When people discover I’m a licensed charter skipper, the first question is almost always, “Where’s the best place to go?” There’s no single answer—everyone wants something different from a bareboat charter—but I enjoy sharing lesser-known destinations that consistently deliver exceptional cruising experiences. The places below have secluded coves, memorable anchorages and unique local flavor that elevate a sailing vacation. Reputable charter operators such as Dream Yacht Charters, The Moorings, Sunsail and Navigare Yachting run fleets of monohulls and catamarans (both sail and power) in many of these regions. These spots tend to be quieter than the British Virgin Islands or the Bahamas, so if you have solid boat-handling skills and an appetite for adventure, you’ll be rewarded with an unforgettable charter.
Tobago Cays & Union Island, Grenadines
The Grenadines stretch along a crescent of Windward Isles in the Caribbean. A practical starting point for many charters is Grenada to the south, which offers better flight connections and more bases than St. Vincent. After clearing in at Union Island, pick up a mooring near Clifton and take a dinghy out to Janti’s Happy Island—a tiny, hand-built isle of conch shells that can only be reached from the water. If a front brings rough seas, shelter in Chatham Bay and try Shark Attack restaurant, famous for its bold slogans and hearty local fare.
Just north of Union are the Tobago Cays, a protected Marine National Park where a horseshoe reef shelters calm anchorage and superb snorkeling. Scenes from the Pirates of the Caribbean films were shot here, and you can snorkel with sea turtles off Baradel Island, haggle for T-shirts with local boat boys, and enjoy a beach barbecue under simple lights. The fresh grilled lobster and local beers are a highlight—bring insect repellent for the evenings.
Pakelni Otoci & Vis Island, Croatia
Croatia’s popularity has grown, but some island groups still feel local and unspoiled. From Hvar’s hilltop fort you can spot Pakleni Otoci (Hell’s Islands), a string of islets favored by Croatian yachties. On Sveti Klement a small cove offers moorings and, by reservation, a chance to dine at The Fisherman’s House—a family-run restaurant set in a charming backyard atmosphere.
Further south, the island of Vis holds wartime tunnels and other remnants of its strategic past. Guided tours reveal passages that once served military purposes and remain electrified. Nearby on Hvar’s western tip is Tito’s submarine tunnel, a striking Cold War relic that evokes cinematic intrigue. Natural wonders include Biševo’s Modra Špilja (Blue Cave) near Vis: you must join a local guide to enter through a narrow opening, and on bright days the cave’s interior glows with an otherworldly blue light.
Expect a colorful local scene—sampling plum brandy and watching fellow sailors’ morning routines are part of the island charm.
Placencia, Belize
Placencia on Belize’s Caribbean coast is an off-the-beaten-path charter base reached by a short flight or a scenic road transfer from Belize City. Skippers must obtain a Belize Port Authority Temporary Certificate of Competency and review local guidance before departure because the area features very shallow waters and abundant coral heads. Keep an eye on charts and the depth sounder while also looking over the side—local knowledge is invaluable here.
Ray Caye is a highlight for its excellent restaurant and protected preserve; snorkeling requires a guide since it’s a national park. Anchoring near local fishing boats is a memorable experience—watch sharks, remoras and giant rays gather when fish are cleaned. The Pelican Cays offer an even more remote option: a family-run beach restaurant living off the grid, where a little WiFi and genuine hospitality make for a cozy stopover.
Sea of Cortez, Mexico
The Sea of Cortez, between Baja California and the Mexican mainland, is often called an underwater paradise. La Paz is a convenient charter base for exploring Isla Espíritu Santo and Partida, part of a UNESCO biosphere reserve. Los Islotes, a narrow channel between rock formations, hosts a lively sea lion rookery—anchor nearby and dinghy in to snorkel with these curious animals, taking care around territorial males.
Beachcombing and desert landscapes make the coastline unique: walk among dried cactus that resemble petrified wood, or explore the mangrove-lined Bahia Amortajada at the southern end of Isla San José by dinghy. For a memorable final night, anchor at La Balandra Cove to swim with bat rays and watch a spectacular mountain-backed sunset. With generally mild conditions outside the coldest winter months and the late hurricane season, the Sea of Cortez offers dramatic scenery and brilliant night skies.
Cyclades Islands, Greece
The Cyclades, south of Athens, deliver classic Greek island scenery and lively sailing conditions. Each island has its own character—expect different landscapes, architecture and coastal features. Navigation can be challenging because places often have multiple spellings and local names, so careful planning and clear charts are essential.
Milos is a standout: follow the early-morning route that local day-boat captains use to find secluded spots like the Sikia cave, a dramatic topless grotto accessed by dinghy, and Kleftiko, with its folded cliffs and sea caves. On the return to the mainland, stop at Paros and hop the short ferry to Antiparos to visit a deep, ancient cave—descending its long stairway rewards you with striking formations and a true sense of discovery. Local tavernas and small wellness spots add to the Greek island charm.
Tahaa and Bora Bora, Tahiti
Charters in French Polynesia typically operate from Raiatea, a short flight from Tahiti. Shallow-draft catamarans are ideal here, allowing easy access across fringing reefs and motus. The shared reef between Raiatea and Tahaa offers protected anchorages and spectacular sunsets behind Bora Bora. Dinghy to motus for drift snorkeling among clams and colorful reef life—bring reef shoes for walking over broken coral and a loaf of fresh French bread if you want to entice the fish.
Bora Bora still has secret corners despite its popularity. Enter through Teavanui Pass, cruise past Vaitape and anchor in the quieter western lagoon for early-morning snorkeling—giant manta rays sometimes feed in the channels at dawn. Huahine is another gem: slightly further and often less visited, it rewards sailors with vivid watercolors and a relaxed local pace.
December 2024