When asking yourself about something to do near me in Chicago with a group of friends or family, consider
On A Boat Sailing - Chicago, IL
Why On A Boat Sailing - Chicago, IL is a fun option when searching for things to do near me with friends and family
On A Boat Sailing offers an exceptional luxury sailing experience along Chicago's iconic lakefront, departing from Navy Pier Marina in downtown Chicago. The business is distinguished by its attention to detail, hospitality, and luxury amenities, making it an ideal place to meet up with friends. Operated by Captain Greg Scannell and First Mate Cait Scannell—seasoned sailors with over 25 years of experience and notable voyages—the company guarantees smooth, world-class sailing adventures on their elegant 37-foot French-built yacht, the S/V Dragonfly. Guests enjoy exclusive access to multiple comfortable seating areas, ample fridge space, and a private bathroom. The experience isn’t just about sailing but also offers opportunities to anchor and swim or relax on Lake Michigan, combining adventure with comfort and style. Having successfully conducted over 700 private charters since 2018, On A Boat Sailing is a trusted superhost for groups seeking a unique and memorable way to experience Chicago’s skyline and waterfront with personalized service and luxury.
Here's what people think of On A Boat Sailing - Chicago, IL
As of recent, On A Boat Sailing - Chicago, IL holds a 5-star rating based on 23 reviews.
Reviews of On A Boat Sailing consistently highlight a perfect 5.0 rating across 23 reviews, reflecting exceptional guest satisfaction. Positive reviews emphasize the welcoming and knowledgeable crew, seamless booking process, and the luxurious quality of the yacht and amenities. Guests particularly appreciate the personalized attention from experienced captains who create a safe, educational, and thrilling sailing environment, making the experience suitable for all ages and groups. The opportunity to swim and relax on the lake during the charter adds a unique aspect that enriches the outing. Negative feedback is minimal, with few mentions of typical weather-related limitations or schedule constraints, which is expected for outdoor activities. Overall, the reviews praise the business for exceeding expectations, valuing the combination of expert sailing, premium amenities, and remarkable hospitality. This feedback affirms On A Boat Sailing as a premier choice for visitors wanting a refined and memorable Chicago sailing adventure.
Highlights from reviewers (Most Relevant)
Nicole Krause
We had the best time this past Saturday evening! Greg was so kind and helpful. The sailing was a lot of fun and it was a beautifully, well-kept boat. We had lots of laughs on board and got some great pictures. It was so relaxing and the city was incredibly beautiful to see out on the lake. Greg found the perfect spot for fireworks. It was easy to get to the dock, easy to book, and we brought more than enough beverages for the 7 of us! I look forward to booking this again!
Charles Wettersten
Capt. Greg's passion for being out on the water is awesome. The yacht is handsome and clean. All in all I say 11/10 recommend for special occasions or if you just want to get out on the boat! Love sailing! This is perhaps the best boat charter I've experienced. Caps off to Greg and Cait for all the work that goes into running On A Boat Sailing
Danielle Lodge
We had a great experience with Captain Greg. The boat was very nice and clean, and we had a great sunset sail! Our kids loved their first sailing experience. Captain Greg even taught my 9 year old how to steer and let all 3 kiddos help with hoisting the sails. Couldn’t have asked for a better night in Chicago!
Elizabeth Stenholt
Not only is Greg's boat beautiful, but he really knows his stuff. We had an incredible night time sail around Navy Pier for the Saturday fireworks. We got to do a little night swimming in front of the skyline with the fun floaties Greg provided, which felt like a once in a lifetime opportunity! Watching the fireworks from the boat was truly awesome. I've never been more excited to watch a firework show, we were so close it was magical! Can't wait to do it again next year!
Haley Petricca
I had the most amazing sunset cruise with On a Boat Sailing! He picked up right in Montrose Harbor which is SO convenient. His boat, Dragonfly, was in pristine shape and it was gorgeous! To top it all off, Captain Greg was incredible! He made me feel very safe and you could tell he was a seasoned professional with a passion for sailing. Overall 10/10 experience! Highly recommend anyone looking to get out on Lake Michigan!
How to reach On A Boat Sailing - Chicago, IL
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Why On A Boat Sailing - Chicago, IL may become Your Favorite Meetup Place for Catching Up, Celebrating or Just Hanging Out
Why rally at On A Boat Sailing with your friends?
Gathering friends and family at On A Boat Sailing in Chicago offers a uniquely memorable way to celebrate, unwind, and connect. Unlike typical venues confined to land, this business provides an immersive experience on Lake Michigan aboard a luxurious 37-foot sailing yacht called S/V Dragonfly. The appeal lies in a blend of unparalleled natural beauty, expert sailing leadership, and exclusive amenities that elevate any group occasion into something truly special. Whether it’s a birthday, bachelor/bachelorette party, or just a casual outing, On A Boat Sailing’s intimate size supports meaningful interaction among guests while still offering plenty of space to relax. The journey itself becomes a shared adventure, enhanced by the evening skies, the shimmering city skyline, and the refreshing lake breeze. Friends create lasting memories as they sail together, swim off the anchored boat, or simply soak in the sunlight atop the deck. The business has a strong reputation, with a perfect 5.0 rating from 23 reviews, reflecting consistent excellence in hospitality and sailing expertise. Captain Greg Scannell and First Mate Cait Scannell, renowned sailors with decades of cruising experience, ensure that guests enjoy a smooth, safe, and exciting trip every time. This attention to detail and commitment to quality make On A Boat Sailing a perfect rallying point when you want to make lasting memories with loved ones.
What activities can you enjoy at On A Boat Sailing?
On A Boat Sailing offers a diverse array of activities specifically tailored for group experiences that combine excitement, relaxation, and luxury. First and foremost is the sailing adventure itself. Guests board the French-built S/V Dragonfly and embark on a 4-hour private charter along Chicago’s stunning lakefront, guided by seasoned captains who can adapt the experience to the group’s preferences. The thrill of navigating open water, handling the sails, or simply watching the sailboat glide through the waves introduces an exhilarating dynamic. Beyond sailing, groups can take advantage of the option to drop anchor and swim in Lake Michigan’s clean, inviting waters—an especially refreshing activity during warm weather, perfect for cooling off and socializing in the water. The sailboat also supports floating and sunbathing on the deck, offering tranquil moments for conversation and reflection amid beautiful scenery. Inside the yacht, guests have access to generous upper and lower cabin seating, ample refrigerator space for drinks and snacks, and a private bathroom, ensuring comfort throughout the journey. The combination of on-the-water adventure and thoughtful amenities shapes this outing into a complete leisure event that serves both active and relaxation-oriented preferences.
Why is On A Boat Sailing ideal for group meetups?
On A Boat Sailing stands out as an ideal venue for group meetups for several powerful reasons, making it an excellent choice for anyone seeking to host memorable gatherings. First, the intimate size of the 37-foot S/V Dragonfly strikes the perfect balance between exclusivity and sociability, comfortably accommodating groups while allowing meaningful interaction in a private setting. Unlike large commercial cruise ships, this yacht feels like a personal escape, making it easier for groups to bond and celebrate together. The all-inclusive nature of the 4-hour private charters removes usual planning hassles; everything from the sailing route to onboard amenities is handled by professional crew with over 25 years of sailing experience, ensuring smooth logistics and attention to guest comfort. The luxury touches, such as spacious seating areas and private bathroom access, add to the sense of indulgence and ease, often uncommon in most boat rentals. Furthermore, the exclusive location on Navy Pier Marina offers stunning views of Chicago’s downtown skyline, providing a gorgeous backdrop for photos and a unique sightseeing opportunity that land-based venues cannot match. For groups looking to combine adventure, luxury, and privacy, On A Boat Sailing offers a rare and enviable package.
How experienced is the crew at On A Boat Sailing?
The crew at On A Boat Sailing brings an exceptional level of sailing expertise combined with passion and dedication to creating memorable guest experiences. Captain Greg Scannell and First Mate Cait Scannell lead every journey with over 25 years of sailing experience between them. Their credentials include an impressive 8-month, 5,500 nautical mile voyage from Chicago to the Bahamas and back, showcasing deep knowledge of both technical sailing and extended maritime navigation. This hands-on experience translates into expert handling of the vessel, ensuring guests experience smooth and safe sailing irrespective of weather conditions or group skill level. Beyond technical skill, the Scannells bring heartfelt hospitality, sharing their passion for the water and Lake Michigan with guests, which elevates the overall atmosphere onboard. Their attentiveness to luxury touches and guest comfort has been refined through 700+ private sailing charters since 2018, marking them as trusted superhosts in the Chicago sailing community. Whether helping guests try their hand at sailing or simply facilitating a relaxing cruise, their seasoned leadership assures an effortless and enjoyable outing.
What amenities and comforts does the S/V Dragonfly provide?
The French-built S/V Dragonfly, which hosts On A Boat Sailing’s charters, is specially designed to combine adventure with comfort and luxury for group excursions. The yacht has spacious upper and lower cabin seating, providing shelter and relaxation options for all guests regardless of weather or desire to be indoors or outdoors. There is ample fridge space onboard, allowing refreshments and snacks to be kept cool and accessible throughout the journey. Unlike many small vessels where bathroom facilities are lacking or inconvenient, Dragonfly boasts a private bathroom, a rare amenity that significantly enhances guest comfort and convenience on a multi-hour voyage. The boat’s deck space is generous enough for passengers to spread out, sunbathe, or float on the water when anchored, yet intimate enough that everyone can engage easily for group activities or conversations. The luxurious design respects both aesthetics and practicality, offering a refined environment that supports long-lasting memories of comfort amid the excitement of sailing.
How does On A Boat Sailing compare to other Chicago sailing options?
On A Boat Sailing distinguishes itself within Chicago’s bustling boating scene through a strong focus on luxury, personalized service, and expert sailing leadership. While options such as Tall Ship Windy deliver impressive large-ship tours emphasizing historic sailing and accommodate bigger crowds, On A Boat Sailing targets intimate private groups seeking a more upscale and relaxed atmosphere. Unlike large public sails with 20+ guests, Dragonfly’s smaller size nurtures closer connections and customization of the experience for each group. Additionally, On A Boat Sailing offers a smooth blend of adventure and relaxation that goes beyond sightseeing—complete with swimming stops and onboard amenities—whereas many other charters focus primarily on tours or racing. Sail Chicago’s community program is fantastic for learning how to sail and joining a volunteer-driven environment but lacks the tailored luxury experience and private group charters that On A Boat Sailing specializes in. Thus, for groups prioritizing exclusivity, comfort, and personalized sailing with a touch of adventure, On A Boat Sailing represents a top-tier choice on Lake Michigan.
What special occasions are ideal for hosting on a boat with On A Boat Sailing?
On A Boat Sailing’s private charters make them perfect for a variety of special occasions that demand a unique, celebratory backdrop combined with luxury and fun. On the top of the list are birthdays and bachelor/bachelorette parties, which benefit hugely from the 4-hour all-inclusive sail where laughter, friendship, and scenic views mingle seamlessly. The boat’s private bathroom and flexible seating add practical benefits that ease hosting responsibilities during celebrations. The environment encourages group bonding through shared sailing adventures, swimming breaks, and relaxed mingling onboard. It is also an excellent choice for small corporate outings or milestone celebrations seeking a private and impressive venue that leaves a lasting impression on colleagues or clients. Other special events like anniversaries, engagements, or simply meaningful get-togethers among friends and families gain from the exclusive experience On A Boat Sailing offers, mixing natural beauty with hospitality and luxury service. Any occasion that deserves a more thoughtful, memorable celebration finds a fitting home on this vessel.
How can you book a group charter with On A Boat Sailing?
Booking a group charter with On A Boat Sailing is straightforward and designed to guarantee ease and confidence for customers. Reservations are made through their official website, which highlights their “Golden Sail” Money-Back Guarantee, reassuring guests of a quality experience or their money back. The process allows groups to choose the date and customize the experience according to preferences, such as incorporating swim stops or dining arrangements. With over 700 private charters hosted since 2018, the company is adept at managing logistics for groups, providing clear communication and professional crew support from booking through the trip. Interested parties can also inquire about any specific needs or requests, ensuring that the sailing adventure fits individual group desires. Given the popularity and limited capacity of the 37-foot yacht, early booking is advised, especially for peak seasons or special dates. The transparent booking process and strong review record make On A Boat Sailing a trusted choice for hassle-free, memorable sailing events.
What makes the location at Navy Pier Marina special for this sailing experience?
Navy Pier Marina is one of Chicago’s most iconic and accessible waterfront points, making it an ideal launch site for On A Boat Sailing’s private charters. Situated in the heart of downtown Chicago, the marina offers stunning panoramic views of the city skyline as you set sail, which becomes a central feature of the entire trip’s visual appeal. Guests gain immediate access to the city’s best waterfront scenery combined with the refreshing expanse of Lake Michigan. The convenience of this location means groups can easily integrate their sailing adventure into a day packed with other downtown activities, from dining to theater, making it an all-around excellent event hub. Navy Pier itself is a vibrant destination with shops, restaurants, and entertainment, adding to the sense of occasion before or after the sailing event. Moreover, the marina’s well-maintained docking facilities and professional staff support seamless boarding and disembarking, contributing to the effortless luxury feel of the overall experience.
What guest feedback reveals about On A Boat Sailing’s quality?
With a perfect 5.0 star rating across 23 detailed reviews, guest feedback strongly highlights the exceptional quality that sets On A Boat Sailing apart as a group outing destination. Reviewers consistently praise the professionalism and friendliness of Captain Greg and First Mate Cait, noting their skill, safety focus, and warm hospitality. Many guests mention the unforgettable nature of the sailing adventure itself — the smooth handling of the boat, the stunning views of Lake Michigan and Chicago’s skyline, and the freedom to swim or relax on the water. The boat’s cleanliness, amenities like the private bathroom, and overall comfort receive recurring positive comments. Beyond logistics, testimonials often speak to the collective joy and connection felt during their private charters, underlining how the experience fostered togetherness and celebration among friends and family. High marks for punctuality, communication, and customization options also reinforce the company’s reputation as a reliable and premium sailing charter provider. This glowing feedback validates the strong recommendation for anyone considering a meaningful group gathering on the water.
How does On A Boat Sailing contribute to sustainable and responsible boating?
On A Boat Sailing complements Chicago’s beautiful natural environment by practicing responsible boating and encouraging guests to appreciate Lake Michigan’s delicate ecosystem. While specific green policies are not detailed publicly, their commitment to careful operation, attention to safety, and respectful navigation of local waters minimizes environmental impact. Sailing itself is a clean mode of transportation powered by wind, reducing reliance on fossil fuels compared to motorized boats. The small size of the vessel also means less wake and disturbance to other lake users and wildlife. Furthermore, Capitan Greg and First Mate Cait’s experience ensures adherence to boating regulations and best practices that protect the lake’s health. Guests are welcomed to engage in immersive, low-impact activities such as swimming and floating that celebrate nature responsibly. By fostering a connection to the water through luxury and education, On A Boat Sailing helps promote a culture of environmental stewardship among Chicago’s boating community and visiting groups. This thoughtful approach enhances the quality of the experience, aligning fun with conservation.