TISBURY BOAT TOUR FIELD GUIDE
Weeklong Liveaboard with Captain Wendy — Private Yacht Voyages from Tisbury to the World
A private, multi-day liveaboard sailing experience from Tisbury with a captain‑guided, customizable itinerary for you and up to 10 guests.
Weeklong Liveaboard with Captain Wendy — Private Yacht Voyages from Tisbury to the World.
Set sail from Tisbury aboard your private vessel with Captain Wendy and Sail the Vineyard LLC, living aboard for multiple days as you move between harbors, secluded coves and waterfront towns; the trip is designed to be personalized around your preferences and sailed with groups of up to ten people.
Highlights
Outing Highlights
Arrive where others cannot — private anchorages and hidden coves
Escape the crowds by arriving under sail and anchoring in quiet coves and hidden beaches, places accessed only by smaller yachts where mornings open to nothing but sea and sky.
A slower rhythm — days set by wind, water and sunset cocktails
Life aboard softens schedules: swim off the transom, dine under the stars, and spend warm days and cool nights moving with the wind — the very pleasures guests say they dream of when picturing a week living aboard.
Fully tailored voyages — your captain plans the details
Every journey is intentionally curated: your captain will help design the itinerary, assist with provisioning, arrange excursions and plan dining so the voyage matches the balance of adventure and relaxation you want.
What the day feels like
What It Feels Like to Live Aboard
This is more than a vacation — it is a life at sea for several days, where each morning can begin with coffee on deck and each evening end beneath a sky full of stars; whether island hopping, snorkeling, or simply drifting at anchor, the trip unfolds at the pace of wind and water and is curated by your captain to match your desires.
Suitability
Who it's for
Who thrives on this trip — and who should consider alternatives.
Practical planner
Details to review before reserving
Provisioning and trip provisioning can be arranged with your captain; the operator assists with provisioning so food and drink needs can be planned ahead of embarkation.
The captain and operator assist with provisioning and dining plans as part of itinerary preparation to ensure meals and excursions match your preferences.
Itineraries are curated and customized with your captain — discuss destinations, excursions and provisioning options in advance so the voyage reflects your priorities.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
Where do trips depart?
Trips depart from Tisbury, Massachusetts.
How long is a typical trip?
These are multi‑day liveaboard experiences — many guests describe spending a week living aboard as the ideal format.
How many people can join a charter?
Charters accommodate private groups of up to 10 guests.
Can the itinerary be customized?
Yes — itineraries are customized and curated with your captain to create the vacation you want.
Who operates the trips and who will be the captain?
The operator is Sail the Vineyard LLC and the advertised trips sail with Captain Wendy at the helm.