Picking your boat is one thing; picking your destination is quite another. Luckily, there’s little chance you’ll go wrong with two of our most popular itineraries. From breathtaking beaches and gorgeous coral reefs to shopping, golfing, and nightlife—sailing the Caribbean on a chartered yacht is the best way to travel!

Flying into St. Vincent and cruising through the Grenadines down to Union Island is one of our most popular itineraries. Flying into Union Island and cruising down to Grenada is another.

St. Vincent and the Grenadines

St Vincent and the Grenadines

Five small, uninhabited islands that make up The Tobago Cays are a must-see for diving and snorkeling enthusiasts

After flying into St Vincent, you’ll take a quick taxi to Young Island Cut, where you’ll meet up with your chartered yacht and begin your sailing voyage. From Bequia to Mustique, Canouan, Mayreau, and the Tobago Cays to Palm Island and Union Island, this is one island-hopping adventure you’ll never forget!

Bequia – an hour’s sail from base

The largest of the Grenadines, this lovely island is a haven for natural exploration, maritime buffs, shopping, and mingling with local sailors. Drop anchor in Bequia and explore one of the 28 dive sites. Catch a glimpse at ghostly shipwrecks and exotic fish; visit the whaling museum and learn about the island’s maritime history; or take a trip to the turtle refuge farm and fall in love with some of nature’s slowest charmers.

Mustique – around two hour’s sail from Bequia

Celebrity spotters take note: this privately-owned island is the playground of the rich and famous. With such noted visitors as Tommy Hilfiger, you never know who you might run into. With no traffic lights, beach vendors, or power lines, sail to Mustique for quiet relaxation on gorgeous beaches, tennis in paradise, and upscale parties—the island is tailor-made for the discerning traveler.

Canouan – about a three hour sail from Mustique

Home to one of the longest barrier reefs, and three major resorts, laid-back Canouan is a great place to snorkel, hike, hit the casino, or just soak up rays on the white sand beaches. Anchor your yacht in one of Canouan’s two beautiful bays, take in the views, and get in a round of golf at one of the best golf courses in the world.

Mayreau – approximately one hour’s sail from Canouan

The smallest inhabited island of the Grenadines, this wee outpost is home to around 300 people and spans just 1.5 miles. You won’t find much hustle and bustle here—just incredible beaches, an abundance of fishermen, and a charming hilltop stone church that offers stunning views of neighboring islands. Visit the salt pond or dock your yacht in Saline Bay, where you can snorkel or dive the wreck of a World War 1 gunboat.

The Tobago Cays – half an hour’s sail from Mayreau

The five small, uninhabited islands that make up The Tobago Cays are a must-see for diving and snorkeling enthusiasts. Much of the Tobago Cays Marine Park is encompassed here and you’ll soon know why if you sail into The Tobago Cays. Sea turtle nesting sites, pristine coral reefs, lobsters, and iguanas are just some of the wonders you’ll see. Hike the trails of James Bay, Petit Bateau and Petit Rameau for amazing views and close encounters with birds and iguanas, or trek to Petit Trabac to see where they filmed “Pirates of the Caribbean: The Black Pearl.”

Palm Island and Union Island

Tiny Palm Island is a great place to dock your yacht for a few hours. Enjoy waterfront dining at one of the resort’s two open-air restaurants, stop in for a massage, or go for a stroll along the island’s five lovely beaches.

Just a quick sail away is the much larger Union Island, a hot-spot for culture and nightlife, with no shortage of great bars and Caribbean restaurants. It seems like there’s always something happening on Union Island—visitors who arrive during Easter Holy Week, late May’s “Maroon” celebration or during one of two major sailing regattas are sure to be treated to a taste of Caribbean culture. But don’t worry—if you sail into Union Island any other time, there’s still an abundance of fun to be had. From turtle watching to shopping, dancing, and diving, Union Island is a gem.