Sail-Away Adventures in Paradise

Four scenic island destinations that are perfect for sailboat charters


Imagine leaving it all behind and setting sail for a tropical island paradise. There, you’d anchor in a remote cove and spend your days swimming over coral reefs, walking deserted beaches and feasting on fresh seafood. This doesn’t have to be a daydream. Not when you book a charter boat vacation.

At some of the world’s most scenic islands, it’s possible to rent a well- equipped sailboat and set your own course for adventure. And don’t worry if you and your crew aren’t seasoned mariners, because these same charter companies can supply a captain to show you the ropes, or become your personal guide for the duration of the voyage. Here are four premier destinations in the Pacific and Indian Oceans where dreams of sailing away can become reality.


These are islands that inspired the artwork of Gauguin, and seduced the crew of the Bounty. Today, the Islands of Tahiti welcome sailing crews, who come to anchor in turquoise lagoons, walk unspoiled beaches and swim over bright coral reefs. Sailing adventures typically begin on the island of Raiatea, which is part of the Leeward group of islands that lies some 100 miles to the west of the big island of Tahiti. This cluster of tall, green islands includes Bora Bora, with it’s world famous lagoon, the quieter sister islands of Tahaa and Raiatea, and the garden island of Huahine. Each offers something different, from traditional villages and coconut groves to world- class resorts and spas. Because these islands are all within an easy day’s sailing of each other, a charter boat crew can island hop, anchoring in a different bay or lagoon each night. Warm, steady trades blow year round, creating easy sailing conditions that will have even new skippers soon feeling like old salts.

Tahiti Sailing

The Tahitian island of Raiatea is the nautical center of French Polynesia. The main town of Uturoa is home to a number of sailboat and yacht charter companies. Photo: Grégoire Le Bacon/Tahiti Tourisme


A thousand miles east of Africa, the remote islands of the Seychelles were known to ancient mariners from Phoenicia, Polynesia, China and the Arab world. Today, only the savviest of sailors know of this magical cruising destination, but the word is getting out. The Seychelles group is hundreds of small, low-lying islands scattered across thousands of miles of ocean. But the star attractions are the larger Inner Islands, which are geological wonders of twisted granite, mountainous and lush with tropical forests that support species of birds found nowhere else on Earth. From the capital island of Mahé, crews can make an easy day sail to a cluster of small islands to the east, where they will find bays fringed by ivory-white sands and clusters of monolithic granite boulders that are an iconic symbol of the Seychelles. Ashore, the islands offer a rich commingling of French, British, Indian, Middle Eastern, and African cultures.

Seychelles Bay

Sailboats ride at anchor in the south bay of the Port Launay Marine Park in the central Seychells. These islands offer dozens of calm coves for overnight stays. Photo: Seychelles Tourism Board


The Kingdom of Tonga is best known for whales. Each year, humpbacks migrate from the Antarctic waters to mate, breed and birth in the warm waters that surround these remote islands, creating a unique opportunity for humans to swim with these 50-foot mammals. That alone would be reason enough to visit these remote and unspoiled islands, but there’s more. In the center of the Tonga archipelago, the Vava’u group of islands provide the ideal sailing conditions that make these waters one of the most appealing cruising grounds in the South Pacific. The green-clad islands sit in close proximity to each other, are ringed in protective coral reefs, and are graced with steady trade winds. Skippers can glide over calm waters, navigating from island to island by sight, with more than 40 calm anchorages to choose from. These same reefs offer exceptional snorkeling and diving in some of the world’s clearest waters, and there are miles of deserted beaches to explore.

Tonga Sailing

A sailboat glides past a small island in Tonga’s Vava’u group. Calm waters, close harbors and steady winds make this region ideal for sailing vacations. Photo: Tourism Tonga


Not many people know of the Phi Phi Islands by name, but most will instantly recognize them by sight. These limestone towers, which rise precipitously from the waters of the Andaman Sea, have served as backdrops for feature films, and have graced thousands of magazine covers and travel brochures. These and the other hundred-plus islands that surround Thailand’s vacation mecca of Phuket are far from unknown, but sailors who charter their own vessels have the advantage over those who come by tour boat. Within the sheltered waters of Phang Nga Bay, there are numerous bays and anchorages on uninhabited islands that aren’t on the main sight seeing routes. The prime sailing season runs from November through April, as cooler, drier northern winds create ideal conditions for relaxing island-hopping passages. Crews can choose to spend nights in quiet coves, or stop in more populous harbors to enjoy shore leave that comes with the warm hospitality that the Thai people are known for.

Thailand Phi Phi Islands

Sailors can explore the dramatic landscapes of Thailand’s Phi Phi Islands, where towering limestone cliffs surround calm bays ringed in white sand beaches. Photo: Flickr