We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Key Sailing

2 Marina Plaza, E-18, Marina Jack, Sarasota, FL 34236
Improve this listing
Ranked #7 of 80 Activities in Sarasota
Certificate of Excellence 2014
Type: Boat Tours
Traveler Description: Key Sailing, at 941-346-7245, is a top 5 star experience on Trip Advisor and 2012 International Business of the Year for the Sarasota Chamber-Reserve... more »
Useful Information: Activities for older children
Write a Review

283 reviews from our community

Visitor rating
Date | Rating
  • English first
  • French first
  • German first
  • Italian first
  • Spanish first
  • Any
English first
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

Was this review helpful? Yes
Cincinnati, Ohio
1 review
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

Was this review helpful? Yes
Philadelphia, Pennsylvania
2 reviews
4 helpful votes 4 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

Was this review helpful? Yes
Senior Reviewer
6 reviews 6 reviews
3 attraction reviews
14 helpful votes 14 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!!

Was this review helpful? Yes
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

Was this review helpful? Yes
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed June 2, 2014 via mobile

What a wonderful time! We had a blast sailing with Jan and Tim. We even got to steer the helm and had wonderful conversation. Even though we didn't see a sunset, we were not disappointed! The cruise was peaceful and relaxing! What sailing is all about! Highly recommended to anyone and everyone!! We will sail with Jan and Tim again!!... More

Was this review helpful? Yes 1
Valparaiso, Indiana
1 review
5 of 5 stars Reviewed May 12, 2014

We have gone with Captain Tim and Janet before and had wonderful sails with them, but this was an incredible experience! We took our two grandsons and they were trained on sailing the boat and got extensive time at the helm. The wind was perfect and we enjoyed the best sailing experience I have ever had. It was the best... More

Was this review helpful? Yes
San Diego, California, United States
2 reviews
8 helpful votes 8 helpful votes
5 of 5 stars Reviewed May 8, 2014

We couldn't have asked for a better time--a beautiful late afternoon sail with a terrific captain and first mate. Our family trio celebrated a reunion, a special birthday-- and made great memories. Thank you Jan and Tim. You're the best! and... Mark Twain was right: "Twenty years from now, you will be more disappointed by the things you didn't do... More

Was this review helpful? Yes
Bridgewater, Virginia
1 review
5 of 5 stars Reviewed May 5, 2014

Had a great time! Very relaxing. I felt so comfortable sailing with Tim and Jan, even got to try my hand at the helm! They were both very friendly and easy-going. Very accomodating. There was never a dull moment and can't wait for a longer sail next time! Definitely got the sailing bug and wouldn't go anywhere else. I'll be... More

Was this review helpful? Yes
Montrose, Colorado
4 reviews 4 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed April 22, 2014

We cruised with Tim & Jan on a glorious evening set to have a wonderful sunset, and a full moon rise. (Blood moon/eclipse) The photos bring a smile to my face, remembering the relaxed evening we spent together with our family. They will accomodate small groups, and their "open" charters are limited to 6 people. (If you get a babysitter... More

Was this review helpful? Yes

Travelers who viewed Key Sailing also viewed

Sarasota, Southwest Gulf Coast
Sarasota, Southwest Gulf Coast
Sarasota, Southwest Gulf Coast

Been to Key Sailing? Share your experiences!

Write a Review Add Photos & Videos

Owners: What's your side of the story?

If you own or manage Key Sailing, register now for free tools to enhance your listing, attract new reviews, and respond to reviewers.

Manage your listing