Based in Jersey City (NYC pickups available), Sailing Islander the most modern luxury sailboat charter in NYC. She is an exceptionally well-maintained and immaculate boat, proudly offered by the only woman-owned charter company in NY Harbor.
We invite you to enjoy Islander's fresh, bright and spacious accommodations...and of course breathtaking views from the harbor!
Host up to six guests on your own private yacht! BYOB beverages & snacks and come sail the epic city sights. The perfect outdoor escape for relaxation with family and friends!
Depending on the time of day, you can experience The Morning Mimosas (owner's fav), The Unforgettable Day Sail, The Sensational Sunset Sailing Tour or The Bright Lights Evening Tour (great after dinner). Take in the glorious Statue of Liberty, NYC's magnificent skyline, Brooklyn Bridge & more.
Ask us about our custom 8-hour day trips to the beach. Sail away for some sun and swim off the boat and beach, enjoy our water toys and paddleboard - and then we arrive back to NYC as the sun sets! An amazing day!!
Islander is a new, modern Beneteau Oceanis 35-foot sailboat, fully equipped for up to six guests. She is the newest, most beautiful boat in the entire NY Harbor rental fleet. Enjoy Islander's multiple entertaining and lounging spaces, outside in the cockpit, up on deck on our overstuffed beanbag and inside her bright, spacious salon. Plug your own music into our sound system. Equipped with a full kitchen and bathroom, Islander allows you to relax in comfort and convenience on the water.
We welcome you with bottled water and sodas and invite you to bring your own food & beverages (BYOB). We offer a Yeti cooler and provide flatware/plates/cups for your use. Islander is a STRICTLY 100% NON SMOKING vessel for the health and safety of all our guests.
Our private sailing tours are a creative venue for special celebrations & milestone moments, such as anniversaries or birthdays. Or an inspiring venue for exclusive corporate events and client entertaining. Islander is also the perfect romantic setting for a sunset marriage proposal!
Book your escape today & come sail away on Islander!
Prices will vary by season and duration and we can customize an event to meet your needs. Please inquire directly through "Message Owner" for exact pricing for your perfect private charter.
Weather Policy: We want your experience on Islander to be exceptional, so if we get bad weather (heavy or sustained rain/lightning) then we will work with you to reschedule your charter. If it is just brief light rain, our guests usually use that time to get under the bimini, grab a drink from the fridge, a snack, adjust the playlist and then back to the fun.
Kids are very welcome on Islander! All kids 12 and under are required by law to wear a life jacket. We have "cool" kids versions that they usually don't mind wearing. Kids also get colorful sailor hats and we will have them soon driving the boat. Our bathroom onboard and multiple lounging areas, indoors and outdoors, makes it convenient for families!
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.
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.
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.
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 :)
Member since June 2020
Hello, I’m Jessica, owner of Sailing Islander! I’m very proud to be the only woman-owned private sailing charter business in NY Harbor.
I invite you to experience sailing on Islander, a beautiful new, modern sailboat, which is immaculate and offers every comfort you could want. We welcome you aboard with complimentary bottle water and sodas. We invite you to bring your own food and beverages (BYOB) and encourage you to relax and make yourself at home. Enjoy lounging in our multiple entertaining spaces, both in the cockpit, on the deck and inside the spacious salon - which also offers a full kitchen and bathroom for your use. Plug in your music and kick back and enjoy the epic sights!
Join us for milestone moments and special celebrations, like birthdays and anniversaries ...or celebrate just being together with family and friends, anytime!
Our licensed, highly skilled, expert and friendly Captain Krista was hand-selected by me to ensure that your cruise is of course safe, but also very fun! We receive fantastic feedback about not only the beautiful boat and experience, but of course Captain Krista! She is happy to also teach you a bit about sailing during your adventure, if you wish! Kids especially thrill at this!
Step aboard Islander and sail off to relax & reenergize!
Usually this boat operates around Jersey City, NJ.
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.