Find your perfect adventure
Trip dates
Wish List
Traveler Stories

Own a Based Fish Mafia NFT?

Save 10% on Your Booking

Sunset cruise

about 1 year ago
Taylor and bailee were amazing! Answered all of our sea questions and made us feel very welcomed. Would definitely do it again with those two!!
Alejandro Sanchez

1st Sailing adventure!

about 1 year ago
We had an amazing time. Capt Taylor and Bailey were wonderful. Felt completely safe with them! Will definitely do this again when we are in Destin
Susan Amaya

Sail experience

about 5 months ago
James was amazing from the moment we got on the boat until the moment we got off!!!
Lisa Salinas

Sailing excursion

about 6 months ago
Excellent sailing!! Kids and adults all loved it!!! We saw dolphins and enjoyed the water and sunshine captain Harbour was terrific highly recommend
Peggy Petrovic

Sunset sail

about 12 months ago
It was perfect! Capt. James and Matt were awesome!!
Kathleen Moore


about 5 months ago
This was a very chill relaxing experiece. We saw several dolphins and our captain was very nice and knowledgeable about the area. The only reason I couldn't give 5 stars was the seating on the boat. It was a long trip with nothing to lean up against.
Cathey H

Just okay …

about 6 months ago
We unfortunately didn’t see any dolphins (I know out of their control but it does list 98% rate so I guess we are the 2%) and was hoping the captain would of been more interactive. He didn’t say much unless we asked.

Fair Winds Sailing Co was great!

about 12 months ago
I booked the sailing trip for me and my best friend for her bachelorette party. We are such chill people, so being able to just drink our wine and relax as we sat at the front of the boat was amazing. The captain was so great, very funny, and very nice. He let us bring the sails down towards the end, and he gave us some recommendations on where to go and what to do in Destin. Hands down the best experience ever.
Dolly Harper

First Time Sailing

about 1 year ago
Capt James and crew were awesome. Sailing was both peaceful and exhilarating. I can sum it up by repeating what my wife said-“the hardest she has ever laughed was when she was holding on for dear life as the boat keeled.”
Robert Driggers

Great Sailing Experience

about 3 months ago
We loved our sail trip! It was a great, peaceful ambiance and fun trip. We all had a wonderful time taking in the sights and relaxing.
Katie Loepp

A little underwhelming

about 12 months ago
I had high hopes for a great experience after reading the reviews. I was looking forward to an engaging captain and learning more about the history of the bay and more about sailing, per the description online. Unfortunately the captain (who never introduced himself so I don’t know his name) was really quiet and only talked when we asked him questions. I also slipped and fell and he did not seem concerned. The positives were that we did see dolphins and my boys enjoyed sailing.
Michael Marsch
about 6 months ago
Nice first time experience, the only bad part is that we experienced the most beautiful sunset driving around in the harbor instead of the lake. I suggest them if they are in a hurry to leave at 5:30-6 pm to get the sunset on the Lake not in the harbor.
Maria Tulba

Best Family Trip!

about 2 months ago
We chose a sailing adventure because we’d never done it before. Sailing at sunset and seeing dolphins was just a plus! It was so peaceful with an amazing breeze; both my husband and I almost fell asleep! Both captains were amazing! So friendly and laid back, very chill and made the whole trip even better! They taught us a little about sailing and what to expect before we even got on board! Highly recommend regardless of who you’re with. It was beautiful!
Heather Crawford


about 1 year ago
This was our first time on a sailboat. And it was amazing! I highly recommend this experience. Captain Harbor was very informative and an experienced sailor. The gulf is calm and the day was hot but beautiful. This is definitely something we will do again.
Theresa Hendrix


about 4 months ago
We really enjoyed our sunset cruise, I was disappointed we did not see any Dolphins, however the sail was great!
Tammie Buice

Highly recommend

about 1 year ago
We truly enjoyed our sunset sailboat cruise and although it started off a little rough because we couldn’t find the slip, parking and traffic was horrific we finally found our captain. The boat needs some TLC but the experience and captain Taylor were awesome. I only wish it started earlier so we could have had more daylight.
Cheryl Wojnar

Fantastic trip!

about 1 year ago
Captain Harbor was awesome! Very knowledgeable. Wonderful experience. We saw lots of dolphins and 3 sharks!
Kimberly Burke

Private sailing

about 1 year ago
It was an awesome experience ! It’s our first time to sail and it’s really a wow feeling and experience . Capt. Harbor was so nice and was very informative. We will be back for sure
Juliet Ocampo

1st Sail

about 2 months ago
We had an amazing sailing experience! The crew were friendly and gave us the freedom to enjoy being out on the open water. The sunset view was spectacular & a dolphin came to visit on our way back to port. This was a great way to end our vacation & it was everyone’s #1 event.
Shirley Varela

10/10 would sail again

about 2 months ago
We had a great time! James and Matt were super friendly, helpful, and informative and made the whole experience very enjoyable. The view at sunset was amazing and made for a very relaxing and memorable evening that was a highlight of our trip to Destin.
Sarah Kennedy


about 7 months ago
Our Skippers were incredible. We brought on snacks and drinks and loved it! The whole Process was so easy and worth every penny! We saw dolphins and experienced the beauty of the Emerald Coast! You must book this trip!!


about 1 year ago
This was the best thing we did the week we were there. The time on the boat was relaxing and wonderful. So happy this was available at the time. Thank you to all on making this a great trip.
Bonnie DAVIS

Awesome trip!!

about 1 year ago
Loved our very educated Captain!! Great trip!! Nice to have a coast guard captain!
Candice Conner

Awesome sailing trip

about 1 year ago
We saw dolphins, turned the motor off and sailed around the gulf. The captain was amazing and was very knowledgeable about the area. He was great to talk to and we learned a lot about the surrounding area. The whole family said it was the most fun they had in Destin. I highly recommend taking the time for a relaxing sail.
James Lockwood

Intimate Sunset Cruise

about 1 year ago
The sunset and dolphin cruise provided by our wonderful Captain Taylor and his first mate was the epitomy of our Florida vacation. The sails raised and billowed over the gulf waters as we were gifted with dolphin sightings, and sunset hues of oranges and purples along the horizon, simply breathtaking. We found ourselves just outside of a sailing race and learned terms and techniquies explained patiently for the Captain. The four of us will never forget this wonderful addition to our vacation on the panhandle of Florida and Captain Taylor provided us a relaxing and skillful sail on the 32' Westsail. I am enamoured with the beauty of the ocean, coastline and inlets of the Florida panhandle and hope to return soon. I'm about the views and experience, not the partyboats, tikihuts or blasters. Looking for an intimate experience, this is the answer. I'm excited to sail with them again next year.
Lori Mofield
This website uses cookies. Please visit our Privacy Policy to learn how we use cookies and how to control your cookie settings. By clicking or navigating this site you consent to our use of cookies.