Viator Rating : 5 (8 reviews)
Milwaukee
Set Sail on Lake Michigan: A 2-Hour Sailing Adventure
120
Overview
Experience a 2-hour sailing adventure on Lake Michigan, perfect for all skill levels. Enjoy stunning views of Racine, and on clear days, Milwaukee and Kenosha. Relax and listen to the waves or learn sailing from a USCG captain and his experienced family crew. An intimate and scenic experience awaits. 
Highlights
Family-Run Experience: Enjoy a personalized sailing adventure with a USCG captain and his family, providing a warm and welcoming atmosphere.
Scenic Views: Take in breathtaking views of the Racine skyline and, on clear days, glimpses of Milwaukee and Kenosha.
Hands-On Sailing: Learn basic sailing techniques and participate as crew, making it an engaging and educational experience.
Perfect for All Skill Levels: Whether you're a beginner or an experienced sailor, this adventure caters to your interests and abilities.
Sentiment Analysis
Relaxing atmosphere
-
Knowledgeable and friendly crew
-
Beautiful scenery
-
Hands-on sailing experience
Weather dependent; clear views not always guaranteed
-
Limited to 6 people, may not suit larger groups
Review Summary
Reviews for the 2 Hour Sailing Adventure in Lake Michigan from Milwaukee consistently highlight the knowledgeable and friendly captain along with attentive family crew as a major positive. Guests appreciate the intimate, private experience with the ability to relax or engage in sailing activities. Scenic views of Racine and, on clear days, Milwaukee and Kenosha add to the enjoyment. Some reviews note that the experience is well suited for beginners, making it accessible to a wide audience. No significant negative comments were noted, but accessibility limitations for those with mobility issues are advised. The flexible cancellation policy and personal touch of the boat crew are frequently praised.
This page is synthesized and developed by Dyvarcity Team
More like this
Chicago
$507.96
Private Sail: Chicago Skyline Views from Navy Pier!
5.0
(70 reviews)
Duration: 120
minutes
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago, offers a memorable two-hour private sailing adventure for up to six people. Guests can relax and enjoy stunning views of the Chicago skyline with a US Coast Guard licensed captain.
The flexibility of a private charter allows guests to customize their experience. From music selection to sailing route, the trip can be tailored to individual preferences. Key sights include the Navy Pier Marina, the iconic Navy Pier itself, the breathtaking Chicago Skyline, Adler Planetarium, Soldier Field, and Buckingham Fountain.
This experience includes the use of Bluetooth speakers, the Navy Pier facility fee, all taxes, and a professional US Coast Guard licensed captain. Food, drinks, gratuities, and parking are not included.
Chicago
$507.96
Chicago Sunset Sailing: Private Lake Michigan Cruise Awaits!
5.0
(27 reviews)
Duration: 120
minutes
Come Sailing at Navy Pier Marina for a stunning sunset sail on Lake Michigan! Enjoy a two-hour private charter for up to six guests, customizable with your choice of music and route. Relax as a licensed captain guides you, offering historical anecdotes and unforgettable skyline views. A perfect, serene escape on the water.
Chicago
$154
Chicago Air & Water Show Boat Tour: Best Views!
5.0
(2 reviews)
Duration: 150
minutes
The Chicago Rainbow Cone Boat Tour Experience offers a front-row seat to the spectacular Chicago Air and Water Show. Perfect for friends and family, this boat tour provides an unforgettable way to experience one of the city's most exciting events from Lake Michigan (Chicago Sailing).
Imagine watching incredible aircraft stunts and water demonstrations from the *best location, as determined by the Captain. This tour takes guests to the heart of the action, ensuring a memorable viewing experience. Alcoholic beverages are included to enhance the enjoyment while taking in the views of the Chicago Air and Water Show Viewing Area.
This tour includes the best views and alcoholic beverages to make the day even better. Please note that this experience does not include food or additional beverages beyond what is specified. With an experienced captain at the helm, guests can relax and soak in the thrill of the show. This is the perfect way to enjoy the Chicago Air and Water Show.
Chicago
$113.73
Chicago Fireworks Cruise Aboard Tall Ship Windy!
4.8
(14 reviews)
Duration: 90
minutes
See a Fireworks Show aboard Tall Ship Windy in Chicago! This special event sail offers an unforgettable way to experience Navy Pier's spectacular fireworks display. Instead of fighting the crowds on land, treat yourself to the best seats in town aboard a magnificent tall ship.
Relax and enjoy a leisurely evening sail on Lake Michigan, taking in the brilliant and beautiful Chicago nighttime skyline. Tall Ship Windy provides a coordinated soundtrack over the ship's sound system to enhance the amazing fireworks show. This unique experience provides breathtaking views of the Chicago Skyline and Navy Pier from the water.
This public tour ensures a memorable experience. Please note that alcoholic beverages are not included. Come aboard Tall Ship Windy, located on Navy Pier in front of the Billy Goat Bar and Grill.
Chicago
$91.23
Chicago Tall Ship Windy: Skyline Sail on Lake Michigan
4.8
(20 reviews)
Duration: 75
minutes
Experience the beauty of Chicago with a sail on the Tall Ship Windy, Chicago's Official Tall Ship Ambassador. This relaxing adventure on Lake Michigan offers stunning views and fresh air.
See Chicago's iconic skyline from a unique vantage point. Guests can join the friendly crew to help raise the sails or simply relax and enjoy the ride. The Tall Ship Windy boasts a full bar and gift shop for added enjoyment. The cruise takes you along the Lake Michigan shoreline, offering views of the Chicago Skyline and the vast expanse of Lake Michigan.
This tour includes access to a restroom on board. Alcoholic beverages, snacks, and gratuities are not included. It's a fantastic way to see Chicago that all ages can enjoy.
Chicago
$35
Chicago's Dazzling Architecture: Interiors Walking Tour
5.0
(1475 reviews)
Duration: 120
minutes
Original Chicago Architecture Interiors Tour: Dazzling Interiors takes guests on a journey through some of the city's most breathtaking interior spaces. Many people pass by these hidden gems every day without realizing what's inside. This walking tour, led by an experienced local guide, reveals the stunning beauty within.
Guests will explore architectural wonders, from turn-of-the-century stained glass mosaics to soaring Art Deco designs from the Roaring 20s. Key stops include the iconic Art Deco Building, Surprise Interiors, and the Chicago Cultural Center. Each location offers a unique glimpse into Chicago's rich history and artistic heritage.
The tour includes a knowledgeable local guide who provides insights and stories about each location. Gratuities are not included. Prepare to be amazed by the hidden beauty that lies within Chicago's architectural treasures.
Nearby Events
Rate Field
Aug 24
6:40 PMChicago White Sox vs. Texas Rangers
Aragon Ballroom
Oct 07
7:00 PMBook Starbomb + Scoochie Boochie Live at Aragon Ballroom
Starbomb with Scoochie Boochie bring their 'Probably The Only Tour Ever' to the iconic Aragon Ballroom in Chicago, delivering a high-energy blend of musical comedy and gaming satire. As the band continues their 2026 tour, fans can expect fresh parodies of video game hits alongside their classic rap-rock antics, creating a unique live experience that appeals to both gamers and comedy enthusiasts. The event showcases the duo's signature style of turning popular gaming culture into hilarious, rhythmic masterpieces, making it a standoutshow for music lovers who appreciate humor and satire.
Starbomb, formed by gaming commentators and musicians, has built a reputation for their clever, music-driven comedy that resonates deeply with the gaming community. Their collaboration with Scoochie Boochie adds an extra layer of comedic depth, as both artists share a passion for turning niche internet culture into accessible, entertaining performances. The Aragon Ballroom, known for its historic architecture and vibrant concert atmosphere, provides an ideal venue for this genre-crossing event, offering a memorable setting where fans can enjoy the show in a space steeped in Chicago's music history.
Ravinia
Sep 17
7:00 PMZiggy Marley & Thievery Corporation at Ravinia
Ziggy Marley with Thievery Corporation lights up Ravinia in Highland Park, IL, blending reggae royalty with downtempo electronica in a world music fusion that promises rhythmic transcendence. Ziggy, son of Bob Marley, brings his Grammy-winning vibes from recent albums like 'Love Is the Drug,' while Thievery Corporation delivers their signature global beats, creating a collaborative setlist of hits like 'Three Little Birds' and 'Lebanese Blonde.'
This pairing celebrates Ziggy's legacy of positive messages and Thievery's innovative soundscapes, drawing fans of conscious lyrics and chill grooves. Ravinia, the legendary outdoor venue, enhances the magic with its pavilion and lawn seating amid lush gardens.
American Family Field
Aug 28
6:40 PMBrewers vs. Rangers: Milwaukee Showdown!
Brewers vs. Rangers at American Family Field: Get ready for an exciting Major League Baseball game as the Milwaukee Brewers take on the Texas Rangers at the iconic American Family Field. This contest will feature a thrilling display of athleticism and tactical maneuvers on the diamond. Expect to witness powerful hitters launching balls into the stands, swift runners stealing bases, and skilled pitchers delivering masterful performances.
American Family Field, the Brewers' home stadium, boasts a distinctive open-air design complemented by a retractable roof, guaranteeing that the game will proceed regardless of weather conditions. The stadium's architecture provides fans with intimate and engaging viewing angles, ensuring an immersive experience. This event is tailored for attendees seeking a relaxed and family-friendly sporting atmosphere, perfect for fans of all ages.
Pabst Theater
Oct 03
8:00 PMLabyrinth In Concert: 40th Anniversary at Pabst
Jim Henson's Labyrinth In Concert brings the cult classic film to Pabst Theater in an immersive live experience. Fans watch the 1986 fantasy on a stunning HD screen while a live band performs the full soundtrack in perfect sync with David Bowie’s iconic vocals, celebrating the movie’s 40th anniversary on a global tour hitting over 60 North American cities.
Jim Henson’s Labyrinth, directed by Henson himself and starring Jennifer Connelly and David Bowie as the Goblin King Jareth, captivates with its magical world of fantastical creatures from Henson’s Creature Shop and timeless songs like “Magic Dance.” This fusion of film and live music revives the sweeping score by Bowie and Trevor Jones like never before. The historic Pabst Theater, a Milwaukee landmark, provides an intimate setting for this nostalgic spectacle.
Ravinia
Sep 13
7:00 PMLos Tigres del Norte at Ravinia 2026
Los Tigres del Norte bring their legendary norteño sound to Ravinia in Highland Park, IL, for an electrifying world music performance. As icons of Mexican regional music with over 50 years of hits like 'La Puerta Negra' and 'Jefe de Jefes,' they continue captivating audiences with storytelling corridos that blend tradition and social commentary.
Formed in 1968, Los Tigres del Norte have sold millions of albums and earned Grammy awards, solidifying their status as norteño legends. Ravinia, one of America's premier outdoor venues, offers a picturesque setting amid gardens and pavilions.
Chicago Best Things to Do: Concerts, Helicopter & Food Tours
The Chicago skyline is hiding a secret- a ton of them, actually. It’s more than a view: it’s got adventures you're meant to explore. Breathe in the winds and excitement of a helicopter tour, party at top concerts, or dive into food and pizza tours. Walk beside history on a gangster mob tour, take a fireboat or bus tour. Looking to get wild tonight? Find events going on sooner than tomorrow, from EDM to country concerts. Check all your bucket list boxes, and live stories you’ll remember forever.
View Chicago Activities