Crewed Yacht Charters

Sailing Itinerary

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14 Night Itinerary

After the morning at our base doing your boat check out briefings and provisioning, head across the Sir Frances Drake Channel to Norman Island, where you can spend the night in the Bight. In the late afternoon take your dinghy around Treasure Point to snorkel at the Caves. Eat ashore at Pirates Bight restaurant that evening, then on to the Willy T for drinks.

Snorkel Sites

  • The Caves

Restaurants & Bars

  • Willy T
  • Pirates

Things to do

  • Hiking Trails on Norman

Set out early and take your boat over to the Indians for a morning snorkel. Then enjoy an upwind sail to Cooper Island, stopping to snorkel at the Wreck of the RMS Rhone, located off Salt Island. Arrive at Machioneel Bay early afternoon to pick up an overnight mooring ball. Once moored, sit back, relax with sundowners on board enjoying the beautiful sunset or head ashore for happy hour drinks and dinner at the Cooper Island Beach Club.

Snorkel Sites

  • The Indians
  • Wreck of RMS Rhone
  • Cistern Point

Restaurants & Bars

  • Cooper Island Beach Club

Things to do

  • Kayaking
  • Stand Up Paddle Boarding

A day to completely relax and unwind enjoying everything that Cooper Island has to offer from the fresh pastries in the coffee shop, the beach amenities, the rum bar and the wonderful sunsets. Set off on your paddle board or kayak to explore the bay. Zip over to Cistern Point on your dinghy to snorkel with the turtles! Or simply relax and unwind on the beach with a craft beer of your choice.

Into scuba? Cooper Island offers scuba experiences for every level – discover underwater gardens, vibrant reefs, shipwrecks and much more!

Snorkel Sites

  • Cistern Point

Restaurants & Bars

  • Cooper Island Beach Club

Things to do

  • Kayaking
  • Stand Up Paddle Boarding
  • Turtle spotting at Cistern Point
  • Diving

Leaving Cooper Island set a course to the Baths on the southern end of Virgin Gorda. Pick up a National Parks mooring ball then swim into the beach to begin the trail through the boulders to Devils Bay. Spend the morning exploring the tunnels, caves and crystal-clear pools through these ancient boulders. Feeling hungry? Head over to the Top of the Baths for spectacular views and a dip in the cool, freshwater pool.

Once you have had you fill, head back to your boat and begin your way up to the North Sound.  Spend the night on an overnight mooring or indulge on dock space with shore power.

Snorkel Sites

  • The Baths

Restaurants & Bars

  • Top of the Baths

You have woken up the amazing North Sound, a mecca for watersports, from flyboarding to jet skiing and snuba! Not into watersports, don’t worry - Leverick Bay boasts a spa, a fresh water pool, a restaurant and beach bar and two boutiques.

Fancy a land adventure? Organise a taxi or hire a car to explore the Gorda Peak Natural Park – one of the last remaining Caribbean dry forest in the region and the home to the world’s smallest lizard! Follow the trail that leads to the look-out tower and be rewarded with a panoramic view of the North Sound.

Hungry? Head to Hog’s Heaven restaurant where you will marvel at the 360-degree view of the islands upto Anegada. Sunset in this location is spectacular, enjoy dinner with the lights of the islands twinkling in the distance.

Snorkel Sites

  • Eustatia Reef

Restaurants & Bars

  • Leverick Bay Restaurant
  • Hogs Heaven

Things to do

  • Watersports
  • Hiking
  • Hire a car

From the Gorda Sound, depart in the morning for the 12 NM mile passage to the Setting Point harbor on Anegada – the only coral island in the Virgin Island’s volcanic chain. Enjoy the evening exploring the beautiful white beaches. And need we say – it must be Anegada Lobster for dinner! Once night falls enjoy a beach stroll under a canopy of bright stars.

Snorkel Sites

  • Loblolly Bay
  • Cow Wreck Bay
  • Horseshoe Reef

Restaurants & Bars

  • The Wonky Dog
  • Neptunes Treasure

Enjoy a taxi tour or rent a scooter to explore the island’s best beaches, Cow Wreck and Loblolly. Take an afternoon eco tour to see the salt ponds, home of a flock of pink flamingos. Also keeping a look out for the islands protected giant iguana.

Anegada is a haven for snorkelers and scuba divers – explore the reef’s mazes, tunnels and drops, rich in stunning marine life! History buffs check out the native Arawak’s ancient conch mounds in the East End or explore the numerous wreckages of galleons and privateers.

Snorkel Sites

  • Cow Wreck

Restaurants & Bars

  • Big Bamboo
  • Anegada Beach Club

Things to do

  • Rent a Scooter
  • Eco-tour
  • Snorkel and diving

Sail from Anegada to Marina Cay, a tiny island off the east end of Tortola. On your way, stop at the Dogs, three small national park islands for lunch and a snorkel or dive. After lunch, head down to the well protected anchorage of Marina Cay. Great spot for an overnight mooring with amazing snorkeling all around.

Need some TLC, head to Scrub Island to luxuriate in the Mariott Resort’s spa, three restaurants and freshwater pool.

Snorkel Sites

  • Dogs

Restaurants & Bars

  • Scrub Island Resort

Enjoy a relaxing morning snorkeling at Marina Cay and Diamond Reef, in the afternoon head over to Trellis Bay on the east end of Tortola. Feel the bohemian vibes at Aragorn’s Art Studio. Have an early dinner and cocktails at the Market at Trellis Bay, the jerk ribs are delicious!

Check your dates… it might be Full Moon and time to party!

Snorkel Sites

  • Marina Cay
  • Diamond Reef

Restaurants & Bars

  • Jeremy’s Kitchen
  • Trellis Bay Market
  • Marche at Trellis Sushi
  • Scrub Island Resort

Cruise down the north shore of Tortola, keeping a look out for dolphins on your way to Cane Garden Bay. If you have time, stop at Monkey Point on Guana Island for some great snorkeling on the way! CGB is the home of much of the BVI’s favourite night life. Enjoy the local scene and dance the night away.

Restaurants & Bars

  • Pusser’s at Myett’s
  • Quito’s
  • Paradise Club
  • Elm’s

Things to do

  • Beach
  • Watersports
  • Tree Top Zipline
  • Callwood Rum Distillery

Head over to Diamond Cay on Jost Van Dyke to pick up an overnight mooring ball. After a spot of lunch at Foxy Taboo’s, hit the trail that leads to the Bubbly Pool – a natural jacuzzi!

Don’t miss Sandy Spit – a perfect white beach in the middle of the blue Caribbean sea  complete with palm trees.

Spoilt for choice – head to Sandy Cay for great snorkeling, palm lined beaches, nature trails and loads of sea birds.

Snorkel Sites

  • Sandy Cay
  • Sandy Spit

Restaurants & Bars

  • Foxy’s Taboo
  • B-Line Bar

A day to explore JVD! After breakfast motor sail around to Great Harbour. This is the home to Foxy’s. Pick up your overnight mooring, then jump in the dinghy and head around the point into White Bay. Enjoy a ‘Painkiller’ (or two) at the Soggy Dollar Bar before heading back round to Great Harbour for dinner. Foxy is well known for his live music and BBQs on the weekends which makes for a great stop for all the family.

Restaurants & Bars

  • Foxy’s
  • Corsair’s
  • Soggy Dollar
  • Hendo’s Hideout
  • Ivan’s Stress Free Bar

Spend a leisurely morning exploring Great Harbour on Jost Van Dyke, before setting out for your short sail to Soper’s Hole on the Western End of Tortola. A great pit stop for water, ice and fuel. Don’t miss out an inventive Indian-Caribbean fusion food at Omar’s and a browse at the Arawak Boutique for that perfect souvenir.

Restaurants & Bars

  • Pusser’s
  • Omar’s

Things to do

  • Shopping at Soper’s Hole

From Soper’s Hole set out for a great upwind sail to Deadman’s Bay on Peter Island. Enjoy this white sand beach before climbing the trail up to view the islands from above. Motor round to Great Harbour for a night under the stars. Great Harbour is ideal for your last night as it is quiet, picturesque and only a short sail back to base in the morning. Dine at the bar and restaurant on the beach called Oceans Seven Yacht Club.

Snorkel Sites

  • Deadman’s Bay
  • Great Harbour

Restaurants & Bars

  • Oceans Seven Yacht Club

Enjoy your last sail as you come back across the Sir Frances Drake Channel into Road Harbour. Arrive mid- morning so that you have plenty of time to make your afternoon flight or ferry back over to St. Thomas. Don’t forget to stop in and buy your Conch Charters T-shirt!