Frequently Asked Questions

Where do you operate from?​

We operate out of Gurney's Star Island (formerly The Montauk Yacht Club), at 32 Star Island Road, slip 412. A Hamptons legacy for over 80 years, Gurney's Star Island Resort & Marina -- A Hamptons full-service resort and spa -- is well known as a Long Island family vacation and New York City weekend getaway.

What happens if there's bad weather?

We reserve the right to determine if the weather will prevent sailing on any given day. Sailing is a water sport and it’s natural to get a little wet. A full refund or rescheduling will be made in the event of small craft warnings on inland waters, heavy rain or high winds. Cloudy conditions, light winds or rain showers will not result in a refund or a rescheduling. ​We do not accept cancellations based on forecasted weather. The charter is rescheduled based on marine weather forecast no earlier than 1 hour before scheduled departure.

When will my credit card be charged?

Your credit card will be charged upon receipt of your reservation to secure your booking. If your time slot is unavailable, your card will not be charged. We will contact you to find an alternate slot. We accept Visa, Mastercard, American Express and Discover. 

What is your cancellation policy?

Cancellations made 3+ days prior to a trip will be refunded 100%, Flotilla Boat Parties are 7+ days. Cancellations or changes made less than 72 hours before a trip and no shows will not receive any refund. Cancellations are confirmed only when acknowledged by a managing member of Sail Montauk

*Sail Montauk reserves the right to cancel a trip due to severe weather. Every attempt will be made to reschedule weather-canceled outings. Trips which Sail Montauk cancels due to weather which cannot be rescheduled will be refunded 100%. If unexpected heavy rain or winds cause Sail Montauk to terminate a sail early (within the first half of your time), a 50% refund OR your sail can be rescheduled for no fee. If Sail Montauk terminates a sail during the last half of your time, your sail may be rescheduled at half price.

Is gratuity included?​

Gratuity is not included on most of our sails. While it is not required, it is customary to tip between 15% and 20% for good service. *18% gratuity will be added to Flotilla Boat Parties.

Can I buy a gift certificate for a sail?​

Absolutely! You can purchase one of our sails, lessons or merchandise, or give a dollar amount to friends and family to use as they wish. If the recipient decides they want a different type of sail, they are welcome to apply the dollar amount towards any of our charters. You can decide to have the certificate sent to you to forward, or send it directly to the recipient. Click here to buy.

Are adult beverages allowed?​

Yes! Adult beverages are BYOB and are allowed on our Private Charters. We keep a cooler on board with complimentary water and ice. If you are enjoying wine on board, please make it white, as red wine can cause stains.


Do you have any age restrictions?

Children of all ages are welcome at Sail Montauk. Children under 12 must wear life jackets at all times, which we will provide.

Do I need any special clothing for sailing?

Most people have all the necessary clothing in their wardrobe. A windbreaker or sweatshirt, t-shirt, and jeans or shorts are generally the most comfortable sailing gear. We recommend sailing barefoot, but if you prefer to wear shoes you should also have some type of non-marking boat shoe or a sneaker with light-soles which will not scuff up the boat.

What kind of boats do you sail on?

We sail on Catalina 22s.  

What are the boats stocked with?

All boats are equipped with coolers stocked with complimentary ice and water. Feel free to BYOB or bring snacks to enjoy. Connect to our speakers with auxiliary jacks or Bluetooth for a custom playlist. Waterguns and pool noodles are kept on board, and we encourage cannonballs, so make a splash!

Do you allow dogs on board?

While we love dogs, unfortunately our furry friends have to stay on land.

Contact Info


© 2011 by Sail Montauk

Open 7 days a week:

Monday-Sunday  8am-8pm

Sailing in Montauk May-September

Sail Montauk

Located at Gurney's Star Island (formerly the Montauk Yacht Club)

32 Star Island Road, Slip 412

Montauk, NY 11954


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