By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.
Page 40 of 41 • 962 listings
969
Miami
Florida
728
Cancún
Quintana Roo
524
Isla Mujeres
Quintana Roo
375
Tampa
Florida
352
Puerto Vallarta
Jalisco
349
Lake Michigan
United States
345
Los Angeles
California
333
Cabo San Lucas
Baja California Sur
333
Miami Beach
Florida
313
Marina
Cabo San Lucas
309
Nuevo Vallarta
Nayarit
281
Chicago
Illinois
250
Cartagena
Bolivar
245
Saint Petersburg
Florida
245
Marina Vallarta
Puerto Vallarta
240
Tampa Bay
Florida
231
Clearwater
Florida
209
Chesapeake Bay
United States
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.
AB
Alan
Dom was a great host. He went above and beyond. We have nothing but good things to say about our experience. Ot was a great experience and we would definitely recommend it for anyone visiting the area or locals just wanting to get out on the water and enjoy the beautiful views.
KD
Katherine
We had an amazing time sailing with Dom! The views of the Toronto skyline were incredible, and we learned so much about the Toronto Islands and about sailing along the way. What we especially appreciated was Dom’s ability to make sailing feel accessible and unintimidating—he cuts through the insider language and conventions and focuses on the practical knowledge that really matters when you’re getting started. It made sailing feel much more approachable and feasible for complete beginners like us. Dom was an incredibly warm and welcoming host, and the whole experience was relaxed, fun, and genuinely informative. We also loved how easy it was to bring our own snacks and drinks. Highly recommend!
GK
Galina
Dom is a great and hospitable captain. He was very kind, he offered drinks, always checked with what we would like to see and was ready to offer alternatives. I would highly recommend his services!
LT
Luc
William Garden 39ft Ketch Sailboat Bar Hop Seattle Experience
Shiva was an incredible captain! Super knowledgeable about sailing, and he made the entire experience super special for my wife and I. He’ll tailor the experience to your preferences — whether you want to stay on the water to dock to drink some wine and explore! Don’t hesitate to book with him and his beautiful sailboat.

Kim
Dominic was incredible! He was so chill and so kind with our family. It was a perfect day out sailing on the water. He taught us so much, shared stories, local history and was genuinely so sweet with our family, taking pictures and showing us points of interest! A PERFECT EXPERIENCE AND A PERFECT DAY!