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    Key Sailing

    4.9 (28 reviews)

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    Judy K.

    We really enjoyed our 2 hour sail with Tim. He was personable and funny. Also, getting it set up and finding it was a breeze. Jan and Donna were both professional and so nice by text and email. It was a gorgeous day for a sail. Our family made some lovely memories.

    Shere G.

    Don't wait for a special occasion! The crew of the Key Breeze will make you feel like a Kardashian even if you're 2 old retirees from Kansas City! Tim, Jan and first mate Becky are pros at customer service! We celebrated our anniversary on their gorgeous sailboat to commemorate our wedding officiated by Tim on the same boat! We waited 12 years, wish we had done it every year! But don't wait for a special occasion!

    Chillin'

    Wow! Tim, Jan & Dawn are all amazing! I wasn't even going to go at first because I'm "nervous Nellie" on motor boats and didn't know what to expect. Tim didn't pressure me to join, told me how smooth the boat is, and why, and that today we'd only go about 8 knots/mph. I joined my family and LOVED IT!! Tim is so chill and included us navigating the boat when we asked to. We will definitely be going out again soon! See you in October & definitely in December at sunset. Thank you from all the Gill's!

    Sailing heaven
    C D.

    HIGHLY RECOMMEND!!! Tim and Jan are wonderful hosts and see to it that you have the ultimate experience. Can an experience be exciting and relaxing?... that's what you'll get! We saw dolphins and the little surprises at the end are a nice touch! You will not be disappointed... relax and enjoy!!

    Chardea N.

    Went out with a big group and had such a fun trip. Jan and Tim were wonderful to sail with!

    Meagan W.

    We had an amazing time sailing with Tim and Jan! They are so welcoming and make you feel right at home on the boat. We took our two children with us on a two hour sail and they absolutely loved getting to take some time and steer the boat themselves! We really enjoyed getting a true sailing adventure for the first time as a family and highly recommend Key sailing to anyone wanting to get a fantastic sailing experience. Tim and Jan have been sailing for many years and are excellent!

    Stunning sunset.
    Mollie L.

    Absolutely wonderful! Captain Tim and Jan were incredible hosts for an evening of sailing at sunset. They were so kind and accommodating and will do anything to make sure you enjoy every moment of your sail. They were super knowledgeable of the area and were great at pointing out some highlights along the way. My husband and I couldn't believe the view from the from of the sailboat as we approached the edge of the Gulf of Mexico. We will never forget it!

    Went for a quick trip to Florida with some college buds, and found this adorable couple who does private charters. It was SO perfect for our group of 6, and Jan and Tim cared for us, down to every detail -- from updating us continually on weather and conditions so we could find the warmest, calmest ride for our seasick-prone crowd, to dressing us up in Snuggies when it got a littler chiller than what we were dressed for. They had awesome stories to tell, perfect ocean music to play, and also made sure to leave us with our own time to chat and just enjoy the sun and water. We were plied with Girl Scout cookies, proffered drinks, and had an awesome time, sailing around and basking in the sun. I would totally sail with them again when I'm back in the area.

    Sunset from the boat!

    From the second we got on the boat--they welcomed us with open arms. They went above & beyond. We were celebrating our honeymoon & the other coupe was celebrating their 43rd anniversary. They only put them on with us & no one else so we would kinda have the boat the ourselves. The captain & his wife gave us flowers, chocolates, drinks, and a treat that said "Happy Honeymoon"--we didn't expect any of it & they did it out of the kindness of their hearts!! We loved every second of it & will go back in a heartbeat. Make sure you tell them if you're celebrating something, because they will make sure they do whatever they can. IT WAS WORTH EVERY PENNY!!!

    Captain Tim and Jan

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    7 years ago

    Awesome time! Tim & Jan are some of the nicest people you'll ever meet. They provide a very personal experience. Would recommend to anyone!

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    10 years ago

    We had a fabulous evening on this sailboat !!! Perfect weather, sunset, and hosts! Will definitely be back !!!!! Thank you Tim and Jan

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    11 years ago

    Great charter! Tim and Jan were informative and entertaining. Our kids can't wait to come back and have more sailing lessons.

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    Review Highlights - Key Sailing

    Both Tim and Jan are special people who care deeply about helping people and providing a wonderful experience.

    Mentioned in 23 reviews

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    Kathleen D Sailing Catamarans

    Kathleen D Sailing Catamarans

    4.6(30 reviews)
    0.1 mi

    What an excellent adventure, especially with Captain Charles (Charlie) Alexander! I met my friends…read morein Sarasota as the family was there on Spring Break and booked this 4-hour catamaran excursion. The harbor area was easy to locate based on the directions given, and a parking pass is provided (as the lot posts a free 3-hour limit). We set sail a little after 1pm. It was a little windy starting out, but Captain Charlie maneuvered the catamaran expertly. He also provided local commentary on the area and made us laugh with his jokes and statements. Sandwiches were provided at the halfway point, and we were allowed to bring drinks and snacks on the catamaran. There were 12 of us in our group and we easily moved around the boat and had plenty of room to stretch out. Captain Charlie even directed us to a small cove area where dolphins played along the seawalls. We got to see a mother, father and baby dolphin frolic in the water as well as one dolphin (probably the dad) swim along and under the catamaran. We all enjoyed that experience! I highly recommend Kathleen D Sailing Catamarans for a fun family day and a great excursion! Hi

    We had great wind but only sailed for about 30 minutes. The captain was great. We did a motor…read morecruise of celebrity houses on bird island and siesta key, I couldn't care less about celebrities 10 million dollar houses. I wanted to sail. The sunset was amazing. Nice catamaran.

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    Kathleen D Sailing Catamarans
    Kathleen D Sailing Catamarans - View of Sarasota from the "No Plans" catamaran.

    View of Sarasota from the "No Plans" catamaran.

    Kathleen D Sailing Catamarans

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    Key Sailing - boattours - Updated May 2026

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