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Page 4 of 10 • 240 listings
24
Detroit
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Michigan
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Norris Lake
Tennessee
281
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Illinois
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Tennessee
78
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Ontario
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Virginia
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69
Toronto
Ontario
19
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165
Potomac River
United States
57
Lake Norman of Catawba
North Carolina
7
Mount Juliet
Tennessee
29
Arlington
Virginia
62
Mooresville
North Carolina
SS
Sonja
44ft Regal Commodore Motor Yacht Charter In Chicago
Robert was awesome! Very communicative, great boat driver, flexible with scheduling changes, professional, and kept us safe! Great value for the experience, good sound system, fun time for my bachelorette, and very experienced! The more flexible refund policy due to weather conditions helped us pick him as well since we didn’t live there but we didn’t need to use it thankfully! Thanks so much for taking care of us. Would book with him again if we lived in chicago!
IC
Isabel
Book "After Hours" today! Sea Ray Sundancer 40ft Motor Yacht In Chicago
We absolutely loved our experience! Our captain, Drake, was wonderful and we were very impressed with the boat. We had 13 guests, and the boat was comfortable for all of us. We went on a Saturday evening and enjoyed the fireworks and city views. Highly recommend!
TF
Todd
Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago
This is the boat to book for a sweet sailing experience in Chicago. Super family friendly. Ocean-worthy vessel and Capt Bob and Gabby have been all over the hemisphere with it. They're more than willing to share as much knowledge as you'd like to know. I even pulled up the main sail! Bob and Gabby were great with our young children. Just wonderful people. Swimming spot they chose was excellent. If you're looking for the real deal, this is it. Loved hearing their stories about open ocean sailing and traversing the Caribbean Islands. Kids loved the aqua chair floaty. Worth every penny and more.
TZ
Ty
Stunning Multi-Level 47’ Carver Yacht for Summertime in Chicago
Our group of 12 people had an awesome time on the boat. Coordination and communication was great throughout and we had a perfect day on the lake with Captain Mike. I would absolutely charter from Tristan again.
QT
QUAN
42ft Trojan Party Yacht Chicago for 12 Guests Every Occasion
DO IT! Highly recommend! Captain Kyle responds quickly and is super accommodating. Our group had a fantastic time and would do again in a heartbeat.

Osamudiamien
Stunning Multi-Level 47’ Carver Yacht for Summertime in Chicago
Had one of the best times I’ve ever had with my closest group of friends. The boat was a beautiful piece of architecture, the captain was very nice, and being in the playpen for a few hours is something special. Can’t wait to book another boat with Tristian in the near future. My only advice to people is that if you’re considering doing this, don’t wait. Book it now.