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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$175-$605
Fishing Charters
Let a captain do the driving while you do the fishing
$40-$250
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$40-$200
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$60-$160
Kayaks
Who says you need a motor to have fun on the water?
$25-$275
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$140-$160
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$115
Sailboats
Set sail with these traditional wind-powered boats
$300
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.
JN
Janet Rose
45 Foot Luxurious Yacht Charter - Unforgettable Toronto Skyline Adventure
Matt S. is a great host! Great communication and his boat is fully equipped; it’s nice and clean and comfortable for a group to cruise around Toronto. We had a ton of fun and he offered to take photos; drove us where and when we wanted; and was so accommodating! I highly recommend. It’s also nice that he’s commercially licensed so we don’t have to worry about skirting around. Thanks Matt!!
SA
Stephy
45 Foot Luxurious Yacht Charter - Unforgettable Toronto Skyline Adventure
We had a great time booking with Matt! We were celebrating a special occasion with friends, and everything was seamless. Matt was on time, friendly, and made us feel instantly welcome with a bottle of prosecco as he helped us board. The yacht departed from Humber Bay, which was super convenient with plenty of public parking, much better than the pricey downtown options. We cruised past the CN Tower, took in the stunning views, enjoyed great music, and shared drinks while relaxing on the water. Matt was the perfect host -easygoing, fun, and great to party with! This was hands down a 10/10 experience. We’d wholeheartedly recommend booking with Matt for anyone looking to celebrate in style on the water!
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!
AS
Arianne
Luxury Electric - 75 Minute Cruise on Belle Isle Breeze
This was an amazing boat ride experience, so peaceful and fun. The boat is very clean and rides very smooth and quiet, the captain and host were both very hospitable, polite, highly recommend!! We definitely want to book 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!