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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$80-$1,385
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$65-$735
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$70-$600
Kayaks
Who says you need a motor to have fun on the water?
$90-$1,715
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$100-$180
Fishing Charters
Let a captain do the driving while you do the fishing
$50-$1,300
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$50-$3,125
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$50-$1,300
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$90-$400
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$60-$425
AD
Alejandro
Charter a 31' Pearson Cruising Sloop, Chicago
Great overall experience. I must advice that I had to adjust my plans from what I initially had in mind. I had to get props for the experience on my own, which complicated the planning and fortunately resulted all right. Also, it wasn’t until after booking my experience that I realized that Captain Joey was thinking of going out for a motorboat ride rather than for a sail, which would’ve been a total bummer - I had to talk him into this plan and he kindly agreed to doing so.
RC
Roman
35ft C&C 35 Sailboat in Toronto
We (dad+mom+7yo son) had an amazing 2-hour trip with Peter in Sep 2024! Enjoyed very much every minute of it. Learned a lot about sailing and had a chance to try it out under the captain's guidance. And we really really enjoyed the conversation with Peter. I definitely recommend Peter and his boat "Restless" !
JD
Jessica
35ft C&C 35 Sailboat in Toronto
I had an amazing experience with Peter and Simon. Would recommend this experience to anyone.
MH
Merna
35ft C&C 35 Sailboat in Toronto
We had so much fun sailing with Captain Peter on the Restless. We booked with Peter for our wedding photoshoot and we had the best time sailing at sunset. Peter was very good at communicating with us prior to the booking to make sure everything went smoothly. Peter is very knowledgeable and kind and we would definitely recommend booking with him!
KM
Kennedy
Morgan 382 Sailboat for charter in Pensacola, Florida
This was so fun! Robert made our sail so enjoyable on his beautiful boat. We enjoyed some sun and stayed out into the evening to watch the sunset. Would highly recommend booking with Robert!
SM
Sachin
35ft C&C 35 Sailboat in Toronto
A very kind, respectable and accommodating person that our captain Peter is, also a man with a vast experience of adventurous travel. He made our sailboat experience a mesmerizing one. Thanks for having us aboard ’Restless’.
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
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October 03, 2022
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August 12, 2021
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July 19, 2021
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December 30, 2019
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December 26, 2019
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