Where We Sail

Caribbean Destinations

Four extraordinary cruising grounds, one boutique fleet. Crews deeply rooted in local culture guide you to the anchorages most people never find.

4Cruising Grounds
22Crewed Yachts
700+Islands & Cays
25+Years Local Expertise
4.9★Guest Rating

Choose Your Horizon

Where Will You Drop Anchor?

From our home base in the US Virgin Islands to the untouched Grenadines, each destination offers its own rhythm. Tap any section below to explore the activities, signature anchorages and insider tips for each.

Home Base

US Virgin Islands

St. Thomas · St. John · St. Croix

Our home waters — easy to reach, effortless to love. Crystal bays, golden sand and the powdery shores of Magens Bay sit minutes from the dock. The perfect first sail.

Best time: Nov – Jul
Sail from: St. Thomas

  • Snorkel the coral reefs of Trunk Bay
  • Paddleboard & kayak calm turquoise coves
  • Sunset cocktails & chef dinner on deck
  • Beach BBQ on a secluded shore
  • Hike the trails of St. John’s national park
  • Dawn swims & sea-turtle spotting

  • Christmas Cove (the pizza boat!)
  • Honeymoon Bay, Water Island
  • Maho Bay, St. John
  • Magens Bay, St. Thomas

  • Best seasonDecember – April for calm seas and sun
  • Getting thereFly into St. Thomas (STT), minutes from the dock
  • Good forFirst-timers — sheltered, beginner-friendly water
  • Travel noteUS territory; no passport for US citizens

The Classic

British Virgin Islands

Tortola · Virgin Gorda · Jost Van Dyke

The world’s most beloved sailing ground, a short hop from our base. Granite boulders at The Baths, legendary beach bars and protected anchorages at every turn.

Best time: Nov – Jul
Sail from: Tortola / USVI

  • Climb the granite grottoes of The Baths
  • Snorkel The Indians & Norman Island caves
  • Painkillers at the Soggy Dollar Bar
  • Scuba dive the wreck of the RMS Rhone
  • Paddleboard sheltered, glassy bays
  • Beach-bar hop to Anegada for lobster

  • The Bight, Norman Island
  • Great Harbour, Jost Van Dyke
  • Cane Garden Bay, Tortola
  • Anegada

  • Best seasonNovember – May
  • Getting thereShort sail or quick ferry from the USVI
  • Good forEasy line-of-sight sailing & beach bars
  • Travel notePassport required (British territory)

Exuma Dreams

The Bahamas

Exumas · Nassau · Eleuthera

Seven hundred islands of impossibly clear water. Swim with the famous pigs of Big Major Cay, dive Thunderball Grotto and drift over sandbars that glow electric blue.

Best time: Nov – Jul
Style: Island-hopping

  • Swim with the famous Exuma pigs
  • Dive the cinematic Thunderball Grotto
  • Snorkel vibrant coral gardens
  • Meet the nurse sharks at Compass Cay
  • Bonefish the shallow flats
  • Stargaze from the deck in zero light pollution

  • Big Major Spot (Pig Beach)
  • Staniel Cay
  • Warderick Wells
  • Shroud Cay

  • Best seasonDecember – April
  • Getting thereFly into Nassau or Staniel Cay
  • Good forAdventurous island-hopping over longer distances
  • Travel notePassport required

Off the Map

The Grenadines

Tobago Cays · Bequia · Mustique

For those who want to sail beyond the crowds. Untouched anchorages, jewel-like islands and barefoot luxury — the Tobago Cays marine park is a snorkeler’s paradise.

Best time: Nov – Jul
Style: Secluded & wild

  • Snorkel the Tobago Cays turtle sanctuary
  • Dive pristine, untouched coral reefs
  • Lobster beach BBQ on a deserted cay
  • Sundowners off glamorous Mustique
  • Kitesurf & paddleboard the steady trades
  • Explore Bequia’s boatbuilding village

  • Tobago Cays
  • Admiralty Bay, Bequia
  • Britannia Bay, Mustique
  • Saltwhistle Bay, Mayreau

  • Best seasonDecember – May
  • Getting thereFly via Barbados to Union Island or Canouan
  • Good forSeclusion, snorkeling and barefoot luxury
  • Travel notePassport required; remote & uncrowded

The Charter Caribe Difference

Sail With People Who Know These Waters

We don’t just charter yachts — we live here. Our captains and crews turn a beautiful itinerary into an unforgettable one.

Local Crews

Captains and chefs who know every hidden cove, the best beach bar, and exactly where the turtles feed at dawn.

Tailored Itineraries

Every voyage is built around you — diving, fine dining, family fun or pure seclusion. Your charter, your way.

Boutique Service

Owner-operated and personal. From first enquiry to final sunset, you’re cared for by a team that takes it personally.

Your Caribbean Awaits

Tell us where you dream of waking up, and we’ll match you with the perfect yacht and crew.

Leigh-Ann

Charter Concierge