Locals call it “The Vineyard,” and once you’ve been on island, you may not want to leave. The sunsets are stunning, the beaches pristine and the handmade wooden sailboats hold a long-standing special place in history on this magical triangle-shaped island. If you can drag yourself away from the mesmerizing maritime history, you'll find that the brightly painted gingerbread cottages, lighthouses at sunset, and magical Flying Horses of America’s first carousel will give you a more than fair shot at the vacation of a lifetime. The celebrity sightings might have you thinking it’s all glitz and glam, but the low-key towns of Vineyard Haven and Menemsha, along with the must-have Black Dog souvenir sweatshirt, offer a casual vacation vibe to visitors. Sail away with us - everyone deserves a slice of a Vineyard vacation.
Phoenix is a 44-foot Classic Islander sailboat. She has a narrow beam vessel with sleek lines. The ever-popular Bob Johnson-designed Islanders, later bought and renamed Island Packets, are known for being well-built, sea-kindly and fast. They are considered by many to be the ideal coastal cruiser.
M.S. Resolute offers two raised stern seats and two comfortable bench seats in the cockpit, as well as plenty of deck space seating. For a more adventurous ride, relax near the mast and feel the rush of the wind and waves as our vessel slides through the water.
Sail away for a few hours or an afternoon. Kick back with a cold drink and work on your tan or take the helm and find your inner Captain Jack Sparrow. Either way, you'll enjoy one of the best days on the island.
Don’t miss the opportunity to sail on a truly classic yacht.
Captain Wendy Lea holds a USCG Master Mariner’s License, sails over 3000 nautical ocean miles annually, and is the only American Sailing Association (ASA)-certified sailing instructor on The Vineyard. She is certified in First Aid, CPR, STCW (which includes Basic Firefighting, Personal Safety & Social Responsibility, Personal Survival Techniques) and as Officer in Charge of Navigational Watch aboard Vessels of 500 or more gross tons. She holds a current certification to teach basic sailing, coastal cruising, bareboat chartering and catamaran sailing as well as 6 certifications from the ASA including Basic Keelboat, Basic Coastal Cruising, Bareboat Chartering, Coastal Navigation, Advanced Coastal Cruising, and Catamaran Cruising. She has sailed the waters of the Pacific Coast from Los Angeles to San Diego as well as thousands of miles along the Atlantic Coast, the inland and offshore waters of the Texas Gulf Coast, the Gulf of Mexico from Florida to Cuba, the East Coast waters surrounding Martha’s Vineyard, and the Caribbean waters in and around Grenada, The Grenadines, the US and British Virgin Islands, and Antigua.
Captain Wendy is a PADI Advanced Open Water SCUBA diver and enjoys beaches, sunsets, photography and music. She holds a Bachelor of Arts degree in Journalism & Photography and offers freelance services in promotional marketing materials as well as marketing copywriting and blogging. She is a member and former Board of Directors officer for the National Women's Sailing Association. She enjoys using her skills and knowledge to help women advance in the sport of sailing.
We are a unique all female sailing team! We hire female crew from all of over the world to bring you a memorable sailing experience. All of our crew are experts in customer service and have been trained by Captain Wendy to flawlessly handle the art of harnessing the wind to make S/V Phoenix perform at her best.
We'll reopen on May 26, 2023. Use our "Book Now" button to reserve your sail for our 2023 sailing season.