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Sailboats
Set sail with these traditional wind-powered boats
$120-$500
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$150
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$325-$500
Fishing Charters
Let a captain do the driving while you do the fishing
$115
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$115
DC
Derek
No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit
Martin and his vessel were very well kept. The list of captains provided were very professional and polite. Martin was very prompt with communication and worked with each change needed through the process of scheduling the trip. I would very much so recommend him and his services. The trip was a success and enjoyable
SA
Shannon
No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit
Martin's boat is great for a day on the water! It fit 12 of us comfortably. We were able to go from Belmont Harbor to the Playpen with plenty of time to swim and relax before having to head back. Also, Captain Matt and Jamie were awesome! They were looking out for both our fun and safety the whole time we were on board which was greatly appreciated.
Sandra
44' Italian Luxury Azimut Premier Party Yacht 13 ppl plus Jet Ski Available
Capt. Tim and crew were very accommodating and helpful. We rented the boat to scatter a loved ones ashes close to Navy Pier. Capt Tim was very receptive to our feelings and knew actually what we needed. We had a great celebration of life on his boat!
Daniya
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
Book Kevin’s boat now! Our captain Hayden was so professional and prompt for our experience. The boat itself is gorgeous and perfect for an all girls getaway . I and my group couldn’t have asked for a better experience.
EL
Erika
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
Kevin was easy to coordinate with, got back to me quickly, and the boat was just as pictured. Captain Justin was accommodating and personable. Couldn’t have asked for a better day on the boat! We’ll definitely be coming back!
KM
KiKi
Cpt included. A perfect blend of comfort and adventure aboard Sea Ray Sundancer.
Diego was a wonderful captain! He took care of me and my girls with such care! And a special shoutout to his wife for making sure we had all the essentials! She’s the real MVP! We will be booking again!
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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October 09, 2023
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November 28, 2022
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May 20, 2021
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December 30, 2019
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