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
Satellite
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:
941-346-SAIL
Website

TripAdvisor Reviewer Highlights

Read all 367 reviews
Visitor rating
  • 341
    Excellent
  • 6
    Very good
  • 5
    Average
  • 5
    Poor
  • 0
    Terrible
Tim and Jan are awesome!

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... read more

Reviewed 5 days ago
Nick S
via mobile
Add Photo Write a Review
Turn Your Opinions into Points!
Turn your opinions into JPMiles
Turn your opinions into PAYBACK Points
*You can enroll in only one programme at a time to earn rewards for reviews.
JPMiles / Payback Arrow
JPMiles / PAYBACK
50

367 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
Language
  • More
Showing 357: English reviews
Level Contributor
5 reviews
3 attraction reviews
Reviewed 5 days ago NEW 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.

Helpful?
Thank Nick S
Level Contributor
2 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
Reviewed 1 week ago 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 

Helpful?
Thank The6thTemp
Madison, WI
Level Contributor
33 reviews
9 attraction reviews
common_n_attraction_reviews_1bd8 10 helpful votes
Reviewed 2 weeks ago

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 

Helpful?
Thank GnC4850
Wheaton, Illinois
1 review
Reviewed 4 weeks ago

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 .

Helpful?
Thank Linda B
Piedmont, NC
Level Contributor
3 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.

Helpful?
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 

Helpful?
Thank Peggy R
Level Contributor
36 reviews
16 attraction reviews
common_n_attraction_reviews_1bd8 14 helpful votes
Reviewed 10 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 

Helpful?
Thank sweenmm
Argyle, Texas
Level Contributor
7 reviews
6 attraction reviews
common_n_attraction_reviews_1bd8 6 helpful votes
Reviewed 9 March 2017

We called last minute and were able to get in for a 2 hour afternoon tour. My son and I had a wonderful time visiting with Tim and Jan hearing about all of their adventures on the boat and in life. We were able to steer the boat the vast majority of the trip. The hospitality was over the top!

Helpful?
Thank PMcAlister
Northville, Michigan
Level Contributor
3 reviews
common_n_attraction_reviews_1bd8 2 helpful votes
Reviewed 26 February 2017 via mobile

We had a private charter for our group on 8 which included our 2 grandkids. It was raining the day we reserved the charter and we could not go out for our sail. Captain Tim and Jan were so accommodating and squeezed us in the next day which was the last day our grandkids were visiting. What a great time!... More 

Helpful?
Thank coopcrew
York, Pennsylvania
Level Contributor
7 reviews
Reviewed 25 February 2017 via mobile

Captain Tim & First Mate Jan are a knowledgeable seafarers with credentials to their vast travel & sailing life experience. Our private 2 hour sail encompassed delightful relaxation. PS Reverend Tim & Jan were involved in ministry as children & now

Helpful?
Thank Susan A

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!

Turn Your Opinions into Points!
Turn your opinions into JPMiles
Turn your opinions into PAYBACK Points
*You can enroll in only one programme at a time to earn rewards for reviews.
JPMiles / PAYBACK
50
JPMiles / Payback Arrow
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?