Sarasota's #1 Sailing Charter

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Gift Certificates Available

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: Will the cruise be cancelled if quota is not met?

A: While some charter companies typically cancel if they don't have a minimum number of guests, we actually cut off our group list at 6 guests. There is no quota. If you have made a reservation on a group charter with us, it will be honored even if that charter is not filled.


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 for four decades. 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 are also 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: You may bring lunch or have us cater, but light snacks are included. We actually have a fold out table attached to the helm station.


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 do have bottle openers and glasses. You are welcome to bring white wine (red can be a bit messy) , champagne or beer. (Hard liquor is not appropriate for a sailing charter.) The Key Breeze is also a "smoke free" vessel.


Q: What if I have young children? Or what if I want to join a group sail with no children?

A: Key Sailing takes young children on private charters only, so that couples on "Date Night" can enjoy a more romantic, quiet experience. Private family charters ARE AFFORDABLE. 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.


And rest assured, when paying a babysitter and making YOUR date night getaway, you will not find the young children of others joining your group sunset cruise.


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: Is Key Sailing on Facebook?

A: We prefer to let you share your Key Breeze experience on your Facebook page with your friends. Your privacy is important to us.


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

The ultimate selfie while enjoying a sunset cruise with Key Sailing Sarasota

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