We use cookies to improve your browsing experience.
And dolphins make us happy. Find out more about our cookies policy here.
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$155-$925
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-$630
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
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$350-$750
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$130-$195
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.
Chloe
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Nijole was a great host and made us all feel comfortable on her boat! It was great to have her dog Piper on board as well! You can bring your own music too. If you like for your captain to be very involved in your experience, this is for you!
SL
Sonam
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
It was a great experience on Nijole’s boat! She made sure everyone was comfortable, and that everyone enjoyed the trip. She was patient, and we had a great conversation! She ensured we had a great time
ST
Sara
41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.
I booked this trip as a surprise for my dear friends Rob and Leslie. This was a first anniversary trip gift. John was amazing to work with and everything went smoothly. Rob and Leslie were so excited and said it is a memory for a lifetime. I would highly recommend John and his beautiful vessel!
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!