Picture yourself aboard a private yacht gracefully gliding through the pristine waters of Sag Harbor, New York. As the wind caresses your face, you’ll find yourself immersed in a world of awe-inspiring beauty and endless fun. Sailacat invites you to experience the ultimate luxury of a private yacht sailing charter, where breathtaking sights, thrilling activities, and lifelong memories await.
Sag Harbor is not only renowned for its rich history, but it also boasts an array of remarkable attractions. As you set sail, you’ll be greeted by the captivating sight of Sag Harbor’s historic whaling port, a reminder of the town’s fascinating past. Take a moment to soak in the ambiance and imagine the tales of sailors past, as the echoes of history surround you. But it doesn’t end there. Our private yacht sailing charter offers an extraordinary opportunity to explore hidden gems and secret beaches that are only accessible by boat. Dive into the crystal-clear waters and discover a vibrant underwater world with snorkeling adventures, where colorful marine life thrives beneath the surface. Alternatively, grab a kayak and paddle your way through the calm waters, exploring serene coves and hidden inlets that hold the promise of untouched beauty.
Sailabrate Summer 2023 with Sailacat, the Hampton’s most sought-after Sailing Yacht Charters! We offer fabulous summer sails for 2 -12 guests from mid-June through Labor Day.
Start the season with a 2-hour midweek special Romance cruise around the Harbor with complimentary signature cocktails. These romantic sails are 2-4 hours, from $1850.
A relaxing sunset sojourn aboard Serenity will set the tone for your best summer ever! Our award-winning 4-hour sails, with a beach break and swim time, are available on weekends and during the week.
Trust our experience and reputation for your special occasion. Team Serene welcomes you aboard as guests, but you’ll leave as cherished friends. Join us! Rates & Dates : 631-682-8288
Mid-June to early September, the Hamptons shine. Sailacat’s dedicated sail team believes customer service is everything. We invite you to experience the difference. Sailacat consistently wins traveler’s choice awards and certificates of excellence, year after year. No other charter company comes close. From mid-June to early September, team Serene is ready to show you and yours the best the Hamptons offers. Everyone’s welcome. It’s time to Sailabrate!
Our Best Seller…
4 hrs : 10 – 2 pm, 4 – 8pm | 2 & 3 hour Sailing charters do not include the optional beach break. Rain dates are rescheduled at no charge at the discretion of the Captain.
Longer custom sail adventures : 5 -6 hours, upon request. Please call for availability .
A 50% non-refundable deposit holds the date. Rates, dates & times are subject to change without notice. 20% service fee additional.
Sailacat offers both full shade and full sun options onboard, as well as complete facilities. The Yacht has been fully customized for your comfort. Sailacat Charters are ideal for special occasions with loved ones, including Birthdays, Anniversaries, Proposals, Bach parties, & Family reunions. Your adventure awaits!
What to Bring: All your friends! Nibbles and drinks, swimsuits & towels, sun lotion, no spray lotion it stains decks and makes decks slippery. Hats that stay on, your favorite bluetooth music , for our bluetooth speaker.
What is Included: Licensed Captain, PFD’s, water toys, and a giant cooler with fresh ice.
NYS Law: Children under 12 must wear PFD’s aboard.
No smoking – No vaping No drugs.
Kal and Bri are amazing and Serenity is a beautiful, clean, well kept boat. My husband and I wanted to kick off our vacation with a sunset cruise and we... read more had such an amazing time that we came back 3 days later with our toddler. The catamaran is great for couples or families.
Boat Trip - Favorite part of my experience was getting engaged on her boat! Captain Kal was so accommodating and enthusiastic through the whole trip! Even broke out some personal celebratory drinks! Would... read more recommend to anyone!
This was our first voyage on the aptly named Serenity. We were with 11 friends for a Saturday afternoon birthday celebration sail. We had a spectacular day! Perfect weather, swimming... read more in crystal clear water and paddle boarding only to be topped off by a gorgeous sunset. What made it so unique were our hosts, Capt. Kal and Brian. Capt. Kal is from the area and knows it inside and out. She handled the boat with ease and had everyone's safety in mind. Brian is clearly an expert seaman as well & both have had quite an adventurous life ( Ask Brian about his experiance with a bull shark).
I agree with the reviewer who stated that Kal and Brian do everything possible to make everyone feel at home. We did feel like they were family by the end of the trip!
Also agree that Brian was always at the ready with food and drink refills. We highly recommend Sailacat. It will be the highlight of your Sag Harbor vacation.
BEST DECISION WE MADE! - My friends and I visited Captain Cal and Brian aboard the Serenity this June for my Bachelorette and it was the best day of the trip! They went above and... read more beyond to accommodate our requests and blended right into our group as part of the party. I highly recommend you book the Serenity to make your vacation unforgettable! We can’t wait to book with Captain Cal on our next trip!
Highlight of our Annual Family Hamptons Trip! - I absolutely cannot recommend Sailacat enough!!! Our now annual charter with my family is the absolute highlight of our year!
The first year we just booked the two hours,... read more which was lovely, but not nearly enough! This year we booked four hours...and STILL extended for ANOTHER TWO hours!!!...just didn't want the day to end!
I also brought a group of friends, who had the most amazing time (not to mention the PERFECT backdrop for Tinder profile pix! ;-)) !!!
Though completely professional and extremely skilled, Capt Kal and Brian really do everything possible to make everyone feel at home and like family. They'll even teach a thing or two to any guests interested in learning about sailing, or participating in the sail.
The cat is perfectly maintained, and we all adore chilling out on the beanbags, and of course netting, where you feel as if flying, midway between sea and sky...I can't think of anything else that provides such a feeling of Zen!
We love the water toys such as paddle boards, noodles, and most of all the 'floating bar' to hold your drinks whilst in the water! My 77 year old mother now experiences balance and swimming challenges as the result of several surgeries, so Brian was gallantly yet discreetly always at the ready to help her around the boat, in & out of the water, along with suited up well to be safe & comfortable in the water....we're also not complaining about his dedication to ensure guests' drinks were never empty!
This year, unfortunately the date I'd initially selected was naturally the ONLY day of the week with poor weather, and they couldn't have been more accommodating to reschedule a suitable rain date.
Also worth mentioning, is the primary reason I'd initially selected a catamaran as opposed to other types of boats, is that some of our guests can get seasick. Given a catamaran is more stable by nature, and Sailcat sails the LI Sound, as opposed to the ocean, not a single one of our guests has ever experienced any issues.
If you're looking for the perfect climax to your Hamptons visit, then do not look any further!!!!
A must do!! - Hands down an amazing experience!! Captain kal and brian were a pleasure to work with and made the entire sunset sail/evening so much fun for my sisters bachelorette party. The... read more perfect day on the water in their beautiful boat!! Will absolutely be doing it again!
It's like a massage for the mind. - We made a birthday celebration an event never to be forgotten by taking it abroad Serenity for an evening cruise with Kal and Brian as our hosts and captains. The... read more sun setting and beautiful quiet bay waters were only disturbed by our laughter and the popping of corks. As a captain myself, I must admit, I have never been as comfortable under sail as sitting on Serenity's bow in those luxurious bean bag chairs. This could become habit forming....and I highly recommend that is should!
The BEST sailing trip, period!! - I always do a lot of research before I book anything, and this is why. Kal and Brian gave us the best sailing trip of our lives. They make everything... read more effortless and relaxed and fun. We spent the afternoon sailing across the bay, stopping in a gorgeous cove off of Shelter Island to swim (and use pool noodles and their stand up paddle boards). And then when we had our fill of swimming, we had a long meandering sail back to the harbor, where we sat in the comfortable bean bag chairs near the bow and watched the beautiful sunset. Kal and Brian are such thoughtful and attentive hosts and their boat, the Serenity, is beautifully appointed and maintained with lots of details that show the level of care they put into every aspect of the trip. Their genuineness and passion for what they do is hard to find, and elevates the entire experience to something truly special. Don't look further, this is really as good as it gets!
P.S. Take their advice about where to stop for sandwiches before you board! They know what they are talking about.
Highlight of our Annual Family Hamptons Trip! - I absolutely cannot recommend Sailacat enough!!! Our now annual charter with my family is the absolute highlight of our year!
The first year we just booked the two hours,... read more which was lovely, but not nearly enough! This year we booked four hours...and STILL extended for ANOTHER TWO hours!!!...just didn't want the day to end!
I also brought a group of friends, who had the most amazing time (not to mention the PERFECT backdrop for Tinder profile pix! ;-)) !!!
Though completely professional and extremely skilled, Capt Kal and Brian really do everything possible to make everyone feel at home and like family. They'll even teach a thing or two to any guests interested in learning about sailing, or participating in the sail.
The cat is perfectly maintained, and we all adore chilling out on the beanbags, and of course netting, where you feel as if flying, midway between sea and sky...I can't think of anything else that provides such a feeling of Zen!
We love the water toys such as paddle boards, noodles, and most of all the 'floating bar' to hold your drinks whilst in the water! My 77 year old mother now experiences balance and swimming challenges as the result of several surgeries, so Brian was gallantly yet discreetly always at the ready to help her around the boat, in & out of the water, along with suited up well to be safe & comfortable in the water....we're also not complaining about his dedication to ensure guests' drinks were never empty!
This year, unfortunately the date I'd initially selected was naturally the ONLY day of the week with poor weather, and they couldn't have been more accommodating to reschedule a suitable rain date.
Also worth mentioning, is the primary reason I'd initially selected a catamaran as opposed to other types of boats, is that some of our guests can get seasick. Given a catamaran is more stable by nature, and Sailcat sails the LI Sound, as opposed to the ocean, not a single one of our guests has ever experienced any issues.
If you're looking for the perfect climax to your Hamptons visit, then do not look any further!!!!
Amazing Experience - This is my second voyage with Captain Kal and it did not disappoint! Her boat is spotless, she makes you aware of everything in case of an emergency, and always... read more encourages us to have time of our lives. Can’t wait to do another!
Kal and Bri are amazing and Serenity is a beautiful, clean, well kept boat. My husband and I wanted to kick off our vacation with a sunset cruise and we... read more had such an amazing time that we came back 3 days later with our toddler. The catamaran is great for couples or families.
Boat Trip - Favorite part of my experience was getting engaged on her boat! Captain Kal was so accommodating and enthusiastic through the whole trip! Even broke out some personal celebratory drinks! Would... read more recommend to anyone!
This was our first voyage on the aptly named Serenity. We were with 11 friends for a Saturday afternoon birthday celebration sail. We had a spectacular day! Perfect weather, swimming... read more in crystal clear water and paddle boarding only to be topped off by a gorgeous sunset. What made it so unique were our hosts, Capt. Kal and Brian. Capt. Kal is from the area and knows it inside and out. She handled the boat with ease and had everyone's safety in mind. Brian is clearly an expert seaman as well & both have had quite an adventurous life ( Ask Brian about his experiance with a bull shark).
I agree with the reviewer who stated that Kal and Brian do everything possible to make everyone feel at home. We did feel like they were family by the end of the trip!
Also agree that Brian was always at the ready with food and drink refills. We highly recommend Sailacat. It will be the highlight of your Sag Harbor vacation.
It's like a massage for the mind. - We made a birthday celebration an event never to be forgotten by taking it abroad Serenity for an evening cruise with Kal and Brian as our hosts and captains. The... read more sun setting and beautiful quiet bay waters were only disturbed by our laughter and the popping of corks. As a captain myself, I must admit, I have never been as comfortable under sail as sitting on Serenity's bow in those luxurious bean bag chairs. This could become habit forming....and I highly recommend that is should!
BEST DECISION WE MADE! - My friends and I visited Captain Cal and Brian aboard the Serenity this June for my Bachelorette and it was the best day of the trip! They went above and... read more beyond to accommodate our requests and blended right into our group as part of the party. I highly recommend you book the Serenity to make your vacation unforgettable! We can’t wait to book with Captain Cal on our next trip!
The BEST sailing trip, period!! - I always do a lot of research before I book anything, and this is why. Kal and Brian gave us the best sailing trip of our lives. They make everything... read more effortless and relaxed and fun. We spent the afternoon sailing across the bay, stopping in a gorgeous cove off of Shelter Island to swim (and use pool noodles and their stand up paddle boards). And then when we had our fill of swimming, we had a long meandering sail back to the harbor, where we sat in the comfortable bean bag chairs near the bow and watched the beautiful sunset. Kal and Brian are such thoughtful and attentive hosts and their boat, the Serenity, is beautifully appointed and maintained with lots of details that show the level of care they put into every aspect of the trip. Their genuineness and passion for what they do is hard to find, and elevates the entire experience to something truly special. Don't look further, this is really as good as it gets!
P.S. Take their advice about where to stop for sandwiches before you board! They know what they are talking about.