Your Floating Home for the Week

Step aboard a spacious 50-foot luxury catamaran designed for comfortable island living, with generous outdoor spaces, a shaded cockpit, room to relax on the bow, and private cabins with ensuite bathrooms.

Unpack once and wake up somewhere new throughout the week. One morning might begin with a swim in a quiet anchorage; another could end at a lively beach bar with a Painkiller in hand.

The boat becomes more than transportation—it’s our home, gathering place, and front-row seat to the British Virgin Islands.

Life Aboard

Mornings begin with breakfast aboard and a relaxed conversation about the day ahead.

Our itinerary stays flexible depending on weather, wind, and what the group is enjoying. We may sail to another island, stop in a beautiful bay for swimming and snorkeling, explore ashore, or stay a little longer somewhere we love.

Lunch is prepared aboard, while evenings may include dinner on the boat or a visit to one of the BVI’s waterfront restaurants and beach bars.

There’s a rhythm to the week, but never a rushed schedule.

Food & Island Flavors

Breakfasts, lunches, and some dinners are prepared aboard by our cook, with fresh, casual meals suited to life on the water.

We’ll also go ashore to enjoy local restaurants, beach bars, fresh seafood, conch fritters, and perhaps a classic BVI Painkiller at sunset.

Island-Hopping Highlights

Depending on weather and sailing conditions, possible stops include:

Cooper Island • Jost Van Dyke • Virgin Gorda • Norman Island & Pirates Bight • Bitter End Yacht Club • Saba Rock • Cane Garden Bay

Swim, Snorkel or Simply Relax

Enjoy daily opportunities to swim and snorkel, along with floats, water toys, and a paddleboard aboard.

Snorkel a reef, paddle around a peaceful bay, float beside the boat—or find a shady spot with a book and enjoy doing absolutely nothing.

Other than sailing with us from island to island, everything else is optional. This is your vacation.

Come Solo, as a Couple or With a Friend

Solo travelers are especially welcome, along with couples and friends.

Many Joyride guests arrive not knowing anyone else aboard. Sailing, sharing meals, exploring islands, and spending time together makes conversation come naturally—and strangers often leave as friends.

No sailing experience is needed. Bring a sense of curiosity, flexibility, and a willingness to embrace life aboard.

Your Captain & Host

Captain Joy Sherman is a USCG-licensed 100-ton Master Captain and has hosted sailing vacations throughout the Caribbean, Mediterranean, Europe, and beyond.

Joyride Charters has been creating sailing experiences since 2004.

Captain Joy handles the sailing, itinerary, logistics, and life aboard so you can relax and enjoy the islands.

This isn’t a large cruise or an anonymous cabin charter.

It’s a personally hosted, small-group sailing adventure—and an unforgettable way to experience the BVI.