Sailing charter weather questions are the ones we hear most, so here is the short answer: if conditions make sailing unsafe, your captains make the call and we reschedule your charter, or you receive a full refund if a new time does not work for your trip. A gray morning or a passing shower does not automatically mean a cancelled sail, and we stay in touch with you as your date approaches.
How we make the sailing charter weather call
Capt. Mason and Capt. Lynne sail these waters all season and make every weather decision themselves. We look at the forecast for wind, sea state, visibility, and thunderstorms, and we watch how the day is actually developing.
New England weather changes quickly, and forecasts for the island are rarely reliable more than two or three days out. We watch the forecast closely in the days before your charter and stay in touch with you by phone or text. When the forecast shifts, we would rather move your start time than cancel early on a shaky forecast, so staying flexible on timing gives you the best chance to sail.
Our rule of thumb is simple: if we would not be willing to take our own mothers out sailing that day, then we are going to aim to reschedule or cancel. Period.
What happens if the weather turns
- Unsafe conditions: we reschedule your charter, or you receive a full refund if a new time does not fit your trip.
- Changed forecast: we may suggest a different start time, departure point, or itinerary so you can still get out on the water.
- Rain but safe: we will talk it through with you. Some guests love a moody, quiet sail; others would rather move the date.
Plan B: a sheltered sail on the lake or lagoon
Sometimes, depending on the weather, we offer a different itinerary instead of cancelling: a sail in a much more protected body of water, such as Lake Tashmoo or Lagoon Pond. These sheltered waters have nowhere near the wind and waves that Vineyard Sound can have on the same day.
Many of our guests are happy to have the chance to still get out on the water. Some enjoy the view and have a party aboard, anchored in a safe, calm spot. Others prefer a limited amount of sailing inside the protected water. Either way, the day is still yours, and we will talk through the options with you.
Rescheduling: what to expect
We always try to reschedule first, but we cannot guarantee the same type of time slot. If rain rules out your sunset sail, we may be able to offer the morning of that day or the next morning rather than another sunset. That is why, when guests ask which day to book, we suggest a date earlier in their stay: it leaves room to reschedule later in the trip if the weather does not cooperate.
What if your ferry is cancelled?
If the Steamship Authority cancels your ferry, call us as soon as you know. If we can move your charter to a later slot the same day or another day, we will. If the weather is bad enough to cancel the ferry, it is often bad enough that we would be cancelling too, in which case we reschedule or you receive a full refund.
What if someone gets seasick?
Most guests are fine. If someone does feel unwell, we can steady the boat by reducing sail or motoring, head for a sheltered harbor, or return to port. If you are prone to motion sickness, tell your captains beforehand so we can build a bail-out plan or a calmer-seas route into your itinerary, and take your preferred remedy before boarding, not after.
Our cancellation policy in brief
If you cancel 14 or more days before your charter, you receive a full refund. Cancelling inside 14 days forfeits 50% of the charter fee, and if we rebook your time slot with another party, that amount is returned to you. See our FAQ for the full policy.
Tips for sailing charter weather days
- Book your charter early in your trip, so there is room to reschedule later if needed.
- Stay flexible on your start time; a few hours can make the difference between a rough sail and a beautiful one.
- Keep your phone handy in the days before your charter and on the day, so we can reach you with any changes.
- Bring a light waterproof layer; it is always cooler on the water.
Ready to plan your sail? See our charters and rates or check availability.
Frequently asked questions (selected from our full FAQ)
These questions are selected from our full FAQ.
How far ahead will we know if the weather will affect our charter?
New England forecasts, especially on the island, are rarely reliable more than two or three days out. We watch the forecast closely and stay in touch with you, and we usually make the call within that window, sometimes on the day itself.
Do you sail in the rain?
A gray morning or light rain does not automatically cancel a charter. If it is safe, we talk it through with you, and you can sail, shift your start time, or move your date.
Who decides if a charter is cancelled for weather?
Our captains make every weather decision, based on wind, sea state, visibility, and thunderstorms.
Can we reschedule instead of getting a refund?
Yes. Rescheduling is our first choice when the weather is unsafe. We cannot always offer the same type of time slot; if rain rules out your sunset sail, we may suggest the morning of that day or the next. If a new time does not work for your trip, you receive a full refund.
Have another question? See our full FAQ for cancellations, what to bring, and more.