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Key Sailing

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Address: 2 Marina Plaza, E-18, Marina Jack, Sarasota, FL 34236
Phone Number: 941-346-SAIL
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TripAdvisor Reviewer Highlights

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Key Sailing? It's social, it's exhilarating, it's relaxing and affordable.

My wife and I stay in Siesta Key during Feburary and March of each year. It has become an annual event for us to spend one afternoon sailing from Marina Jack in Sarasota. Some... read more

5 of 5 starsReviewed December 18, 2015
James T
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320 Reviews from our TripAdvisor Community

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Rose Creek, Minnesota
Level Contributor
9 reviews
common_n_attraction_reviews_1bd8 4 helpful votes
4 of 5 stars Reviewed 3 weeks ago via mobile

Booked at the last minute and was surprised to get a quick response a few hours later that we were booked for an evening sail. No money required to save spot which was nice and received a text from capt the morning of to let us know it was still a good sailing day. Met the other passengers (limit of... More 

Helpful?
Thank Z37
Level Contributor
17 reviews
common_n_attraction_reviews_1bd8 10 helpful votes
5 of 5 stars Reviewed December 18, 2015

My wife and I stay in Siesta Key during Feburary and March of each year. It has become an annual event for us to spend one afternoon sailing from Marina Jack in Sarasota. Some times we have family with us, other times it may be with a couple friends. We have sailed on a couple other boats but nothing has... More 

Helpful?
1 Thank James T
Sarasota
Level Contributor
5 reviews
common_n_attraction_reviews_1bd8 8 helpful votes
5 of 5 stars Reviewed December 2, 2015

My husband and son booked this sunset cruise for us as a birthday surprise. It was absolutely wonderful! Captain Tim & Jan were the perfect hosts. They welcomed us with kindness and lots of Sarasota history. As locals, this is the kind of activity that's always put aside for "some other time". If you're visiting or you live here full... More 

Helpful?
Thank Wren2000
Sarasota, Florida, United States
Level Contributor
5 reviews
common_n_attraction_reviews_1bd8 7 helpful votes
3 of 5 stars Reviewed November 28, 2015

I have lived in Sarasota for many years and have frequently been out on the water so I may be a bit spoiled. I wanted my visiting family to experience the beauty and tranquility of water here in Sarasota. Captain Tim appears to be an expert sailor and he did an excellent job of showing us the intercostal where we... More 

Helpful?
Thank David M
Overland Park, Kansas
1 review
5 of 5 stars Reviewed November 7, 2015

We celebrated our anniversary with a sunset cruise with Captain Tim and First Mate Jan. They were amazing hosts and made this truly a romantic evening. From the moment we stepped aboard we felt at home, as Jan shared Sarasota's rich history to the peaceful sound of the wind filling the sails we enjoyed our cruise. We look forward to... More 

Helpful?
Thank Doug M
Northfield, Ohio
Level Contributor
3 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 4 helpful votes
5 of 5 stars Reviewed October 11, 2015 via mobile

Captain Tim and Jan helped to make our anniversary even more special when we came aboard their sail boat in Sarasota Bay. It was a beautiful evening as we watched the sunset and sailed across the bay. They even supplied snacks, chocolates and flowers.. We will be back to sail again!

Helpful?
Thank Stuart F
Louisville, Kentucky
Level Contributor
14 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 7 helpful votes
5 of 5 stars Reviewed October 6, 2015

Easy to locate at the Marina Jack's with plenty of parking close by. The captain and Mrs. T meet us at the dock and we proceeded on our sail as scheduled. Our first time sailing and it was a beautiful evening and we plan on returning again.

Helpful?
1 Thank KYsailormom
Epping, New Hampshire
1 review
5 of 5 stars Reviewed September 10, 2015 via mobile

We called last minute for a sunset cruise and they were able to get us on and with just two other couples! We were in our honeymoon along with another couple on the same cruise. Tim and Jan were so very nice and accommodating. The weather was great and they were so thoughtful and endearing through the whole cruise. I... More 

Helpful?
Thank LinzL5682
Cincinnati
Level Contributor
3 reviews
common_n_attraction_reviews_1bd8 6 helpful votes
5 of 5 stars Reviewed September 9, 2015

Had a great sailing experience with Jan and Tim. The weather was great and there was a breeze so they could use both sails. They are great hosts.

Helpful?
Thank Dianna Y
Italy
2 reviews
5 of 5 stars Reviewed August 29, 2015

Amazing afternoon. Tim and Jan are very kind and friendly. And the boat is really nice! We had a good time. Higly recommended!!!

Helpful?
Thank Marco D

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Questions & Answers

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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?