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.
Milwaukee
$89.75
Milwaukee: Tandem Kayak River Adventure!
4.9
(9 reviews)
Duration: 240
minutes
Milwaukee Tandem Kayak Rental offers a fun way to see Milwaukee! People can paddle down the Milwaukee River at their own speed.
Rent a tandem kayak for up to 4 hours. It costs only $85! As people paddle, they will see the pretty city and can stop to get out of their kayak. Many people like to stop at the local restaurants or breweries along the river. These kayaks are easy to get in and out of. They are also good for holding a cooler. People also get life vests and instructions.
Explore downtown Milwaukee by kayak. Paddle on the Milwaukee River, where it is easy to kayak. People can also stop at many public docks to get food or a drink.
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.
Nearby Events
Coronado Theatre
Oct 04
7:30 PMLabyrinth In Concert 40th at Coronado Theatre
Jim Henson's Labyrinth: In Concert 40th Anniversary lights up the Coronado Theatre in Rockford, IL, with a live band performing the iconic score from the 1986 cult classic film starring David Bowie, synced perfectly to the on-screen action while preserving his original vocals. This massive 2026 tour, following a triumphant run across nearly 100 cities, celebrates the film's 40th anniversary by immersing audiences in the Goblin King's fantasy world through epic music and visuals.
Jim Henson's Labyrinth captivates with its timeless puppetry, enchanting songs like 'Magic Dance' and 'As the World Falls Down,' composed by Bowie and Trevor Jones, drawing fans into Sarah's quest to rescue her brother. The Coronado Theatre, a historic 1927 movie palace known for its Spanish Renaissance architecture and starry ceiling, provides an atmospheric backdrop for this unforgettable cinematic concert experience.
Wrigley Field
July 31
1:20 PMChicago Cubs vs. New York Yankees Tickets
Chicago Cubs vs. New York Yankees at Wrigley Field brings two of baseball’s most recognizable franchises together in one of the sport’s most storied settings.
With the Cubs continuing to draw major attention at Wrigley and the Yankees carrying the weight of one of MLB’s most successful legacies, this matchup offers a high-demand blend of tradition, rivalry energy, and marquee-team appeal. Wrigley Field is famous for its ivy-covered outfield walls and classic ballpark atmosphere, making it one of the most iconic places to watch a game in Chicago.
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.
Chicagoland Speedway
July 04
5:00 PMNASCAR Cup Series Chicagoland Speedway Tickets
The NASCAR Cup Series races at Chicagoland Speedway in Joliet, Illinois, delivering high-octane motorsports action that captivates racing enthusiasts from across the region. This premier event showcases the sport's most competitive drivers battling for position on one of the circuit's most challenging tracks, combining speed, strategy, and pure adrenaline in a spectacle that defines American motorsports culture.
NASCAR Cup Series events represent the pinnacle of stock car racing, featuring elite drivers competing at speeds exceeding 180 mph in vehicles engineered for peak performance. Chicagoland Speedway, located just outside Chicago, is renowned for its 1.5-mile D-shaped oval configuration that creates intense side-by-side racing and memorable moments throughout the race.
Allstate Arena
July 17
8:00 PMMelanie Martinez Live at Allstate Arena
Melanie Martinez - HADES: THE SACRIFICE at Allstate Arena brings one of pop’s most theatrical and visually driven artists to Rosemont for a night built around immersive storytelling, dark-pop style, and fan-favorite songs. With Martinez’s distinctive aesthetic and emotionally charged performance approach, the show is poised to draw listeners who want a concert that feels as cinematic as it does musical.
Melanie Martinez has built a devoted following through concept-driven albums, bold visuals, and a sound that blends pop, alternative, and theatrical performance. Allstate Arena is one of the Chicago area’s best-known live entertainment venues, widely used for major concerts and large-scale touring productions, making it a fitting setting for a high-demand Melanie Martinez event.
United Center
Jun 27
8:00 PMWeird Al Yankovic Chicago: Tickets & 2026 Tour
“Weird Al” Yankovic is bringing his Bigger & Weirder 2026 Tour to the United Center in Chicago, IL! This event promises an evening of hilarious musical parodies and unforgettable stage antics from the reigning king of comedy rock. Expect a career-spanning setlist packed with fan favorites and deep cuts, showcasing Yankovic's unparalleled ability to transform popular songs into comedic masterpieces.
“Weird Al” Yankovic is a pop culture icon known for his clever song parodies and high-energy performances. He has sold millions of albums and won multiple Grammy Awards, solidifying his place in music history. The United Center, a renowned multi-purpose arena in Chicago, is home to the Chicago Bulls and Chicago Blackhawks, and is known for hosting world-class entertainment events.
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