Top Travel Days of 2020, Sailing to Anse La Roche on the Island of Carriacou
South of St. Lucia and west of Barbados, St. Vincent and the Grenadines are known as the world’s best cruising grounds. With a prevailing northeasterly trade wind, you can sail at a good 9 to 10 knot clip, zipping through the swells while watching the fly fish take flight. But what makes this 100-mile sail from St. Vincent to Grenada so enjoyable are the anchorages, wondrous sheltered bays ridged by the hillside and lined with often desolate crescent sand beaches. These are the sights Lisa and I, friends Amy and Josh, and our highly competent 24-year-old Captain Bry, would savor on our weeklong joint in early February. We chartered the 48-foot Andiamo Piano from Horizon Yacht Charters out of St. Vincent, the same outfitter we used two years prior when sailing the British Virgin Islands.
This is the Caribbean of yore, where you anchor and then go snorkeling with turtles near the shoreline or with the multi-colored fish at one of the most pristine reefs in this part of the world. If terra firma calls your name, you can simply swim over to the beach and walk in the sand, practically deserted except for the lone fishermen sewing his nets. At twilight, you zodiac over to the requisite beachside bar and restaurant, dig your feet in the sand, and have a stiff rum punch spiced with local nutmeg, before dining on freshly caught lobster, conch, and red snapper.
We had many memorable meals on this trip, but my favorite dinner was at Anse la Roche Bay on the Grenada island of Carriacou. After another day of fantastic sailing, we dined barefoot in the sand on a sublime stretch of secluded beach lit up by torches. We devoured our last grilled lobster of the trip and ended the night with the chef’s special potion, a shot of homemade liquor that burned my throat called “Under the Counter.” It’s no surprise that Forbes chose our trip as one of the best bucket list trips in the world.
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.
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 
South Seas Island Resort
Maine’s 2,500-mile stretch of granite coast is custom-made for sailing. No other sport gives you the freedom to anchor in a pristine cove, hike on an anonymous island, and sleep with seals by your window. Some 2,000-plus pine-studded islands, more than in the Caribbean or Polynesian archipelago, welcome sailors from around the globe. If you’re feeling a wee bit intimidated to tackle the sport in these salty waters, take a refresher course at 
Don’t fret. While still under the beastly spell of winter here in New England,