Viator Rating : 5 (70 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
$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
€605
Experience Chicago's Festive Christmas Lights: A Magical Holiday Journey
5.0
(1 reviews)
Duration: 120
minutes
Chicago’s Festive Lights: A Magical Christmas Journey immerses you in the Windy City's holiday spirit. Starting at 875 N Michigan Ave, explore seasonal displays and the Christkindlmarket. This walking tour offers stunning views and cultural experiences. Perfect for experiencing the city's joy and beauty during Christmas.
Chicago
$35
Uncover Chicago's Dark Past: A Murder Mystery Adventure!
5.0
(724 reviews)
Duration: 120
minutes
The Chicago Murder Mystery Tour blends history and intrigue as you solve a fictional crime. Explore famous neighborhoods, delve into true crime legends, and play detective. Enjoy interactive gameplay and souvenir mugshot photos. Perfect for history buffs and true crime fans seeking a unique, immersive city experience, requiring walking and observation skills.
Chicago
$85.5
Chicago Art Institute: Skip-the-Line Private Tour
5.0
(271 reviews)
Duration: 150
minutes
Private Art Institute of Chicago Skip-the-Line Guided Tour. This is a special walking tour for people who love art and want to see the best pieces at the Art Institute of Chicago without waiting in long lines. The tour is just for the group and a guide, so it feels personal.
What to Expect: The tour visits famous artworks like 'Paris Street, Rainy Day' and 'Sunday on La Grande Jatte'. People will also see 'Nighthawks' and 'The Old Guitarist'. The guide shares stories about the art and artists. The Art Institute of Chicago is a very big museum with lots of famous art. It has art from all over the world and different times in history.
This private tour lasts for 2.5 hours and includes a professional tour guide just for the group. It also includes all entrance fees. The tour is wheelchair friendly. This tour does not include hotel pickup or drop-off, but the guide suggests using UBER or a taxi. Gratuities (tips) are not included in the price.
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
$64
Glide Through Chicago: A Lakefront Segway Adventure!
5.0
(345 reviews)
Duration: 120
minutes
The 2-Hour Chicago Lakefront and Museum Campus Segway Tour offers a unique way to explore Chicago's iconic landmarks. Effortlessly glide through Grant Park, visit Buckingham Fountain, and explore Museum Campus. This tour blends sightseeing with adventure, perfect for experiencing Chicago's highlights. Requires basic balance; training provided.
Nearby Events
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.
Fiserv Forum
Apr 03
7:00 PMBucks vs Celtics Tickets at Fiserv Forum
Milwaukee Bucks vs. Boston Celtics ignites Fiserv Forum in a high-stakes NBA showdown featuring Giannis Antetokounmpo’s dominance against Jayson Tatum’s scoring prowess. This Eastern Conference clash pits the playoff-contending Celtics, boasting a strong 21-12 record, against the home-standing Bucks aiming to rebound from their 15-20 start with crowd energy.
The Milwaukee Bucks, led by Giannis Antetokounmpo averaging 30.4 PPG and 11.9 RPG, face the Boston Celtics powered by Jayson Tatum’s 26.8 PPG in one of the league’s fiercest rivalries. Fiserv Forum, the Bucks’ state-of-the-art home since 2018, offers premium sightlines and electric atmosphere for every slam dunk and three-pointer.
Soldier Field
May 16
7:30 PMBruno Mars Romantic Tour Chicago Tickets
Bruno Mars - The Romantic Tour with Leon Thomas and DJ Pee .Wee at Soldier Field in Chicago brings the Grammy winner’s first full global stadium tour in nearly a decade to one of the Midwest’s biggest stages. The Romantic Tour celebrates his upcoming album The Romantic*, pairing arena-sized production with intimate, love-soaked storytelling in a pop, funk, and R&B spectacle fans have waited years to see.[1][4][7]
Bruno Mars, the 16-time Grammy-winning hitmaker behind “Uptown Funk,” “24K Magic,” and “Leave the Door Open,” returns to solo touring as he debuts new songs from *The Romantic* alongside a career-spanning set of fan favorites.[1][6][7] Leon Thomas and DJ Pee .Wee (Anderson .Paak’s DJ moniker) add soulful vocals and groove-heavy DJ sets to the night, while Soldier Field—Chicago’s historic lakefront stadium known for hosting major concerts and NFL games—provides an open-air backdrop with sweeping skyline and lake views.[2][5]
The Chicago Theatre
Sep 26
7:00 PMBassem Youssef: The Belly of the Beast Tour
Bassem Youssef: The Belly of the Beast Tour brings the Egyptian-American comedian and satirist to The Chicago Theatre for an evening of sharp political commentary and observational humor. Known globally as the "Egyptian Jon Stewart," Youssef has captivated audiences worldwide with his fearless approach to comedy that blends social critique with intelligent wit. This tour marks his continued expansion into English-language stand-up, where he applies the same uncompromising satirical lens that once drew 40 million weekly viewers to his groundbreaking television show.
Youssef's journey from cardiac surgeon to internationally acclaimed satirist has made him one of the most influential comedians of his generation. His ability to tackle complex political and social issues with humor has earned him recognition as one of Time magazine's 100 most influential people. The Chicago Theatre, one of America's most iconic performance venues, provides the perfect backdrop for an artist who has spent his career challenging authority and sparking meaningful conversation through comedy.
Coronado Theatre
Aug 22
7:30 PMJimmy Failla Live at Coronado Theatre
Jimmy Failla brings his razor-sharp stand-up comedy to the historic Coronado Theatre in Rockford, IL, delivering his signature humor drawn from his journey as a former New York City cab driver turned Fox News host. Known for his nationally syndicated radio show Fox Across America and hosting Fox News Saturday Night, Failla's performances blend everyman wit with timely takes on politics, pop culture, and everyday absurdities, as showcased in his stand-up special They're Just Jokes on Fox Nation.
Jimmy Failla, a New York Times bestselling author of Cancel Culture Dictionary, captivates audiences with relatable stories from driving cabs in NYC to opining on major Fox News programs like Hannity and Gutfeld. The iconic Coronado Theatre, a 1920s movie palace famed for its Spanish Revival architecture and superb acoustics, provides an intimate backdrop for his high-energy show.
United Center
May 01
8:00 PMDemi Lovato: It's Not That Deep Tour at United Center
Demi Lovato brings her highly anticipated 'It's Not That Deep Tour' to the iconic United Center in Chicago, promising an unforgettable night of pop anthems and raw, emotional performances. Known for her powerful vocals and candid stage presence, Demi is set to showcase new music and fan favorites in one of the city’s most celebrated arenas.
Demi Lovato continues to captivate audiences with her evolving artistry and resilience, making each concert a deeply personal experience. The United Center, home to the Chicago Bulls and Blackhawks, is renowned for its state-of-the-art acoustics, vibrant atmosphere, and history of hosting legendary concerts.
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