10 Winter Destinations to Charter a Catamaran

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An Aerial view of Abacos

An aerial view of Abacos

If you want to get your catamaran vacation fix this winter (or next summer) and want a unique experience, consider one of the following 10 destinations. Maybe you’ve only got a week and want to stay close to home. Or perhaps you have loads of time off and don’t mind a long flight. Either way, here are some ideas that will get you to some new cruising grounds that are guaranteed to make your twin-hulled excursion an adventure.

Bahamas, Sea of Abaco

Starting close to home for East Coasters, the Bahamas are an amazing chain of over 700 islands, but the most compact place to cruise (and seemingly the only place to charter) is the Sea of Abaco. The sea, which is like a giant lake, offers protected water no matter what the Atlantic is cooking up outside. Although there are no coral heads, there are coral flats that love to nip at even shallow cat keels.

Don’t miss Man-O-War Cay, a small and tightly knit community with families that have been there since the settlement was established in the 1700s. Visit Albury’s Sail Shop, where handmade canvas bags have been sewn for three generations. Spend a couple of days in Hope Town, a camera-friendly harbor with a 130-year-old candy stripe lighthouse. A trek up the 200-plus steps inside this still-manned, kerosene-fueled beacon is a must-do, if only for the fantastic views from the top. For a cheeseburger in paradise, visit Nippers on Great Guana Cay. The colorful bar has a pool, or you can shoot down to the windward-side beach to catch some waves.

When to Go: The best months to visit are April through June, and again in October through November. Winds are usually 10 to 25 knots.

Charter Companies:

Cruise Abaco; cruiseabaco.com

Tropical Yacht Charters; abacoyachtcharters.com

The Moorings; themoorings.com

Sunsail; sunsail.com

Dream Yacht Charter; dreamyachtcharter.com


With the barrier reef running north-south and the trade winds coming from the east, the sailing conditions are close to perfect in Belize. The snorkeling is phenomenal, and Ambergris Caye is called the “Beautiful Island” for a reason.

Ambergris Caye (originally a fishing village and coconut plantation), as well as the rest of Belize, is protected by the second largest barrier reef in the world, so the sailing is protected. But it’s not just about the sailing. Belizeans love to party, and there are events throughout the year with live bands, contests, karaoke and restaurants of all kinds. You won’t want to miss diving the world famous Blue Hole or snorkeling at Hol Chan Reserve and Shark/Ray Alley. 

Belize remains relatively undiscovered as a sailing location with only two companies offering bareboat charters. At press time, it was also the only country in the Caribbean to require proof of enhanced training and capabilities. You must apply for a temporary certificate of competency, so submit your resume and qualifications early to make sure you’ll be able to charter.

When to Go: It’s best to visit in the dry season, from late November to the middle or end of April. The rainy season runs from June to November.

Charter Companies:

The Moorings; moorings.com

Sunsail; sunsail.com

Come for the parties and stay for the pink sand beaches and sunsets of Antigua

Come for the parties and stay for the pink sand beaches and sunsets of Antigua

Antigua & Barbuda

Come for the parties and stay for the pink sand beaches and sunsets. Antigua is known for its annual race week (April) and nonstop festivities. Great restaurants, interesting historical sites and plentiful rum make Antigua a great winter destination in the Caribbean. Antigua’s western side has dozens of pristine beaches with gently lapping waves. One stretch of foliage-bordered beach that also makes for a great anchorage for cruising and charter boats is Ffryes, where you can while away the day on a beach towel or stop by the Dennis Cocktail Bar for refreshments.

When you’re ready for a break from all the social activity, sail five hours north to the sister island of Barbuda. Nearly undeveloped, Barbuda’s one town, Codrington, is home to most of the island’s 1,500 inhabitants, while Low Bay, on the western coast, offers 11 miles of white and pink beaches and spectacular sunsets. Snorkel with turtles or visit the Frigate Bird Sanctuary, especially if it’s nesting season.

Don’t miss the ruins of the Codrington estate named Highland House, and be sure to climb the 56ft Martello castle and tower, a fortress that was used as a vantage point from which to spot valuable shipwrecks on the outlying reefs.

When to Go: Antigua is a year-round destination. In the winter months it’s crowded with vacationing Brits, but between May and November you’ll still get good weather and the anchorages will be much less crowded.

Charter Companies:

Sunsail; sunsail.com

Dream Yacht Charter; dreamyachtcharter.com

Horizon Yacht Charters; horizonyachtcharters.com

The Grenadines

Farther southeast in the Caribbean, St. Vincent and the Grenadines form one country that stretches along 40 miles in a northeast-southwest direction. The better known of the Windward Isles includes Bequia, Mustique, Canouan, Tobago Cays, Mayreau and Union Islands. However, there are many small spits of sand and one-boat anchorages in between that are idyllic.

The wind is a little stronger, and the waves are a little bigger down here, so a bit of sailing confidence and familiarity with reefing is needed. If you are lucky and the weather is amenable, you may be able to sail both north and south on a beam reach. The rewards for intrepid sailing include snorkeling with turtles in the Tobago Cays, visiting a turtle sanctuary on Bequia and having a cocktail at Janti’s Happy Island bar (a spit built entirely of conch shells) in Clifton Town on Union Island.

The Grenadines have a “boat boy” culture where entrepreneurial men and women come out in skiffs to help you catch a mooring or bring ice and fresh croissants in the morning.

They’re indispensable for island information and assistance, so take care of them with tips and they’ll take care of you with just about everything else.

When to Go: You can sail here year-round, though there’s a slight risk of hurricanes between July and November. Most of them pass north of the Grenadines.

Charter Companies:

Dream Yacht Charter; dreamyachthcarter.com

The Moorings; moorings.com

Horizon Yacht Charters; horizonyachtcharters.com

Sunsail; sunsail.com

America’s largest estuary gets busy in the short summer season

The Chesapeake Bay, America’s largest estuary gets busy in the short summer season

Chesapeake Bay

OK, so Chesapeake Bay in winter won’t be much fun. But America’s largest estuary gets busy in the short summer season, so start thinking this December about making a reservation for next July. Nearly 200 miles long and from three to 30 miles wide, Chesapeake Bay has over 11,000 miles of shoreline, so there’s much to explore. Many shoals require a close eye on the chartplotter, but that’s where cats excel with their shallow draft.

A weeklong charter should include Annapolis, where many charter companies are based, and St. Michaels, which is approximately 25 miles to the southeast. This seaside resort on the Eastern Shore is a must for history buffs, crab lovers and amateur photographers, being the kind of place that never takes a bad picture. Be warned, in the summer, the population of St. Michaels swells beyond its 1,500 residents and getting a guest dock can be like winning the lottery, although you can always anchor out.

Maritime museums abound throughout the bay area, and the outstanding Chesapeake Bay Maritime Museum is world-renowned with its 18 acres of exhibits and restored boats. Don’t miss Solomons Island, a former boatbuilding and seafood-packing town, and Smith Island where you can sample its famous 15-layer cake.

When to Go: May through November. It can get steamy on the bay in July and August, but at either end of the season the sailing is good and the crowds are gone.

Charter Companies:

Cruise Annapolis; cruise-annapolis.com

Annapolis Bay Charters working with Dream Yacht Charters; annapolisbaycharters.net

Sail Away Catamarans; sailawaycatamarans.com

Mexico, La Paz

Strangely, La Paz may be the only place to charter a bareboat catamaran in Mexico. Dream Yacht Charters has a base in Marina Costa Baja, the closest marina to open water and the spectacular Sea of Cortez. The sea is nearly 700 miles long, but your Baja charter will be concentrated in a small area, mostly within 80 miles of La Paz. The island of Espiritu Santo with its coves and beaches is a highlight. Make sure to stop at Los Islotes, the tiny islets at the northern tip of Espiritu Santo that serve as a sea lion rookery.

La Paz is much quieter and very different from Cabo San Lucas, with lots of history as well as a great expat cruiser community that is always ready to share a cerveza and some sea stories. Provisioning opportunities in town are excellent, but nonexistent on the nearby islands, so stock up.

Sailing around Baja is desert cruising at its best, with snug coves, pristine beaches and red-hued mountains. However, the best thing about a Baja charter is the sea life, with dolphins, whales, manta rays and whale sharks in abundance, which is why Jacque Cousteau called the area the Aquarium of the Pacific.

When to Go: December to February can get cold but book for late March or April and you’ll be in heaven.

Charter Companies:

Dream Yacht Charter; dreamyachtcharter.com


For a truly exotic sailing destination, consider the French Society Islands, which are like nowhere else on Earth. Palm trees swaying with the trade winds, white sand beaches, dramatic mountains rising from aquamarine waters—why it must be Tahiti.

Bora Bora is the most developed island of this cruising ground, but that should not keep you away. Mount Otemanu dominates the crystalline lagoon, and the island loves the camera. After a quick stop to provision at the town dock in Vaitape, it’s a 90-minute motor to the backside of the lagoon for the quintessentially Polynesian experience.

Anchor in 10ft to 30ft of calm water behind the protective fringing reef and swing gently to the breeze that keeps things cool and mosquito-free. A terrific drift snorkel is in the coral garden near the southeastern tip of the motu (reef island) chain. Just walk up the beach (with reef shoes) and then drift back to where you started. Along the way, you’ll see eagle rays, turtles and hundreds of clams with iridescent mantles.

Due to the shallow water (and steady winds) sailing cats have become immensely popular here, so it’s easy to get one from the multiple charter companies all based on the island of Raiatea, a 45-minute flight from Papeete.

When to Go: The high season is in winter, from May through October, when temperatures and humidity are lower. From October through April there’s a greater chance of rainfall the wettest months are December and January.

Charter Companies:

Dream Yacht Charter; dreamyachtcharter.com

Tahiti Yacht Charters; tahitiyachtcharter.com

The Moorings; moorings.com

Sunsail; sunsail,com

The Kingdom of Tonga is in the South Pacific between Tahiti and Fiji

The Kingdom of Tonga is in the South Pacific between Tahiti and Fiji


The Kingdom of Tonga is in the South Pacific between Tahiti and Fiji and is made up of 171 islands. The Vava'u island group is the focal point of the beautiful cruising grounds that are only about 15 miles end to end. Like in the British Virgins, the islands here are close together, and the winds are constant (10 to 20 knots) from the southeast, so the sailing is easy.

The protective outer reefs create calm, turquoise water that is perfect for scuba diving. The main town of Neiafu has many resorts and restaurants, so it’s not that remote, but drop the hook at a quiet beach nearby and you can gaze at the same isolated vistas as Captain James Cook when he sailed by in the 1770s.

Tonga is a year-round destination known for its easy conditions and relaxed and friendly locals. Even if you’re relatively new to sailing, you’ll be comfortable in the cruising grounds of this kingdom. Note that charters here do not begin or end on Sunday, so plan your flights accordingly. That said, if you’re going to fly that far, you might as well take an extra day on either end to enjoy this island paradise.

When to Go: Winter runs from June through October, when temperatures are milder, and you’re more likely to get rain between November and March.

Charter Companies:

The Moorings; moorings.com

Sunsail; sunsail.com


If you’re really up for a long flight and want to go where most of your friends have never been, try the Maldives. In the middle of the Indian Ocean, just about at the equator, lie a spectacular archipelago made up of nearly 1,200 coral islets grouped into 26 atolls. This string stretches 500 nautical miles and is made up of the tops of a submerged mountain ridge.

White beaches to port and starboard descend into water that is every imaginable shade of blue and green. The area is becoming popular with surfers, so bring your board—cowabunga, dude.

Tourism is the main driver of the Maldivian economy, so luxury resorts (where the Muslim culture is less evident) abound. The Maldives are your destination if you appreciate natural beauty and phenomenal swimming and snorkeling. Don’t be surprised if you have a superyacht or two sharing the anchorage with you.

When to Go: The rainy monsoon season is June to August, but the winter is the time that diving is fantastic.

Charter Companies:

Dream Yacht Charter; dreamyachtcharter.com

British Virgin Islands (BVIs)

The BVIs are a compact playground that is often the first place anyone dares to charter on their own. Short distances, steady breezes and lots of places to stop to eat, drink and shop, make the BVIs very popular. The anchoring is easy, and the navigation is line-of-sight with only an hour or so between islands.

Two must-dos are the island of Anegada and The Baths on Virgin Gorda. Arrive at The Baths early in the day before it gets crowded, and then swim ashore to explore the caves and tunnels. Bring your reef shoes because the rocks and wooden ladders get slippery. That night, have dinner on Saba Rock across from the Bitter End Yacht Club.

On the horizon, the 11-mile island of Anegada beckons. The island’s 18-mile-long Horseshoe Reef is dramatic, but the entrance into the lagoon is well marked with buoys, so it’s easy to visit this quiet spit of sand, even if just to get away from the BVI party scene. Hook up to a mooring in the lagoon and take a taxi to the windward side to snorkel or have a drink at Cow Wreck Beach. A romantic dinner can be had at Anegada Reef Hotel, but be sure to make reservations, especially if you want one of their big lobsters on the grill.

Charter Companies:

Dream Yacht Charter; dreamyachtcharter.com

The Moorings; moorings.com

Sunsail; sunsail.com

Horizon Yacht Charters; horizonyachtcharters.com

CYOA (out of St. Thomas, USVI); cyoacharters.com

TMM Yacht Charters; sailtmm.com

BVI Yacht Charters; bviyachtcharters.com

Conch Yacht Charters; conchcharters.com 

See more photos for 10 Winter Destinations to Charter a Catamaran, here.

MHS Fall 2016


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