CHICAGO'S PREMIER ​PRIVATE SAILING CHARTER
PHONE:  708-824-SAIL (708-824-7245)
EMAIL:  Info@ComeSailing.us

Custom Charters

​We would like each sail to be a fun and memorable event for every person. In order to provide that unique and personalized experience, we will make every effort to provide additional services like decorating, photography, and catering upon special request. Please ask for pricing.​

Custom Sailing Charters​

 All charters are private.  The passenger list is at your discretion.

  • Private sailing charter
  • Up to six passengers
  • Flexible departures
  • Departs from Monroe Harbor
  • Choice of sailboats
  • USCG licensed captain provided
Call for Pricing
STEP 1 - CHOOSE A SAILBOAT
Sailing Vessel Bernard
Max Passengers:           6
Manufacturer:                Catalina Yachts
Length over deck           36 feet
Notes:         
​
  • Sloop design with modern roller furling mainsail
  • ​Modern design built for cruising with a small family
  • Instant booking confirmation for standard charters
  • Great for entertaining friends
Sailing Vessel Druid
Max Passengers:           6
Manufacturer:                Shannon Boat Co.
Length over deck           28 feet
Notes:         
​
  • Cutter design with traditional full batten mainsail and full batten staysail
  • Semi-custom bluewater sailboat built to cross oceans
  • Hull #28 of the 55 Shannon 28's ever built

/

  • 1
  • 2
  • 3
  • 4
  • 5
We had an excellent charter with Michael! A group of girl friends and myself went for a weekend afternoon charter and had a blast sailing along Lake Michigan! They have every accommodation on board (cooler, restroom, seating area, below deck seating) that you could need for a sail. Michael and his crew were professional and friendly to sail with- I highly recommend booking your charter here!

Robyn Szablewski - Facebook Review

/

  • 1
  • 2
  • 3
  • 4
  • 5

/

  • 1
  • 2
  • 3
  • 4
  • 5
I recently went on an afternoon charter with some friends on Bernard with captain Michael, it was amazing! Michael made our group feel comfortable, safe, and helped make our time on the lake very memorable. This is the boat you want to be on to have a great time sailing along one of the world's prettiest skyline views! I would highly recommend them!

​Jamie Delos Reyes - Facebook Review

/

  • 1
  • 2
  • 3
  • 4
  • 5

/

  • 1
  • 2
  • 3
  • 4
  • 5
Had a WONDERFUL birthday sailing with my family and Captain Mike was friendly and knowledgeable!!...we will definitely be sailing with him again!!#bestbirthdayever!!

​Shawn Jeffries- Cullens - Facebook Review

/

  • 1
  • 2
  • 3
  • 4
  • 5

/

  • 1
  • 2
  • 3
  • 4
  • 5
Captain Mike took us out mid day and we have a beautiful day for sailing. He was so accommodating to us. He was there but you barely knew it. The boat was clean & he had refrigerator space and ice for us. We packed like we were going to two days, not two hours, and the boat didn't seem crowded. We had so much fun and can't wait to go out again! Thank you Come Sailing! Also - an added bonus is that if you park in the Millennium .....

Colleen L. - Yelp Review

/

  • 1
  • 2
  • 3
  • 4
  • 5

/

  • 1
  • 2
  • 3
  • 4
  • 5
​Captain Mike made or experience so easy and amazing! We were a bit confused where to go on arrival, but another friendly boater gave us a lift to Mike's sailboat. We rented Mike's sailboat for our friends 26th birthday for a few hours on a sunny Monday, and we already cannot wait to go again. There is space in the back section of the boat to sit on benches, but me and the ladies spent the majority of our sail sprawled and sunning on the front section .....

Rebecca C. - Yelp Review

/

  • 1
  • 2
  • 3
  • 4
  • 5

/

  • 1
  • 2
  • 3
  • 4
  • 5
A Fantastic Experience!  We've done a number of the Chicago boat tours, including several of the different architectural tours on large boats with crowds of people.  This was SO MUCH better!  We took my in-laws, who were visiting from out of town, on the 2-hour sunset cruise for six (the maximum allowed by the Coast Guard), and just sailed up and down the lake along the skyline. We loved it!  We lucked out with fantastic weather .....

C P. - Yelp Review

/

  • 1
  • 2
  • 3
  • 4
  • 5
  • 0
  • 1
  • 2
  • 3
  • 4
  • 5

PRIVATE SAILING CHARTERS
SUNSET SAILS • FIREWORKS • SPECIAL OCCASIONS

Contact - 708-824-7245 or Info@ComeSailing.us
Location - Monroe Harbor, Chicago, IL 60603
Copyright © 2018.  All Rights Reserved.  Come Sailing, Inc.