Escape & Enjoy
At Always Dreaming, we specialize in private full day, half day, sunset sails on Tampa Bay. We start the day with an invigorating sail 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. The bar is open on Always Dreaming. We serve complimentary wine, beer, soft drinks and bottled water. Relax on our hammock, enjoy our floats on the water, lay out in the sun, try your hand at sailing Always Dreaming, and enjoy the beautiful Florida sunset.
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Sunset Sail (Our most popular)There is nothing quite like soaking in a beautiful Florida sunset out on the water. Whether you are with family, friends or colleagues, our trip around Tampa Bay will offer you the best views of the setting sun, all while you enjoy the natural splendor of the Bay. Complimentary food and drinks are provided, along with our personal first class service. Priced at only $100 a person, the Sunset Sail is for those looking to escape and enjoy the great outdoors and the romance of the setting sun.
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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 six 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!! :)
