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Sailing Chicago's Gorgeous Lakefront

Chicago, United States

Check local COVID-19 restrictions before booking

Experience hosted by Dan And Jen

3 hours
Includes food, drinks, equipment
Up to 6 people
Hosted in English

What you'll do

Experience Chicago from the Lake - beautiful anytime day or night!!! We sail from DuSable Harbor to favorable winds. Captain Dan takes care of the sailing but you're welcome to lend a hand anytime if you'd like...he's a great teacher. Please let us know if you don't see the time you're looking for on the schedule, we'll do our best to accommodate you.

Wednesday and Saturday night sailors will experience a special treat - fireworks off of Navy Pier right above your head and Jennifer singing an all-American patriotic song... or two!

We'll cruise Chicago's Navy Pier, world-renowned Field Museum, Shedd Aquarium, and Adler Planetarium. We'll visit the "playpen", a secluded cove where boaters mix and mingle - it's a floating party. On warmer days we can cool off with a swim in the lake.

We're here to share Chicago's best side - lakeside!
Other things to note
- Please be on time, we can only wait a few mins past scheduled time -thanks!
-Will cancel trip one hour ahead of time if there's extremely bad weather and/or lightning in area.
Experience Chicago from the Lake - beautiful anytime day or night!!! We sail from DuSable Harbor to favorable winds. Captain Dan takes care of the sailing but you're welcome to lend a hand anytime if you'd like...he's a great teacher. Please let us know if you don't see the time you're looking for on the schedule, we'll do our best to accommodate you.

Wednesday and Saturday night sailors will experience a special treat - fireworks…

Dan And Jen's commitment to safety

This host committed to Airbnb’s COVID-19-related safety and cleaning guidelines—including adhering to social distancing guidelines, practicing good hygiene, and ensuring that all participants wear a mask.
Learn more

What's included

  • Food
  • Drinks
    BYOB
  • Equipment
    Toilet onboard, small fridge and coolers, sunscreen, lifejackets, towels, b...
From $160
/ person

Meet your host, Dan And Jen

Host on Airbnb since 2019
  • 43 Reviews
  • Identity verified
We are Dan and Jennifer and we share a love for sailing, music and our beautiful city, Chicago!

Captain Dan holds a Coast Guard OUPV Master Captain's license from USCG and has over 20 years of experience in cruising, racing, boat chartering, water sports and over-night cruises across Lake Michigan to Wisconsin, Indiana, and Michigan.

First mate Jennifer is a professional opera singer and has lived and performed throughout Europe and the US. She is fluent in Italian and "fun".
To protect your payment, never transfer money or communicate outside of the Airbnb website or app. Learn more

Where you'll be

We'll first head north to see Navy Pier, Chicago's "playpen", Oak Street Beach and North Avenue Beach. Then head South to cruise past the Shedd Aquarium, the Adler Planetarium, the Field Museum, and Soldier Field. All the while taking in Chicago's stunning skyline!!!

Rated 4.88 out of 5 from 43 reviews.

Ronny
October 2020
This was such a great experience. Jen, Dan and Martin made us feel comfortable and safe. They truly are experts in sailing, showed us a good time and were fun to hang out with. This is a must do while in Chicago and we’d definitely do it again! Don’t hesitate to book.
This was such a great experience. Jen, Dan and Martin made us feel comfortable and safe. They truly are experts in sailing, showed us a good time and were fun to hang out with. Thi…
Edina
August 2020
Wow! What an experience! Captain Dan was so knowledgeable, accommodating and made us feel extremely welcoming. During the trip we got to learn a lot about the nuance of sailing process and a bit about Chicago. Overall, I would absolutely recommend anyone to try this experience!
Wow! What an experience! Captain Dan was so knowledgeable, accommodating and made us feel extremely welcoming. During the trip we got to learn a lot about the nuance of sailing pro…
Ana
October 2019
This was a very unique experience which definitely transformed our first stay in Chicago and make us want to come back! The boat is comfortable and has everything you need and the view is AMAZING .. but without that special and gorgeous crew it wouldn’t have been the same! So a big big thank you to Jen, Bryan, Dan and Jerry ... can’t wait to see you all again!!
This was a very unique experience which definitely transformed our first stay in Chicago and make us want to come back! The boat is comfortable and has everything you need and the…
Lydia
October 2019
We happened to pick a perfect day to sail and Dan gave us his history of sailing and Chicago. It was a great 3 hours and well worth the cost.
Mike
October 2019
Fantastic experience. Got to see the city in a way we never could’ve imagined. The hosts and captain treated us like family and were very accommodating.
Erica
September 2019
This was our first experience with Airbnb and it was perfect. Dan and Jen were perfect with communication, asked our group what we were expecting out of our sailing time and made it happen. Being able to go sailing on Lake Michigan with the backdrop of Chicago for such a reasonable price and 3 hrs was amazing. I am already planning my next trip just to go sailing with them again. They are extremely friendly and make you feel welcomed instantly!!!
This was our first experience with Airbnb and it was perfect. Dan and Jen were perfect with communication, asked our group what we were expecting out of our sailing time and made i…

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    Activity advisory

    Expert industry partners
    Every adventure follows industry guidelines. We partnered with the Adventure Travel Trade Association, expert leaders in adventure travel, to define best practices and standards for safety.
    Know your comfort level
    Please note outdoor activities carry risks, and you may be exposed to dangerous situations as part of this experience. Make sure you can participate safely given your abilities and the conditions (such as location, weather, and equipment).

    Things to know

    Cancellation policy

    Any experience can be canceled and fully refunded within 24 hours of purchase, or at least 7 days before the experience starts.

    Government ID

    You’ll need to take a picture of yourself that matches the photo on your ID. This is so Airbnb can confirm who’s actually going on the experience. You’ll only have to do this once.

    Guest requirements

    Up to 6 guests ages 5 and up can attend.

    What to bring

    Sunscreen/sunglasses

    Windbreaker/sweatshirt