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Taste of Sailing in Montauk

Rated 5.0 out of 5 from 4 reviews.Montauk, United States

Paused until 31 July.

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Experience hosted by Alexandra

2 hours
Includes drinks, equipment
Up to 1 people
Hosted in English

What you'll do

*Base price of $250 includes 2 guests. Each additional adult is $60, and each additional child is $40. Up to 5 guests max. This is a private sailing experience with your group and the captain.

Meet us dockside at Gurney's Star Island Yacht Club, located in Montauk. Step aboard your private sailboat and start your adventure.

You're welcome to BYOB or bring snacks to enjoy, we keep a cooler onboard with complimentary ice and waters, along with cups and bottle opener for your convince. Connect to our bluetooth speaker for custom tunes during your sail.

Your Taste of Sailing experience is a hands on activity. Your captain can show you how to steer the boat and trim the sails to harness the power of the wind. If you prefer to sit back and relax, your captain can sail the boat while you enjoy the beautiful scenery.

On this 2 hour sail you'll first visit Lake Montauk, then tour Montauk harbor, and finish the sail in Block Island Sound. We love being tour guides, so be sure to ask us where the best places to eat/drink/do in the area. Come Sail Montauk with us!
*Base price of $250 includes 2 guests. Each additional adult is $60, and each additional child is $40. Up to 5 guests max. This is a private sailing experience with your group and the captain.

Meet us dockside at Gurney's Star Island Yacht Club, located in Montauk. Step aboard your private sailboat and start your adventure.

You're welcome to BYOB or bring snacks to enjoy, we keep a cooler onboard with complimentary ice and…

What's included

  • Drinks
    Cooler filled with ice & waters. BYOB or bring snacks to enjoy. We also sto...
  • Equipment
    Bluetooth speaker. All required safety equipment.
From £205
/ person
Sat, 1 Aug
11:00 - 13:00
£205 per person
£205 per person
Sat, 1 Aug
14:00 - 16:00
£205 per person
£205 per person
Sat, 1 Aug
18:00 - 20:00
£205 per person
£205 per person

Meet your host, Alexandra

Host on Airbnb since 2019
  • 4 Reviews
  • Identity verified
Ahoy! We are a small family owned Sailing School and Charter company in Montauk, New York. We're a husband and wife team(Alexandra and Darius Ali) that have owned Sail Montauk for 10 years. We're ASA Sailing Instructors, hold USCG Captains Licenses, and trained in CPR & First Aid. We love sailing and can't wait to share our passion with you. Whether you'd like to sit back and relax or have an informative sailing lesson, we'll make your experience one of kind.
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Where you'll be

The boat departs from Gurney's Star Island in Montauk. We'll then venture into Lake Montauk, Montauk Harbor, and surrounding waters.

Rated 5.0 out of 5 from 4 reviews.

Helen
August 2019
Loved the sailing tour! So happy we got to go on this experience. Our guide was totally chill! Brought us around all the spots cool spots of Montauk with some history lessons. Highly recommended for anyone looking to just chill out or sail. I hung out at the edge of the boat for sometime while my boyfriend chatted with our guide. Lots of fun, highly recommended.
Loved the sailing tour! So happy we got to go on this experience. Our guide was totally chill! Brought us around all the spots cool spots of Montauk with some history lessons. High…
Sumi
July 2019
I’d decided to take a friend to our first-ever sailing experience and was excited, though a bit apprehensive as deep ocean water and I are not exactly friends, ha. Alexandra was very prompt and helpful in answering all of my questions for pre-planning, so by the time we met, I knew that I was dealing with someone who was both meticulously professional and kind. Her vast expertise, knowledge, and passion for sailing was immediately apparent from the jump. She answered every single one of our newbie questions and involved us every step of the way, which was our request, explaining the hows, whats, and whys (and ever the professional, never tiring of my curiosity, hehe). Though we were involved in getting a small taste of actual hands-on sailing, which was really fun, the experience was amazingly relaxing. We brought some wine and snacks, wore our bathing suits, and mostly chilled out to Alexandra’s music playlist which was fantastic. She was so open and personable, we had lots of fun conversations, and she was also very encouraging. I was a bit nervous to climb up to the bow to take a view from the front, but after a while, she made me feel so at ease, I even surprised myself by deciding to try it! She cheered me on as I crawled to the front, and I was truly amazed at how peaceful and enjoyable it was! It takes a special guide to help someone overcome their fears, and though Alexandra never signed up for this part, she helped me just by her breadth of training, professionalism, friendliness, encouragement which made me feel so comfortable and most of all, extremely safe. There was a couple who sailed at the same time we did, but were on their own boat with Alexandra’s husband, and it was so fun to meander a bit near their boat from time to time and to also watch their hands-on sailing instruction across the water. You honestly can’t go wrong with Taste of Sailing in Montauk, and although I’m sure that her husband is an equally wonderful captain and guide, I can only speak to the great experience that my friend & I had with Alexandra. I would absolutely highly recommend this experience in every way, and would love to sail again soon! Thank you for everything, Alexandra!
I’d decided to take a friend to our first-ever sailing experience and was excited, though a bit apprehensive as deep ocean water and I are not exactly friends, ha. Alexandra was ve…
Christine
June 2019
This sailing experience was so fun! We learned all about sailing and participated. The instructors are a wonderful duo who accommodated our requests. We would definitely do it again!
Robert
May 2019
Sailing with Ali was a wonderful, relaxing experience - I would highly recommend the trip to anyone!!

Choose from available dates

24 available
1 / 2
  • Sat, 1 Aug
    11:00 - 13:00
    £205 per person
  • Sat, 1 Aug
    14:00 - 16:00
    £205 per person
  • Sat, 1 Aug
    18:00 - 20:00
    £205 per person
  • Sun, 2 Aug
    11:00 - 13:00
    £205 per person
  • Sun, 2 Aug
    14:00 - 16:00
    £205 per person
  • Sun, 2 Aug
    18:00 - 20:00
    £205 per person
  • Mon, 3 Aug
    11:00 - 13:00
    £205 per person
  • Mon, 3 Aug
    14:00 - 16:00
    £205 per person

Activity advisory

Expert industry partners
Every adventure follows industry guidelines. We partnered with the Adventure Travel Trade Association, expert leaders in adventure travel, to define best practices and standards for safety.
Know your comfort level
Please note that outdoor activities carry risks, and you may be exposed to dangerous situations as part of this experience. Make sure you can participate safely given your abilities and the conditions (such as location, weather, and equipment).

Things to know

Cancellation policy

Any experience can be cancelled and fully refunded within 24 hours of purchase, or at least 7 days before the experience starts.

Guest requirements

Up to 1 guest of all ages can attend.

More tips

These are private experiences. Just your party & the Captain!
$250 base price includes first 2 guests.
$60 each additional adult and $40 for kids under 12.
Up to 5 guests max.

What to bring

Light jacket

BYOB & Snacks