Not long ago I watched as a pair of newlyweds hired my 12-year-old to teach them how to sail. We were on vacation and my two boys had been zipping across the horizon for over an hour and as they sailed the Hobie Cat back onto the sand the newly married couple negotiated a chartered cruise right on the spot. My son, ever the opportunist, jumped aboard, handed them life vests and explained where the couple would sit. He then had his younger brother give them a gentle push off the shore. Just like that, the couple was on a cruise of the warm waters of the Caribbean with their own private skipper.
I don’t recommend getting on a boat with a 12-year-old that you don’t know.
What you should do is get your own sailing certification. ASA 101 gives you the basic knowledge so that when you are sipping mai tais on a secluded beach and you see a boat for rent you will have the confidence to sail it all on your own.
These are five spots where you will encounter the right amount of wind, the right size boat and the perfect place for you to test out the sailing skills that you gained in ASA 101.
Charles River – Boston
Sit alongside the Charles River in the middle of summer and you’ll see the sailboats darting across from the Longfellow bridge up to the Massachusetts Ave bridge. Community Boating located on the south shore just a few steps from the Hatch Memorial Shell rents boats daily. You can choose from 4-person Cape Cod Keel Mercury and 5-person Rhodes 19 sailboats. Rentals are on a first come first served basis and are available to anyone over the age of 18 with prior sailing experience. Candidates are interviewed by the dock master on duty.
When your sailing day is done make sure to take a walk around the Boston Commons, follow the Freedom Trail or just pop into the Cheers Bar for a selfie at the bar, all are within walking distance to the dock.
Southern California
If you like the ease of setting off within the protected waters of a harbor or marina these spots in Southern California make for an easy day of getting on the water and working your ASA 101 skills. Both offer rentals by the hour and they each are located in protected waters that help you stay focused on keeping your sails full. In San Diego, they also offer larger boats for multi-day cruising for the more experienced sailor who has moved into ASA 103 or ASA 104.
Marina Del Rey
When your sailing day is done in Marina Del Rey venture to the nearby Abbot Kinney neighborhood for posh lunch spots and eclectic shopping options. You can’t miss a stroll through the canals of Venice or a walk along the infamous Venice boardwalk.
San Diego
In San Diego, the Gaslamp quarter is home to a bevy of options that range from romantic dinner spots to high energy gastropubs that feature the regions popular craft beer scene. Also within walking distance from the water is San Diego’s Little Italy that boasts patios alive with diners, plenty of pedestrian-friendly piazzas and Waterfront Park where the view of the bay is almost as good as being on the water.
Turks and Caicos
Push off the sand in Grace Bay and you’ll be hard pressed to keep your eye on the horizon as the clarity of the water creates an optical illusion and you’ll feel like you are sailing along in shallow depths. The shades of blue mixed in with the white sand below make for a feast for the eyes. The wind is dependable and with very little current or swells, the Hobie cats in this area can get moving at an exhilarating speed. All along this tourist corridor, you will find small activities shacks that offer up sailboat rentals by the hour. A few hotels on Grace Bay have their own fleet that are free to use for guests of the hotel. This is not uncommon in the Caribbean from the Bahamas to Barbados.
Lake Champlain Vermont
Your visit to Burlington, Vermont will be enhanced with a few hours on the lake sailing a 23’ Sonar across Burlington Bay. Community Sailing Center rents an assortment of boats from entry level dinghies for one to two people up to 23-foot keelboats for up to six sailors. Summer rentals are popular and they take reservations for their keelboats in 2-hour time slots.
When your sailing day is done you’ll have to visit Church Street Marketplace in downtown Burlington. With what seems like an endless supply of food, shopping and entertainment options the marketplace is great for a full day of window shopping and snacking. Craft beer is popular in these parts and of course Ben & Jerry ‘s got their start nearby.
Florida Keys
Sail the calm waters of the Florida Keys and utilize your ASA 101 talents as you embark on an adventure near Key Largo. They even offer a cottage and sail package where you fill your day with unlimited daysailing and end the night in a beachfront cottage. If you wanted to work on your sailing education they are an ASA school as well.
When your sailing day is done explore the Florida Everglades by kayak or by airboat. You can indulge in conch at one of the many restaurants along the overseas highway or watch the sunset from a beach bar with a view of Pelican Key.
