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Fort Walton Beach-Okaloosa Island Sailing Charters

Getting the best experiences for you...
6 Passenger Private Catamaran Sailing Charter in Choctawhatchee Bay

6 Passenger Private Catamaran Sailing Charter in Choctawhatchee Bay

65 ratings
Sail away and enjoy the area's stunning emerald green waters. Customizable...
Great weather, experienced Capt. Karl and Dodi made this a perfect afternoon sailing. Very personable staff. Plenty of space and 32 ft. Gemini catamaran is super stable on the water.
The boat was great people are awesome can’t wait to go back
My husband and I took a sunset sail and Carol and Dorothy made the trip wonderful. We were alone on the beautiful water watching the sunset with champagne, what could be better? I would highly recommend booking this excursion, 5 stars all the way!
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$250
Private Sunset Sailing Cruise from Okaloosa Island

Private Sunset Sailing Cruise from Okaloosa Island

7 ratings
Duration2 Hrs.
Sunset on the water is one event that will never go out of style. Now you can amplify your enjoyment with an extra...
Surprise proposal, and wedding ceremony all on a perfect sunset sail. Captain Ladd and first mate Tracy were very helpful and willing participares in a perfect surprise wedding under sail.
It was great never been on anything like that before
Moby’s Captain and Staff provided a personal and private tour of one of the best sunset sails we ever been on. They also included some fishing instructions for my family and we even caught some nice size blue fish. To end it with some dolphin viewing near the Destine crab island. This was a spectacular day at sea for our Family.
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$290
Sights & Sunsets Private Sailing Cruise

Sights & Sunsets Private Sailing Cruise

3 ratings
Duration3 Hrs.
Set sail for an enjoyable evening on the beautiful waters of the Gulf of Mexico and Choctawhatchee Bay looking at...
We had an amazing even out. It was perfect could not have asked for a better experience!!!
We had a great time with Thad and Sebastian- they made the trip enjoyable. The water was rough so we only saw 2 dolphins- but they took us to a nice cove and we snorkeled for crabs! Great time. Only negative was that trip shock required that I pay extra for one person- but Thad didn’t receive the money and only charges a flat fee.
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$375
Private Sail and Play Day Cruise

Private Sail and Play Day Cruise

5 ratings
Duration5 Hrs.
Set sail for adventure with the friendly folks today! Customization for your sailing cruise means you get to go and do...
We had a fabulous time with Tracey and Captain Ladd. They took us dolphin watching, which we saw a bunch of, we got to do some fishing, which we caught fish as well, we got to snorkel and saw some great creatures. They took us by crab island so we could see what all that was about. We just had a great experience! They were very accommodating!
The captain and first mate were awesome. Fun family time is all that you can ask for. They definitely made our experience memorable. We will definitely do this again!
This was the highlight of our trip in Destin! Well worth the money. From being up close to the dolphins, to catching fish, to the beautiful sunset. This was an AMAZING TRIP!
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$550
Private Sailing Adventure (6 Person) Departing from the Destin Harbor

Private Sailing Adventure (6 Person) Departing from the Destin Harbor

36 ratings
Duration2 Hrs.
INCLUDES UP TO 6 GUESTS!
Climb on board for an authentic sailing experience on this Private Sailing Tour in Destin. Voyage through the clear...
We had a wonderful experience sailing and even got to help out being a first mate. Captain Max was very knowledgeable and also pointed out dolphins and sea turtles along the way. I highly recommend this charter for a nice relaxing sailing excursion!
Very relaxing, informative and personable. Highly recommended. Captain Max is a blast!
Delightful Experience! We had a great experience on our first sailing trip. Captain Max is very friendly and knowledgeable on sailing, He made the trip fun and exciting. Everyone in my family really enjoyed it! Defiantly recommend sailing with him.
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$240
4-Hour Private Daytime Sailing Adventure

4-Hour Private Daytime Sailing Adventure

9 ratings
Duration4 Hrs.
Spend a half day among the wind and the waves of Joe's Bayou in the heart of Okaloosa Island. This 4-hour sailing...
Friendly and knowledgeable staff!! Lad and Tracy are amazing! We will definitely do this again!
This was a great trip! Very nice staff that allowed us to pick what we wanted to do, they even let us catch some fish which was a nice surprise:) Would definitely recommend!!
It was a great experience! They were so kind and laid back and friendly. We saw lots of dolphins and were able to get in the water as well.
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$440
Destin Sailing Cruise Aboard The Daniel Webster Clements

Destin Sailing Cruise Aboard The Daniel Webster Clements

187 ratings
Duration2 Hrs.
Set sail aboard one of the very last schooners in the Destin Harbor, the Daniel Webster Clements! Enjoy aqua waters and...
What a wonderful time spent. Well worth the money compared to other options. It was an intimate setting, crew was accommodating and polite answered questions and though it wasn’t promised we saw several dolphins. I will take this tour again for sure. So glad we did this.
The Captain was very informative. The crew was awesome and visited with most everyone for a time. The trip itself was one of the most incredible experiences we have ever had. We cannot wait to bring our family and have them experience this along with us. Pure AWESOMENESS!!
It was a beautiful cruise!
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$42
Swim & Sail Aboard the Daniel Webster Clements

Swim & Sail Aboard the Daniel Webster Clements

35 ratings
Duration3 Hrs.
The Daniel Webster Clements is a great way to start the day in Destin, Florida! This is a 3 hour excursion where you can...
Mitch and others are great Nice add on to a vacation .
We enjoyed our stay at the Beach House. The location was perfect and the place had everything we needed.
The crew was great, the water was amazing, the music perfect, and the sail boat was everything I thought it would be. The only thing that could have made it better is a better place (to short of an area, not much to see) to snorkel and going further out into the ocean.
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$38
Destin Harbor Private Sunset Sailing Excursion
There is no better way to experience the beauty of this area than sailing and the possibilities are endless. We love...
Swim and Sunset Sailing Excursion From the Destin Harbor
Start out sailing to a popular spot to swim and snorkel. Enjoy the beautiful emerald green water and look out for...
Sail and Swim From the Destin Harbor
Sail and snorkeling charters offer a great way to experience the amazing marine life and beautiful waters of Destin...