Into the details? We got you!

What sights will I see? Where do I go to board? What if it rains? How many guests can I bring? What if I arrive late?  Is there a bathroom? Can I bring alcohol onboard?

you've got questions, we've got answers!

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read our crews' rave reviews!
view 20+ most FREQUENT QUESTIons

"This is the best of the best sailing companies in NY, based on my experience. If you are looking for something magical and wonderful you should absolutely choose Sailing Islander. I was just speechless - the team is so professional they will make you feel like you are in a Hollywood movie."


"You guys are the best of the best"

Book Your Yacht Today!

don't miss your special date!

Why wait? There's is zero risk to book now for your special date. Cancel with full refund within 14 days of your sail. Sunsets and weekends go very quickly in the summer season in busy NYC: Sailing Islander will be a memory you and your crew will treasure for years!

We have the newest, most modern sailboat in NY Harbor and the newest, fastest powerboat on the Hudson River, providing bright and spacious surroundings for you to take in the epic sights.

Our yachts offer the next level of comfort, both indoors and out, with multiple lounging spaces, from the comfortable cockpits, outside on the decks and front bows and inside the spacious salons. Plug in/Bluetooth your own music to our sound system and rock out to what you wish!

The Sailing Islander Difference

New, Modern Yachts

Next-Level Comfort



We welcome you aboard with a complimentary selection of bottled water and sodas. We invite you to bring your own food and beverages (BYOB) and we provide drinkware/flatware. We also offer free Sailor’s hats to all children (take a fun photo while they "steer" the boat!) and a sparkly tote bag to remember your cruise!

Refreshments & Fun Gifts


We invite you to enjoy access to our entire yacht, including the inside lounging areas, galley (kitchen) and, of course, full head (bathroom) - so no worrying about this necessity, just relax and enjoy your time on the water! The only restricted space is the bedrooms.

Access Full Amenities


what sets us apart as the #1 yacht RENTAL in nyc?

Book your private yacht in three simple steps on our website

How does this sound?

Alert your fab five crew (max of six passengers) and start the countdown...




Assemble your BYOB - will it be Rose all Day or a cold beers? Consider picnic-style snacks.


Get your 48-hour advance email confirmation and share with Crew!


Grab your sunglasses, Yacht Rock playlist and step onboard for an epic experience!



"We were absolutely shocked and stunned at the beauty that we were able to witness on the Hudson River in this world-class sail boat."




"If I could afford to do it every weekend I would...I believe everyone should experience this at least once."





How It Works

Chose your experience (day cruise or sunset cruise), date and time. Book it before someone else does!


You will receive an instant email confirmation. Your spot is locked in. Inform your lucky guests!


48 hours before your charter, you will receive a personal email with Captain contact details. It's go time!



There are only 24 Saturday sunsets and 24 Sunday brunch spots available each season!

If your date is special, better book it now!

"At night the city looked like it was floating on water & the views were absolutely breathtaking…"

"We had an amazing time on Jessica’s boat & the Captain was very accommodating.  Made both my girlfriend & I cry it was so magical (and we’re not criers lol) The sailboat was very clean & we will definitely rent with Jessica again!" - ALEXANDRA, 5-star rating on GetMyBoat



Yes, Sailing Islander is that great! Read what our crews say...

"This has become a summer tradition for our group-we really loved the attention to detail on the boat."

"An absolute pleasure sailing on Jessica's lovely boat - and fab skill sets of the captain, who is fun & professional! The booking process with Jessica is an absolute breeze. Highly recommend this beautiful, private sailing experience to one & all around the NY harbor." - OLIA, 5-star rating on Yelp



"It is probably one of our favorite things we've ever done while visiting NY."

"Surprised my fiancé with sailing islander for his birthday and celebrating our engagement. I can tell you it is probably one of our favorite things we've ever done while visiting NY. We try to come to NY a few times a year and will absolutely be doing this again!" - CHRISTINE, 5-star rating on Yelp



"Ummm, yeah....I totally deserve this!"


"What an amazing experience!! Booked the 3-hour day tour for a family birthday celebration! The captain was punctual and great company. Our party of 6 fit perfectly in the front and back of the sail boat comfortably! IF you are looking for a unique experience in NYC area look no further :)"

— shannon, yelp

"for a unique experience in NYC look no further!"

"My girlfriend was over the moon with the proposal experience on Islander. Jessica guided me through the whole process and I felt relaxed and ready - what a memorable setting!"


"It doesn't get more romantic than this!"

"We had the incredibly unique New York moment of watching the fireworks on July 4 from vantage of this special sailboat - it was absolutely surreal!" 


"Truly a once in a lifetime opportunity!

Permission to come aboard & see her!

BYOB & sail NYC's epic sights in style with the only woman-owned private charter and #1 most popular private sailing experience in NY Harbor. The perfect spot to gather your crew and celebrate, Islander is the newest & cleanest sailboat in NY Harbor - host your guests in comfort and class as you sail the city sights.


Never been on a sailboat?

Sailing Islander was highlighted last summer as NYC’s only woman-owned private charter business. With great thanks to the CBS News NYC Crew and of course, our epic customers who shared their experiences Sailing Islander…including a proposal!

Watch our CBS News New York story to see Islander live in action!




Proposals on Islander - all YES!


Sailing seasons since opening in 2020


Guests and counting! Many repeat x2 or 3x!


5-star reviews!

Islander     for you if:






It's probably       for you if...




She's probably
for you if...

How much does it cost?

Our sailing experiences suit various budgets, depending on your schedule and your party size, starting as low as $400 for a specially priced 2-hour day sail for couples. We offer 2-, 3-, 4- or 8-hour day sails, sunset sails, evening bright lights sails and extended evening sails! See our pricing page for details.

Islander/Sailboat: Frequently Asked Questions

Will I be sharing the boat with other people?

Never! Your experience aboard Islander is always private and exclusive to just you and your five lucky guests. We don’t offer “per person” individual bookings to fill our boat. Islander is yours and yours alone!

Where do I meet the boat to get onboard?

You will board Islander at Liberty Harbor Marina in Jersey City, NJ - 100 Marin Blvd. - just 10 minutes from NYC by ferry or 15 minutes by PATH train. See easy directions on our contact page or click here for a map for GPS. We provide an email confirmation with all necessary details at your booking - as well as an email the day before your charter with your Captain’s name and number. Please text or call your Captain upon arrival at the Marina, and they will greet you at the Marina main house and escort you to Islander on her dock. For driving or via Uber, please set your GPS to 100 Marin Blvd. to reach our lot right in front of our dock (“M DOCK”). For PARKING for your car(s) you will need to first drive (or walk) about half a block further up Marin Blvd. to the Liberty Harbor Marina office (white trailer on your right at end of street/security guard can guide you) to buy a parking pass for your car(s). They are $5 each. Place it on your dashboard. You can then return to the private parking lot at 100 Marin Blvd for parking closer to the boat. 

What if I am late for my tour?

Guests are requested to arrive 10 minutes early for their tour to ensure an on-time departure. Any amount of time you are late will reduce your booked time. For example, if you book a 2-hour sail and are 30 minutes late, we can only make the duration of the voyage 1 hour and 30 minutes. This policy is created with respect to keeping other tours on time for guests who have voyages later in the day. Please keep in touch with your Captain if you are running late.

Is there a bathroom I can use on the boat?

Absolutely! A full bathroom (on a boat it is called a “head”) is available and you are welcome to use it. Unlike some other charters, we appreciate that when you have to go, you have to go :) and we don’t want you to be uncomfortable at any point during your journey. Ours is a modern, electric marine toilet.

Should I tip the Captain?

That’s very kind of you to ask! A gratuity (12-15%) for excellent service is common in the tour business - and, moreover, greatly appreciated by our hard-working crew. If our Captain has delighted you with an exceptional experience, they will be grateful for a tip/gratuity! You can add to booking in advance or cash is always welcome!

What is the cancellation policy?

Guests may cancel up to 14 days before the tour date to receive a 100% refund minus a 10% service fee. Cancellations made fewer than 14 days before tour date will be able to rebook/reschedule the cruise within one year, but will not be refunded. Operator cancellation, due to severe inclement weather or mechanical issues, will be rebooked/rescheduled at no additional charge. Read our detailed weather policy (below), as Operator - not guest - will make the judgment on inclement weather cancellations. 

What if the weather is bad or rainy during the day/night of my sail?

The Captain (and only the Captain) will make the call as to whether a tour is cancelled due to inclement weather. We will proactively reach out to you as far in advance as the forecast allows. We do continue to sail in hot, humid weather. As for rain, we want your experience on Islander to be exceptional - and that does not mean forcing you out on a rainy day. If it is raining the few hours prior to your charter, we are happy to rebook/reschedule the cruise within one year, but it will not be refunded. If you wish to continue with the cruise, Islander comes equipped with a very large bimini (cockpit cover) and we also welcome you to enjoy our bright, spacious inside lounging area. If the National Weather Service declares a small craft advisory, or if we otherwise expect excessive wind or rain, we reserve the right to cancel a tour for the safety of our guests.

Where does Islander sail to?

Islander can go wherever you like in New York Harbor - it’s really up to you! However, to see many of NYC’s famous landmarks and iconic sights, the Captain most typically sails Islander across the Hudson River, down past the Statue of Liberty, over to Governor's Island and up the East River, passing under the Brooklyn Bridge. On Islander, we customize our cruise, so if you want to spend more time in and around a particular spot, just let the Captain know.

Is sailing safe? Do I need to wear a life jacket?

Leisure sailing is a very safe activity, happily enjoyed by thousands of people around the world! With a basic level of common sense, you can relax and completely enjoy your time on Islander, even sitting up on the bow, which we encourage! Islander is a very safe and secure, modern sailboat with all the conveniences of the latest technology, and is fully equipped with all US Coast Guard safety equipment and a life raft. Moreover, Islander’s Captain is highly experienced, with a USCG Master license and thousands of hours sailing New York Harbor. Your sailing experience will begin with a brief, but important, safety review on basic and essential precautions. Lifejackets are available/provided for all guests - but they are REQUIRED by New York and New Jersey state law for children age 12 and under.

Can I play my own music?

Nothing goes better than pairing your favorite music with a relaxing sailing voyage. Islander is equipped with a great sound system and you can Bluetooth or plug directly into our system, which will play your music outside as well as inside the cabin/salon space. 

Can I smoke on the boat?

We invite you to have a smoke before coming aboard Islander, as smoking of any kind is NOT permitted on Islander. Additionally, Islander has a zero tolerance policy for drugs of any kind. This includes usage by those in possession of a medical marijuana card, which will still not permit drug use aboard Islander. The US Coast Guard does not recognize any flexibility to this rule, regardless of state law. We will immediately return to the dock and conclude the sail if drugs are discovered aboard - with no refund for time not used.

Can I bring my dog aboard?

We love dogs (and cats!) but no animals of any kind are permitted on Islander.

Can children come sailing?

Absolutely: We even give complimentary Sailor’s hats to all “Mini Crew of Islander” and invite you to take a fun photo of them while they enjoy “steering” the boat! Children will thrill with the experience of sailing on Islander! We love children and welcome them warmly, however in the case of very small children, it is of course essential that parents/guardians monitor them at all times, in particular, moving about the boat. Lifejackets are required for children age 12 and under, by state law.

Can I take photos while underway sailing?

You will be sailing past some of the most epic and iconic sights in America - OF COURSE you can take as many photos as you wish! There will be plenty of Instagram-worthy moments as we sail past such iconic sights as the Statue of Liberty, Brooklyn Bridge, the downtown skyline and more. 

Why is there a maximum of six passengers permitted?

The US Coast Guard prohibits passenger boats of Islander’s size from carrying more than six passengers (in addition to the Crew) at any time. This applies to most private boat charters in NY Harbor. There are larger boats available (per ticket, by person), taking hundreds of guests, but you lose the intimacy and exclusivity of having your own private tour and will often encounter the crowded experience - from which we want to take you away during our relaxing sailing excursions. So treat yourself and up to five more family and friends to this iconic experience!

What kind of food can I bring on Islander?

You are welcome to bring whatever snacks and beverages (alcoholic or nonalcoholic) as you wish. We encourage you to think “picnic-style” for your food choices - finger foods and snacks that can be easily eaten on a moving boat. Large tinfoil food trays take up precious space and won’t stay in place as the boat moves. Simple foods are best. We provide a Yeti cooler, drinkware and can supply limited ice upon request. We also provide a complimentary selection of bottled water and sodas for every charter. 

Can I bring alcohol onboard?

You are welcome to bring any additional snacks and beverages (alcoholic or nonalcoholic) as you wish. Please no red wine, due to the high potential of stain damage while drinking on the moving water! We provide a Yeti cooler, drinkware and limited ice. Please note, the Captain will request ID from guests, as needed - no drinking is permitted by anyone under age 21.

Will I get sea sick?

Feeling seasick during a short charter around New York Harbor is rare for our guests. However, the Harbor is quite active with ships and ferries, so it will not be “smooth as glass.” You can expect to feel movement. If you are prone to motion sickness, we recommend Dramamine, or a similar type medication, available at drug stores all over the city. Or you may wish to purchase the “Sea Band” online. It is important to take the medication in advance of boarding - meaning BEFORE you get to the tour. These medications do not work if you take it “in the moment,” after you begin to feel sick.

Should I wear any special clothes for sailing?

No special clothes are required for sailing - though we will ask you to remove your shoes upon boarding and wear just socks or go barefoot, that’s the Islander way! High heels or other types of shoes can cause damage to the boat. Also, depending on weather, we of course encourage appropriate jackets, or sweaters/sweatshirts. We provide cozy blankets for use in the outdoor cockpit, should it be chilly.

Can I help sail the boat?

We are happy to teach some of the basics of sailing during your tour - and of course give you a turn at the wheel! Upon request (certainly never an obligation!) you can also participate in operating the sails, adjusting lines (ropes) or helping with fenders/dock lines upon departure and arrival. All of our USCG Captains are also ASA Sailing Instructors, so feel free to use the experience to learn some new skills. We welcome you to be involved as much or as little as you wish!

Can I swim in the water from the boat?

Swimming in NY Harbor is strictly forbidden by the US Coast Guard. But if you wish to engage Islander on an extended full-day sail, we can certainly take you to nearby beaches, where we can anchor. There, you can swim, or enjoy our paddle board, water toys and floating beanbag raft.

Will I have fun sailing?

Without a doubt you will have an epic experience on Islander! Sailing is an energizing and yet serene activity, and we predict that once you try it for the first time, you will want to experience it again and again! So, YES, absolutely you will have fun sailing - and generally, you will be thrilled to absorb the sights, sounds and action around you in New York Harbor. It will provide you with the memories of your trip to NYC that will last a lifetime.

I loved my experience! Can I give the gift of sailing on Islander to someone else?

Yes! We agree - a sailing experience is the perfect gift! Consider a gift certificate for that newlywed couple, top performing team at work, or as a special surprise to help someone celebrate a milestone occasion, such as an anniversary or birthday. You can tailor the gift to any amount, or purchase an experience from our menu of options. See our pricing page for selection and purchase.

Wait - I have other questions!

Great! I have answers! Please just reach out to me on email or text us at 646.866.8549. I am happy to address any questions you have :)


What are you waiting for? Grab your crew and some bottles and BOOK YOUR SAIL TODAY!

If not now, then when?