Viator Rating : 5 (73 reviews)
Dyvarcity Score : 9.1/10 (Verified Excellent)
Chicago
Private Sail: Chicago Skyline Views from Navy Pier!
120
Overview
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. 
Experience DNA Fingerprint
Scores are shown on a scale of 1 to 10, 1 = lowest score, 10 = highest score.
What People Love
Crowd Density (9 - Empty / Light) : Very few people, free movement
Safety (9 - Secure) : Strong feeling of safety and control
Upsell Risk (10 - Transparent) : No upsells or hidden costs
Logistics (9 - Seamless) : Smooth and well executed
Mobility (8 - Easy / Accessible) : Comfortable for most people
Pacing (9 - Balanced) : Smooth and comfortable timing
Instagram Factor (9 - Iconic) : Highly photogenic and memorable
Guide Quality (9 - Exceptional) : Engaging and memorable
Guide Reliability (10 - Dependable) : On time with strong follow-through
Highlights
See Chicago's Skyline: Enjoy amazing views of the city from Lake Michigan.
Private Sailing Trip: It's just for your group, up to six people.
Customize Your Trip: Pick your music and the route you want to sail.
Relax on the Lake: Let a licensed captain take you for a smooth ride.
Sentiment Analysis
Customers loved the amazing views of the Chicago skyline.
-
Many enjoyed the relaxing and smooth sailing experience.
-
The captains are often praised for being friendly and knowledgeable.
-
Groups appreciate the customization options to create a personalized experience.
Some mentioned additional costs can add up, like drinks and gratuity.
-
A few customers experienced issues with booking times.
The Journey
Navy Pier Marina
Begin your nautical adventure at Navy Pier Marina, the launching point for an unforgettable sailing experience on Lake Michigan. Before setting sail, receive a comprehensive safety briefing and prepare to be captivated by the boundless possibilities that await. With a flexible itinerary tailored to your preferences, you have the freedom to explore iconic landmarks, discover hidden gems, and create cherished memories against the backdrop of Chicago's breathtaking skyline.
Navy Pier
Experience the vibrant energy of Navy Pier, a beloved Chicago landmark and popular tourist destination. As you sail past its eastern end, marvel at the grandeur of the Grand Ballroom and capture stunning architectural photos. With a rich history dating back to 1916, Navy Pier has served various roles, including its significant contribution during WWII. Beyond its picturesque facade, this iconic pier holds a captivating story that resonates with the heart and soul of Chicago.
Chicago Skyline
Witness the awe-inspiring beauty of Chicago's magnificent skyline from the tranquil waters of Lake Michigan. Ranked among the world's most beautiful waterfront cities, Chicago's architectural marvels and engineering feats come to life from this unique vantage point. Customize your experience by selecting the stories you wish to hear, allowing our knowledgeable captains to guide you through the city's captivating history and landmarks. Alternatively, simply relax and soak in the breathtaking views as you create unforgettable memories with friends and loved ones.
Adler Planetarium
Behold the iconic dome of the Adler Planetarium, an architectural gem nestled on the northeast corner of Northerly Island. Established in 1930, this public museum dedicated to astronomy and astrophysics provides an enchanting setting for exploration and discovery. From the lake, uncover a hidden perspective of the structure, including the lakeside Doane Observatory with its accessible telescope. Immerse yourself in the wonders of the universe as you admire the Adler Planetarium's timeless beauty and scientific significance.
Soldier Field
Discover the storied past of Soldier Field, the iconic home of the Chicago Bears, opened in 1924. This historic stadium has played host to numerous significant events throughout the years. As you glide along the water, catch a glimpse of the original colonnades, a testament to the stadium's enduring legacy. Immerse yourself in the rich history and tradition of this beloved Chicago landmark, a symbol of sportsmanship and civic pride.
Buckingham Fountain
Sail past the historic Queen's Landing, the site where Queen Elizabeth II embarked on her royal visit to Chicago in 1959, and prepare to be mesmerized by the majestic Buckingham Fountain. This iconic centerpiece of Grant Park, donated by Kate Buckingham in memory of her brother Clearance, is one of the world's largest fountains. Capture the perfect photo opportunity as you admire its intricate design and cascading waters, a symbol of Chicago's artistic and philanthropic spirit.
Know Before You Go
This private sailing experience includes the use of Bluetooth speakers, Navy Pier facility fees, all applicable taxes, and a professional US Coast Guard licensed captain. What is excluded is gratuities, food and drinks, and parking at Navy Pier. The meeting point is at the Navy Pier Marina. Make sure to coordinate meeting time and location with the operator before arrival.
Hot Tip
Many reviewers suggest bringing your own drinks and snacks to enjoy on the boat. Also, confirm the exact meeting location at Navy Pier with the operator a day or two before your sail to avoid any confusion.
Review Summary
Travelers consistently praise the private sailing experience for its stunning skyline views, flexible itinerary, and friendly, knowledgeable captains. Many highlight the opportunity to relax and enjoy the lake breeze while customizing the route and music. Some note that the experience is more about leisure than in-depth guided commentary. The main drawbacks mentioned are the lack of wheelchair accessibility and the fact that food and drinks are not included, which some guests expected.
This page is synthesized and developed by Dyvarcity Team
More like this
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.
Chicago
$89
Chicago's Best Bites: A Delicious Bike & Brews Tour
4.9
(731 reviews)
Duration: 270
minutes
Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour lets people taste all the best Chicago foods on two wheels! This 4 1/2-hour guided bike tour, led by the experts at Bobby’s Bike Hike, takes riders on a fun and yummy adventure. It was even ranked in the Top 20 tours in the world by TripAdvisor!
The easy 13-mile ride explores Chicago's famous eats, including deep-dish pizza and a Chicago-style hot dog. Sample local craft beers while seeing cool spots like the Gold Coast, Lincoln Park, and Wrigleyville, home of the Chicago Cubs. Night tours light up with Buckingham Fountain, Millennium Park, and downtown sights. Pedal along the Lakefront Trail, a top bike path, and discover the heart of Chicago.
This experience includes an expert local guide, a water bottle to stay hydrated, a bicycle, a helmet for safety, and delicious food and beer samples. The tour does not include the suggested $15 guide gratuity per person, payable via cash, Venmo, or PayPal. Get ready to roll, taste, and learn on this unforgettable Chicago adventure!
Chicago
$100.95
Chicago Food, History & Architecture Walking Tour
4.9
(1152 reviews)
Duration: 270
minutes
Chicago in a Day: Explore Food, History, and Iconic Architecture. This walking tour takes people through the heart of Chicago, showcasing its food, history, and buildings. It's a tasty way to see the city and learn some fun facts.
Visitors will walk along the Riverwalk, see the Wrigley Building, and snap photos at Millennium Park by Cloud Gate, also known as 'The Bean'. The tour also explores hidden spots like the Chicago Pedway and the bustling energy of Chicago's Main Artery. Expert local guides share stories about Chicago's past, from the Prohibition era to the Great Fire.
This tour includes stops at the Chicago Theatre, City Hall-County Building and the Loop. It includes Chicago's famous eats like deep-dish pizza, a Chicago-style hot dog, and Italian beef. The tour is limited to a small group of 12, making it personal and relaxed. This experience is run by a certified B Corp, which means they care about ethical and responsible tourism.
Chicago
$87
Chicago Food Tour: Bites, History & Secret Dishes!
4.9
(867 reviews)
Duration: 180
minutes
Chicago Walking Food Tour With Secret Food Tours lets one savor the Windy City's vibrant flavors! This isn't just a food tour; it's a delicious journey through Chicago's history and culture, one bite at a time. This walking tour explores the famed Chicago Loop District, showcasing world-renowned architecture and public art. See landmarks like the Harold Washington Library Center, walk along LaSalle Street, admire The Flamingo (Calder Sculpture), and catch a glimpse of the Willis Tower (Sears Tower), The Rookery Building, and the Palmer House Hilton.
What can visitors expect? The tour includes the city's biggest food hits, many with roots dating back over 150 years. Imagine tasting the iconic deep-dish pizza, sinking your teeth into an amazing Italian beef sandwich, munching on gourmet popcorn, and savoring other treats. There's also a mouth-watering secret dish that’s revealed only on the day of the tour! The local guide will provide insights along the way.
The tour includes an Italian Beef Sandwich, a brownie, a Chicago-style Hot Dog, a delicious Secret Dish, Deep Dish Pizza with Sausage, and Gourmet Popcorn. It excludes hotel pickup and drop-off, and gratuities (optional).
Chicago
$84.99
Chicago Food Tour: Deep Dish, Hot Dogs & Hidden Gems
4.8
(1957 reviews)
Duration: 180
minutes
The Chicago Favorites Ultimate Food and Walking Tour is perfect for anyone who wants to taste Chicago's famous foods and see the city's best sights. This tour takes you through downtown Chicago to try the Windy City's favorite eats! You'll get to taste deep-dish pizza, a Chicago-style hotdog, Italian beef, popcorn, and brownies.
What to Expect: This walking tour, led by expert guides, explores iconic landmarks like Millennium Park and the Chicago Theatre Marquee. Guests will see the Cloud Gate ('The Bean') and the Pritzker Pavilion, stroll along the Chicago Pedway/Loop Promenade and visit the First Chicago Skyscraper. They'll also see the Chicago Historic Water Tower and Holy Name Cathedral. Plus, they'll visit Max's Take Out and sample an Original Recipe Brownie. It's a tasty way to learn about Chicago's food history!
This experience includes 4-5 food stops, a free 2-hour bike or kayak rental (weather permitting), and insider tips on what to see and do in Chicago. It excludes hotel pickup/drop-off and a recommended gratuity for the guide. It's important to note that alcoholic beverages are not included. With Bobby's Bike Hike, whose food tours are ranked Top 10 in America (USA Today) & Top 20 in the world (Tripadvisor), this tour promises a fun and delicious adventure, usually with small groups.
Chicago
$59
Chicago's Iconic Landmarks: A Riotous Bike Adventure
4.9
(233 reviews)
Duration: 180
minutes
Chicago's Ultimate City Bike Tour offers an engaging exploration of iconic landmarks like Millennium Park and the Museum Campus. Led by Bobby's Bike Hike, the leisurely 3-hour ride suits all skill levels. Gain intimate knowledge of Chicago's treasures, perfect for first-time and returning visitors.
Nearby Events
The Chicago Theatre
Nov 21
7:00 PMGEORGE LOPEZ
The Auditorium
Nov 22
7:00 PMDaniel Sloss: BITTER Tour at The Auditorium
Daniel Sloss: BITTER brings the Scottish comedy powerhouse to The Auditorium in Chicago for his brand new tour. Known for Netflix specials like DARK and Jigsaw, Sloss delivers dark, incisive humor on topics from religion to politics, building on his record as the youngest comedian to sell out London's West End and perform on Conan ten times.
Sloss's provocative style has earned critical acclaim worldwide, with 13 solo shows across 55 countries and massive tours like HUBRIS. The Auditorium, a premier Chicago venue, hosts this unmissable stand-up event.
Rialto Square Theatre
Nov 15
2:00 PMBe Like Blippi Tour!
Milwaukee Improv (Main Room)
Nov 05
7:00 PMRussell Peters Live at Milwaukee Improv
Russell Peters performs at Milwaukee Improv (Main Room), bringing one of the world’s most recognizable stand-up voices to Brookfield for a sharp, fast-paced night of comedy. He is actively touring in 2026 with his Relax World Tour, continuing to draw audiences across major cities with his observational humor, crowd work, and globally informed storytelling.
Peters has built his reputation as a major international comedy headliner with sold-out tours, a large online following, and a style that blends cultural commentary with quick improvisation. Milwaukee Improv (Main Room) is known as a dedicated comedy venue in the Milwaukee area, giving audiences an intimate setting that suits live stand-up and keeps the focus on the performance.
The Lerner Theatre
Nov 08
7:00 PMBERT KREISCHER: PERMISSION TO PARTY
United Center
Jan 07
8:00 PMMatt Rife Stay Golden Tour Tickets Chicago
Matt Rife: Stay Golden World Tour rolls into the iconic United Center in Chicago, delivering a fresh, high-energy comedy experience. Known for his sharp wit and engaging crowd work, Rife’s 2026 tour boasts a unique 360° in-the-round stage setup that immerses fans by surrounding the performer from all sides.
Rife has skyrocketed to fame with his viral humor and stand-up charisma, making this tour one of the most anticipated comedy events of the year. The United Center, famed for hosting major entertainment and sports events, offers a premier venue setting that enhances every moment of this dynamic 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