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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$160-$915
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$50-$600
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$120-$650
Fishing Charters
Let a captain do the driving while you do the fishing
$25-$995
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$20-$1,050
Kayaks
Who says you need a motor to have fun on the water?
$10-$425
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$45-$375
Canoes
A classic option for leisurely paddling
$10-$25
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$130-$195
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$350-$750
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!
RB
Richard
41' Morgan Classic Sloop in Muskegon, Michigan!!! Min $135 pp 2 persons
This was our second time sailing with Jim My wife and I had a great time. Jim was easy to contact and responded very quickly to questions before the sail. We had to change our scheduled date and time because of weather, but Jim was very flexible and accommodating. We had a great conversation with him and heard some great stories about his sailing past. He even let me take the helm for a while, which i really enjoyed,
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!
April 17, 2024
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