Fort Walton Beach-Okaloosa Island Sailing

Climb aboard for a daytime or sunset sail in Fort Walton Beach, FL. Enjoy the sapphire-blue waters around you as you look for area marine life in the waves. Revel in the beauty of the open water and feel the wind in your hair. From leisurely cruises to exhilarating adventures, discover the magic of the open water with expert crews guiding your voyage. Sail, swim, and enjoy the warm salty breeze on a sailing charter to remember.

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Nov 20 - Nov 26
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Private Trip
Swim Friendly
Cruise Only
Restroom
Captain Included
1-6 passenger
Half Day Trip (if duration 3-6 hour)
Kid Friendly
Morning Departure (5am-11:59am)
Afternoon Departure (12pm-4:49pm)
Evening Departure (4:49-11:59pm)
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2 Hour Destin Day Sail

6 ratings
2 Hrs.
Hop aboard your very own 2 Hour Destin Day Sail and enjoy some time out on the aquamarine waters of Destin, Florida. Cruise around on a Stiletto 30-foot catamaran and see the area like never before with the wind steering your path. Take in the sights of marine life and maybe even see a dolphin or two. Enjoy the sounds of the sea birds and feel the wind in your hair. Perfect for families, celebrations, or romantic engagements. Don't miss out, book your sailing charter today!
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Destin Gulf Sunset Sailing Cruise

1 rating
2 - 3 Hrs.
Set sail on this Gulf Sunset Sailing Cruise in Destin, Florida. Relax on the top deck of this 45-foot Beneteau Sailing Yacht as you feel the Gulf breeze in your hair. Cruise the emerald water of the Gulf Coast as you take in the natural beauty around. Keep an eye out for the playful dolphins swimming beneath the water and jumping above the waves. Witness the sun set beyond the horizon as the sky erupts in an array of colors. Create lifelong memories with family and friends and experience a sunset like never before! Book your Destin Gulf Sunset Sailing Cruise today!
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Private Destin Catamaran Sunset Cruise

47 ratings
2 - 3 Hrs.
If you are looking for a beautiful way to end your day, this Destin Sunset Cruise is the perfect match for you! This cruise includes an experienced captain that will take you on an exclusive adventure aboard a Stiletto 30-foot catamaran. Experience the magic and romance of sailing at dusk as you sip, relax, and unwind while watching out for dolphins and other marine wildlife in the surf. Perfect for families, celebrations, or a date-night. Don't miss out on seeing the painted sky of another Destin sunset, book today!
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Destin Dolphin, Sailing & Snorkeling Charter

28 ratings
3 - 4 Hrs.
Climb aboard your very own Destin Dolphin, Sailing & Snorkeling Charter and enjoy a day out on the sapphire-blue waters of Destin, Florida. Sail on a Stiletto 30-foot catamaran and see the area like never before, with the wind at your back. Have the opportunity to take in sights of the area marine life, snorkel and swim, and maybe even see a dolphin or two. Don't miss out, book your private charter today!
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Private Destin Sunset Sailing Cruise

28 ratings
2 Hrs.
Don't miss a stunning cotton candy [sunset cruise on the water in Destin, Florida](https://www.tripshock.com/attractions/destin/sunset-cruises/ "sunset cruise on the water in Destin, Florida"). Set sail on a 35 foot catamaran cruise and enjoy the fresh salt air around you as you watch the sun disappear into the endless horizon. Let your captain take your worries away as you relax, enjoy the sunset, and watch dolphins play in the surf! Don't miss a gorgeous way to say goodbye to the day on this Private Sunset Sailing Cruise from Destin!
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Private Gulf of Mexico Sunset Sail

34 ratings
2 Hrs.
Experience the serene beauty of an Emerald Coast sunset on a Private Gulf of Mexico Sunset Sail. Enjoy a breathtaking cruise around Destin, gliding through Choctawhatchee Bay and Destin Harbor. Relax as you let go of life’s worries and watch dolphins play against a stunning cotton candy sky. Whether with a loved one or friends, this unforgettable sunset sail offers a perfect vacation moment. Don’t miss your chance—hop on the catamaran and sail into the sunset today!
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Discover Destin Private 3 Hour Swim & Sail

59 ratings
3 Hrs.
Experience Destin like never before with Discover Destin Swim & Sail. Board a 30-foot Stiletto catamaran to cruise and snorkel at your own pace along the stunning Emerald Coast. Explore hidden beaches and encounter fascinating marine life, including sand dollars, blue crabs, sea turtles, and dolphins. This is your chance to immerse yourself in the beauty of the coast—don't miss out! Book your [Destin sailing charter](https://www.tripshock.com/attractions/destin/sailing-charters/ "Destin sailing charter") today!
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6 Passenger Private Day Time Sailing Cruise

96 ratings
2 - 4 Hrs.
Climb aboard an authentic sailing cutter for an experience to remember on this Private Sailing Tour in Destin, Florida. Cut through the clear water of the Destin Harbor and along the stunning Emerald Coast spotting dolphins, sightseeing, and enjoying the warm salty breeze. An entertaining tour guide and sailing captain will teach you all about the history of the area as you explore. Put some wind in your sails and customize your private sailing tour today! Book yours now!
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Private Destin Dolphin, Sailing & Snorkel Charter (for up to 6 guests)

16 ratings
3 Hrs.
Don't miss an exciting day on the water in Destin, Florida. Set sail on a 35-foot catamaran cruise and enjoy the fresh salt air around you as you and up to 5 of your closest friends or family members watch as the sun dances on the waves. Let your captain take the helm as you relax, take a dip, hang out at Crab Island, enjoy some snorkeling, and watch pods of dolphins play in the surf! Get an up-close look at fascinating aquatic life like hermit crabs, dolphins, and colorful shells. Maybe even catch a few fish as you troll fishing lures while sailing along if you like. Book your trip today and make some memories to last a lifetime!
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Discover Destin Private 2 Hour Sail

22 ratings
2 Hrs.
Experience Destin like never before. Get up close and personal with everything the exciting Emerald Coast has to offer with this Discover Destin Sail. Set out on this 30' Stiletto catamaran and soak up the rays and the sights around you as you cruise at your own pace. There are so many intriguing places to visit along the coastal beaches, places that cannot be reached by car. Nestled in these hidden treasures are places to explore and get an up-close look at fascinating aquatic life. Experience the amazing marine life and beautiful water. Don't miss the boat! Book today!
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Destin Gulf Sailing Adventure

21 ratings
3 Hrs.
Explore the Emerald Coast in style on 45-foot Beneteau Sailboat in Destin, Florida. Enjoy an authentic sailing experience from the deck aboard your own private sailing yacht. Sit back and feel the warm Destin breeze, see dolphins play in the water, and unwind as you sip on your favorite beverage. Don't miss out on the beautiful sights of the Destin Harbor, book your Destin Gulf Sailing Adventure today!
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5 Hour Swim, Sail, & Snorkel Charter

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5 Hrs.
Experience the ultimate adventure in Destin with a Swim, Sail, & Snorkel Charter. Relax as your captain takes the helm, allowing you to enjoy a customized adventure. Dive into the clear water at Crab Island, snorkel among vibrant marine life, and watch dolphins play in the surf. This charter offers personalized tours based on your preferences. Perfect for family fun or a relaxing day out, this Destin charter is your ticket to an unforgettable experience on the emerald water of the Gulf Coast. Book your ultimate Destin water adventure today!
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6 Passenger Private Swim & Sail Adventure

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3 Hrs.
Climb aboard an authentic sailing cutter for an experience to remember on this Private Swim and sail adventure in Destin, Florida. Cut through the clear water of the Destin Harbor and along the stunning Emerald Coast spotting dolphins, sightseeing, and enjoying the warm salty breeze. An entertaining tour guide and sailing captain will teach you all about the history of the area as you explore. Put some wind in your sails and customize your private sailing tour today! Book yours now!
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6 Passenger Private Sunset & Fireworks Sailing Cruise

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3.5 Hrs.
Climb aboard an authentic sailing cutter for an experience to remember on this Private Sunset & Fireworks Sailing Cruise in Destin, Florida. Cut through the clear water of the Destin Harbor and along the stunning Emerald Coast spotting dolphins, sightseeing, and enjoying the warm salty breeze. Take in the sky as it erupts in color as you witness the breathtaking sunset. As the sky darkens, enjoy a firework show as your entertaining tour guide and sailing captain will teach you all about the history of the area as you explore. Put some wind in your sails and customize your private sailing tour today! Book yours now!
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