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Chicago Skyline Sunset Sail Aboard a Tall Ship

4.8 (28)
Chicago, US
4.8 (28)
Chicago, US
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Experience the breathtaking beauty of the Chicago skyline on the famous Tall Ship Windy sunset sail. As you sail across Lake Michigan, you'll be treated to stunning views of the city's iconic skyline. This unforgettable journey aboard the official flagship of Chicago, the 148' S/V Windy, is perfect for a romantic evening or a special event. Capture the perfect photo backdrop as the ship turns towards the skyline, creating a picture-perfect moment. Sit back and relax, listen to soothing music, and let the dramatic sunset complete your day. And if you book a sunset sail on Monday evenings, you'll be treated to the Monday Night Blues Summer Concert Series, featuring live blues music and an extended sail time. Don't miss out on this truly famous and unforgettable experience.

About this experience

  • Free Cancellation For a full refund cancel at least before the start of your booking
  • Admission Included
  • 1 hours 15 minutes
  • Suitable for 1-15 Participants
  • Private Tour, Small Group Tour
  • Guided Experience
  • Breathtaking sunset views of the Chicago skyline
  • Sailing on Lake Michigan aboard a historic four-mast Schooner
  • Relaxing atmosphere with soothing music on board
  • Opportunity for stunning photos and memorable moments
  • Upgrade to Monday Night Blues Summer Concert Series
  • WiFi on board
  • GST (goods and services tax)
  • Landing and facility fees
  • Restroom on board
  • Alcoholic beverages
  • Snacks
  • Gratuities

Popular Hotels Closeby

More about this experience

Introduction

Experience the breathtaking beauty of the Chicago skyline from the deck of the official flagship of Chicago, the 148' S/V Windy. Embark on a sunset sail aboard the iconic Tall Ship Windy, a four-mast Schooner that has been captured in numerous world-renowned photos and is often chosen as the backdrop for special events and weddings. This unforgettable tour offers the perfect way to spend an evening out, whether you're seeking a romantic outing or simply a relaxing escape.

What to expect?

During the Chicago Skyline Sunset Sail, you can anticipate a serene and captivating experience. As you set sail on Lake Michigan, the magnificent S/V Windy will gracefully turn towards the Chicago skyline, allowing you to witness a truly awe-inspiring sunset. Sit back, relax, and let the soothing music create the perfect ambiance as you sail into the golden hour. This magical moment will provide you with an unforgettable memory to cherish.

Who is this for?

This sunset sail is designed for anyone who appreciates the beauty of nature, the allure of the open water, and the charm of the Chicago skyline. Whether you're a local looking for a unique way to spend an evening or a visitor seeking an authentic Chicago experience, this tour is for you. Couples looking for a romantic outing, friends searching for a memorable adventure, or solo travelers seeking tranquility will all find solace and delight aboard the Tall Ship Windy.

Why book this?

Embarking on the Chicago Skyline Sunset Sail is an opportunity to escape the hustle and bustle of the city and immerse yourself in the serenity of Lake Michigan. This unique experience allows you to witness the picturesque Chicago skyline as it is bathed in the warm glow of the setting sun. The Tall Ship Windy offers an unparalleled vantage point, ensuring that you capture the perfect photo or simply revel in the breathtaking views. Let the gentle sway of the ship and the soothing music transport you to a state of pure bliss.

Good to know

During your sunset sail, you'll have access to WiFi on board, ensuring you can share your stunning photos and experiences with friends and family in real-time. The ticket price includes GST (goods and services tax) as well as landing and facility fees. Additionally, there is a restroom available on board for your convenience. Please note that alcoholic beverages, snacks, and gratuities are not included, allowing you the freedom to personalize your experience according to your preferences.

Reviews

Guests who have previously embarked on the Chicago Skyline Sunset Sail rave about the experience. They express their awe at the unparalleled beauty of the Chicago skyline at sunset, and they emphasize the tranquility and relaxation that comes with sailing on the Tall Ship Windy. Many visitors mention that this tour provided them with unique and stunning photo opportunities, allowing them to capture memories that will last a lifetime. Overall, individuals who have experienced the sunset sail aboard the Tall Ship Windy express their complete satisfaction and recommend it as a must-do activity in Chicago.

How long before the event do I need to book?

  • You can book at any time before the event

Vouchers accepted in the following formats

  • Mobile

Is an adult required for the booking?

  • At least one adult or senior required per booking

Your Itinerary

Navy Pier

148' Tall Ship Windy departs from historic Navy Pier, the entertainment venue in Chicago

Lake Michigan

Tall Ship Windy will sail from Navy Pier into Lake Michigan and at the perfect time, turn so our guests may see the glorious sunset behind the Chicago Skyline.

Admission Included

Chicago Skyline

As you sail on Tall Ship Windy, guests will have a phenomenal view of the Chicago Skyline.

Admission Included

Reviews

(28)

4.8 (28)

Richa_B

Sunset sail was amazing- was incredible weather, staff was great and their was plenty of room to move around and get great pictures of the sunset

Olga_P

The crew was amazing. They were very entertaining and made the experience truly enjoyable. Having a bar on board and bartender with a great sense of humor is definitely a plus!!

Meander04733761196

The evening cruise was the perfect family activity for our weekend trip to Chicago. We set sail on time and enjoyed a smooth ride as we enjoyed sunset views of the city. The crews’ upbeat personalities, Caribbean drinks, and fun music added to a relaxing and fun vibe!! I highly recommend!!

rogerhF9326SW

Honestly, a perfect experience. Exactly on-time departure and arrival. Perfect boat - size and look. The Captain and crew were friendly and knowledgable. My son raised the sail. Hard. Fun. An experience. The frozen drinks and cold beers were excellent. The views? Wow. A great soundtrack plays during the excursion at perfect volume level. A great time for all ages of Pirates. I guess I liked it :) Just do it. Thank me later.

csseng1

We’ve been to Chicago many times but have never experienced the city from this perspective. We were blown away at how beautiful the skyline is at sunset.

Lynn_O

The girl that did the commentary was pretty funny. And good. Was nice that we actually sailed. Even though it was for a short time was still nice!!

Delilah_T

The crew, boat and evening were perfect. The crew was engaging and lively which added to the wonderful experience.

Bonnie_F

Beautiful views, great music, peaceful boat ride! Definitely would go again! My family really enjoyed it!

Barbara_S

We had a fabulous time with 4 generations of our family on the main deck for a Monday sunset sail! It was so beautiful and the live musician added so much to the experience! The crew were extremely helpful in providing extra care for my nearly 90 year old granny and my mom who is a bit frail in between her cancer surgery and start of chemo.

K4620WOchristinem

The views from the sailing vessel were wonderful. The tour would benefit from some historical narration rather than silly nautical songs and pretend pirate characters. You are on your own trying to figure out landmarks and such.
Collected by Evendo, Tripadvisor & Viator
2024-05-23 13:24