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Find Tours on the Water Near You

4.9
(9,540 Reviews)

Page 2 of 10240 listings

Sail & Swim from a Luxury Sailing Yacht
Sailing in Chicago · 7 guests

Sail & Swim from a Luxury Sailing Yacht

5.0
Superowner
$200+/hour
Instant Book
Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.
Sailing in Chicago · 6 guests

Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.

5.0
Snoozed - Active 02 Jan 2026
No tie ups - BIG BOAT for up to 36 people - at NAVY PIER MARINA
Events in Chicago · 36 guests

No tie ups - BIG BOAT for up to 36 people - at NAVY PIER MARINA

New
$735/hour
Instant Book
Sailing Lessons with Chicago's #1 Rated Sailing School
Tours in Chicago · 6 guests

Sailing Lessons with Chicago's #1 Rated Sailing School

New
Superowner
Best of 2025
$175+/hour
Make no mistake. She is clean with plenty of room and monster sounds. 40’ searay
Events in Chicago · 12 guests

Make no mistake. She is clean with plenty of room and monster sounds. 40’ searay

New
$400/hour
46' luxury yacht for up to 12 people - DUSABLE Harbor
Events in Chicago · 12 guests

46' luxury yacht for up to 12 people - DUSABLE Harbor

New
$280/hour
Instant Book
No tie ups - 40ft Premium Yacht - lots of room group of for 12 - DuSable Harbor
Events in Chicago · 12 guests

No tie ups - 40ft Premium Yacht - lots of room group of for 12 - DuSable Harbor

New
$250/hour
Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
Events in Chicago · 12 guests

Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht

5.0
Best of 2025
$200/hour
Instant Book
Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht
Powerboats in Chicago · 12 guests

Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht

5.0
Best of 2025
$210/hour
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
Powerboats in Chicago · 12 guests

Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!

5.0
Best of 2025
$170/hour
Instant Book
Cpt included. A perfect blend of comfort and adventure aboard Sea Ray Sundancer.
Powerboats in Chicago · 6 guests

Cpt included. A perfect blend of comfort and adventure aboard Sea Ray Sundancer.

5.0
$225+/hour
No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit
Sailing in Chicago · 12 guests

No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit

New
$245/hour
Instant Book
27' Chris Craft with Water Toys plus Jet Ski Available
Powerboats in Chicago · 6 guests

27' Chris Craft with Water Toys plus Jet Ski Available

4.9
Superowner
$240/hour
Instant Book
44' Italian Luxury Azimut Premier Party Yacht up to 13 plus Jet Ski Available
Events in Chicago · 13 guests

44' Italian Luxury Azimut Premier Party Yacht up to 13 plus Jet Ski Available

5.0
Superowner
$575+/hour
Instant Book
40ft Formula 40 Performance Cruiser in Chicago
Tours in Chicago · 13 guests

40ft Formula 40 Performance Cruiser in Chicago

5.0
$349/hour
Lake Michigan Fishing Charters and Cruises on 36' Tiara Yacht
Fishing in Muskegon · 4 guests

Lake Michigan Fishing Charters and Cruises on 36' Tiara Yacht

New
$150/hour
Explore the Beauty of Lake Michigan & Duck Lake by Kayak!
Adventures in Michigan · 2 guests

Explore the Beauty of Lake Michigan & Duck Lake by Kayak!

New
$35+/hour
Niagara ‘s Boat Adventures Start Here
Tours in St. Catharines · 6 guests

Niagara ‘s Boat Adventures Start Here

New
$179+/hour
2019 Lund 2175 Pro-V - Niagara River Fishing Charter!!
Fishing in Niagara Falls · 4 guests

2019 Lund 2175 Pro-V - Niagara River Fishing Charter!!

New
$2,700/hour
Water Fun with the Swan (Lake Anna, Va)
Fishing in Richmond · 11 guests

Water Fun with the Swan (Lake Anna, Va)

New
$165/hour
SAIL aboard "RED WITCH III" -- Kenosha's TALL SHIP RED WITCH'S little brother
Sailing in Kenosha · 6 guests

SAIL aboard "RED WITCH III" -- Kenosha's TALL SHIP RED WITCH'S little brother

New
$175/hour
SeaRay Sundancer 36ft Captained Yacht Charter in Toronto!
Events in Etobicoke · 10 guests

SeaRay Sundancer 36ft Captained Yacht Charter in Toronto!

New
$287/hour
Instant Book
27 Foot Sailboat for a Day of Fun in the Sun in Toronto
Sailing in Toronto · 6 guests

27 Foot Sailboat for a Day of Fun in the Sun in Toronto

5.0
$90+/hour
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
$146/hour

Local Tours Reviews

  1. S

    Sandra

    Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.

    Captain Russell was incredibly hospitable and entertaining, making this Afternoon Delight even more special. On the yacht was pure bless -- sunshine, bevies, great music and stunning Lake Michigan views. Plus there's a huge Yeti Tundra hard cooler onboard with ice... just bring your fav adult beverages. Highly recommend for a fun, luxe day with your besties.

  2. J

    Jeff

    Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.

    What a WONDERFUL experience!! Capt. Russell was truly amazing, our 2 hour cruise Friday could not have been better! His attention to detail, coupled with a strong focus on safety didn't go unnoticed. We had 1 person in our party that was a little nervous about being on the open water. The Capt. was able to sooth their apprehension with his vast knowledge of sailing, peppered with humor...it was the needed medicine. We will be back soon, next time we'll book a 4 hour cruise, 2 hours was clearly not enough time. 5 star recommendation, only because 6 stars was not an option.

  3. AC

    Alicia

    Sail & Swim from a Luxury Sailing Yacht

    When I say I celebrated my 36th birthday on this beautiful boat, it was AMAZING!! Cait was so incredibly helpful and prompt with any questions I had. Her husband Greg was the coolest captain you could possibly meet. I wish I could rate this 10 stars, for it was truly a wonderful experience! You can’t go wrong if you book with them!! Thank you again!!

  4. RM

    Raymond

    Sail & Swim from a Luxury Sailing Yacht

    Cait was a lifesaver! Another captain canceled on me less than 40 hours from a booking on a Saturday! The horror of potentially having 10 guest in my crew with that time of letdown was so disappointing. Luckily Cait answered my bat signal and things happen for a reason because we got her amazing sailing yacht and awesome husband, captain Greg, to take care of us which was such a great upgrade! Thank you for taking such good care of us! We will be back and recommending you to all our friends!

  5. rb

    ryan

    Sail & Swim from a Luxury Sailing Yacht

    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.

  6. GL

    Georgia

    Sail & Swim from a Luxury Sailing Yacht

    Cait and Greg are an amazing duo! We had a fantastic sunset cruise with our young girls. Greg was our captain and was excellent- he was also very kind, understanding of the girls and flexible with the route. The boat is beautiful- really clean and well kept as well. We wouldn’t hesitate to do this again for another special occasion. Thank you, C+G!