Bareboating 101: Set a course for sailing adventure
A live-aboard sailing vacation offers unmatched appeal. Craft your own itinerary, explore remote islands and spend quiet mornings at anchor with nothing more pressing than choosing the next island to visit.
But it does come with a notable prerequisite: Someone onboard must know how to operate a sailboat. Charter companies require candidates to fill out a sailing résumé, which will help determine what type of boat they can manage.
"Anyone who likes to boat and is comfortable operating boats themselves will enjoy bareboating," says Melody Delgado of Virgin Island Sailing. "Basically, to qualify, you have to have experience operating a similar powered vessel."
Those with borderline experience or lacking confidence in their ability can hire a captain for the first day to get acclimated to the vessel and its systems, and get a refresher in managing a boat. Some charter rentals include a captain for up to four hours.
Those with no experience at all can hire a captain for the entire charter for an additional $180-$250 a day, plus room, board and gratuity. Some companies accommodate the sailor wannabe with various levels of sailing classes that cover everything from the rudiments of operating a vessel to offshore, "bluewater" sailing.
"In choosing a type of boat, it depends on how many people are in your charter," says Beth Weinstein of The Moorings, a leading charter company. "For couples or families, catamarans have more spacious berths, more en-suite baths and more living space below and on deck to enjoy."
Monohull sailboats have been the workhorses in traditional charter fleets, but catamarans have had a surge in popularity. Multihulls now make up about 35% of wordwide charter fleets.
But for the traditionalist and the adventurous who don't mind life on the tilt, monohulls still win the day.
"Adventurers should choose a large monohull," Weinstein says, "to get that feeling of slicing through the water and bringing out their inner sailor."
Weinstein cautions that everyone coming along should share the same expectations and the overall plan for accommodations, activities and, especially, the sailing destination.
"I think it's good to choose a destination you really want to see at the end of the day," Weinstein says. "It's the experience you are paying for."
Cathy Parsons of Medford, Ore., who has chartered in the Abacos, British Virgin Islands, Grenada and Tahiti, agrees. "For us, the first thing we look at is if we can get there easily," Parsons says. "We don't want to spend three or four days on a plane."
Parsons looks for areas that have many islands close together for easy island-hopping. She also identifies an ancillary benefit to sailing: "It's a chance to get the kids away from the electronics and get some rich family time."
We've rounded up a trio of sailing regions perfect for a bareboat vacation.
British Virgin Islands
The British Virgin Islands, or BVIs, are perennially the No. 1 bareboat destination, because they offer the trifecta for inexperienced sailors: protected waters, a moderate climate with consistent winds, and a variety of islands clustered tightly together.
"It's an easy sailing destination," Delgado says. "Even fairly new sailors can sail there. It's all line-of-sight navigation. You're always in sight of land."
The mountainous archipelago, a string of more than 60 islands, provides enough contrast to satisfy even the most diverse crew. You can spend one night anchored off a remote, unpopulated island and the next in a sprawling mooring field with bustling restaurants and beach bars just a dinghy ride away.
Jost Van Dyke's bay, one of the most popular stops, could grace any vacation brochure with its brilliant white beach, shockingly turquoise water and walk-up beach bars complete with hammocks swaying beneath palm trees.
At Virgin Gorda, one of the larger islands, you can sport your best resortwear at the Bitter End Yacht Club on the North Sound, accessible only by boat. Or, on the southern end, you can anchor near the Baths, where you can take endless and enviable selfies among the supersized boulders.
Florida Keys
For the first-time bareboater who wants turquoise water and teeming reefs without the hassle of international travel, the Florida Keys at the southernmost tip of the state are a convenient option. You can charter in Miami near the top of the island chain, or in Key West at the southwest end. The shallow inside waters are perfect for tiptoeing between tiny islands and discovering your own secret spots — keeping a wary eye on the depth sounder. Or, the more adventurous can make open-ocean jaunts between inlets — keeping a wary eye on the weather. Either way, you're likely to be greeted by dolphins, the cheerful welcoming committee on every sail along the Florida Keys.
The storied stretch of islands is long on variety. Before reaching the Keys, sailors can enjoy ostentatious South Beach and the hunting (and haunting) houses of Stiltsville in Biscayne Bay en route to Key Largo, Islamorada and the deserted islands of the Dry Tortugas. The brilliantly clear turquoise water and crisp breezes will make you forget you're still in the continental USA.
If your skills and the weather permit, you can charter in Key West and head for the Dry Tortugas, a group of seven islands just 64 nautical miles west of Key West. The main island, now a national park, is home to Fort Jefferson, abandoned by the military in 1888. Unique birds populate the islands, and offshore, coral reefs teem with sea turtles and tropical fish.
San Juan Islands
For the more experienced sailor, the San Juan Islands in Washington meet all the requirements for bareboating: protected waters, lots of islands close to one another and plenty of opportunity for adventure.
Designated as a National Monument by President Obama in 2013, the San Juans are a diverse archipelago of more than 450 islands in the northern reaches of the Puget Sound. Sandwiched between Vancouver Island on the west and mainland Washington on the east, the San Juans showcase the diverse beauty of the Pacific Northwest and are home to a diverse array of wildlife, such as the black-tail deer, otter, mink, rare birds and a butterfly once thought to be extinct. The waters are rich with marine mammals, including majestic orcas and playful seals and porpoises — all with the backdrop of mountain peaks in the distance.
Though the San Juans are only 100 miles north of Seattle, they get an average 247 days of sun in a year and less than half the rainfall of Seattle. The Olympic Mountains and Vancouver Island form a "rain shadow" that protects the islands, making it warmer and drier than the surrounding area and earning it the nickname Banana Belt of the Pacific Northwest. Chartering is typically favorable from May through October.
Although every foray onto the water should be approached with caution, cruising the San Juans requires some extra vigilance. Strong currents, submerged rocks and occasional fog demand extra skills from mariners and skillful use of instruments and charts.
Before you sail
• Check cruise ship routes and schedules so you can plan your itinerary to avoid the crowds.
• Download nautical navigation and GPS apps to your tablet or phone to map your route and get familiar with the waters before you sail.
• For several couples chartering together, consider renting an additional dinghy so everyone can move about more independently.
• Investigate costs of transportation from the airport to the boat. Some charter companies provide free transportation depending on your arrival time.
• Ask about reduced fees for staying onboard your boat the night before your charter begins. Staying aboard is usually less expensive than putting up the crew at a hotel.
• Get a nautical guide to your destination, which will serve as a reference for sightseeing and offer advice on anchorages, sea states and hazards in the area.
PRICES
Cost estimates for seven-day charters in three areas. Prices vary by season and boat type. Provisioning estimates do not include alcohol.
British Virgin Islands
Boat (41-foot monohull for seven days, high season)
Three-cabin, two-head monohull: $4,700
Taxes and fees: $89
Insurance: $399
Extra night/early check-in: $505
Total boat rental: $5,693
Food
Split provisioning, $29 per person per day, breakfast and lunch and half of dinners: $812
Dinners out, three nights with average $30 per person: $500
Welcome provisions for first evening snacks, including wine and beer, and continental breakfast (optional and not applicable without early check-in): $85
Total food: $1,397
Transportation (in addition to round-trip airfare to St. Thomas)
$100 round-trip per person taxis and ferry from St. Thomas: $400
$15 per person departure tax for ferry passengers: $60
Total transportation: $460
Mooring
$20 per night, optional three nights: $60
Total mooring: $60
Grand total: $7,610 ($1,902.50 per person, seven days' room and board)
San Juan Islands (Anacortes)
Boat (39-foot monohull for seven days, high season)
Three-cabin, two-head monohull: $3,540
Insurance: $480
Washington sales tax: $326.40
Extra night/early check-in: $200
Dinghy outboard, $15/day: $105
Total boat rental: $4,651.40
Food
Essentials kit (condiments, paper goods, cleaning supplies, charcoal, etc.): $110
$38 per person per day full meals four days: $608
$28 per person per day three days: $336
Dinners out, three nights with average $30 per person: $500
Total food: $1,554
Transportation (in addition to round-trip airfare to Sea-Tac airport)
$68/per person round-trip transport from Seattle Airport to charter marina (with advance reservation): $272
Total transportation: $272
Grand total: $6,477.40 ($1,619.35 per person room and board, seven days)
Key West
Boat (41-foot monohull for seven days, high season)
Two-cabin, two-head monohull: $4,400
Taxes and fees: $330
Insurance: $350
Extra night/early check-in: $350
Total boat rental: $5,430
Food
$38 per person per day full meals four days: $608
$28 per person per day three days: $336
Dinners out, three nights with average $30 per person: $500
Total food: $1,444
Transportation (in addition to round-trip airfare to Key West)
Taxi $7 per person each way from airport: $66
Total transportation: $66
Mooring
Two nights at $22 per night in Marathon: $44
Total mooring: $44
Grand total: $6,984 ($1,746 per person room and board, seven days)