We use cookies to improve your browsing experience.
And dolphins make us happy. Find out more about our cookies policy here.
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$105-$700
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$55-$600
Fishing Charters
Let a captain do the driving while you do the fishing
$100-$700
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$30-$500
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$100-$700
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$150-$225
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$150-$500
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$130
AC
Alicia
37' Luxury Sailing Yacht in Downtown Chicago
When I say I celebrated my 36th birthday on this beautiful boat, it was AMAZING!! Cait was so incredibly helpful and prompt with any questions I had. Her husband Greg was the coolest captain you could possibly meet. I wish I could rate this 10 stars, for it was truly a wonderful experience! You can’t go wrong if you book with them!! Thank you again!!
RM
Raymond
37' Luxury Sailing Yacht in Downtown Chicago
Cait was a lifesaver! Another captain canceled on me less than 40 hours from a booking on a Saturday! The horror of potentially having 10 guest in my crew with that time of letdown was so disappointing. Luckily Cait answered my bat signal and things happen for a reason because we got her amazing sailing yacht and awesome husband, captain Greg, to take care of us which was such a great upgrade! Thank you for taking such good care of us! We will be back and recommending you to all our friends!
Hitesh
Charter a 31' Pearson Cruising Sloop, Chicago
Captain Joey was great! Gave very clear directions on how best to meet up with him and is clearly an expert at what he does. Would highly recommend him!
JW
Jessica
Captained Charter 30' Sailboat in Milwaukee, Wisconsin
Our group of six women celebrating girl's weekend had the most memorable and special outting on Scott's boat. He is very friendly, accomodating, generous, and easy going. His background as a Navy search and rescue swimmer coupled with his confident sailing abilites assured the group that safety was never an issue. He perfectly integrated into or out of our conversations, highlighting is flexible nature. We all highly recommend!
ruby
Privat 30’ Luxury Sailing Yacht in Mazatlan Bays & Islands
Had such a great time, captain D went above and beyond to make sure we were having fun and comfortable. Lunch was delicious and drinks were awesome. The boat was clean and nice. I will book with him again when back in town.
rb
ryan
37' Luxury Sailing Yacht in Downtown Chicago
Booked this as a last night surprise for my family and friends. On the day, it ended up being super cloudy and rainy but Cait was so great at letting us reschedule. Her communication was excellent throughout. We ended up pushing by a few days and got perfect weather. We had an amazing sunset sail. The boat was clean and comfortable. We sailed and stopped to swim as well. Captain Greg (Cait’s husband) was super friendly and knowledgeable. He was a pleasure to be around. I would highly recommend booking this trip. For us, it was a life changing experience.
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
August 01, 2023
Read Article
October 03, 2022
Read Article
August 12, 2021
Read Article
July 19, 2021
Read Article
December 30, 2019
Read Article
December 26, 2019
Read Article