When asking yourself about something to do near me in New York with a group of friends or family, consider
True Sailing
Why True Sailing is a fun option when searching for things to do near me with friends and family
True Sailing offers a unique and personalized sailing experience that caters to individuals and groups seeking memorable outings on the water. Founded in 2017 by Captain Nate, True Sailing began with a vision that sailing should be accessible, fun, and engaging for everyone. Capt. Nate's passion for sailing traces back to his childhood summers spent on Lake Winnipesaukee, which informs his approach to creating exceptional sailing adventures. Originally based in New York City, True Sailing later relocated its operations to the Hamptons, specifically the quaint sailing town of Sag Harbor, offering a serene setting that complements the experience. The business specializes in customized day charters, ensuring that each sailing trip is tailored to the specific needs and desires of its clients, making each outing flexible and unique. True Sailing places a strong emphasis on sustainability; their sailboats run on environmentally friendly wind power supplemented by solar panels, and they maintain a rigorous waste management plan to minimize pollution. In addition to offering sailing excursions, True Sailing provides yacht management services, with Founder Nate personally overseeing all aspects including maintenance, deliveries, and shipyard projects. With a focus on professionalism, expert navigation, and personalized care, True Sailing creates a welcoming atmosphere perfect for meeting friends, celebrating special occasions, or learning to sail in an eco-conscious manner.
Here's what people think of True Sailing
As of recent, True Sailing holds a 4.8-star rating based on 39 reviews.
User reviews of True Sailing consistently highlight the exceptional quality of the sailing experience and the professionalism of Capt. Nate and his crew. Guests have praised the beautiful and comfortable boats along with the warm, friendly, and knowledgeable nature of the captain, which contributes to a welcoming and enjoyable atmosphere. Many reviewers note the scenic routes taken, with many memorable views around the New York Harbor and the Hamptons. Positive reviews often cite the personalized attention and flexibility in tailoring the sailing trips that cater to various group preferences and occasions. Guests feel that the experience exceeded their expectations and many express eagerness to return for future sailing adventures. On the other hand, negative reviews are minimal and infrequent, with no significant recurring complaints. Any minor concerns tend to revolve around availability or scheduling during busy periods, but these do not appear to affect the quality of the experience once on board. Overall, the high rating of 4.8 out of 5 based on 39 reviews reflects a strong customer satisfaction and a well-regarded reputation for True Sailing. The reviews collectively underline True Sailing’s commitment to making sailing an accessible, sustainable, and memorable experience for all its clients.
Highlights from reviewers (Most Relevant)
jeunesse awad
I've been chartering with Captain Nate in Sag Harbor and the USVI for years, and every time I book a trip, it's always an unforgettable adventure. He's very detail-oriented -- some may even say calculated. If you're looking to be adventurous he'll take you to a hidden gem. If you'd prefer a chill night in town, at a local restaurant or bar he'll recommend the best spots. AND THE CREW! The crew is always the best part; from the deckhands to the chefs I've enjoyed many meals and made new mates.
Nina Kuntz
This U.S. and British Virgin Islands sailing trip was a dream. The boat was so luxurious, like a 5-star hotel, and the week was a perfect mix of fun and relaxing. I drank an iced coffee every morning while tanning and admiring the natural beauty of the USVI/BVI coves, and would spend the rest of the day sailing, swimming to the nearby beaches, snorkeling, and relaxing on one of the boat’s many decks. Captain Nate is wonderful. I was traveling with a small group of women and we felt super safe and comfortable around him the entire time. 100/10 would recommend
Emma Hines
With Captain Nate we went on a Charter in the Caribbean for one week and visited many different islands. He knows the islands so well and picked out the best anchorages, restaurants and hikes for us. The captain for sure knows what he's doing and you can tell that sailing is his big passion. Looking forward to the next Charter in May with True sailing (and the new drinks and snacks catering service!😍)
Joseph Pollarine
The 2-hour cruise around lower Manhattan was amazing. Captain Nate is not only a great captain, he is also the kind of guy you can have a drink with afterwards. From the minute he meets you at the dock he is warm and inviting and you can tell he loves what he does and he wants you to love it to. I love taking photos and Nate was very accommodating making sure he got me to the best places to shoot an epic sunset over lower Manhattan. This honestly was one of the best experiences I have ever had and I can’t recommend it enough. It is worth every penny!
Katy Hunter
We are so happy we chose to book with Nate! The communication was clear and concise, we knew exactly where to go when our trip came! Nate and crew were beyond accommodating and the boat is so charming! This made our trip so special!
How to reach True Sailing
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Why True Sailing may become Your Favorite Meetup Place for Catching Up, Celebrating or Just Hanging Out
Why rally at True Sailing with your friends?
Gathering your friends for an unforgettable day can be a challenge—finding a venue that combines excitement, relaxation, and shared experience is key. True Sailing in the Hamptons offers exactly that: a perfect blend of adventure and leisure on the water, tailored for groups seeking a unique way to connect. With its outstanding 4.8-star rating from nearly 40 reviews, this sailing charter is not just a trip; it’s an experience that invites camaraderie and celebration under the open sky. From the moment you arrive, you are welcomed with drinks and refreshing cold towels, creating an atmosphere that is both uplifting and welcoming. The personable captain and crew make everyone feel at ease, balancing professionalism with a laid-back vibe. This ensures that whether you’re an experienced sailor or a first-timer, your group feels involved and engaged. The spacious boat provides ample room to both relax and socialize, with above and below deck options that let everyone find their ideal spot, from sunbathers to those wanting a quiet nook. Together, these features transform a simple meetup into a memorable adventure that strengthens friendships and family bonds against the picturesque backdrop of the Sag Harbor coastline.
What activities can you enjoy at True Sailing and why are they ideal for group meetups?
True Sailing goes beyond just transport on the water; it’s a hub of varied activities that cater to all interests within a group. One of the most engaging activities offered is sailing itself—under the guidance of Captain Nate, a highly experienced and approachable sailor, attendees are invited to helm the boat and learn about the mechanics of sailing. This creates interactive fun and a shared sense of accomplishment. Beyond the sailing lessons, the boat often visits secluded beaches perfect for swimming and snorkeling, adding a refreshing and adventurous element to the day. This allows groups to split their time between the thrill of navigation and the calm of nature, ensuring everyone finds enjoyment. The crew also offers tasting sessions or casual gatherings with drinks onboard, fostering a relaxed atmosphere where stories are shared and memories made. The boat’s design ensures comfort during these moments, with plenty of space for lounging, socializing, or enjoying a meal. For families, the experience is educational and safe, with attentive staff who readily engage children in the sailing experience, making the day enjoyable for all ages. This combination of active adventure, warm hospitality, and diverse leisure options makes True Sailing an ideal venue for group meetups that want more than just a typical outing.
How does True Sailing create an unforgettable social atmosphere?
The social vibe at True Sailing is a significant draw for anyone looking to host an event with friends or family. This is achieved through a combination of the crew’s personality and the setting itself. Captain Nate and his team bring a warm, fun, and knowledgeable presence that makes guests feel like part of a community rather than just passengers. Their attention to detail and friendliness encourage mingling and participation, creating a lively but comfortable atmosphere onboard. The setting on the water naturally promotes relaxation and conversation, away from the distractions of city or daily life. With stunning views of the Hamptons coastline, the experience feels exclusive and special, perfect for celebrating birthdays, reunions, or simple get-togethers. The onboard environment also supports flexible gatherings, from intimate chats in cozy nooks below deck to group activities in open sunlit spaces. The seamless combination of expert service, scenic beauty, and the thrill of a sailing adventure ensures that every meetup feels personalized and memorable.
What makes True Sailing’s boat and crew stand out in the Hamptons?
True Sailing’s vessel, Elizabeth, is a standout for its spaciousness and comfort, offering more room than most standard day charters. With plenty of seating and open areas both on deck and below, the boat allows guests to spread out and find their preferred space to relax or engage. The boat is meticulously maintained, clean, and equipped to provide a premium experience. But it is the crew that truly elevates the experience—they are described as super friendly, professional, and deeply knowledgeable about sailing and the local waters. Captain Nate, in particular, is praised repeatedly for his skill and convivial nature, making guests feel safe and entertained simultaneously. His ability to tailor the experience to the group's interests—whether teaching sailing basics, pointing out local sights, or offering swimming stops—demonstrates excellent personalized service. This combination of a high-quality vessel and exceptional crew ensures that every group receives the best blend of comfort, adventure, and expert guidance.
Why is True Sailing recommended for families and kids as well as adult groups?
While True Sailing caters brilliantly to adult groups and friends, it is equally suitable for families with children. The crew’s patient and engaging approach makes learning about sailing accessible and fun for kids, turning what could be just a boat ride into an educational adventure. Stories from the captain, hands-on opportunities to steer, and safe swimming breaks at private beaches allow kids to be both involved and entertained. The boat’s size and layout provide safe, comfortable areas where families can gather without feeling cramped. Parents appreciate the attentive crew who ensure safety without compromising on fun and discovery. The experience fosters shared learning and connection across ages, making it a wonderful way for families to bond outside of typical routines. True Sailing’s reputation for being welcoming and accommodating to all ages further assures peace of mind for families looking to create cherished memories on the water.
How does the location of True Sailing enhance the overall experience?
Situated in Sag Harbor in the Hamptons, True Sailing benefits from one of the most beautiful and coveted coastal environments in the Northeast. This prime location means that guests are treated to stunning panoramic views of the shoreline, historic harbor spots, and serene, less crowded beaches that only a boat can access. The quiet coves and clear waters invite exploration and leisurely swims, enhancing the day’s relaxing vibe. Sag Harbor itself is a charming and picturesque town, adding to the allure of setting sail from this locale. The proximity to both New York City and the rest of Long Island makes True Sailing easily accessible for day trips or weekend outings, perfect for escape from urban life. The surrounding natural beauty amplifies every moment onboard, whether it’s a sunset cruise or midday adventure, ensuring the environment complements the flagship service and activities offered by True Sailing.
What do customer reviews highlight about True Sailing’s service and value?
Customer reviews for True Sailing consistently emphasize the exceptional quality of service, the friendliness and professionalism of the crew, and the overall value of the experience. Many reviewers note how Captain Nate and his team go above and beyond to accommodate their group’s needs, making everyone feel comfortable and well cared-for. The mix of education, entertainment, and catering to individual preferences is frequently praised. Clients appreciate the attention to detail, from welcome drinks and clean towels to the seamless coordination throughout the sailing trip. Reviewers highlight the boat’s comfort and cleanliness as standout features. Overall, the glowing feedback underscores that True Sailing provides a premium experience that justifies its reputation as the best sailing company in NYC and the Hamptons. The high rating, based on dozens of detailed reviews, reflects consistent customer satisfaction, making it a trustworthy choice for any group seeking a memorable outing on the water.
In what ways is True Sailing customizable for special events and celebrations?
True Sailing is well-suited to hosting special events like birthdays, anniversaries, or casual celebrations with friends and family. The crew is flexible and willing to tailor the itinerary, making stops that suit the group’s interests, whether that’s swimming, sightseeing, or just relaxing onboard with drinks and snacks. The boat’s spacious design allows for comfortable mingling or intimate conversation. Because of the crew’s accommodating nature, guests can communicate specific needs prior to their trip to ensure everything from music preferences to dining options matches their vision. The picturesque setting and professional hospitality create a unique backdrop for creating unforgettable memories. Whether it’s a lively party atmosphere or a tranquil escape, True Sailing adapts to provide an experience that matches the occasion perfectly. This ability to customize makes it ideal for those looking to celebrate in style with a group that values exclusivity and personal touches.
How does the combination of adventure and comfort at True Sailing satisfy different personalities in a group?
Groups often contain a wide range of personalities—from thrill-seekers looking for adventure to those who prefer to relax and savor the scenery and company. True Sailing balances these needs expertly. For the adventurous, the opportunity to steer the boat, learn about sailing, and explore hidden coves and beaches offers excitement and engagement. Meanwhile, the comfort-focused will appreciate the generous relaxing spaces, the attentive service, and the ability to enjoy food and drinks while taking in peaceful water views. This duality ensures that no one feels left out or unfulfilled. The crew’s experience in reading the group’s dynamics allows them to adjust the pace, activities, and vibe so that everyone enjoys their ideal outing. This makes True Sailing an inclusive destination that caters to diverse tastes while fostering group harmony, perfect for friends and family seeking an outing where every member’s preferences are respected and celebrated.