An intentional, intimate sailing experience aboard our original 44' vessel
Set sail from Vineyard Haven aboard Phoenix, a restored 44' classic for private day or sunset charters. Small groups, a local female captain, and customizable routes across Holmes Hole and Vineyard Sound make this a hands-on, scenic island experience.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2–8 hours
Fitness Level
Light: able to step on/off a dock, handle short stairs, and tolerate mild boat motion.
Wildlife
History
Vineyard Haven (Tisbury) has long served as a working harbor and ferry gateway to Martha’s Vineyard, shaping local maritime craft traditions.
Conservation
Respect shorebird nesting zones and anchor only in designated areas; minimize wake near shallow habitats and follow leave-no-trace principles while ashore.
Sail the Vineyard LLC
An intentional, intimate sailing experience aboard our original 44' vessel
Sail the Vineyard LLC is a Tisbury, Massachusetts–based sailing company offering a curated collection of public and private nautical experiences around Martha’s Vineyard and beyond.
The company operates the classic boat Phoenix for public sunset sails, brunch cruises, themed events and private day or sunset charters, and also provides private liveaboard sailing vacations to worldwide destinations for groups of up to 10 guests. Signature experiences include a crowd-free Martha’s Vineyard 4th of July Sail from Vineyard Haven to Edgartown with anchoring near the fireworks barge for front-row views; a Phoenix Public Sunset Sail highlighting vibrant island sunsets; a Grand Illumination Fireworks Event sail into Vineyard Sound for a community celebration; and a Phoenix JAWS-Themed Sail spotlighting the film’s local filming sites.
Every sailing experience emphasizes personalized service, local knowledge and safety. The Phoenix sails with a skilled female captain who provides narrated island insights, attentive guest care and optional catering for private charters. Liveaboard vacations pair a private vessel and captain for customizable itineraries to exotic ports, combining onboard comfort with expert seamanship. Reservations are available for scheduled public sails and for bespoke private charters, making these sea-based experiences accessible for couples, families and friend groups visiting Martha’s Vineyard.
Public sails, themed events and private charters together create a wide range of options for visitors seeking scenic cruises, memorable celebrations and small-group maritime adventures on and off the island.
Location
Tisbury, MA
Home base on Martha’s Vineyard
Vessels
Phoenix + private
Classic boat and private liveaboards
Tours Offered
7 trips
Public sails and private charters
Events
Fireworks & themed sails
Fourth of July and Grand Illumination
Book public seats on the Phoenix or request a private charter or liveaboard vacation with Sail the Vineyard LLC for an unforgettable island experience.
Dress in layers
Even summer evenings can be cool and windy on deck; bring a windproof layer and a warm mid-layer.
Bring motion-sickness remedies
If you’re prone to seasickness, take preventative medicine or bring ginger; conditions can change quickly offshore.
Book sunset slots early
Sunset sails are popular—reserve in advance for weekend summer dates to secure the best departure times.
Protect your gear
Use a polarizing filter and secure camera straps; spray and sunlight can be harsh on lenses and electronics.
Windproof jacket
Blocks spray and the evening breeze—critical for comfort during sunset sails.
summer
Non-slip deck shoes
Protects your feet and improves traction on wet wood or fiberglass surfaces.
Polarizing camera filter
Reduces glare and deepens skies for better coastal photos.
Seasickness remedy
Helps ensure a comfortable trip if you’re sensitive to boat motion.