img0 img1img2img3img4
Left Arrow
Right Arrow
img1
img2
img3
img4
Rating Star

Viator Rating : 5 (70 reviews)

Dyvarcity Score Icon

Dyvarcity Score : 9.1/10 (Verified Excellent)

Location Icon Chicago

Private Sail: Chicago Skyline Views from Navy Pier!

Clock

120

Overview

Experience Intelligence

Highlights

Sentiment Analysis

FAQs

Location

Overview

Quotes Logo 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. Quotes Logo

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)

Crowd Density (9 - Empty / Light) : Very few people, free movement

Safety (9 - Secure)

Safety (9 - Secure) : Strong feeling of safety and control

Upsell Risk (10 - Transparent)

Upsell Risk (10 - Transparent) : No upsells or hidden costs

Logistics (9 - Seamless)

Logistics (9 - Seamless) : Smooth and well executed

Mobility (8 - Easy / Accessible)

Mobility (8 - Easy / Accessible) : Comfortable for most people

Pacing (9 - Balanced)

Pacing (9 - Balanced) : Smooth and comfortable timing

Instagram Factor (9 - Iconic)

Instagram Factor (9 - Iconic) : Highly photogenic and memorable

Guide Quality (9 - Exceptional)

Guide Quality (9 - Exceptional) : Engaging and memorable

Guide Reliability (10 - Dependable)

Guide Reliability (10 - Dependable) : On time with strong follow-through

Highlights

Highlight Icon

See Chicago's Skyline: Enjoy amazing views of the city from Lake Michigan.

Highlight Icon

Private Sailing Trip: It's just for your group, up to six people.

Highlight Icon

Customize Your Trip: Pick your music and the route you want to sail.

Highlight Icon

Relax on the Lake: Let a licensed captain take you for a smooth ride.

Sentiment Analysis

  • Positive Highlight Icon Customers loved the amazing views of the Chicago skyline.

  • Positive Highlight Icon Many enjoyed the relaxing and smooth sailing experience.

  • Positive Highlight Icon The captains are often praised for being friendly and knowledgeable.

  • Positive Highlight Icon Groups appreciate the customization options to create a personalized experience.

  • Negative Highlight Icon Some mentioned additional costs can add up, like drinks and gratuity.

  • Negative Highlight Icon A few customers experienced issues with booking times.

The Journey

1

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.

2

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.

3

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.

4

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.

5

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.

6

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.

Frequently Asked Questions

This page is synthesized and developed by Dyvarcity Team

From $508 Price

Book Now

As a Viator affiliate partner, we may earn a commission on purchases made through our platform.

Book Now

As a Viator affiliate partner, we may earn a commission on purchases made through our platform.

More like this

Chicago Sunset Sailing: Private Lake Michigan Cruise Awaits!

Location Icon Chicago

$507.96

Chicago Sunset Sailing: Private Lake Michigan Cruise Awaits!

Low Last Minute Supplier Cancellation Rate Likely to Sell Out Day Cruises

Rating Star 5.0 (27 reviews)

Duration In Minutes 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.

Details

Book Now

Chicago's Culinary Gems: A Private Foodie Adventure

Location Icon Chicago

$288

Chicago's Culinary Gems: A Private Foodie Adventure

Food & Drink City Tours Likely to Sell Out

Rating Star 5.0 (6 reviews)

Duration In Minutes Duration: 240 minutes

The Chicago Private Foodie Tour dives into Windy City favorites. This half-day experience, led by a local guide, explores iconic landmarks while indulging in Chicago's famous eats, including deep-dish pizza and Italian beef. Bottled water and fees are included. Perfect for food lovers seeking culture and delicious memories.

Details

Book Now

Uncover Chicago's Dark Past: A Murder Mystery Adventure!

Location Icon Chicago

$35

Uncover Chicago's Dark Past: A Murder Mystery Adventure!

Walking Tours Crime Tours Cultural Tours

Rating Star 5.0 (724 reviews)

Duration In Minutes 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.

Details

Book Now

Chicago Art Institute: Skip-the-Line Private Tour

Location Icon Chicago

$85.5

Chicago Art Institute: Skip-the-Line Private Tour

Historical Tours Museums Low Last Minute Supplier Cancellation Rate

Rating Star 5.0 (271 reviews)

Duration In Minutes 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.

Details

Book Now

Chicago Food, History & Architecture Walking Tour

Location Icon Chicago

$100.95

Chicago Food, History & Architecture Walking Tour

Likely to Sell Out Food & Drink Viator Experience Award 2023

Rating Star 4.9 (1152 reviews)

Duration In Minutes 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.

Details

Book Now

Glide Through Chicago: A Lakefront Segway Adventure!

Location Icon Chicago

$64

Glide Through Chicago: A Lakefront Segway Adventure!

Cultural Tours City Tours Excellent Quality

Rating Star 5.0 (345 reviews)

Duration In Minutes 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.

Details

Book Now

Nearby Events

Bulls vs Trail Blazers: United Center Tickets

Location Icon United Center

Feb 26

7:00 PM

Bulls vs Trail Blazers: United Center Tickets

Basketball NBA Sports

Chicago Bulls vs. Portland Trail Blazers ignites the United Center with high-stakes NBA action, pitting the home-standing Bulls against a Trail Blazers squad surging on a three-game win streak led by Deni Avdija's explosive scoring outbursts.
Both teams battle in the tight Western and Eastern Conference standings—Bulls at 17-19 with a solid 10-9 home record, Trail Blazers at 17-20 but riding momentum after blowouts like their 137-117 rout of the Jazz. The iconic United Center, known for hosting legendary Bulls eras, delivers unmatched energy for this clash.

Details

Book Now

Romeo Santos & Prince Royce Live at Allstate Arena

Location Icon Allstate Arena

Apr 02

8:00 PM

Romeo Santos & Prince Royce Live at Allstate Arena

Latin Music

Romeo Santos and Prince Royce ignite the Allstate Arena with their Mejor Tarde Que Nunca Tour 2026, a powerhouse collaboration between bachata legends delivering hits like 'Propuesta Indecente' and 'Stand by Me.' This rare joint tour celebrates their decades of chart-topping success and sold-out shows, promising an explosive mix of romantic rhythms and high-energy performances that have defined Latin music.
Romeo Santos, the King of Bachata, rose to fame with Aventura before launching a solo career with multi-platinum albums, while Prince Royce modernized bachata for global audiences with his soulful voice and crossover appeal. Together, they bring unmatched charisma to fans. Allstate Arena, a premier Chicago suburb venue, hosts top-tier concerts with excellent sightlines and vibrant energy.[1][6]

Details

Book Now

Lion King in Concert: Milwaukee Tickets

Location Icon Miller High Life Theatre

Mar 22

12:00 PM

Lion King in Concert: Milwaukee Tickets

Music Film

The Music of The Lion King – Live in Concert brings the iconic Disney soundtrack to life at Miller High Life Theatre with a symphonic orchestra, dynamic percussionists, and soaring choral harmonies from star soloists of the original Broadway productions.
This multisensory tribute features timeless hits like “Circle of Life,” “Hakuna Matata,” and “Can You Feel the Love Tonight,” enhanced by immersive visuals, state-of-the-art lighting, and vibrant projections that capture the majesty of the African savanna. Performed by the Broadway Symphonic Orchestra & Choir, it delivers the emotional depth and cultural richness of the beloved film and musical. Miller High Life Theatre, a historic venue in Milwaukee's Wisconsin Center District, provides an elegant backdrop for this captivating performance.

Details

Book Now

Bucks vs Heat Tickets: Fiserv Forum NBA Clash

Location Icon Fiserv Forum

Feb 24

7:00 PM

Bucks vs Heat Tickets: Fiserv Forum NBA Clash

Basketball NBA Sports

Milwaukee Bucks vs. Miami Heat ignites Fiserv Forum in a high-stakes NBA showdown between Eastern Conference rivals. As Bucks defend their 2024 Emirates NBA Cup title and Heat ride a hot streak with 19-15 record, fans anticipate explosive plays from stars like Bucks' Giannis and Heat's sharpshooters in this pivotal matchup[1][3].

Milwaukee Bucks and Miami Heat share a fierce rivalry history, with both teams vying for playoff positioning amid Bucks' homestand push and Heat's road resilience. Fiserv Forum, the Bucks' state-of-the-art home hosting 22 weekend games this season, delivers premium sightlines and electric energy[3].

Details

Book Now

Theresa Caputo Live! The Experience at Genesee Theatre

Location Icon Genesee Theatre

Feb 04

7:30 PM

Theresa Caputo Live! The Experience at Genesee Theatre

Community/Civic Miscellaneous

Theresa Caputo Live! The Experience brings the renowned Long Island Medium to the historic Genesee Theatre in Waukegan, IL, for a night of unforgettable psychic readings and heartfelt connections. Fans can expect an intimate, emotionally charged evening as Theresa delivers messages from loved ones, blending humor, compassion, and the supernatural in her signature style.

Theresa Caputo has become a household name through her hit TV show and sold-out tours, captivating audiences with her authenticity and warmth. The Genesee Theatre, a beautifully restored 1920s venue, adds to the magic with its elegant ambiance and excellent acoustics, making it the perfect setting for a memorable live experience.

Details

Book Now

Peso Pluma Dinastia Tour: Chicago Tickets

Location Icon United Center

May 07

8:00 PM

Peso Pluma Dinastia Tour: Chicago Tickets

Latin Music

Dinastia Tour by Peso Pluma & Friends lights up the United Center with the Mexican superstar's fully reimagined live spectacle, featuring elevated production, immersive creative elements, and surprise appearances by his rotating lineup of friends.[2][4] Named after his chart-topping album DINASTÍA, which debuted at No. 1 on Billboard’s Top Latin Albums and Regional Mexican Albums charts, this tour showcases Peso Pluma's evolution as a global Música Mexicana phenomenon following two sold-out U.S. runs.

Peso Pluma has redefined the genre with hits that dominate Spotify’s Global Albums chart and Billboard’s Global 200, blending raw corridos tumbados with massive stadium energy.[2] The United Center, Chicago's premier arena home to the Blackhawks and Bulls, delivers world-class acoustics for this epic night.[6]

Details

Book Now

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