Sailing

Sailors know the British Virgin Islands as legendary cruising grounds. Here, in places like Virgin Gorda, Peter’s Island, and Tortola, you’ll find sheltered marinas where you can dock or throw down your anchor, shopping, restaurants, and small hotels that are popular with yachters. Even better, you can sail to these various islands without going outside the reefs into the open ocean. But you won’t have to worry about navigational charts on VOYAGE Charters 7-night night cruise around the BVIs, because a skipper comes with you. Their 44 to 60-foot luxury catamarans, which sleeps 8 to 10 guests in queen or king bedded guest cabins with private bathrooms, also comes with a Chef and liquor to make this the ideal all-inclusive package. The catamarans are perfectly suited for 4 or 5 couples or 2 families since the yacht comes equipped with water toys, like kayaks, a dinghy, water skies, tube, floats, and noodles. The weeklong jaunt starts in Tortola and includes snorkeling with sting rays in the caves of Virgin Gorda, a stop at Cane Garden to listen to the steel band play at Stanley’s, and a night anchored off Norman Island, the treasure island author Robert Louis Stevenson made famous in his book. Cost of the trip starts at $4595 per couple, including meals, a berth onboard, and, of course, transportation.  

South Seas Island Resort on Captiva Island, Florida, (right next door to the better known Sanibel Island) will once again be offering three and five-day Learn to Sail packages for those looking to earn sailing certification while on vacation. Overseen by the renowned Colgate’s Offshore Sailing School, the courses can be taken in a fast-paced three-day curriculum with full eight-hour days or a more relaxed five-day schedule in half-day sessions. We prefer the latter, so you have time to bike through the alligators at Ding Darling National Wildlife Refuge, look for seashells on the spanking white Gulf Coast beaches, and search for manatees in the waters. Rates for the three-day Learn to Sail package start at $1,350 per person including the sailing certification course, resort accommodations, textbooks, Colgate Day Sailing certification, diploma and logbook, based on double occupancy. Courses are open to all skill levels, minimum age seven with adult.

If you truly want to feel like a local on Mount Desert Island, take a day sail on a Friendship Sloop from Northeast or Southwest Harbor. Sail Acadia offers the opportunity to take a 3-hour guided sail on three Friendship Sloops, vessels that were used during the late 1800s to fish for lobsters along the Frenchman Bay shoreline. We sailed on the Helen Brooks, a replica designed with sailing in mind. Under the skilled guidance of Ryan at the wheel and his sidekick Savannah, we motored past the estates lining the Northeast Harbor shores and a seal that popped his head out of the water. Near the lighthouse perched atop Bear Island, Jeff and I helped hoist the sails. Winds were strong. In fact, there was a small craft advisory in effect, so Ryan had already reefed the mainsail and we chose to use only the staysail instead of the stronger jib. Soon we were gliding at a good 5-knot clip past Great Cranberry Island and the many lobstermen picking up their traps. 

One of the most unique opportunities in the Caribbean is the chance to race aboard authentic America’s Cup yachts used in the actual competition. In the three-hour sailing fantasy camp called the Sint Maarten 12 Metre Challenge, you have the rare opportunity to step into Dennis Conner’s soft-soled shoes. After an introductory talk about the history of the America’s Cup, four captains choose teams and off you go to your respective boats. The boats include the winning Stars & Stripes yacht which Connor used in the 1987 America’s Cup in Fremantle, Australia; his back-up, Stars & Stripes ’86; and two Canadian yachts, Canada II and True North IV. Once aboard your boat, the captain designates crew assignments. You could be chosen to be a primary grinder (grinding a winch as fast as possible so that the foresail can change direction), timekeeper, or handler of the mainsheet or rope. Simulating the America’s Cup, you sail against one other yacht around a triangular course, about one-tenth the size of the actual race. Afterwards, you’ve earned your rum punch. 

To celebrate my 50th birthday, my wife, Lisa, set up a glorious day in Portland, Maine—biking along the shoreline, only to be topped by a private sunset sail with family and close friends. Thankfully, the weather was perfect. Norman Patry, owner of Summer Feet Cycling, led my family of 10 along the scenic shoreline of South Portland and Cape Elizabeth to five lighthouses. They included such picturesque gems as Bug Light, the smallest lighthouse in operation in America, and Portland Head Light, painted by the likes of Edward Hopper. Near Portland Head Light, we bought lobster rolls from a food truck and dined overlooking Portland Harbor. The lobster rolls were excellent, chockful of fresh meat, and you could order them Maine-style (with mayo), Connecticut-style (lightly buttered), spiced with curry (loved it) or wasabi. Washed down with locally made Eli’s Blueberry Soda and topped off with ginger molasses cookies from Standard Bakery in town, it was a perfect Portland meal. The ride ended at Kettle Cove, a small beach, just past Two Lights State Park.

This past May, the historic whaling ship, Charles W. Morgan, left Mystic Seaport for the first time in more than 70 years and sailed to several New England ports of call, giving folks from New London to Provincetown an unprecedented opportunity to explore the ship. Built in New Bedford in 1841, the Morgan is the last remaining wooden whaling ship in the world and the oldest merchant ship in America. In its heyday, the Morgan traveled across the globe in search of whales, the source of oil for illumination and lubrication in the 19th and early 20th centuries.

A day of salty air and pulling on ropes can build up an appetite. Fortunately, the Windjammers are known for their hearty meals. And if you’re expecting Navy grub, you’ll be surprised to know that Windjammer food is so cherished that no less than three of the boats have already published their own cookbooks. The Captains source local harvested ingredients and often provide their own produce from home, like flowers, syrup, honey and eggs. Fresh baked breads are cooked in a cast-iron wood stove, with stews and salads another staple of the seafaring diet. 

Aboard an historic schooner sailing the Penobscot Bay islands of Maine’s mid-coast, modernity slows to a more languid pace. Cruising amidst the anonymous pine-topped islands, stopping at the occasional seaside village, you can’t help but relax aboard these yachts of yesteryear. Help hoist the sails, read a good thick book, or partake in an increasingly popular activity aboard a windjammer, photography. Lately, these schooners have been offering specialty cruises that cater to one particular passion.

If you’ve followed me on Twitter @ActiveTravels all week, you’ve learned about some of the specialty cruises. I’ll also be writing an upcoming article for The Boston Globe on the subject. Here is a small sampling of this summer’s offerings. For a full listing, visit the Maine Windjammer Association:

“Heave Ho!” went the cry as all hands pulled down on a thick rope to haul up the mainsail. “Heave Ho!” the crew chanted again and the schooner headed upwind, all sails gleaming white against a cloudless blue sky. The Captain took the wheel as the boat quickly gained momentum passing another anonymous island crowned with pines and rimmed with the ubiquitous Maine granite. Behind us was the vast expanse of the Atlantic, dotted with multi-colored lobster buoys and lined with the only mountains on the coast north of Brazil. The crew were passengers from around America and Europe who delighted in the chance to hoist the sails, bilge the pump, even take a turn at the wheel sailing this big boy.