Save to Wishlist

What you offer

Hours per week

Help out and collaborate with your host only a few hours per week.

Painting & Decorating

Help to maintain the appearance inside and outside the building.


Help with a wide range of repairs.

Learn more

What you get

Days off per week

Have some time off for yourself, go explore the city or rest for a while.

Shared Dorm

Be ready to meet people while staying in a shared dorm.

Cook your own meal

Feel free to prepare your own meal here

Free Tours

Don’t miss a thing! Get free tours and explore.


Worldpackers team will guide and advise you before, during and after your trip.

Verified hosts
Verified Hosts

Every host in the community is checked and approved by our team.

Worldpackers Insurance

Did something not go as planned? Contact our team.

Learn more
Learn more

The Experience

This is a great position on a sailboat, docked in downtown Chicago! Its a lot of fun, but there is always work to do :) We take the boat out a lot so theres lots of good times and you can learn to sail! This summer we have several initiatives going: - Refinishing the wood pieces on the outside of the boat. - Electrical work - Some touch up painting For food we usually use the grill. There are a lot of great options to eat in Chicago.

Learn more


  • Fluent English

  • Between 18 and 40 years old

What's not included

Flights, Travel Insurance, Internal Transportation and Visa

Learn more


Stay at least
1 day
Stay up to
2 weeks

Talk to those who have lived the experience

3 Reviews

Host & Staff

Hours & Tasks


Learning & Fun


Amazing experience at The Isabella, Karl is a really nice guy and made me feel at home all the time. Thanks for being there and making my trip amazing! Lara

over 1 year ago


The experience on the boat was absolutely different to any experience I have had before. The Isabella is a small boat, but pretty good to spend a few weeks enjoying the lake and the city. I could met good people, have fun and enjoy the amazing view from the harbor. Wake up and have breakfast slowly in front of the lake and the big buildings of Chicago... it was one of my favorites moments in this city.

over 1 year ago


The idea of staying in a boat in Chicago sounds cool already. But staying at The Isabella, that's when you see that all the other stuff are boring. Karl is an awesome, easy going guy who made it all to make me feel at home. He's not at the boat all day, so he let you do the things at your time and he's fair with the tasks.
Also the harbor is a good place to meet new people and Karl has a lot of friends who are always around.

over 1 year ago

About The Isabella

  • Hosted by Karl

  • New
    Recently Online
  • Response Rate: 0%

About the host

You'll sail beautiful Lake Michigan, and sleep on the boat, spend time in the world class city of Chicago, and hang with cool people. The Isabella is a great boat and we take her out a lot. So be prepared to have an unforgettable experience!

About the host

Want to live this experience?

Travel exchanging your skills for accommodation in hostels, NGOs, ecological projects and so much more.