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Sailboats
Set sail with these traditional wind-powered boats
$430
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$415
Fishing Charters
Let a captain do the driving while you do the fishing
$2,700
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$2,700
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Alaina
45 Foot Luxurious Yacht Charter - Ask about end of the season special.
If you're contemplating any other boat for reasons aside from capacity, don't look any further. Matt is your guy. The whole party showed up at varying times, he let us get going on the boat to get the vibes started. He was such a great host. We felt extremely welcome. He definitely upped the vibe of the whole party. I'm so glad I chose him to host us. I would 100% recommend him to anyone I know looking to book a boat and I'll certainly book with him again myself when the opportunity arises again. 11/10!
Salara
44' Luxury Double Decker in Toronto for any Occasion / Event
Booked a trip for my birthday in august. We had a great time, Jay was an excellent caption and we have no complaints at all. Would definitely book again and would recommend him to anybody looking for a special and fun way to celebrate any event
Marijka
45 Foot Luxurious Yacht Charter - Ask about end of the season special.
We took a sunset boat ride with Matt to celebrate my 25th birthday. Our experience was absolutely wonderful and surpassed all of our expectations! Matt was so friendly and accommodating taking us downtown to look at the Toronto skyline, blasting karaoke and partying in the rain. Thank you for making my 25th such a memorable night Matt!
SM
Sarah
45 Foot Luxurious Yacht Charter - Ask about end of the season special.
I threw a birthday party on a yacht, and it was honestly one of the best decisions ever! The vibe was perfect right from the start. The yacht was super sleek and spacious, with incredible views as we cruised around. Everyone was having such a great time that we decided to extend the party! Matt was awesome—super chill but made sure everything ran smoothly, so we could just focus on enjoying ourselves. We had great music, food, and drinks, and the whole atmosphere was just next level. Afterward, we headed to La Vecchia for dinner, which was the perfect way to wrap up the day. If you’re looking for an epic celebration, I can’t recommend Matt enough. It was definitely a day to remember!
MC
Mike
Sailing NYC aboard 34' Catalina
Great experience to see the city! Ian is awesome and knows the city well. Besides the pictures and views, sailing towards the Statue of Liberty was a moving experience. Would definitely recommend to anyone in the area. Thanks Ian!
Katie
45 Foot Luxurious Yacht Charter - Ask about end of the season special.
Matt was a fantastic captain who took us on a wonderful boat ride. The boat was beautiful and well-maintained, making our trip even more enjoyable. Matt's knowledge of the city and his warm hospitality made the experience truly memorable. Thank you so much we had a blast!!!
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!