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Flotilla Adventures

Looking for a new way to enjoy a charter sailing vacation with friends and family? Join SAIL on a Flotilla Adventure in the British Virgin Islands, where a SAIL host will guide you through a week of fun and relaxation with new friends. Traveling aboard a fleet of Sunsail charter boats out of Tortola, we’ll explore BVI hot spots, visiting old favorites and discovering new

Looking for a new way to enjoy a charter sailing vacation with friends and family? Join SAIL on a Flotilla Adventure in the British Virgin Islands, where a SAIL host will guide you through a week of fun and relaxation with new friends. Traveling aboard a fleet of Sunsail charter boats out of Tortola, we’ll explore BVI hot spots, visiting old favorites and discovering new surprises. With SAIL as your host, you’ll spend less time planning the itinerary and more time enjoying the scenery.

Our next Flotilla Adventure sets sail December 9, with host Chris Museler aboard. Join Chris for a week of hands-on sailing, windsurfing, diving, stand up paddling, kayaking and snorkeling. We'll host a regatta around the Dogs, dinghy races at the Bitter End Yacht Club, and much more. Space is limited, so sign up soon.

Before you go, here are the FAQs:

What’s a flotilla?

A charter flotilla is a unique type of sailing vacation in which eight to ten boats sail together for one week. We all follow the same itinerary, but boats are free to sail at their own pace, coming and going as they please. Each evening, we gather for a briefing of the next day’s activities and a chance to socialize with the rest of the group.



Who can participate?

Flotillas are open to charter groups of any size and experience level. Rookie skippers will enjoy the safety of following a Sunsail lead boat, while experienced skippers will benefit from the knowledge and expertise of the SAIL host and Sunsail crew. All sailors, regardless of age and experience, will enjoy the camaraderie of new sailing friends in the relaxed environment of the islands.

What will the Adventure Watersports Flotilla be like?

This December, SAIL’s Adventure Water Sports Flotilla will be the ideal winter vacation for charter guests seeking a thrill and a challenge. Picture sipping cocktails at anchor with your new sailing friends as you recount the days' activities: kayaking through the Baths, scuba diving on the Wreck of the Rhone, snorkeling at the Indians and racing around the Dogs. The itinerary will allow for plenty of quality time aboard your own boat as well as opportunities to socialize with other like-minded charter guests. It’s a winter vacation you will not soon forget.



What’s the role of the SAIL host?

SAIL’s host Chris Museler will work with the Sunsail lead crew to ensure you have a plethora of charter knowledge at your fingertips. Chris is a multiple national and international sailing championship winner and a former professional bowman on ocean racing yachts. Between his racing expertise and Sunsail's charter knowledge, you'll have a wealth of knowledge to tap into. They will make sure your boat and crew are safe and happy throughout the week. They’ll also keep your crew entertained with daily activities ranging from windsurf trips to cocktail hours, big boat regattas to Pirate Parties.



Where do I sign up?

To learn more about the trip and to reserve your boat today, visit sunsail.com/sail.

Still not sure if a flotilla’s for you?

Neither was SAIL’s editor Peter Nielsen. But one flotilla with his family was enough to convince him, and it soon became a beloved Nielsen family tradition. Check out his experience here.

What’s on the itinerary?

Friday, December 9: Gather at Sunsail’s Tortola base to get settled on your boat and enjoy the Caribbean’s premier yacht charter resort.

Saturday, December 10: Sail to the Caves for top-notch snorkeling before setting off for The Bight on Norman Island. That evening, gather at the Willy T for a Pirate Party and to learn the Rules of Engagement for the week’s Treasure Hunt.

Sunday, December 11: Sail to the Baths for a day of scrambling on the rocks, hiking to Devil’s Bay and snorkeling in the surrounding crystal waters. That evening, sail to Marina Cay to shop at the Pusser’s store, then gather on the beach for a group dinner.

Monday, December 12: In the morning, join Sail Caribbean Divers for a lesson in Scuba diving in Marina Cay (min age 10). In the afternoon, sail to the Dogs for snorkeling and windsurfing before making your way to Virgin Gorda Yacht Harbour, a short walk to Spanish Town. After tonight’s briefing, throw it down for family-style dining in town.

Tuesday, December 13: Participate in an all-flotilla regatta up and around the Dogs before embarking on a quick sail to the Bitter End Yacht Club. Spend the day racing aboard the Club’s dinghies, windsurfers, Hobie Cats and Standup paddleboards. That evening, gather for dinner and dancing at the Yacht Club’s Jamaican Barbecue.

Wednesday, December 14: Sail a pleasant 21 miles downwind to Cane Garden Bay, a gorgeous white-sand beach known for its terrific nightlife. Here you’ll find great food, plentiful bars and awesome live music.

Thursday, December 15: Spend your final day in paradise sailing leisurely back to base. Consider a stop at Deadman’s Bay on Peter Island with excellent swimming, beachfront hammocks and ice-cold beverages, but be sure to make it back in time for the Treasure Hunt prize-giving ceremony and wrap-up party.

Friday, December 18: Swap notes with your new friends, enjoy a last swim at the Mariner Inn pool or a pre-journey spa treatment and start planning for next year!

To learn more about the trip and to reserve your boat today, visit sunsail.com/sail.

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