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
Booking unavailable on TripAdvisor

Want other options you can book now?
All photos (224)
Full view
Certificate of Excellence
Traveller Overview
  • Excellent96%
  • Very good1%
  • Average1%
  • Poor1%
  • Terrible1%
Travellers talk about
“captain tim”(78 reviews)
“sunset sail”(32 reviews)
Providing private and group daytime and sunset sailing charters. Husband and wife crew has over 40 years of sailing experience together.
2 Marina Plz # E-18, Marina Jack, Sarasota, FL 34236-8919
Improve This Listing
Recommended experiences in and around Sarasota
from USD 50.00
More Info
from USD 40.00
More Info
from USD 15.00
More Info
from USD 360.00
More Info
Reviews (418)
Filter reviews
407 results
Traveller rating
Traveller type
Time of year
More languages
Show reviews that mention
All reviews captain tim sailing experience sunset sail sarasota bay great sail hour cruise marina jack amazing experience small group sailboat jan helm skiing sailed solomon sails dolphins
Updating list...
1 - 10 of 407 reviews
Reviewed yesterday via mobile

Tim and Jan are a most capable and enjoyable owners and crew. They have a beautiful boat, but what makes sailing with them so special is that they limit the number of guests to 6, unless it's a private party. They obviously are more concerned...More

Date of experience: March 2019
Thank Bill G
Reviewed 1 week ago

We had our own private group for the sunset. It was fun, relaxing and very enjoyable. The ride goes out to the edge of the Gulf where you watch the sunset and then back into port with a 2 hour cruise. Captain Tim and Jan...More

Date of experience: March 2019
Thank MarciaKay
Reviewed 2 weeks ago

Captain Tim and his wife Jan were wonderful hosts on a fantastic sailing day. Their friendly, enthusiastic demeanor brought a small group of strangers together sharing their life experiences with a sense of humor. My husband and I are looking forward to revisiting the Bay...More

Date of experience: March 2019
Thank Pioneer823649
Reviewed 2 weeks ago

We sailed with Captain Tim and first mate Jan for my wife's birthday. It was a beautiful late afternoon charter with perfect winds and temperature. We couldn't have asked for more gracious and knowledgeable hosts. We have lived in Sarasota for 20+ years and have...More

Date of experience: February 2019
Thank jnichols777
Reviewed 3 weeks ago via mobile

We went on a sunset sail with Captain Tim and Jan. They were very gracious even though we were the fourth sail of the day and the other group that was to be on the boat cancelled and there was only two of us. They...More

Date of experience: February 2019
1  Thank restahl
Reviewed 11 February 2019

Beautiful weather and a great sail. Tim and Jan are wonderful and provide information about Sarasota, their yacht, and answer questions without reserve. Service is excellent and Tim even brought out his guitar! I'd recommend Key Sailing to ever regardless of age.

Date of experience: February 2019
1  Thank Barbara M
Reviewed 23 January 2019

My husband and I scheduled a sailing day with Tim and Jan, we let them know that we planned to bring some friends that are originally from South Africa. We had the perfect day! We were lucky as the winds were up so the sailing...More

Date of experience: February 2018
2  Thank KJWeeks
Reviewed 30 December 2018 via mobile

We had a perfect day sailing on the bay with Captain Tim and Jan. They were warm and welcoming and made us all feel at home. They also lovingly taught the kids ( ages 14 & 9) about sailing. Can’t wait to go out again...More

Date of experience: December 2018
1  Thank Stefr5050
Reviewed 7 October 2018 via mobile

Thanks so much to Captain Tim and Jan! We had a wonderful time and they were the kindest and most accommodating hosts.

Date of experience: October 2018
Thank OnAir290322
Reviewed 27 September 2018

My best friend and I booked this while on a girls weekend away. Jan and Tim were awesome. They were very timely in their communication with us and even offered to adjust the time of our sail in order to avoid some potentially bad weather....More

Date of experience: September 2018
Thank Molly G
View more reviews
Nearby HotelsSee all 55 nearby hotels
The Westin Sarasota
415 reviews
.28 km away
Art Ovation Hotel, Autograph Collection
163 reviews
.31 km away
Aloft Sarasota
370 reviews
.45 km away
Embassy Suites by Hilton Sarasota
60 reviews
.48 km away
Nearby RestaurantsSee all 1,208 nearby restaurants
Selva Grill
883 reviews
.32 km away
The Coolinary
167 reviews
.34 km away
Caragiulos Italian American
479 reviews
.34 km away
Marina Jack
1,524 reviews
.12 km away
Nearby AttractionsSee all 478 nearby attractions
Bayfront Park
188 reviews
.33 km away
Unconditional Surrender Sculpture
943 reviews
.07 km away
AlexArt International Art Gallery
15 reviews
.38 km away
Questions & Answers
Ask a question
10 February 2019|
Response from keysailing1 | Property representative |
We offer several sailing cruise options. Please call me at your convenience at 941-346-7245. We look forward to having you sail aboard the Key Breeze with us! Captain Tim, Key Sailing