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.
The latest reviews. The lowest prices. The perfect place to shop for hotels.
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Get directions
Address: 2 Marina Plz # E-18, Marina Jack, Sarasota, FL 34236-8919
Phone Number:

TripAdvisor Reviewer Highlights

Read all 370 reviews
Visitor rating
  • 344
  • 6
    Very good
  • 5
  • 5
  • 0
Thank you!!

Jan and Captain Tim Thank you so much for such a beautiful sail. Everyone that went along for our sail with the two of you made a point of telling me how awesome it was for them... read more

Reviewed 2 days ago
Catherine Rose A
via mobile

Similar Things to Do in Sarasota

Add Photo Write a Review

370 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
  • More
Showing 360: English reviews
1 review
Reviewed 2 days ago NEW via mobile

Jan and Captain Tim Thank you so much for such a beautiful sail. Everyone that went along for our sail with the two of you made a point of telling me how awesome it was for them, and honestly it was - personal, beautiful, easy for us riders and relaxing to the extreme. I am sure that all 6 of... More 

Thank Catherine Rose A
Cincinnati, Ohio
2 reviews
Reviewed 3 weeks ago

I contacted several charters and so happy that I chose Key Sailing for my mother's service at sea. Captain Tim and his wife Jan were so accommodating and respectful of our wishes that day. Captain Tim took us just off the northern tip of Siesta Key where we spread my mom's ashes and each shared a favorite memory of my... More 

Thank ckb2000
1 review
Reviewed 4 weeks ago via mobile

Captain Tim and Jan made our sunset sail a special trip. Captain Tim shared his wealth of sailing knowledge while we enjoyed "friendly" winds with the motor off. Jan was so very welcoming and enthusiastic. It is obvious they love this life aboard the Key Breeze. Thanks for the memories! We will be back. Christy.

Thank Christy M
Level Contributor
5 reviews
3 attraction reviews
Reviewed 21 April 2017 via mobile

If you are in the Sarasota area and looking to get out on the water, sailing with Tim and Jan is the way to go. All around amazing experience. Will definitely be sailing with them again when my wife and I are back in the area.

Thank Nick S
2 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
Reviewed 13 April 2017 via mobile

My wife and I along with my parents went out for an afternoon sail with Tim and Jan and they made us feel like family! They both have hearts of gold and truly make the trip so relaxing and enjoyable! We had the perfect weather for our trip and it was EVERYTHING I was hoping it would be for our... More 

Thank The6thTemp
Madison, WI
Level Contributor
33 reviews
9 attraction reviews
common_n_attraction_reviews_1bd8 11 helpful votes
Reviewed 5 April 2017

We booked a two-hour tour with Key Sailing and it was a truly memorable experience. Captains Tim & Jan made it enjoyable and it was a learning experience. It was easy to sit and listen to their stories of Sarasota when it was a "Mayberry Town" or to check out the fine points of sailing or to just sit back... More 

Thank GnC4850
Wheaton, Illinois
1 review
Reviewed 27 March 2017

We had a great time sailing with Key Sailing. It was very pleasant and relaxing to be on the water. The boat is beautiful and Tim and Jan are great hosts and knowledgeable about the area. We plan to sail with family and friends when they visit .

Thank Linda B
Piedmont, NC
Level Contributor
4 reviews
common_n_attraction_reviews_1bd8 3 helpful votes
Reviewed 16 March 2017

Captain Tim and Jan made all of us feel so welcome, relaxed, and engaged in our fun hours of sailing together. We saw dolphins, beautiful blue skies and clouds, and a delightful breeze as we enjoyed the bay and all its sights and sounds.

Thank OrchardMountain
Forsyth, Illinois
2 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
Reviewed 11 March 2017

Sailing on the Key Breeze with Captain Tim and Jan is one of our favorite ways to spend a leisurely afternoon. The two hour sail is the best way to relax and enjoy the quiet of the water and the views of Sarasota and the surrounding Keys ( Siesta, Lido, Bird, Longboat). First mate Jan and Captain Tim make sure... More 

Thank Peggy R
Level Contributor
36 reviews
16 attraction reviews
common_n_attraction_reviews_1bd8 14 helpful votes
Reviewed 11 March 2017

My husband and I booked an afternoon sail. The day was predicted to have some fairly strong winds 15 - 20mph. Captain Tim called beforehand to see if we were comfortable with that. I know you need wind to sail, but I was a bit apprehensive. Capt Tim was very reassuring and we decided to go ahead. So happy we... More 

Thank sweenmm

Travellers who viewed Key Sailing also viewed

Sarasota, Southwest Gulf Coast
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

Is This Your TripAdvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing

Questions & Answers

Here's what previous visitors have asked, with answers from representatives of Key Sailing and other visitors
2 questions
Ask a question
Questions? Get answers from Key Sailing staff and past visitors.
Posting guidelines
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?