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Key Sailing
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Certificate of Excellence
Traveller Overview
  • Excellent96%
  • Very good1%
  • Average1%
  • Poor1%
  • Terrible1%
Travellers talk about
“captain tim”(67 reviews)
“sunset sail”(30 reviews)
Providing private and group daytime and sunset sailing charters. Husband and wife crew has over 40 years of sailing experience together.
2 Marina Plz # E-18, Marina Jack, Sarasota, FL 34236-8919
Most Helpful Positive Review
Reviewed 25 November 2011

What a terrific experience. Our family recently moved to Sarasota and went sailing with Key Sailing as part of our own "getting to know the area." We had the greatest time. We saw all the sights of Sarasota Bay (including dolphins!) and our trip was...More

2  Thank Ken S
Most Helpful Critical Review
Reviewed 11 July 2010

It's hard NOT to enjoy a sail in Sarasota, it's a beautiful place. Unfortunately, I found this one way overpriced, and the captains talked on and on about themselves (and their religion). I felt obligated to listen and engage in small talk with them, when...More

7  Thank beachfront914
Reviews (410)
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All reviews captain tim sailing experience sunset sail sarasota bay sailboat ride dove chocolates great sailing hour afternoon perfect afternoon marina jack saw dolphins jan helm skiing sailed solomon sails
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1 - 10 of 400 reviews
Reviewed 7 October 2018 via mobile

Thanks so much to Captain Tim and Jan! We had a wonderful time and they were the kindest and most accommodating hosts.

Thank OnAir290322
Reviewed 27 September 2018

My best friend and I booked this while on a girls weekend away. Jan and Tim were awesome. They were very timely in their communication with us and even offered to adjust the time of our sail in order to avoid some potentially bad weather....More

Thank Molly G
Reviewed 26 July 2018 via mobile

Our trip with Tim and Jan is one that our family will never forget. They were incredibly hospitable and treated us like family. I would recommend Key Sailing to anyone looking for a memorable family experience. We will be back! -Keith Hurt

1  Thank Keith H
Reviewed 12 July 2018 via mobile

Tim and Jan were spectacular hosts! My family of 10 took a 4 hour trip with them. They exceeded every expectation we had! The boat is beautiful and we had plenty of room for everyone-some wanted sun and some needed shade. This excursion was everyone’s...More

Thank Missi S
Reviewed 21 June 2018 via mobile

We went on the cruise with Jan and Tim after our original plans fell through. Well, we couldn’t have asked for a better anniversary celebration. It was a beautiful night for sailing and Jan and Tim couldn’t have been more hospitable. They did everything to...More

Thank audreyrigot
Reviewed 16 June 2018 via mobile

My husband and I took a private 2 hr late afternoon sailing cruise with Tim & Jan and it turned out to be way more then we expected. They were the most gracious people and we felt so comfortable with them right away. Hearing about...More

Thank Denise W
Reviewed 13 June 2018 via mobile

We had an evening sail and it was beautiful. Both Capt Tim and Jan explained several aspects of sailing to us and pointed out landmarks surrounding us. My birthday was the following day and Capt Tim played the guitar and sang for me while Jan...More

Thank mlwalker1
Reviewed 10 June 2018 via mobile

We were impressed by Capt Tim and Jan's warm hospitality. They were genuinely friendly and worked well together. We felt absolutely comfortable with their competency on the sailboat as well as their flexibility and professionalism booking it. Our originally scheduled date was rained out so...More

1  Thank V5470PHmarye
Reviewed 8 June 2018 via mobile

Family outing on a sunny Thursday afternoon. The boat comfortably held six of us ( husband and wife boat owners included). Jan offered some local history.....and Dove chocolates! Tim strummed and sang “Happy Birthday” to the “ birthday girl” on his guitar. The sailboat ride...More

1  Thank tdl253
Reviewed 5 June 2018 via mobile

Capt Tim surprises us with his guitar talent for my upcoming Birthday. This our fourth time out sailing with Jan & Capt Tim. They let us take the helm, relax on deck, or converse whatever topics come to mind. The choice is always ours. We...More

1  Thank sherrysea620
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