When asking yourself about something to do near me in Chicago with a group of friends or family, consider
The Salty Dog Sailing Co.
Why The Salty Dog Sailing Co. is a fun option when searching for things to do near me with friends and family
The Salty Dog Sailing Co. offers an exceptional sailing experience on the scenic waters of Chicago, making it a fantastic place to meet up with friends for relaxation and adventure. This sailing company is known for its welcoming atmosphere, expert Captain Kirk, and his friendly companion Woody, a well-mannered sailing dog who adds to the charm of the trips. Whether you are new to sailing or an enthusiast, The Salty Dog Sailing Co. ensures everyone feels comfortable and safe during the journey. Guests can enjoy stunning views of the Chicago skyline while feeling the cool breeze on the water, which provides a refreshing and unique way to explore the city from Lake Michigan. The company caters to small groups and families as well, making it a versatile option for various kinds of social gatherings. The tours are praised for being relaxing yet engaging, with Captain Kirk providing insightful commentary about the sights and sailing techniques. Renting a sailboat here is not only about the ride but also about the memorable moments shared with friends or loved ones in a beautiful outdoor setting.
Here's what people think of The Salty Dog Sailing Co.
As of recent, The Salty Dog Sailing Co. holds a 5-star rating based on 150 reviews.
Reviews of The Salty Dog Sailing Co. consistently laud the professionalism and friendliness of Captain Kirk, highlighting his knowledge and accommodating nature, which help newcomers and experienced sailors alike feel at ease. Reviewers particularly appreciate the clean, well-maintained boat and the involvement of Woody, the captain’s dog, who is beloved by guests and adds a fun, homey touch to the sailing experience. Positive feedback often mentions the breathtaking views of Chicago’s skyline, the enjoyable and safe sailing environment, and the personalized attention from the captain, making it ideal for couples, families, and friends. Many reviewers recommend this as a top way to see Chicago from the water, especially appreciating the cool weather gear provided on chillier days and the relaxed yet informative atmosphere. Negative reviews are very rare given the strong 5.0-star average rating but some guests mention mild seasickness, which Captain Kirk addresses thoughtfully with remedies and support. Overall, the reviews paint The Salty Dog Sailing Co. as a must-try adventure that leaves clients eager to return, confirming its reputation as a unique, pleasurable, and safe sailing experience on Chicago’s lakefront.
Highlights from reviewers (Most Relevant)
Gretchen Scheidler
We took a spur-of-the-moment morning sail with Kirk, Woody, and our family of 5, with kids aging from 5-11. Was amazing, easy, peaceful, and a great way to see the city we live in and love in a whole new way. Reservation, parking, payment, and all was super simple. Thanks so much, Captain Kirk! We will definitely be back!
BA_Inspire Fire
As a sailor myself I was looking to experience Lake Michigan, not as a tourist, but true sailing. Captain Kirk and Peony were awesome! He is a top notch captain, and the boat handles so well! She is agile and spunky! Well appointed, clean and beautiful. Having a boat dog along was the cherry on top! The marina is convenient, nice, with good food and music Apre-sail! I can’t wait to go out again asap!
Travis Swiatlo
Had an awesome experience sailing with Kirk and his co-captain Woody (his friendly dog). The views were absolutely spectacular and am so thankful to Kirk for making my birthday sail so special. Booking, parking, and getting aboard were seamless. Will definitely be coming back in the future!
Tom Gamull
We had an amazing private sailing experience with Salty Dog Sailing! It was just us and Captain Kirk on the beautiful Peony, sailing Lake Michigan with incredible views of the Chicago skyline. Everything was safe, well-explained, and perfect for both experienced sailors and first-timers — I’ve sailed before but my fiancée hadn’t, and she loved it. Visiting from Atlanta, this was the highlight of our trip. Highly recommend to anyone in Chicago looking for a fun, unique way to see the city!
Andrea Pfarrer
A fantastic evening on the water! Sunset, skyline, music and fireworks! The captain had lots of good stories for our son who loves sailing. A little choppy but great weather. We ❤️ Woody! Thanks, Salty Dog!
How to reach The Salty Dog Sailing Co.
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Why The Salty Dog Sailing Co. may become Your Favorite Meetup Place for Catching Up, Celebrating or Just Hanging Out
Why rally at The Salty Dog Sailing Co. with your friends?
Gathering your friends or family at The Salty Dog Sailing Co. in Chicago offers a uniquely refreshing and memorable experience unlike any traditional meetup spot. This sailing company has earned a flawless 5.0 rating out of 150 reviews, signaling consistent customer satisfaction and exceptional service. What makes it truly special is the opportunity to escape the bustle of the city and enjoy a private sailing adventure on Lake Michigan, with spectacular views of the Chicago skyline providing a stunning and ever-changing backdrop. Whether you're celebrating a special occasion or just seeking quality time together, the Salty Dog’s intimate and customizable charters create the perfect setting for connection, conversation, and unforgettable moments. The experience is accessible even to those with no sailing experience, thanks to the knowledgeable and friendly captain, often praised for making guests feel safe and comfortable. Plus, with the added charm of "Woody," the four-legged mascot and unofficial canine captain, the vibe is welcoming and fun. The blend of outdoor adventure, scenic beauty, attentive service, and private setting makes The Salty Dog Sailing Co. the ideal rally point for friends and family seeking to make lasting memories on the water.
What activities does The Salty Dog Sailing Co. offer for group meetups?
The Salty Dog Sailing Co. specializes in private sailing charters that promise an intimate and customizable adventure on Lake Michigan. Their primary activity is the private boat sailing experience, where groups can relax and soak in the panoramic views of the Chicago skyline, Navy Pier, and Lake Michigan’s vast blue waters. These charters last about two hours, perfect for activity-packed yet not exhausting outings. During the cruise, the captain handles all sailing responsibilities, allowing guests to fully unwind, socialize, and enjoy the breeze and sunshine. Many guests enjoy bringing their own snacks and drinks onboard, turning the sailing trip into a floating party or celebration. The boat's layout supports comfortable socializing, spreading out, and enjoying time together whether in small or larger groups. While not inherently a sport activity, the sailing experience still offers gentle motion on the water and can be a new, exciting experience, especially for those who have never sailed before. The presence of Captain Kirk, noted for his professionalism and friendly demeanor, ensures a safe and educational experience that can include learning about sailing terminologies and lake conditions, making it both fun and informative.
Why is The Salty Dog Sailing Co. perfect for a group meetup?
The Salty Dog Sailing Co. stands out as an excellent venue for group meetups due to a combination of privacy, convenience, customization, and ambiance. Each charter is private, meaning your group will have exclusive use of the boat and captain, free from outside crowds or distractions. This level of privacy is particularly appealing for family gatherings, celebrations like birthdays or proposals, or simply close friends wanting uninterrupted time together. The company provides several group size options designed to fit small to medium-sized parties comfortably—ranging from intimate two-person outings ideal for couples to larger six-person charters that accommodate bigger groups. Free harbor parking adds to the convenience, removing stress about where to leave your car. The sailing company’s flexibility allows groups to shape the outing according to their preferences, whether a casual cruise with light refreshments or a festive, photogenic celebration against Chicago’s iconic skyline. Moreover, the boat’s gentle motion and scenic routes work well for all ages and experience levels, making it inclusive for families with kids or older guests. The attentive and personable captain, along with the charm of the boat itself, delivers an experience that bonds groups over shared adventure and enjoyment in a unique setting.
How do the rates and group sizes at The Salty Dog Sailing Co. accommodate different gathering needs?
The Salty Dog Sailing Co. offers straightforward and transparent pricing designed to accommodate various group sizes and gathering purposes with clear options suitable for couples, double dates, families, or small parties. The pricing is based on a two-hour private charter that includes a professional captain, ensuring an inclusive experience with no hidden costs. For solo or duo outings, the rate is $300, perfect for couples seeking a romantic or intimate outing, such as proposals or anniversary celebrations. Groups of 3-4 people can book for $400, an ideal setup for double dates or small friend groups wanting to share the experience without feeling crowded. Larger parties of 5-6 are accommodated for $500, making it a fantastic option for families or slightly bigger gatherings wanting to spread out comfortably on the boat. This tiered pricing model ensures groups pay a fair rate relative to their size, maximizing value for the experience. Additionally, all groups benefit from free harbor parking, which simplifies logistics and adds to the overall convenience of meeting at this waterfront destination.
What are the safety and comfort considerations that make The Salty Dog Sailing Co. an appealing choice?
Safety and comfort are paramount at The Salty Dog Sailing Co., contributing significantly to its perfect review scores and consistent recommendations. The boat operates under full licensing and regulation by the U.S. Coast Guard, the State of Illinois, and the Chicago Park District, confirming it meets all safety standards for passenger charters. Guests repeatedly mention Captain Kirk’s professionalism, reassuring demeanor, and readiness to accommodate any needs, including helping those prone to seasickness with useful advice and remedies like seasick bands. The boat is well-maintained and spacious enough to allow guests to move around, sit comfortably, and enjoy the ride without feeling cramped, which is essential for longer outings and groups with varying comfort levels. The calm waters of Lake Michigan, especially close to shore, usually provide a stable sailing experience, making it accessible to guests of all ages and physical conditions. The presence of the friendly canine mascot Woody adds a relaxing and lighthearted atmosphere, which many guests find comforting and enjoyable. This blend of top-tier safety protocols, attentive captaining, and warm hospitality creates a secure and pleasant environment perfect for group outings.
How does the location of The Salty Dog Sailing Co. enhance its appeal for meetups?
Located at 1559 S Lake Shore Drive in Chicago, The Salty Dog Sailing Co. benefits from a prime urban waterfront location that combines convenience with scenic beauty. Being right on Lake Michigan’s shore provides easy access to expansive water routes that offer unparalleled views of Chicago’s iconic skyline, Navy Pier, and the skyline’s architectural gems, making for a visually spectacular outing. This central location makes it accessible by car, public transit, or bike, giving diverse groups a straightforward way to reach the venue without hassle. Free harbor parking further enhances accessibility, alleviating a common urban challenge and allowing guests to focus on enjoying their meetup. The waterfront setting also means you can balance your outing with nearby activities on shore, such as visiting lakefront parks, dining at local establishments, or simply enjoying a walk along the shoreline before or after your sail. This prime location thus combines metropolitan convenience with natural beauty and outdoor adventure, strengthening its appeal as a top-tier venue for gatherings of friends and family.
What kind of groups and occasions is The Salty Dog Sailing Co. best suited for?
The Salty Dog Sailing Co. is highly versatile and suitable for a wide range of groups and occasions. It is ideal for couples seeking intimate, romantic outings, including special moments like proposals or anniversaries. Friend groups enjoy it as a fun and unique way to celebrate birthdays, reunions, or just casual get-togethers with an adventurous twist. Families with children or multigenerational groups find the sailing experience inclusive and manageable, as the boat’s comfortable size and calm sailing conditions make it safe for kids and older adults alike. The private charter format also appeals to corporate groups or small teams interested in low-key team-building or client entertainment in a relaxed, scenic setting. Because every charter is tailored and private, it works equally well as a special celebration spot or simply as a weekend leisure activity to break the routine with a splash of excitement. The adaptable nature of the setting and service means groups looking for anything from peaceful sails with scenic views to lively social occasions can find what they need here.
How does customer feedback reflect the overall experience at The Salty Dog Sailing Co.?
Customer feedback overwhelmingly praises The Salty Dog Sailing Co. for its professional, friendly service and outstanding sailing experience. Reviews frequently highlight Captain Kirk’s welcoming attitude and expert handling of the boat, which reassures novices and seasoned sailors alike. Many customers report feeling perfectly safe and cared for throughout their trips, even those who initially felt nervous or experienced seasickness. The presence of Woody, the friendly four-legged companion, is repeatedly mentioned as adding a charming and unique element to the sailing experience, enhancing the warm and personal atmosphere. Guests appreciate the stunning city views and the chance to get a fresh perspective on Chicago from the water, often describing the trip as a highlight of their visit or a perfect way to celebrate a special day. The consistent 5.0 rating across 150 reviews reflects a pattern of delight and satisfaction, indicating that the sailing company delivers reliably excellent experiences that meet or exceed expectations for group outings.
What should you know before booking a trip with The Salty Dog Sailing Co.?
Before booking your private charter with The Salty Dog Sailing Co., it is useful to know that all bookings come with an important email confirmation that contains details you need to prepare for your sailing adventure, such as meeting location and time. It’s recommended to check your spam or junk mail folder in case the confirmation email does not appear in your inbox. The company welcomes communication and offers text or phone support to ensure a smooth booking and preparation process. Knowing the rate structure upfront helps manage expectations on cost relative to group size, and understanding that all charters are private events allows you to plan your guests accordingly. The company’s licensed status and adherence to safety protocols ensure a secure outing, but it’s also wise to consider typical weather conditions on Lake Michigan during your chosen date to dress appropriately and bring necessary items like sunscreen or light jackets. Bringing your own refreshments is allowed, so you can personalize your onboard experience with snacks and drinks to suit your group’s tastes and occasion. Being prepared with these insights ensures that your time on the water is as seamless and enjoyable as possible.
What makes The Salty Dog Sailing Co. a unique Chicago experience for visitors and locals alike?
The Salty Dog Sailing Co. offers a singular blend of adventure, relaxation, and cityscape beauty that is difficult to find anywhere else in Chicago. Unlike crowded tourist hotspots or land-based venues, this sailing company lets groups experience the city from a fresh, invigorating vantage point on Lake Michigan’s serene waters. For locals, it provides a serene escape and a way to rediscover familiar city views under different light and weather conditions. For visitors, it presents a bucket-list attraction that combines sightseeing, leisure, and the thrill of sailing—an enriching way to connect with the city’s maritime heritage. The personable, approachable style of the captain and crew transforms what could be a formal charter into a warm, memorable outing with an intimate friends-and-family vibe. The presence of friendly Woody the dog adds distinctive character rarely found in other boating experiences. The combination of professionalism, personalized service, spectacular setting, and the novelty of private sailing on an iconic lake makes The Salty Dog Sailing Co. a uniquely compelling choice to anchor any social gathering in Chicago.