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 Plz # E-18, Marina Jack, Sarasota, FL 34236-8919
Share
Save
Review Highlights
Anniversary cruise

We went on the cruise with Jan and Tim after our original plans fell through. Well, we couldn’t... read more

Reviewed 5 days ago
audreyrigot
via mobile
Perfect Experience

My husband and I took a private 2 hr late afternoon sailing cruise with Tim & Jan and it turned... read more

Reviewed 1 week ago
Denise W
,
Huntington Beach, California
via mobile
Read all 406 reviews
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Overview
More
Providing private and group daytime and sunset sailing charters. Husband and wife crew has 40 over years of sailing experience together.
  • Excellent96%
  • Very good1%
  • Average1%
  • Poor1%
  • Terrible1%
Travelers talk about
“key breeze” (53 reviews)
“captain tim” (71 reviews)
LOCATION
2 Marina Plz # E-18, Marina Jack, Sarasota, FL 34236-8919
Write a ReviewReviews (406)
Traveler rating
Traveler type
Time of year
Language
All reviews
"key breeze"
in 53 reviews
"captain tim"
in 71 reviews
"sailing experience"
in 42 reviews
"sunset sail"
in 31 reviews
"private charter"
in 16 reviews
"sarasota bay"
in 42 reviews
"great sailing"
in 7 reviews
"love sailing"
in 4 reviews
"hour afternoon"
in 4 reviews
"perfect weather"
in 6 reviews
"wonderful sunset"
in 4 reviews
"perfect afternoon"
in 4 reviews
"siesta key"
in 21 reviews
"amazing experience"
in 7 reviews
"marina jack"
in 6 reviews
"gulf of mexico"
in 8 reviews
"highlight of our trip"
in 5 reviews
Filter

1 - 10 of 396 reviews

Reviewed 5 days ago via mobile

We went on the cruise with Jan and Tim after our original plans fell through. Well, we couldn’t have asked for a better anniversary celebration. It was a beautiful night for sailing and Jan and Tim couldn’t have been more hospitable. They did everything to...More

Thank audreyrigot
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 1 week ago via mobile

My husband and I took a private 2 hr late afternoon sailing cruise with Tim & Jan and it turned out to be way more then we expected. They were the most gracious people and we felt so comfortable with them right away. Hearing about...More

Thank Denise W
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 1 week ago via mobile

We had an evening sail and it was beautiful. Both Capt Tim and Jan explained several aspects of sailing to us and pointed out landmarks surrounding us. My birthday was the following day and Capt Tim played the guitar and sang for me while Jan...More

Thank mlwalker1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
See more reviews
Reviewed 2 weeks ago via mobile

We were impressed by Capt Tim and Jan's warm hospitality. They were genuinely friendly and worked well together. We felt absolutely comfortable with their competency on the sailboat as well as their flexibility and professionalism booking it. Our originally scheduled date was rained out so...More

1  Thank Mary E
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 2 weeks ago via mobile

Family outing on a sunny Thursday afternoon. The boat comfortably held six of us ( husband and wife boat owners included). Jan offered some local history.....and Dove chocolates! Tim strummed and sang “Happy Birthday” to the “ birthday girl” on his guitar. The sailboat ride...More

1  Thank tdl253
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 3 weeks ago via mobile

Capt Tim surprises us with his guitar talent for my upcoming Birthday. This our fourth time out sailing with Jan & Capt Tim. They let us take the helm, relax on deck, or converse whatever topics come to mind. The choice is always ours. We...More

1  Thank sherrysea620
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 3 weeks ago

My bf mentioned one day that we would like to go sailing, so I looked online for different options and Key Sailing came up. I booked my trip in Nov '17 for my bf's bday April '18. It was TRULY an amazing time!!! The weather...More

1  Thank carajae00
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 3 weeks ago via mobile

We got to experience this beautiful sunset sail on a day that looked like the only thing we were going to see was clouds. We were all surprised when we came across this sunset. This sailboat tour is for groups of 6 or less. Even...More

1  Thank Joy G
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 4 weeks ago via mobile

We didn't think we were going to be able to go because of bad weather but luckily it cleared up and we got to enjoy a lovely sunset sailboat outing. They were wonderful to us and made us feel very special.

1  Thank Jenedwards1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed April 26, 2018 via mobile

We took a 2 hour afternoon sail around the beautiful harbors around Sarasota/ Siesta Key. It was an extremely enjoyable and relaxing experience. They made us feel welcome. My wife and I relaxed on deck while we sailed around the bay enjoying the views of...More

1  Thank MikkFun
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Nearby
Nearby HotelsSee all 53 hotels in Sarasota
Aloft Sarasota
312 reviews
.15 miles away
Art Ovation Hotel, Autograph Collection
43 reviews
.30 miles away
The Westin Sarasota
195 reviews
.33 miles away
Quayside Inn
1 review
.46 miles away
Nearby Restaurants
Owen's Fish Camp
1,791 reviews
.23 miles away
Selva Grill
820 reviews
.21 miles away
First Watch
316 reviews
.26 miles away
Caragiulos Italian American
440 reviews
.15 miles away
Nearby Attractions
Bayfront Park
161 reviews
.04 miles away
Unconditional Surrender Sculpture
841 reviews
.18 miles away
Massimo Meda Art Gallery
5 reviews
.27 miles away
Questions & Answers
Get quick answers from Key Sailing staff and past visitors.
Note: your question will be posted publicly on the Questions & Answers page.
Posting guidelines
Submit
;