Woman-owned luxury with transparent pricing - read our 5-star reviews!

I chose this boat because it said woman owned but it was a man captain, so I'm not sure what happened there. The boat was clean and the ride was pleasant.

My experience was great! I proposed on the boat and Captain Dan got nice pictures of the moment with the skyline in the background. The trip itself was very scenic and the whole experience was one to remember.

This was my second trip on the Islander and it was just as fun as the first time! The boat is great, very comfortable and has all of the amenities you would want. The captain was very friendly and helpful, and we were lucky to have great weather. Would definitely recommend for a fun activity with friends or family.

So much fun!

Outstanding and thoroughly enjoyable

We had a lovely time sailing with Sailing Islander. The boat was beautiful and Captain Dan showed us a great time. We certainly would love to do this again with friends and family.

Everything was great! The boat was on time, clean and as described, the captain was friendly, and the communication beforehand was comprehensive. We had a wonderful time and would 100% book again with Jessica.

Side note - Unfortunately the water was a bit choppy that day due to the wind so I recommend bringing some Dramamine just in case anyone in your party is prone to seasickness!

Thank you so much Jessica and Captain Dan! We had a great day on the water! The crew was excellent communicating with us, especially when there was a chance of some inclement weather. We did hit a rainy patch, but we made the best of it. The boat is beautiful and clean! Don't hesitate to book this experience!

What a great experience! A knowledgeable and very fun captain took us around the harbor with incredible views!

Thank you, Jessica and Captain Dan, for a wonderful Mother’s Day excursion. It was a beautiful and relaxing time, and our little family got in some good cuddle puddle time on the bean bag mat on the bow!

Super communicative owner. Our first booked trip was rescheduled bc it was rained out. She was super flexible on rebooking dates if open. We sailed on Friday, September 14 instead and everything was wonderful. Our captain was friendly and took a few pics of us. It was a beautiful sunset sail. The inside cabin was so pretty and clean. I'd definitely book again. Highly recommend.

This was an amazing sail!! This was my first sailboat in NYC I usually do boat in other countries, only because I wasnt expecting much- boy I was wrong! I rented the sailboat for my husbands birthday and a few of our friends, The sailboat was fabulous- super clean, looked just like the pictures sailed beautifully, the captain Michelle was a joy to be around her energy was just great (definitely would recommend her for my next sail), Jessica was fast with her response when booking and also accommodating she even put up a happy birthday sign!
Jessica did tell me I was going to love it and I REALLY do!! Definitely doing this next summer!

Had the best time. Our skipper Kevin was great!
5 stars all round!!!!!

Kevin was great, very enjoyable.
Everything was just right, thank you.

Look forward to our next sail.

Kindest Regards
Jesus Garcia

This was exactly how I envisioned the 2 hours to be, so much fun! The boat is beautiful and our Captain Michelle was awesome! So welcoming ❤️
Jessica is quick to respond and very accommodating. Will definitely book again!

The captain was rude and disrespectful and I don’t appreciate that at all

Great experience. Captain Kenny was great. Only thing was the bathroom wasn’t working bc of the prior trip.

Highly recomended! Great host an captain!!

If you're debating doing this, do it. Book it. Whatever concern it is, this trip will exceed expectations. I promise you! The Islander team is amazing, the area is so easy to get to and you wont regret it.

Celebrated my 35th birthday with friends. Absolutely the best experience I have had in so long !! The captain was great , communication was great, I couldn’t be happier!! Kudos to both Kristen & Jessica. Thank you for making my birthday a great time!!

Fantastic trip! Highly recommend

Perfect sail boat trip!
The boat is new and very well equipped, the captain was a pleasure to sail with and the owner is super responsive and accommodating - helped us change dates on the last minute with courtesy and ease.
Wonderful experience - highly recommended!

Our skipper Krista made the experience perfect.
We got lucky with the weather and could relax and let Krista sail the beautiful yhat while we relaxed and enjoyed the sights of lady Liberty and the Manhattan skyline.
We highly recommend Islander @sailingIslander.com

We were scheduled to sail last week however, the hurricane arrived and we had to rebook. Jessica & Krista made rescheduling seamless and pleasant. We sailed on a beautiful Sunday (with a bit of an overcast) but still pleasant. Krista was the Captain and very knowledgeable and open to sharing and answering all of our questions. Upon our return to dock, Jessica met us and that added a special touch- to meet the owner. Such a fantastic duo!!’ Thank you Jessica & Krista for making our sail a special one we will Never forget. We highly recommend sailing with this company. Gracias!!!!

Super fun! The yacht was amazing, Capt Krista was extremely helpful and would recommend friends for this!

Captain Krista was the absolute best, so welcoming, sweet, and professional. She was very attentive to us and made sure we felt comfortable and had fun. Will def book with her again!!

Super captain jack!! Very friendly and accommodating!! Would highly recommend them. Excellent sail boat.

Captain Krista was so awesome and helpful! Love the Jersey City location which was really easy to get to and Jessica was very communicative.

It was AMAZING!!! Krista, the captain, was so friendly and made us feel comfortable all the tine!
Jessica also made an easy process to book it
Thank you all!!! I’m very happy

I couldn’t have asked for a better captain
Krista was awesome. Extremely accommodating friendly and warm, just a super relaxed vibe. Boat owner Jessica does an excellent job in communication to set up reservations
Would definitely highly recommend if you had been second guessing yourself I would say don’t rob yourself of this wonderful experience. Myself and the girls plan to do this way more often.

This plan is casual, unique, fun and destined to bring yours close friends out for a good time. I am so glad, I picked Jessica's Sailboat to celebrate my 30th Birthday.

Not only was this a lovely boat, the captain and owner were wonderful to communicate with. They had drinks on board they had lovely cups they gave us a nice gift bag and the experience was absolutely wonderful. I will 100% book again. Wonderful ladies couldn’t be happier

Awesome service thank you Jessica & Dan for your wonderful hospitality

Excellent Boating experience

Jessica and captain Krista were absolutely wonderful. She was very accommodating with all my requests about my proposal idea. They were very communicative and supportive. We had such a great time and they made our day that much more special! I would recommend 1000 times over. Thank you!

We had such an amazing experience! Jessica and Captain Krista were both very accommodating, and such a pleasure to talk to. We sailed during the sunset hours per Jessica’s recommendation, and it was one unforgettable experience with beautiful views of the New York City and Jersey City skyline. We got close enough to Statue of Liberty and were able to take plenty of pictures. We’ll definitely be back soon! Thank you!

Sailing Islander was such an amazing experience for our family for Father's Day. My dad kept saying thank you for the boat and my husband really enjoyed hanging out on the water with our kids. Jessica was super helpful and communicative and Captain Krista was delightful to sail with particularly with so much experience and insights to share.

Will definitely share with friends and do this again in future!

Amazing trip! We celebrated my wife’s birthday with a group of close friends. It’s such a clean and beautiful boat (even more so than the pictures) and Captain Krysta is so sweet. We’ve lived in the city for a while now but the skyline at night was still quite something to see! 10/10

The caption was awesome the boat was clean and the experience was amazing. Will definitely book again for a longer time next time

My family and I celebrated my husbands birthday and my daughters birthday. It was myself, my husband and 4 kids. The captain Dan was super nice and informative. The owner Jessica came out and met us and was super nice to us. The view was amazing and Dan even let my my 13 year old son be co-captain. The boat was very clean, they had a speaker if you want to hook up your music. It was worth the money and a awesome day to celebrate someone’s birthday 🥳

Thank you Jessica and Captain Krista for helping me with my proposal. It was an amazing experience and you really made sure it was carried out exactly how I imagined. The day was beautiful and the ride was smooth. The boat was an absolute beauty and my fiancé and I had a great time. Captain Krista was so friendly and very accommodating by asking us for refreshments and giving me advice for when to propose with the best view. The proposal was executed perfectly. Thank you again!

I had an amazing time on this terrific sailboat with my friend! Such a great experience! The boat was so clean, and its 25 years experienced captain is so lovely. Jessica tries to make everything perfect to make your moment special with your loved ones. I'm looking forward to being on this boat again!

Had a beautiful birthday weekend! Jess was so helpful and made the booking process so easy and smoothly. Definitely would recommend and do another trip

this boat was amazing, we had a great time the captain made sure we got to see everything we wanted!!!

Had a great time sailing along New York City! Captain was patient and welcoming. 10/10 would recommend!

This was the most AMAZING experience!

We took a sunset trip around the city for my GF's bday. Jessica was very helpful with questions I had setting things up. Capt Krista was so knowledgeable and friendly, couldn't have asked for a better Captain. We had such an amazing time.

If you're thinking about doing this, DO IT!! It's an unforgettable adventure.

What an amazing experience! The sunset cruise was the perfect way to celebrate. Our group of 3 adults and 1 child had an exceptional evening. The boat is stunning - comfortable and clean. Capt Krista is competent, thoughtful and courteous. We did not want the evening to end and are already planning to sail again soon. I highly recommend booking a sail on Islander.

We had a phenomenal time on this boat. It thoroughly exceeded our expectations. Krista was an incredible and very kind captain.

I highly recommend the sunset trip. You will see New York harbor in a totally new light. I cannot overstate how gorgeous the skyline is.

Great trip, Krista was so helpful and amazing!

Jessica was very nice to work with. Thanks for making my husbands 40th birthday 🥰. Captain Krista was amazing. Looking forward to doing it again in the spring.

Excellent trip. Super sweet and friendly captain. Very family friendly. Beautiful boat.

The boat was better than the pictures and really clean! We had a great time and the view was AMAZING and the captain was so nice! Would definetly recommend!

This yacht was all around perfect in every way, there is nothing to complain about. Our captain Krista was phenomenal and always made sure my group & I were accommodated, took pictures of us & gave a an beautiful tour of NYC. Definitely planning my trip to relive this amazing experience again.

We had an amazing time sailing with Capt Krista! She was very friendly and accommodating and the boat was beautiful! We appreciate all the amenities they had aboard the boat. Booking with Jessica was very straightforward and east and I really appreciated how quick she was to respond to my questions. I definitely would recommend this for anyone looking for a daytime adventure with beautiful views. We would love to sail with you again in the future! Thank you for a great day!

Jessica was great to work with, open communication and prompt responses during the booking process.
Capt Krista was excellent - and managed our evening brilliantly - maximized our time on the water - and got us to dock seconds before a thunderstorm. She even voluntarily took great pics of our group on the lovely boat.
Highly recommended!

Best experience ever especially for the proposal. The Captain was great clean boat and very helpful. It is memorable moment and the price was great.

Captain Krista was amazing! We had a lot of fun with her. 10 out of 10! Highly recommend!

everything was so surreal! Krista knows exactly what she’s doing!

FABULOUS TRIP! CAPTAIN KRISTA WAS AMAZING! We had a blast. Clean boat, comfortable setting! We were in our own little paradise and world! Loved it! Doing it again for sure!

Captain Krista was amazing! She made our experience one of a kind and made it feel like it was our own personal boat. I appreciate her time in taking pics of my husband and I . She didn’t have to but she was more than willing . The boat was gorgeous. Just as the picture. Overall great experience. Would do it again for sure!

Krista was a fantastic Captain! We felt safe and she was very accommodating and helpful. We could tell she had years of experience and was a pro! We all had fun and Captain Krista made sure we were safe and no one was sea sick. She took the birthday girl to the best spots for photos too! Thanks Krista for making sure we came back safely to the marina with nothing but fun filled memories!!

Capi Mike is great! He is professional and kind. The birthday sailing was memorable!

We had trip on August 8th 2020 with captain Krista and her boyfriend. It’s was a lot of fan. They took us in Sandy Hook beach in New Jersey, we jumped from boat, cooked barbecue and just simply enjoy the view and weather. Definitely will rent this boat again! Thank you captain Krista and her team to gave us such high service 🤗😀

Truly a 5-star experience. The boat was in like-new condition, the owner was helpful and responsive throughout the booking/planning process, and Captain Krista was skilled, safety-conscious, patient, communicative, flexible and cheerful. Highly, highly recommended!

Captain Krista was so polite and very knowledgeable!
She made the experience all the better!

The boat was very clean and well maintained. Will definitely have to book it again!

Jessica and Captain Krista were amazing. Captain Krista was so incredibly nice and accommodating and was able to schedule around a pending thunderstorm. We all were very comfortable aboard, and Krista made the experience so much better and unforgettable even taking group pictures for us at one point. I would recommend this 100 times over, thank you so much!

Had a fantastic time celebrating my birthday. Cruised to Brooklyn Bridge and Statue of Liberty. Boat was gorgeous and Krista was the absolute best - so good at her job and attentive to us. Would recommend in a heartbeat!!

An amazing evening with such a beautiful view. We were celebrating a 30th birthday and it was everything we expected plus more. Very easy to book and the Captain Krista was very helpful/attentive. Cannot wait to book another tour.

Amazing time ⭐️⭐️⭐️⭐️⭐️Thank you

I’ve been on many boats before but my experience with Jessica was by far the most amazing time! She was so attentive so respectful so outgoing also the boat itself is stunning! The photos do it no justice! Jessica was the best host she met us in the parking lot, offered to help with the luggage and gave us a tour of the boat

Awesome!! Krista is super nice! Great experience!

Truely a fantastic New York experience! We had Captain Katrina and she was just so pleasant. Would 100 % recommend these guys. Super nice boat. Very professional. Clean.
Just perfect.

The experience was beautiful . My boyfriend enjoyed it! I was very pleased and the captain was super friendly.

Captain Mike made us feel welcome as soon as we got on board. We had very specific requests regarding where we wanted the boat to be at certain time with sunset coming on - we had photographers and make up artists and models on the boat and they are not the easiest to please - but he great in doing everything possible to get the locations we wanted. The boat was clean and new and very nice overall. Thanks!

Great Trip! Great Captain, Highly recommend!

My birthday trip was amazing!! Krista was the best! We will be booking again!!

Loved every minute of it. Great Captain, Great Boat!

This was the BEST experience ever! Captain Krista was amazing, attentive, & FUN! Jess was very responsive and easy to contact. The boat is beautiful, well maintained. We will definitely be booking again.

It was a wonderful trip on a beautiful day. Both Jessica and her crew were attentive and professional. The boat was clean and well maintained with PPE available

Boat was awesome! We had a storm the night of our trip, but both the captain and owner were flexible and communicative. We were able to push back the boat time in order to avoid choppy waters. We brought wine and food- there was a table that pulled out so the 6 of us could enjoy. The captain was careful navigating the choppy storm water/wind.

I found both Jessica and her staff to all be very accommodating and responsive. We had a wonderful trip the boat was clean. Staff appropriately wore masks and sanitized the boat and equipment, and remained socially distanced, yet still attentive. It was wonderful and I definitely plan to book again.

Great afternoon on the water. My kids really enjoyed the sailing experience and learning from Krista. I would highly recommend this boat and captain.

Awesome!!!

This experience was perfect! I could not have asked for a better day. Our captain for the boat was very attentive and extremely sweet ! Her communication was excellent and made sure everything was safe and comfortable for us! Thank you so much again for this amazing time and a perfect Sunday.

Our boat trip was amazing. From the beginning Jessica was super responsive and easy to talk to before booking. After we booked she sent over all the details which made everything so smooth the day of the trip. The Captain, Micheal, was very nice, respectful and most of all very patient with our little one. He was very easy to get along with and answered all our questions. The boat itself is very beautiful, clean and comfortable. We went on a sunset ride and it was absolutely gorgeous. Would definitely recommend booking with the Islander.

It was my best birthday ever! What an incredible experience! Capt Krista was amazing! Thanks a lot!

I reserved this amazing boat for Father’s Day, a party of 6 and when I tell you the experience is unbelievable!! The views, the hospitality, the boat, the winds & even other boat riders along the way ! Who would of thought you don’t even have to go to Miami to get this type of VIEW here into own City .. amazing!! The owners of the boat names are Jessica and Michael and what a coincidence that my fiancé and I names are Jessica and Michael haha ! We’ll be back again :)