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 10 of 38 • 912 listings
823
Miami
Florida
670
Cancún
Quintana Roo
489
Isla Mujeres
Quintana Roo
380
Tampa
Florida
361
Los Angeles
California
349
Lake Michigan
United States
321
Puerto Vallarta
Jalisco
298
Miami Beach
Florida
288
Chicago
Illinois
284
Nuevo Vallarta
Nayarit
273
Cabo San Lucas
Baja California Sur
257
Marina
Cabo San Lucas
253
Saint Petersburg
Florida
240
Tampa Bay
Florida
235
Clearwater
Florida
226
Cartagena
Bolivar
226
Marina Vallarta
Puerto Vallarta
209
Chesapeake Bay
United States
AS
Andy
Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago
What a wonderful time out on beautiful lake Michigan with Captain Bob! First time my family and I have been on a sailboat and we learned so much! The views of the city coupled with the hospitality onboard made it a day to remember for sure! A+ Highly recommend!
TW
Ted
Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago
I was impressed that everything went according to plan. Met Captain Bob right on time and boarded what looked like an almost brand new boat. Very well maintained and extremely clean. First mate was first of all and offered water and refreshments for myself and my guest. Leaving the marina was professional and uneventful. The wind was light and variable and made for rather slow sailing but it was a great opportunity to hear some of the fine stories connected to Helios. For anyone that wants a true sailing experience and an opportunity to talk to some people that have been there done that, charter this sailboat! Thank you Captain, maybe we can have another adventure later in the summer.
ES
Edward
Hunter 43 Sailing Yacht in Oakville, Ontario for 5 Guests
Our whole family, 3 generations, had a wonderful time. Skipper Dave is a knowledgeable, caring, and thoughtful host on his well equipped boat.
SL
Sarah
Private Sailing Tour in San Diego
5 star! Great communication and helped me out in a last minute pinch. Captain Paul was amazing!!!! Made the trip! Will def use them if ever back in San Diego!
AS
Ali
Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago
We had a wonderful time on Bob's boat! We felt safe and loved seeing the beautiful skyline! Would definitely do it again!

Eric
Sailing Lessons with Chicago's #1 Rated Sailing School
I had a four hour private lesson with Doug and small crew. All were very helpful and knowledgeable, it was a great learning experience. I look forward to joining them again.