Sailing NYC with us!!

 5.0 (75)

Catalina Standard (1994)


  • 34 feet

  • 6 guests

  • 3 cabins

  • 1 heads

  • Captained



See amazing views of the city during this top rated sailing experience for up to six passengers! Join our friendly and knowledgeable captains and take fantastic photographs from the comfort of a 34’ sailboat.

- Statue of Liberty
- Manhattan Skyline
- Ellis Island
- Brooklyn Bridge
- Freedom Tower
- Governors Island
- Seaport

Daily Times: 9:00am, 11:30am, 2:30pm, 5:00pm, 7:30pm.

We have a full drink menu available: Champagne, White Wine, Rose, Beer, Hard Seltzer

Our qualified captains are knowledgeable, experienced, professional, and fun! We adhere to all USCG rules, and have all required safety equipment on board.

What happens if it rains? If I have to cancel for any bad weather there is a full refund. Generally I play it safe and we only sail if there is a good chance of clear skies. Usually the weather report improves closer to the date and we will never sail if it is unsafe.

Can I reschedule my sail? You are allowed to 1reschedule 72 hours or more before your sailing reservation. No reschedules are allowed within 72 hours of your reservation.

Can I cancel my sail? You are allowed to cancel and receive a full refund 7 days or before your sailing reservation. No refunds for cancellations within 7 days of your reservation. No refunds if you are more than 30 minutes late or miss your sail. No penalty for any cancellation caused by a government shutdown.

Where are you located? Brooklyn Bridge Park

How many people can I bring? Groups up to six passengers. 6 passengers is a legal maximum.

Can I bring a 7th person, they are really cool? No, six passengers is a legal maximum.

Do kids or babies count as passengers? Kids and babies legally count as passengers.

Can I bring kids or babies? I provide life jackets for any kids or babies12 or younger that will have to be worn the entire sail. Please let me know if you plan to bring anyone under13 to make sure I have the correct number of life jackets.

Can I bring drinks or food? Passengers are welcome to bring any food or drink—please no red wine or anything that stains or is messy. There is bottled water available.

Is there a working bathroom? You are welcome to use the bathroom at any time.

Are there speakers for playing music? There are 2Bluetooth speakers guests can use to play music.

Is there a refrigerator or ice? There is an ice box with light refrigeration for any food or drinks.

Is smoking allowed? Smoking is not allowed during the sail although a vape is ok from the front of the boat.

Are you available next weekend? You can check available days on the calendar and see a "Add Extras" with 'message owner'


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


Hi my name is Ian. I've lived in Brooklyn for ten years and love to share my joy of sailing and nature with guests. I’m the owner of Enchantress, a beautiful 1994 Catalina 34 sailboat. I have a USCG (United States Coast Guard) Master sailing license, I'm certified in CPR, and have spent years living and sailing around the Atlantic East Coast. I once solo sailed the Bahamas for a Winter and had friends visit me along the way. I look forward to meeting you and going out for a sail around NY Harbor! Hi my name is Andrew. I’ve been living in Brooklyn for almost twenty years. My brother Ian introduced me to sailing in 2008 and since then I’ve sailed the Atlantic Coast, Bahamas, and New York Harbor. I have a USCG (United States Coast Guard) captain’s license as well as a sailing endorsement, and I’m certified in CPR. I have lots of information to share about New York City and its landmarks, just ask! I look forward to meeting your group and going out for a sail. :)


  • GPS
  • Dining
  • Cocktail parties
  • VHF Radio
  • Speakers on deck
  • Depth finder
Navigation & Safety
  • GPS
  • VHF Radio
  • Depth finder
  • Life jackets
  • Fire extinguisher
  • First aid kit
  • Torch light
  • Speakers on deck
  • Electricity
  • Dining
  • Cocktail parties

75 Reviews

  • Darya
    Oct. 11th, 2023

  • broox
    Oct. 3rd, 2023

    This experience was a 10/10!!! We sailed shortly after I proposed to my partner. It was 100% the highlight of the day and nothing short of magical. I recommend taking the sailboat during the sundown. It was stunningly unreal!!!

    We sailed with Ian's brother, Andrew, who is super chill, kind, respectful and just had all around good energy! He knew a ton about all of the surroundings - it was fascinating to learn some NYC history from him.

    I can't recommend Brooklyn Sail enough. It's not just about the sailboat, which was beautiful, but more importantly who you travel with and the experience they give you. Andrew - you're AWESOME!!! :) Can't wait to sail again!

  • Jessica
    Sept. 11th, 2023

    This was our first time sailing and it was something we’ve always wanted to do. I have to say it was the highlight of our weekend as it was an amazing overall experience. Our captain Andrew was phenomenal and I couldn’t have asked for a better trip, the boat was beautiful and would love to sail with them again in the future. We were all very pleased

  • Andres
    Aug. 25th, 2023

    Ian was amazing. The entire experience (from booking, inquiries, and the sailing itself) was great. He was kind, careful, and very attentive to safety protocols.

    He shared great stories and facts at different points of the trip, and made the experience very enjoyable.

    I would recommend him every day of the week.

  • Brendan
    Aug. 13th, 2023

  • The Jungle Upstairs
    The Jungle Upstairs
    June 23rd, 2023

    Captain Andrew was awesome, we had the best time!

  • Andrew
    Sept. 25th, 2022

    We had a great time! 10/10 would sail again.

  • Lindsey
    Sept. 14th, 2022

  • Talisman
    Aug. 16th, 2022

    Beautiful boat. Fabulous Captain - knowledgeable and friendly. The sail was just stunning and we hope to ride again, soon.

  • paul
    Aug. 6th, 2022

    We had a wonderful two-hour sail with Ian's brother, Andrew. He was extremely considerate and responsive to the needs of his passengers, a skilled sailor, and just great company throughout.

    He charted a route from Pier 5 in Brooklyn heading north up the East River and coming about under the Manhattan Bridge. From there we continued south through Buttermilk Channel passing close by Governor's Island, Liberty Island, Ellis Island, and then returned near the Battery back to the pier.

    I cannot recommend this captain and boat more highly. It was a wonderful to be on the water and see the islands from this unique perspective.

  • Jeffrey
    Aug. 1st, 2022

  • Ingrid
    July 26th, 2022

    So much fun! Brought my parents who were visiting, the trip was so special! Would definitely recommend a trip with Ian. Boat is great, captain is knowledgeable and it's just great fun sailing around Manhattan

  • Alexa
    July 25th, 2022

    Great experience. Would definitely recommend and hope to do again soon!

  • Sarah
    July 22nd, 2022

    Ian was a delightful captain. He was friendly and knowledgeable which was helpful to my guests who have various sailing skills and interest.
    Ian was timely and courteous, ensuring we started promptly and also enjoyed a nice long sail.
    Ian's boat is comfortable, clean and well sized for a group of 6.
    I recommend you book with Ian for a lovely, leisurely time.

  • Rachel
    July 18th, 2022

  • Hayley
    July 17th, 2022

    We had the best time on the boat! The captain was great. We felt welcomed and safe. So much fun. We'll definitely do it again.

  • Haley
    July 5th, 2022

    We took a perfect trip over the holiday weekend. We are all local and all agreed it was one of our favorite NYC days, ever. Beautiful, easy, chill and a different way to enjoy our gorgeous city. Both Ian and Andrew are great to work with and captain the boat. We will 100% do it again.

  • Kevin
    July 4th, 2022

    Fantastic trip. Ian is an awesome captain. Very knowledgeable and the boat was great. Clean and very nice. We will absolutely be using him again, Highly recommend!

  • Clara
    Oct. 29th, 2021

    We sailed with Ian's brother Andrew, and he was a pleasure to be around. The boat was clean and stocked with ice and water. We brought our own food and drinks, and it was a wonderful day sailing on a beautiful boat.

  • William
    Oct. 12th, 2021

    Great ride around NYC. Ian was so quiet the whole time we forgot he was there, which was perfect. He was happy to take some photos of us as a group when we asked as well. Always in a good mood and just wanted us to enjoy ourselves safely on the boat. The excursion was 2.5 hours, an extra half hour than other were offering, and left from an ideal location out of Brooklyn. 5 stars

  • Mohammad
    Oct. 5th, 2021

    Ian was amazing! Proposal to my gf went extremely well. Ian was very accommodating and understanding! Will definitely book again! 5 *

  • Renata
    Sept. 27th, 2021

  • Gautam
    Sept. 6th, 2021

    Ian was very flexible about scheduling when a thunderstorm threw off our plans! My friends were able to use the reservation at a later date and even brought another person— very happy with the value of this booking! They had a great evening with city views, saw the Statue of Liberty up close, hopefully I’ll be able to join next time!! Communication was great as well!

  • Karla
    Aug. 14th, 2021

    We were planning to sail during sunset time but thanks to Ian who was very responsible about our safety, moved the sailing date to another day because a storm just showed up.

    Then we we sailed at 9am which was a very good idea since the weather was beautiful out there.

    We met Andrew, he was our captain and he explained everything we needed to know about our safety.

    Then we sailed and everything went smoothly. Andrew was so kind and he took some pictures of us.

    We enjoyed so much. We were 4 people. The boat is neat and equipped with all you can need to expend our time out there.

  • Tobi
    Aug. 5th, 2021

    Great experience Ian was great!

  • Vibhu
    July 26th, 2021

    The trip was amazing! I highly recommend it for everyone.

  • Dalune
    July 20th, 2021

    It was great! Thank you so much ,Ian!

  • Alyssa
    July 16th, 2021

  • Alexis
    July 14th, 2021

    Ian was wonderful! We had a great boat ride! If you’re thinking about booking but haven’t yet, just do it! Definitely worth it and such a cool experience with friends!

  • Max
    June 25th, 2021

    We had an incredible time on Ian’s boat. Looks just like the pictures and Ian is a great captain/host. Would recommend to anyone

  • Colleen
    June 21st, 2021

    A huge THANK YOU to Ian for an awesome sail! Ian was extremely accommodating and enjoyable. Ian is very knowledgeable and able to answer our many questions. We will definitely look him up again for future sails!

  • Kelsie
    June 14th, 2021

    Ian was accommodating to our special requests and took us on a great trip! Will definitely book again.

  • Djahna
    June 3rd, 2021

    It was super great! Loved every moment. Beautiful boat and Ian was great! Thank you so much!!

  • Miljacic
    May 25th, 2021

    Andrew was amazing!! 5 of us had a great experience!!! Definitely would recommend and we plan on doing it again!

  • Shira
    May 24th, 2021

    The boat ride was lovely and could not have gone better!

  • Alexis
    May 11th, 2021

    My family and I had an amazing time enjoying all of the great information Ian shared. He was very kind and is very passionate about sailing. The boat was clean and had all sorts of amenities to keep his passengers comfortable. Would 100% recommend going and I will personally be booking again!!!

  • Kate
    May 8th, 2021

    We sailed with Ian to celebrate my husband's 30th birthday and it couldn't have been better! A beautiful sunset sail around lower manhattan and the statue of liberty was the perfect way to celebrate with friends. Also very covid safe since it was just our group on the boat! Ian was great and we had a blast. Now I just need to find anther excuse to sail again! Highly recommend.

  • Logan
    April 20th, 2021

    Highly recommend!!

  • Meliza
    April 18th, 2021

    Everything was UUHMAZING ! I cannot eait to book again. I am so happy i booked Ian!

  • Anirudh
    April 12th, 2021

    We had such an amazing experience! The enchantress was clean and spacious. Ian is really helpful and tries his best to accommodate any requests you have. We will definitely book again in the future.

  • Naimi
    April 11th, 2021

  • Ayanna
    April 9th, 2021

    Ian, was extremely responsive and accommodating for our trip. In addition, he was friendly and offered knowledgeable information/tips for sight seeing along the way.

  • Pony
    April 9th, 2021

    Ian’s the best!

  • Adam
    Oct. 25th, 2020

    Ian was great! He was prompt, communicative and just fun to talk with! He handled everything so we could just enjoy being on the boat and sailing!

  • Audrey
    Oct. 25th, 2020

    It was an amazing trip!! Thank you very much Ian for all!
    We will come back for sure!!

  • kin
    Oct. 23rd, 2020

    Excellent day trip.. Ian was great and kept us nice and dry
    Would do it again.

  • B
    Oct. 15th, 2020

    Ian was the absolute BEST. I had tried to find a few places to rent a tour last minute (literally 1-2 day notice) to surprise my older brother for his birthday! Everyone was a bust. But the universe led me to Ian. He was so kind enough to be flexible and create a time slot that he didn’t have originally to help with the timing of us having an engagement after our ride. That meant the world to me because I was trying SOOOOOOOOOOOOOOO hard to make it work with a boat tour for my brother birthday. The ride itself was so cool! It was a first for me being on any type of boat. But Ian was super nice, professional, chill, funny and cool. He was extremely knowledgeable about the sea and landmarks. He answered all million of my questions with no problem! He made this a memorable experience for my whole family. I would book with him again in a heart beat! Thank you sooooo much again.

  • Jacob
    Oct. 13th, 2020

  • Monica
    Sept. 26th, 2020

    Highly recommend Ian and this trip!!

    Ian is a super safe and wonderful captain and his sailboat is pristine and beautiful. He was waiting for us and made this birthday trip unforgetable.

    He will sail around and highlight NYC in a way you will never forget. Thank you, Ian!

  • Jennifer
    Sept. 22nd, 2020

    Had the absolute best birthday boat trip. Ian is safe, knowledgeable and fun and his boat is the perfect size and layout for 6 people. Would absolutely recommend and can’t wait to get back on board. Thank you!

  • Mackenzie
    Sept. 21st, 2020

    Had a great time on Ian’s boat! He was a great captain and the boat was perfect!

  • Rebecca
    Sept. 20th, 2020

    We had the most fantastic afternoon on the water! Ian was wonderful and the boat was truly stunning. Incredible way to celebrate a birthday and I will absolutely be coming back for another trip!

  • Maria
    Sept. 14th, 2020

    I couldn't recommend Ian more. Everything was perfect. Best birthday ever!

  • Jodi
    Sept. 8th, 2020

    Our sail with Ian was beautiful, relaxing, and really fun.
    Ian was quick to respond and really accommodating to me and my group. We definitely look forward to sailing with Ian again.

  • Amanda
    Sept. 5th, 2020

    Ian was an excellent steward for the private sail afternoon trip around Manhattan, nothing short of spectacular. I surprised my partner with a private tour of NYC for our anniversary and this incredible experience exceeded my already high expectations. I will definitely be back to enjoy the marvelous views of this beautiful city again!

  • Sarah
    Aug. 24th, 2020

    Ian was helpful, timely and responsive and we all had a great evening aboard the Enchantress! Thank you!

  • Arturo
    Aug. 24th, 2020

    Ian gave us the most perfect farewell to NYC. His boat is beautiful and spacious. He was extremely professional and we had a pleasant time.

  • Ankita
    Aug. 16th, 2020

    We had a super great boat ride with Ian! He is an experienced sailor, and fun guy. The boat was super clean and comfortable. Highly recommend sailing with Ian!

  • Laura
    Aug. 15th, 2020

    We had the best time! Ian was a wonderful captain and host. We will definitely be doing this again!!

  • shesapriima
    July 28th, 2020

    Ian was a fantastic Captain! He drove smoothly, was very accommodating & made sure we had a great time. His boat was clean and well kept. I would definitely book with Ian again. Great experience! :)

  • Mia
    July 21st, 2020

    We are so grateful to Captain Ian! He truly made our day. We had a small party of 4 (3 adults, 1 toddler) and had the best time during the sunset cruise around Manhattan, Governor's Island, Statue of liberty and up the Hudson. Captain Ian was very kind, professional, accommodating, and has a great sense of humor. Being able to use his blue tooth speaker was a plus as we were able to curate our own vibe. We truly had the best time and hope to book him again soon!

  • Steve
    July 15th, 2020

  • Chastity
    July 10th, 2020

    Great boat ride Ian was very patient and made us very comfortable. Definitely booking again

  • Andy
    July 4th, 2020

    Ian was a great captain and host. Very accommodating and friendly. The boat is beautiful and clean. The sail was Very smooth And I would recommend to anyone to sail with Ian. I definitely will be again. My friends and I really enjoyed ourselves. Thanks Ian.

  • Ebony
    June 30th, 2020

    Our experience was amazing! From start to finish Ian made us all feel comfortable and safe. We got to see some beautiful views! If you’re looking for a great social distancing activity I highly recommend booking with Ian. Would definitely book again.

  • Chelsea
    June 30th, 2020

    Ian was great! Overall very easy to get in contact with during the booking process and friendly once on the boat. Everyone had a great time!

  • Damien
    June 26th, 2020

    Ian was an amazing captain. Filled with interesting stories and very professional, we enjoyed the sail to celebrate our anniversary. We will do it again!

  • Sandra
    June 23rd, 2020

    We had a great sail with Ian on Father’s Day. There were 5 of us and there was plenty of space. The weather was perfect and the harbor was beautiful for a sunset sail. The boat is in great shape and Ian is a terrific captain. Highly recommend. Best charter out of Brooklyn Bridge Park.

  • felicia
    June 23rd, 2020

    thank you so much for having us me and my husband had a great time the smile on my husband face was priceless. Ian was super cool i’m going to do it again and I’m gonna to book it with him Definitely Made us feel comfortable and safe Thank you again😌

  • Joanna
    June 22nd, 2020

    Highly, highly recommend Ian and his beautiful sailboat! I surprised my husband with a sailboat ride around downtown NYC, Statue of Liberty, Ellis Island, Governor's Island, etc for Father's Day and it was such a perfect, fun afternoon. Ian was so easy to book with and he was so professional - we felt incredibly safe while also having the freedom to explore the boat as we pleased. We brought our one-year-old son and Ian had a special infant life-jacket for him. He loved it. We are definitely going to book again with Ian. Thank you!!

  • Tykeisha
    June 22nd, 2020

    My family and I had a great time. Ian was awesome he answered all of our questions. He informed us on where we located when sailing around. It was a really great Father’s Day surprise for my husband. The trip was very relaxing.

  • Yechezkel
    June 20th, 2020

  • Kimberly
    June 14th, 2020

    My kids and I had a great time! Captain Ian is a pro!

  • Alie
    June 1st, 2020

    What an AMAZING time!!! Ian is the best captain!! He was easygoing and made sure we were comfortable every step of the way. The boat is beautiful and clean. Definitely will be taking another trip with Ian soon!!

  • Raph
    May 31st, 2020

    You will absolutely enjoy the trip around the NYC Harbor with Ian.

    I chartered him for a private trip to create a magical evening under the gorgeous summer sunset. He was kind enough to take a few photos as I proposed to my girlfriend under the Brooklyn Bridge.

    Definitely take advantage of laying down at the front of the ship to really feel the boat's movement. Ian even let us steer the ship for a minute, to get a sense of the boat.

    Fantastic new way to see the Statue of Liberty, lower Manhattan, Governor's and Ellis Island for natives and tourists alike.

Boat Owner


Member since June 2019

Hi my name is Ian. I've lived in Brooklyn for nine years and love to share my joy of sailing and nature with guests. I’m the owner of Enchantress, a beautiful 1994 Catalina 34 sailboat. I have a USCG (United States Coast Guard) Master sailing license, I'm certified in CPR, and have spent years living and sailing around the Atlantic East Coast. I once solo sailed the Bahamas for a Winter and had friends visit me along the way. I look forward to meeting you and going out for a sail around NY Harbor!

Response rate: 99.5%
Response time: within 3 hours
Message owner

Location and Destination Guide

Usually this boat operates around Brooklyn, 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.


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.