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
Huntington Bank Pavilion at Northerly Island
Jun 25
6:30 PMMartin Garrix Americas Tour Chicago Tickets
Martin Garrix brings his biggest Americas Tour to Huntington Bank Pavilion at Northerly Island in Chicago. The Dutch DJ and producer delivers his world-renowned high-energy live production, featuring massive drops and crowd-pleasing anthems across his 16-city North and South American run launching in May 2026.
Known for global hits like 'Animals' that propelled him to stardom at age 17, Martin Garrix continues to dominate electronic music with innovative sets and collaborations. Huntington Bank Pavilion at Northerly Island offers stunning lakeside views amid Chicago's skyline, enhancing the immersive concert experience.
Soldier Field
Aug 02
3:00 PMLiverpool FC vs Leeds United at Soldier Field Tickets
Liverpool FC vs Leeds United ignites Soldier Field in a fierce pre-season showdown between two historic English soccer rivals. As Liverpool, the 2024/25 Premier League champions, gear up under Arne Slot, they face a battle-hardened Leeds United side that went undefeated against the Reds last season, promising high-stakes action and tactical previews for the 2026-27 campaign.
This clash highlights the deep rivalry between Liverpool FC, with over 26 million US fans and the fastest-growing Premier League base in America, and Leeds United, returning to the US after 29 years. Soldier Field, Chicago's iconic NFL stadium home to the Bears and Chicago Fire, offers a massive stage with pristine pitch conditions optimized for elite soccer.
Allstate Arena
Jun 27
8:00 PMJosh Groban & Jennifer Hudson at Allstate Arena
Josh Groban with special guest Jennifer Hudson lights up Allstate Arena in Rosemont, IL, as part of their 'Two Legendary Voices, One Unforgettable Evening' tour. This pop and adult contemporary powerhouse pairing promises soaring vocals and emotional depth, drawing from Groban's classical crossover hits like 'You Raise Me Up' and Hudson's soulful anthems from her Grammy-winning career and Dreamgirls legacy.
Josh Groban, known for his tenor range and over 25 million albums sold worldwide, joins forces with Jennifer Hudson, the Emmy, Grammy, Oscar, and Tony-winning powerhouse whose powerful voice has captivated audiences in film, TV, and stage. Allstate Arena, a premier Chicago suburb venue famed for major concerts, offers prime sightlines and easy access.
NOW Arena
July 15
12:00 PMBulgaria vs Poland VNL Tickets at NOW Arena
Men's Volleyball Nations League: Bulgaria vs. Poland ignites NOW Arena in Hoffman Estates, IL, with elite international volleyball action. This thrilling matchup in the 2026 FIVB tournament's preliminary phase pits Bulgaria against powerhouse Poland, the defending champions and FIVB world No. 1, known for their Olympic silver and World Championship bronze.
The Men's Volleyball Nations League features 18 top teams in intense pool play across global host cities, with each squad battling in 12 high-stakes matches to secure Final 8 spots. NOW Arena delivers an electric atmosphere for fans craving world-class spikes and blocks.
United Center
Jun 20
8:30 PMROSALÍA LUX TOUR 2026: Chicago Tickets
ROSALÍA brings her *LUX TOUR 2026** to the United Center in Chicago, delivering a groundbreaking fusion of Latin rhythms, flamenco innovation, and electronic beats that has redefined modern music. Known for chart-topping albums like *Motomami* and *El Mal Querer*, the Spanish superstar captivates with her raw vocal power and boundary-pushing performances, promising an immersive spectacle blending cultural heritage with futuristic visuals.
ROSALÍA's rise from flamenco roots to global icon status has earned her multiple Grammy Awards and billions of streams, making her one of the most influential artists in Latin music today. The United Center, Chicago's premier arena renowned for hosting legendary concerts, provides the perfect stage for this unmissable event.
United Center
Aug 03
8:00 PMAriana Grande Tickets Chicago United Center 2026
Ariana Grande's The Eternal Sunshine Tour arrives at Chicago's United Center, delivering a dazzling pop music experience. This highly anticipated 2026 tour supports her seventh studio album, Eternal Sunshine, marking her triumphant return to the stage with a vibrant setlist from both new and classic hits.
The Eternal Sunshine Tour showcases Ariana's iconic vocals and dynamic performance style, combining cinematic visuals with intimate and energetic moments. The United Center, renowned as Chicago's premier arena for top-tier concerts and sporting events, provides an electrifying backdrop for this unforgettable show.
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