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Key Sailing

Address: 2 Marina Plaza, E-18, Marina Jack, Sarasota, FL 34236
Phone Number: 941-346-SAIL
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96%
Ranked #9 of 144 Activities in Sarasota
Certificate of Excellence 2014
Useful Information: Activities for older children
Attraction details
Useful Information: Activities for older children

Hotels near Key Sailing

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288 reviews from our community

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Date | Rating
  • English first
  • French first
  • German first
  • Italian first
  • Spanish first
  • Any
English first
Orlando, Florida
2 reviews
5 of 5 stars Reviewed January 8, 2015

My wife and I had the wonderful opportunity to spend an afternoon with Tim and Jan on their beautiful sailboat. It was absolutely the highlight of our week in Siesta Key. They are as gracious and accommodating as they could possibly be and they make sure that every need is met. The sailing was amazing, it was the first time... More 

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Indianapolis, Indiana
2 reviews
5 of 5 stars Reviewed January 5, 2015

My husband, son and his wife along with our two young grandchildren had the greatest time sailing with Key Sailing! The couple that own and operate this trip are the people that took us out- it was nothing short of magnificent! The trip would be just perfect for a couple, a family with little ones or teens, or friends. Tim... More 

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Reviewer
3 reviews 3 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed December 22, 2014

Wow! I was surprised by my husband with a sailboat experience I never could have dreamed! Captain Tim and Jan made sure we had all our needs met with cheese and apples and beverages. Jan was sharing information about the Keys and taking pictures and video to ensure we captured this memory in more then our hearts. We enjoyed intimate... More 

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2 reviews
5 of 5 stars Reviewed December 22, 2014

My wife and I enjoyed a nice sunset cruise with Jan and Tim for a 2nd honeymoon and our 10th anniversary. It was a simple, but memory filled cruise concluding with Tim, as a Capt and an ordained minister, helping us to renew our vows. They served a simple fruit and cheese plate and soft drinks, which was perfect for... More 

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Huddersfield, United Kingdom
1 review
5 of 5 stars Reviewed September 26, 2014

Wonderful afternoon sailing. Tim and Jan were friendly and attentive hosts. Nothing was too much trouble. They really tried hard to compliment our family reunion holiday and gave us a memorable experience. This is a fun and affordable holiday TREAT.

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1 review
5 of 5 stars Reviewed July 30, 2014

Best experience ever! Amazing surprise for our 11th anniversary from my brother. Tim and Jan were awesome and we will return again. We will be moving to Florida next summer and we plan to frequent Key Sailing

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Cincinnati, Ohio
Reviewer
3 reviews 3 reviews
5 of 5 stars Reviewed July 26, 2014

My husband and I have sailed 4 times with Tim and Jan. We have sailed with our grown children and by ourselves, sunset and day cruises, and each time is better than the last. Jan and Tim give very personal attention and are very knowledgeable about the area. They will leave you alone if you like, or converse at length... More 

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Philadelphia, Pennsylvania
2 reviews
5 helpful votes 5 helpful votes
5 of 5 stars Reviewed July 14, 2014

Before our vacation to Lido Key, I booked a group sunset sail on the Key Breeze as a surprise for my boyfriend's birthday. We enjoyed a nice dinner beforehand at Marina Jack and brought a bottle of champagne for the sail. Since we arrived first, Jan suggested we claim our spot at the front of the boat and provided bean... More 

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Senior Reviewer
7 reviews 7 reviews
3 attraction reviews
15 helpful votes 15 helpful votes
5 of 5 stars Reviewed June 24, 2014

What a nice relaxing time. Just the sails and wind. Captain Tim was great and was so nice with my questions. I had never sailed and he was so interesting and enjoyable to talk with. Great down time on the vacation to get away from it all!!

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Fort Lauderdale, Florida
Senior Reviewer
7 reviews 7 reviews
5 helpful votes 5 helpful votes
5 of 5 stars Reviewed June 17, 2014 via mobile

Captain Tim & First Mate Jan are warm, gracious hosts & an impressive sailing team to watch. Our early afternoon cruise was one of the highlights of a wonderful family reunion trip to celebrate our parents 50th Anniversary. The cruise was lovely & relaxing. Captain (& chaplain) Tim surprised us by generously offering to officiate in an impromptu ceremony for... More 

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Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
  • How should I dress for this tour?