An intentional, intimate sail aboard Phoenix — Vineyard Haven’s restored 44' classic

TISBURY BOAT TOUR FIELD GUIDE

An intentional, intimate sail aboard Phoenix — Vineyard Haven’s restored 44' classic

Private day and sunset charters aboard a beautifully restored classic sloop, tailored to your group and guided by an experienced captain — this guide explains what to expect and how to plan.

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An intentional, intimate sail aboard Phoenix — Vineyard Haven’s restored 44' classic.

Duration
2,3,4,6, and 8 Hour Options
Location
Tisbury
Operator
Sail the Vineyard LLC
Category
Boat Tour
Robert Eric Crews
Founder & Editor, The Adventure Collective
Published Verified

Sail the Vineyard’s Phoenix is a classic, restored 44-foot sloop offering private day and sunset sails out of Vineyard Haven. The operator emphasizes luxurious exclusivity, personalized service with a favored local female captain, and routes that showcase Martha’s Vineyard’s coastline, lighthouses, historic homes and beaches.

Highlights

Outing Highlights

THE BOAT

A restored 44' classic sloop

The original, beautifully restored classic sailboat — Phoenix — is the centerpiece of these private charters, offering a sleek, timeless platform for coastal cruising around Martha’s Vineyard.

THE CREW

Vineyard Haven’s favorite female captain

Trips are led by an experienced local captain who delivers personalized service and local knowledge that shapes each tailored private sail.

THE SAIL

Tailored private excursions

Each private sail is customized for your group, responsive to guest requests while still guided by wind and current to curate an ideal outing.

What the day feels like

How the day unfolds

You board in Vineyard Haven and set out aboard a classic 44-foot sloop for a private sail that can last a few hours or a full day. The operator offers multiple duration options and crafts each voyage around wind and current while honoring guest preferences — whether a relaxed sunset cruise or an extended day exploring the island’s beaches and coastal landmarks.

Suitability

Who it's for

Who this sail suits — and who might look elsewhere.

1
Private groupsIdeal for couples, families or small groups seeking an exclusive, private sailing experience tailored to preferences.
2
Sightseeing enthusiastsA strong match for travelers wanting a coastal perspective on lighthouses, historic homes and Vineyard beaches from the water.
3
Students of sailingGood for guests who want to feel the wind and learn about sailing — guests may participate and observe sailing techniques aboard the classic sloop.
4
Those wanting low-impact relaxationWell suited to travelers who want to unplug, breathe salt air, and enjoy a relaxing, curated time on the water.

Practical planner

Details to review before reserving

Timing & Duration

Private charter durations available in 2-, 3-, 4-, 6- and 8-hour options; departures operate out of Vineyard Haven.

Meeting point

Boarding location: 1 Water St, Vineyard Haven, MA 02568.

Customize your sail

All sails are private and curated for your group; the captain takes guest requests into account while navigating by wind and current.

Booking Notice

Review cancellation policies before reserving.

Frequently asked questions

Planning Your Outing

How long are the sailing options?

Charters are offered in 2-, 3-, 4-, 6- and 8-hour options.

Where do we meet for the sail?

Boarding is at 1 Water St, Vineyard Haven, MA 02568.

Is this a private charter?

Yes — these are private sails tailored exclusively for your group.

Who runs the charters and who is the captain?

The sails operate out of Vineyard Haven with a locally based captain noted as a favorite among island guests.

Can the itinerary be adjusted during the sail?

Yes — while the captain takes guest requests into account, routes are influenced by wind and current and are customized accordingly.