Islands.

    • Day 1-2

      NORMAN ISLAND

      Stop 2
      • NORMAN ISLAND

        8 NM from the last port

        Start your adventure on one of our BVI yacht charters on Norman Island, an uninhabited rocky island, considered by some one of the hidden gems of the British Virgin Islands. Time to grab your snorkeling gear and explore the bountiful marine life or swim in the spectacular coastal caves.

    • Day 2

      COOPER ISLAND

      Stop 3
      • COOPER ISLAND

        8 NM from the last port

        Then you will visit the Virgin Gorda. Here there is opportunity both for Hiking and beach views. If you want to try both, you can hike along the boulders that end on a beautiful white sand beach.

    • Day 3-4

      VIRGIN GORDA

      Stop 4
      • VIRGIN GORDA

        16 NM from the last port

        A must on your to do list when sailing on one of our BVI yacht charters is a stop at Virgin Gorda. Go for a hike along the boulders or relax on the picture-perfect, white sand beach.

    • Day 5

      JOST VAN DYKE

      Stop 5
      • JOST VAN DYKE

        20 NM from the last port

        On your way to Jost Van Dyke make a stop to visit Guana Island - famous for the seven different white powdery beaches. Go snorkeling the reefs, relax in a hammock, or set up your own private picnic on land. And if you are in the mood for a walk, explore the tropical forest. Then set sail to the smallest of the four BV Islands - Jost Van Dyke - the perfect stop with an overnight to join the happy, laid-back crowd at the Soggy Dollar Bar or at Foxy’s. Drop anchor in White Bay and don’t miss your chance to try one of the signature rum cocktails at Foxy’s!

    • Day 6

      CANE GARDEN BAY

      Stop 6
      • CANE GARDEN BAY

        6 NM from the last port

        Don’t miss your chance to stop and enjoy the Sandy Cay - a deserted island with a fantastic beach where you can relax and take in the breathtaking tropical view. Drop anchor and go for a swim or grab your snorkeling gear and explore the crystal clear Caribbean waters. After lunch, set sail to Cane Garden Bay on Tortola for your overnight anchorage.

    • Day 7

      ROAD TOWN

      Stop 7
      • ROAD TOWN

        15 NM from last port

        Head back to Road Town Tortola for the end of your journey. We hope you had an amazing time on one of our BVI yacht charters and we hope to see you soon back on the water!

    5

    British Virgin Island - Sailing Holidays in the Caribbean

    6 Days Itinerary from Road Town
    • DAY 1

      ROAD TOWN

      STOP 1
      • ROAD TOWN

        Starting point

        Get aboard on one of Sailo’s BVI yacht charters in Road Town and start your tropical nautical adventure!

    • DAY 2

      NORMAN ISLAND

      STOP 2
      • NORMAN ISLAND

        8 NM from the last port

        Set sail to your next stop at Bight Bay (formerly known as Man of War Bay). This sheltered inlet is perfect for your first overnight. Explore Norman’s island water level caves and go snorkeling in the crystal blue water.

    • DAY 3

      PETER ISLAND

      STOP 3
      • PETER ISLAND

        3 NM from the last port

        Your next stop - Peter Island - is famous for some of the best beaches in the British Virgin Islands. Drop anchor at Little Harbour: a quiet spot usually not so crowded. White Bay and Key Bay are the best anchorage spots on the south shore. Hop off and try the local Caribbean cuisine.

    • DAY 4

      SALT ISLAND AND COOPER ISLAND

      STOP 4
      • SALT ISLAND AND COOPER ISLAND

        3 NM from the last port

        Spend the day exploring these two little charming islands. Salt is famous for the Wreck of the Rhone and the surrounding reefs - a spectacular snorkeling and diving spot. Cooper island has a protected anchorage, picture-perfect white sandy beaches and some of the best snorkeling sites in the BVIs (tip: try the crystal clear waters around Cistern point).

    • DAY 5

      VIRGIN GORDA

      STOP 5
      • VIRGIN GORDA

        6 NM from the last port

        Your voyage on one of our Caribbean yacht charters must include a stop at the famous Baths. Indulge in the natural jacuzzis and go hiking the beachside boulders for an amazing view of the bay waters.

    • DAY 6

      NORTH SOUND

      STOP 6
      • NORTH SOUND

        2 NM from the last port

        North Sound is a cluster of small islands off the northern tip of Virgin Gorda. Take advantage of the protected anchorage and the calm waters to try out watersports. A fun way to check the area is to glide the turquoise waters on a hobie cat! For a gourmand dinner with a fantastic view, make a reservation at the gorgeous and secluded Biras Creek resort (dress code required).

    • DAY 7

      ROAD TOWN

      Ending point
      • ROAD TOWN

        15 nm from last port

        Head back to the home port carrying wonderful memories of your sail on one of BVI yacht charters from Sailo!


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