What an amazing experience! Our family recently enjoyed an afternoon sail with Tim & Jan in Sarasota Bay. We've sailed with them before and this sail didn't disappoint. They pointed out several landmarks along the way and even let us take turns at the helm. Both Tim and Jan are special people who care deeply about helping people and providing a wonderful experience. Thanks for a great afternoon, we will be back! read more

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Took an amazing sail boat ride with Jeremy out into the Sarasota Bay. The ride was beautiful, Jeremy was chill and knowledgeable about the surrounding area. I would definitely go with Key Sailing again. read more

Key Sailing - Sarasota Bay - Boat Tours Near Me - Sarasota, Florida

Comfortable and easy for seniors! Would sail again soon. Looking forward to another great experience read more

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. read more

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Epic evening on the sunset cruise ... really nothing else like it. I reserved the entire boat for my date and I with Captain Tim at the helm. Everything Jan advised in advance was exactly what we experienced. Tim and Jan are delightful and professional. The experience made our hearts soar with the beauty of the bay and the sunset and the full moon. We fell in love on a perfect evening! read more

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! read more

Key Sailing - Boat Tours Near Me - Sarasota, Florida

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! read more

Key Sailing - Chillin' - Boat Tours Near Me - Sarasota, Florida

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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!! read more

Key Sailing - Sailing heaven - Boat Tours Near Me - Sarasota, Florida

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

Key Sailing - Boat Tours Near Me - Sarasota, Florida

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! read more

Key Sailing - Boat Tours Near Me - Sarasota, Florida

My wife and I had a wonderful cruise with Jan & Tim. We had a wonderful sailing experience with the best weather and the best sailing ever. They made it my best birthday ever! They pay attention to the weather and know the best time to go sailing! read more

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! read more

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Awesome trip! I highly recommend using Tim and Jan for some cool sailing in Sarasota - the service is so much more personable then any other business in the area! I had inquired about a sailing trip the day before we left Sarasota. They didn't have any availability for a group trip but took down my number. Within 30 minutes, they called back and were able to take us out the next morning. When we arrived, they informed us that we would be the only ones on the boat! AWESOME! We were able to customize the trip as it progressed, which was really neat. Highly, HIGHLY recommend. This was the most fun we had in Sarasota. read more

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. read more

Key Sailing - Boat Tours Near Me - Sarasota, Florida

5 of 5 bubbles Reviewed December 4, 2016 This was a great sunset excursion from the marina across the bay and out Big Sarasota Pass for a sunset on the Gulf of Mexico. Tim and Jan were superb hosts. We took the trip with two close friends who were visiting us in Sarasota and they enjoyed it very much. We highly recommend this trip for couples. read more

This was the best sailing trip I've ever been on. Tim and Jan were incredibly easy to talk to and were nothing short of encouraging to me and our team. I would recommend this trip to anyone! read more

Best sailing experience ever. My wife and I were on board to help celebrate my brother and his wife's 25th anniversary. Jan and Tim go beyond all expectations to make your trip a once in a lifetime experience. All of us, including their 20 year old daughter and 18 year old son, enjoyed the adventure, right from the time you arrive at the dock. If you are in Sarasota or in the area, this is something you do not want to miss. We will do this again. read more

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!!! read more

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What a great evening with captain Tim and 1st mate, Jan! We did a charter with them to celebrate the engagement of our children, and to celebrate our 30th wedding anniversary. Such an enjoyable time for all! They made sure we were comfortable and took a number of photos for us. No lacking for detail with beverages, chocolate,cookies and flowers given. We even got to steer the sailboat and saw a number of dolphins. A perfect celebration for all. We will definitely do it again! Thanks Tim and a Jan for making this such a wonderful time to remember. read more

My husband and I had the delight of being Captain Tim and Jan's guests today for a perfect sailing adventure. What a precious couple sharing the seas with visitors expertly! Thank you so much! read more

Key Sailing - Captain Tim and Jan - Boat Tours Near Me - Sarasota, Florida

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I'm really glad I stopped in here on a whim. They were super friendly and excited about sharing the sailing experience. Have a nice variety of packages for groups larger or small. In previous chapters of my life, I used to go sailing and boating pretty frequently. Beginning to feel a little landlocked even though I was still a Floridian. Putting this on my to-do list for this year! read more

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

I did the sunset cruise with my boyfriend and his family and we had the pleasure of having Tim and Janet be our guides. Janet allowed us to take turns driving and Tim was a great teacher when my boyfriend asked a bunch of questions about sailing and sailing terms. They were extremely personable, kind, experienced and worldly. They had flowers for all the girls on the boat, snacks, sodas and Janet made sure to take pictures of everyone so we could have fun memories to look back on later. Some of my favorite photos from the entire vacation were from the cruise with the beautiful sunset behind us. I didn't want the cruise to end when it was time to dock and would absolutely recommend this to everyone. I will definitely be doing this again on my next return to Siesta Key. read more

There are so many positives to share about sailing with Captain Jim and Jan on Dec 29. First, they are extremely welcoming and ensure everyone is comfortable. Even though I was a solo traveller it seemed I was traveling with family. Delicious snacks, including chocolates were shared and we received helpful information about iconic landmarks we passed. The best part, and most unexpected part of the trip was the wonderful, and heartfelt stories shared. Sailing with Captain Jim and Jan was the highlight of my entire vacation. read more

Great three hours with Jan and Tim. We had six in our party so we had the boat to ourselves. We didnt get to do a ton of sailing, more motoring but only mother nature can control that! Brought subs on board and Jan did everything to make us feel at home. Fun day, but not something I would bring kids on. Next time we would book a longer sail so we could get out on the gulf and do some sailing! read more

Thank you Tim and Jan for an absolutely wonderful sunset sail last month. It made our anniversary week complete! We enjoyed ourselves immensely, it was beautiful and we enjoyed your company so very much. Blessings to you this Christmas and in the New Year. We will see you again in the future. And thank you for the rose. That was a nice gentle touch. Thrilled and blessed, David and Kiki read more

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

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