Classic beatuiful sailboat in the heart of NYC.

 5.0 (38)

Hinckley Custom Pilot 35 (1964)


  • 35 feet

  • 6 guests

  • 1 cabins

  • 1 heads

  • Captained



PRICES INCLUDE FUEL AND CAPTAIN: We have a set schedule for two hours maximum: 10am, 12:30pm, 3pm, 6pm and 8:15pm. Price is $660.

1964 Hinckley Custom Pilot 35 sailboat, completely renovated and upgraded for your comfort. Enjoy a relaxing sail aboard. Bring your family and friends for a truly unique boat ride in New York City. Feel free to bring up to six passengers and any food or drinks you like on board.


  • Manufacturer
  • Model
    Custom Pilot 35
  • Year
  • Guest Capacity
  • Cabins
  • Single Beds
  • Double Beds
  • Bathrooms
  • Number of engines
  • Horsepower per engine


Capt. David started company in 2013 to share his joy of sailing with his customers. At the age of 16 he learned to sail on the south shore of Long Island and was an avid sailboat racer. Please join him as he shares with you his love for the water and his excitement for the city. Capt. David is a USCG Licensed Master.


  • USB Connection
  • VHF Radio
  • Speakers on deck
  • Teak deck
  • Depth finder
  • Life jackets
Navigation & Safety
  • VHF Radio
  • Depth finder
  • Life jackets
  • Fire extinguisher
  • First aid kit
  • Torch light
  • Binoculars
  • USB Connection
  • Speakers on deck
  • Teak deck

38 Reviews

  • Claire
    Aug. 31st, 2023

    This was an amazing trip! Our Captain was engaging, kind, and patient as I was seasick (still 5 stars)! Was a pleasure to have around our group sailing. Highly recommend sailing on this beautiful boat... but if you get motion-sick like me, I would take the necessary precautions.

  • Midas
    Aug. 24th, 2023

    We had an amazing time with Captain Matt. David was incredibly responsive leading up to the experience. All-over, we had a great time and would definitely consider booking again. Thank you!

  • Berna
    Aug. 7th, 2023

    Although we were not lucky with the weather , the captain did his best to take us around in the most convenient and safest way! He is great with kids, explains in detail and involves them if they are interested. Once again many thanks for welcoming is in your beautiful sailing boat !

  • Adriana
    July 25th, 2023

    Una experiencia unica, aunque sin viento el calor fue impresionante. Gracias por el super buen servicio

  • Charley
    June 11th, 2023

    Captain Levi was an excellent captain and David’s boat is wonderful.

  • Crawford
    May 30th, 2023

    We had a wonderful trip! Captain Matt was subbing for David and was very friendly and knowledgeable. We would recommend to others looking for a great activity on the water.

  • Kyleigh
    May 19th, 2023

  • Kayla
    May 19th, 2023

    Wonderful trip around the Statue and into Buttermilk Channel. We had a great time.

  • Alex
    May 16th, 2023

    David was perfect. We booked our time with David last minute the day before Mother’s Day. He was a perfect mix of hospitality and guide as we sailed to the Statue of Liberty and then Brooklyn bridge. Definitely will be returning for another sail.

  • Christy
    Oct. 11th, 2022

    David was great! Punctual, friendly and the boat was beautiful

  • Lashawnda
    Sept. 3rd, 2022

    The ride was amazing Captain will was awesome he joked with us sang with us and took one of the best pictures of the night i would definitely book this again as

  • Sadie
    Aug. 23rd, 2022

    We could not have had a better time! The boat was beautiful and we all loved every minute. Everything went smoothly from start to finish. Will definitely look to book again in the future!

  • Julia
    June 13th, 2022

  • Ivania
    June 1st, 2022

    Thank you so much to Captain David and Captain Levy! You guys made our trip to NYC so memorable aboard Tara!

  • Peter
    Aug. 23rd, 2021

  • Arthur
    Aug. 1st, 2021

    David was a terrific captain, he shared wonderful local knowledge. Took us right up to the Statue of Liberty, then around Governor's Island. Great trip, gained a ton of local knowledge from David.

  • Anna
    June 27th, 2021

    David was very communicative while booking and prior to the sail.

    We had great wind during our sail so my group opted to sail the entire time and had an absolute blast and felt very safe! David sailed us all around the tip of the island—from the Statue of Liberty to buttermilk channel. We enjoyed his humor and his great knowledge of city & its sights. Would highly recommend for a group just looking for a fun sail or even groups with sailing knowledge or experience like ours. David caters to whatever experience you are looking for!

    May 30th, 2021

  • Tiffany
    May 16th, 2021

    Great experience! Beautiful boat, beautiful views and great customer service. Highly recommend!

  • Christian
    Nov. 10th, 2020

    Captain David is amazing and Tara (Sailboat) is an absolute beauty. Highly recommend this trip to anyone. I propose to my GF (now fiancé) last weekend and it was unbelievable. If you have to opportunity to do this trip next season, do it. I would give them 6 stars if i could.

  • Sepideh
    Oct. 8th, 2020

    We rent this boat for 2 hours, it was very nice and we enjoyed our trip! Highly recommend this beautiful boat for ur events :)

  • Bethany
    Sept. 12th, 2020

    Great boat ride, beautiful sights! Thanks Captain David

  • Lisa
    Sept. 9th, 2020

    We had a great time with Felix on the Hudson! Highly recommend.

  • pedro
    Aug. 18th, 2020

    Simply great we went on a 2 hour sail for our anniversary and it was perfect. Captain Dave was AMAZING. His boat TARA is absolutely beautiful we are definitely going to be back! Thanks David

  • George
    Aug. 8th, 2020

  • Mustafa
    July 18th, 2020

    Simply great - David was so nice and the boat is absolutely beautiful. We had fantastic time celebrating my husband’s birthday.

  • Alison
    July 13th, 2020

    We enjoyed a wonderful 3 hour sail with Captain David. He was attentive and kept us well informed about the weather. It ended up being a beautiful day. We will for sure be back for another sail!

  • Jess
    July 9th, 2020

    We went on a 2 hour sail for our anniversary and it was perfect. David is fun to talk to and very knowledgeable about the city, and accommodating...gave us a Bluetooth speaker for music, a cooler bag, cups etc. Vibes were great and we will definitely be back!

  • Yadid
    July 6th, 2020

    Our trip with David was great! Smooth sail in a beautiful and well kept boat. Definitely recommend the captain well - very nice, upbeat, responsive and responsible making sure everyone knew the dos and don'ts of sailing. Recommend the trip and would definitely book another sail! Thanks David for a great birthday sail! :)

  • Mark
    June 22nd, 2020

    Was the perfect afternoon on the water. Captain Dave was tremendous and we will definitely be back!

  • Brian
    June 15th, 2020

    My wife and I rented for a sunset cruise for our anniversary and everything was perfect. Amazing boat and captain. Very easily accessible slip. Highly recommended!

  • Brian
    June 14th, 2020

    Me and my wife took a trip for our anniversary and everything was perfect. Highly recommended.

  • Alain
    Sept. 7th, 2019

    We had a magnificent trip. The ship is beautiful and the captain is great !
    Highly recommended !

  • Craig
    Aug. 6th, 2019

    The Tara is beautiful and unique. Quite a bit of fun. Terrific for small groups. Captain Dave knows the boat and the waters very well , and is pretty gifted at finding a wind to sail on when everyone else appears becalmed. Great experience.

  • Shaoyi
    April 19th, 2019

    It was a great experience! David was so nice, patient, and professional. He's very cooperative throughout the whole process. The boat is lovely, tidy and beautiful! We will definitely consider it again in future.

  • Nagibe
    Nov. 3rd, 2017

    David contacted me very quickly after I had email him. He is very attentive and friendly. His boat "TARA" is cozy and comfortable we had a very memorable sailing afternoon along lower Manhattan. The accommodations were great for our family. I would highly recommend him to anyone interested in a sailing tour in NYC.

  • Martha
    Dec. 7th, 2015

    My family is still talking about our "Black Friday" 2015 sailing excursion while they were visiting NYC for the holidays. Captain David was skilled not only at sailing, but offered us very interesting stories and history as we sailed the Hudson and East River. So fun. Also, the Hinckley boat was simply spectacular! Every aspect of our day was "ship-shape" start to finish! Glorious experience!

  • Yasemin
    Sept. 19th, 2015

    This was a surprise birthday gift for my boyfriend and it was a huge success. Captain David was absolutely wonderful. Very knowledgable, helpful and genuine. Would certainly recommend!

Boat Owner


Member since April 2015

I am a passionate sailor, boat owner and USCG licensed captain. I started sailing as a boy on the south shore of Long Island where I learned how to race. I've managed a sailing school and I am also a professional sailing instructor. I love taking people out on my boat as it allows me to combine my passion for sailing and my dream of introducing people to the art and enjoyment of being on the water.

Response rate: 98.9%
Response time: within 1 hour
Message owner

Location and Destination Guide

Usually this boat operates around New York, NY.

New York City looks great from the ground, but that view from the water is something else! Jump aboard a Sailo boat rental from the Big Apple and experience the thrill of the sea - and snap plenty of incredible pictures. Sailing in NYC is a must on your summer bucket list, whether you are visiting or a New Yorker.

It might not be the first thing you think of when finding things to do in New York City, but renting a boat for a full day or just a few hours is a truly memorable experience.

Customer Questions & Answers

Ask general questions about this boat. For questions related to a specific booking request click here to Message the Boat Owner directly.


Where does the boat pick up and drop off?


0 votes
The location of this boat is located at North Cove Marina at 225 Liberty Street. On the corner of Liberty and South End Ave you will find a ramp leading down to the marina behind a security barrier. You are in the right location when you see three large flag poles at the bottom of the ramp.
by Janet on July 3rd 2018


What happens if there is bad weather?


0 votes
Unless extremely adverse weather conditions prevent us from leaving the dock for safety reasons, we will sail in the rain, heat, cold, humidity, etc. It is obvious that your captain will not take you out if conditions are dangerous. That being said, please keep in mind that a few clouds, or a slight chance of rain will likely not be grounds for cancellation or rescheduling. On the day of your sail, if you have any questions regarding the weather, please do not hesitate to contact the captain.
by Janet on July 3rd 2018


Does the price include gratuity?


0 votes
No, gratuity is not included in the price above and is at your discretion. It is recommended between 10% - 20%.
by Janet on July 10th 2018


Will I receive a refund if there is bad weather?


0 votes
If weather conditions are deemed to be unsafe, please contact the boat owner to reschedule or work out a refund.
by Janet on July 10th 2018


How can I rent for a number of hours not available in the dropdown menu?


0 votes
Get in touch with us at We will help you with customizing the duration of your booking.
by Janet on July 16th 2018


Cancelation policy - Standard
Full refund if renter cancels 6 days or more before the trip start date.
No refund if renter cancels 5 days or less before the trip start date.