Escape & Enjoy
At Always Dreaming, we specialize in private full day and half day sails on Tampa Bay. We start the day traveling Northwest up the Manatee River. On Always Dreaming, the journey is up to you. We can make way as far as your heart desires or anchor for some fun in the water. Whatever floats your boat (pun intended). Once we get the yacht moving and everyone gets settled, we will treat you to a special platter of cheeses, charcuterie, dips and crackers. Relax on our hammock, enjoy our floats on the water, lay out in the sun, take pictures of the wildlife including Egrets, Dolphins, and Sting Rays, try your hand at sailing Always Dreaming, and enjoy the beautiful Florida sunset.
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Half-Day SailLooking to enjoy an afternoon or evening out on Tampa Bay? Look no further. Always Dreaming will help you create your half-day itinerary to ensure your party enjoys any and all activities you have planned. Whether you want to drop anchor and enjoy a dip in the refreshing waters near Anna Maria Island, Egmont Key or Passage Key or lounge on the boat and enjoy complimentary food and cold beverages, we will work closely with you to ensure we are tailoring our quality services to your specific needs.
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Full-Day Private SailThere is truly no better way to recharge and rejuvenate your spirits than feeling the wind in your face and soaking in the Florida sun. For the greatest sailing adventure, experience our full-day private sail, in which your private party (don't worry, there won't be any strangers), will enjoy eight hours out on Tampa Bay including a beautiful Florida sunset. Let's go where you want, anchor and swim, sunbathe, relax in the hammock. Complimentary lunch, dinner and drinks are provided. We look forward to having you out on our boat for an experience you will remember for a lifetime!
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Taylor Strohl
1 review
★★★★★ 5 months ago
this was a first-time sailing experience for me, and it was amazing!! captain Guy and his wife are absolutely wonderful; such sweet and welcoming company to have around. they kept in close touch before our sailing date to discuss plans, foods, and drinks. they truly went above and beyond everything I had expected. I will most definitely be returning!! :)
1 review
★★★★★ 5 months ago
this was a first-time sailing experience for me, and it was amazing!! captain Guy and his wife are absolutely wonderful; such sweet and welcoming company to have around. they kept in close touch before our sailing date to discuss plans, foods, and drinks. they truly went above and beyond everything I had expected. I will most definitely be returning!! :)
