Sarasota's #1 Sailing Charter

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Key Sailing - Sarasota's #1 Sailing Charter - Fresh Air, Fine Chocolates, and a few hours of Peace on Earth!

941-346-7245 (SAIL)



Q: OK, how do I make my reservation?


Q: What methods of payment do you accept?

A: We accept credit cards, debit cards, checks or cash. No deposit is necessary.


Q: I want to purchase a gift certificate. How does that work?

A: Gift certificates are available by phone or email, and are valid for one year. Certificates make great stocking stuffers. Some people attach them to a cap/hat or toy sailboat and give them as anniversary or birthday gift. Realtors often purchase them for closing gifts.


Q: What if the weather doesn't cooperate? What is your cancellation policy?

A: Because we do NOT take a deposit, there are no worries if your plans change or if the weather changes your plans. But don't wait for the sun to shine to make your reservation. Although you can sometimes sail with us on the same day you call, and it is always worth a try, we take reservations weeks and months in advance, and some dates are already booked for the next several years.


Q: What sailing experience can I expect from the captain and crew?

A: U.S. Coast Guard Master Captain Tim Solomon has been sailing together with his wife Jan since 1975. They first studied their craft in high school at the Sarasota Sailing Squadron. Many boats later, international experience includes Australia, the Caribbean, the Coast of South Africa, and over 3,000 miles in the Pacific Ocean. Now Tim and Jan have returned to their hometown roots. The Key Breeze sails across from the bay front veteran's park named in honor of Jan's father, Chaplain J.D. Hamel. Key Sailing IS the hometown team.


Q: Can I take the helm?

A: As an Official Educational Vessel of Sarasota County, free sailing lessons are offered by request to guests of all ages. Classes have been offered through the adult education program of Sarasota County. Sailing certificates are awarded on our longer sailing experiences.


Q: Can I just relax?

A: We customize the route, snacks, music, and experience, even on group charters. Whether you want real estate knowledge or privacy at sunset, Key Sailing is all about meeting YOUR expectations, so let us know what they are!


Q: My friends want to sail in the sun, but I need to sail in the shade. Do you have both?

A: The shady area alone under the Key Breeze bimini top has room for ALL guests to sit comfortably if that is their desire. If you prefer fun in the sun, our vessel is equipped with pillows, bean bags, and cushy cushions with backs to relax out front and catch those rays. You are free to move around during the cruise as you wish, and because we don't crowd the yacht, there is more room to roam in both sun and shade.


Q: Can we eat on the yacht?

A: Yes! We actually have two refrigerators, ice, cups, plastic plates, silverware, and a fold out table attached to the helm station in the shade. You may bring lunch or ask us about local take out and catering options to make the experience unique. Birthday cakes are fine, but no candles, please! If you let us know in advance, we can provide some birthday or anniversary treats, and even sing for the guest with the guitar on board! Also, no need to buy items like bottled water, soft drinks or chocolates. They are included.


A word to the wise: We have noticed that first time guests generally bring everything but the kitchen sink. Repeat guests, especially those who have been with us more than a couple dozen times, often come aboard “their yacht” with nothing more than a smile and a camera or cell phone.


Q: So snacks are included? Are adult beverages allowed on the Key Breeze?

A: We serve soft drinks, iced tea, lemonade, and bottled water. We have been known to buy coffee for morning sails and customize the snack selection. All sails include CHOCOLATE. You may bring any other snacks you wish, including adult beverages. We have bottle openers and glasses.


You are welcome to bring white wine, champagne or beer, but the Key Breeze is a relaxing vessel and not the venue for becoming inebriated. In that spirit, hard liquor is not appropriate for a sailing charter. Also, red wine can be a bit messy, so is no longer allowed due to stains.  In addition, the Key Breeze is a, “smoke-free” vessel.


Q: What if I have young children?

A: Jan loves children and holds a graduate degree in education. There is a playpen type area near the helm in the shade and Captain Tim often teaches the little ones to sail while their parents sample the chocolates. Life jackets are available in all sizes. The Key Breeze is a safety first vessel. Tim and Jan are grandparents now, and it shows in their love for the little ones on board! Morning sails are ideal for young families.


Q: What about restroom facilities?

A: We have two heads (bathrooms) on board, and as the captain says, "Two heads are better than one."


Q: Will I get seasick?

A: It's not likely! One of the main reasons is that monohull vessels have a heavy keel under the vessel that provides incredible stability. The Key Breeze has 8,500 pounds of lead in her keel, under the water line. We also only go into the Gulf by request, and can spend all day in the nice breezes of Sarasota Bay if that is your desire (most guests actually prefer the bay sails).


Q: How old is too old to sail?

A: You can enjoy sailing at any age. Please call us if you have any physical limitations or health concerns. 941-346-7245.


Q: Will I get wet or need a towel?

A: The Key Breeze is a deep water yacht, so we do not anchor during your charter. We are a cruising vessel built for "smooth sailing." Although you won't be swimming or getting wet, some guests prefer to add a personal towel over our cushions out front when tanning.


Q: Is it true that the key to the City of Sarasota is on board the Key Breeze?


Q: Does Captain Tim really speak Spanish? Where is he from?

A: Captain Tim was born in the Midwest but grew up in South America and speaks Spanish like a native. Jan is also fluent in Spanish. They both enjoy learning other languages as time and travel permit.

Frequently Asked Questions

Affordable private sailing charters in Sarasota Bay
Affordable private charters in Sarasota Bay

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