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4 Hour Private Daytime Sailing Adventure
$525
Duration4 Hrs.

Destin Sailing Charters

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2 Hour Sunset Sailing Charter

2 Hour Sunset Sailing Charter

23 ratings
Duration2 Hrs.
Take a relaxing, leisurely cruise through the emerald waters of Destin, Florida and see the local sights, feel the warm...
This was the best and most fun!!! Captain Chris and his mate made my husband’s birthday the best!!! Saw lots of dolphins—but the two sailors were what made our sail so great!!! We highly highly recommend this wonderful experience!!!
Beautiful boat, mother nature at her best, 2 first time sailors, great captain n crew.....tequila Recipe for an unforgettable night! Thanks SpaceDancer, we will be back!
Myself and three of my best friends took this wonderful sunset cruise with Captain Chris and his first mate Tighe (sp?) It could not have been better. Wanted to do it again the next night.
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$400
2 Hour Destin Sunset Cruise (for up to 6 guests)

2 Hour Destin Sunset Cruise (for up to 6 guests)

25 ratings
Duration2 Hrs.
If you are looking for a relaxing way to end your day, this Destin Sunset Cruise for 6 is the perfect match for you!...
We chose this cruise for a relaxing sunset cruise and we were not let down. Captain Bill was amazing . His hospitality and knowledge was 2nd to none. Our only regret was we did not know he offered so many things to do but we will certainly use him as our one stop place to do our activities in the future. Five stars for him for sure . You will never go wrong using him and his services ! We were so pleased !
Perfect trip, very calm and relaxing. Great for our 17th anniversary!
Captain Bill was a great host and captain. I proposed to my girlfriend, now fiancé on his sunset sailboat cruise and couldn't be happier with how it turned out. Choose Captain Bill with Southern Country Charter and you will not be disappointed!
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$325
2 Hour Destin Day Sail

2 Hour Destin Day Sail

New to TripShock
Duration2 Hrs.
Climb aboard your very own 2 Hour Destin Day Sail and enjoy some time out on the aquamarine waters of Destin, Florida....

New to TripShock

from
$300
Champagne Brunch Cruise

Champagne Brunch Cruise

New to TripShock
Duration1.5 Hrs.
Want to add little sweet and savory to your vacation? This private champagne brunch experience is perfect for those who...

New to TripShock

from
$400
Private Sailing Adventure (6 Person) Departing from the Destin Harbor

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

69 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...
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.
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.
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
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$275
Discover Destin Private 3 Hour Swim & Sail

Discover Destin Private 3 Hour Swim & Sail

41 ratings
Duration3 Hrs.
Experience Destin like never before. Get up close and personal with everything the exciting Emerald Coast has to offer...
Our family loved this sailboat experience! J.D. was an excellent host with lots of knowledge and experience. There was a pod of dolphins the very first spot that he took us. We followed the pod for about 30 minutes with 10 or so dolphins, and then found a great place to relax, swim and snorkel. There is something very peaceful about being out on the water with wind in the sails verses loud motors! We have a wide range of personalities in our family, but this was a highlight of our Florida trip.
Captain J.D. was an awesome host on the boat, we were very well taken care of. He made the experience fun & pleasurable for our entire family esp my 3 young granddaughters. He interacted with them alot which they really enjoyed. He took us to some great places & we saw tons of dolphins. It was a great time.
Captain JD was great host. We saw dolphins in the gulf and had a great swim in the bay. Very relaxing.
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$400
Destin Sunset Sailing Cruise Aboard The Daniel Webster Clements

Destin Sunset Sailing Cruise Aboard The Daniel Webster Clements

56 ratings
Duration2 Hrs.
Set sail aboard one of the very last schooners in the Destin Harbor, the Daniel Webster Clements! Enjoy aquamarine and...
We were over all very impressed with the experience! We will definitely be back!
From the time we boarded until the time we left it was amazing! The crew was knowledgeable as well as personable and the views were awesome. Will definitely book on my next visit.
Was a very pleasant and fun 2 hour sunset cruise. The crew was excellent. I have already recommended the cruise to several people.
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$45
Destin Daytime Sailing Charter

Destin Daytime Sailing Charter

15 ratings
Duration2 Hrs.
Explore the Emerald Coast in style on the 45-foot Space Dancer. This stunning sailboat features a top deck, restrooms,...
We bad a great trip!!! Very good staff. No complaints at all.
We thoroughly enjoyed our morning cruise. Captain Chris was great, very personable and knowledgeable. Our teens were able to Bluetooth their music and even got to drive. We had dolphins swim along beside us. The whole experience was relaxing and enjoyable (and easy…from booking to finish). Highly recommend! We will definitely book with East Pass Sailing the next time we are at the beach.
Captain Chris and first mate Dawson were personable, funny and always in control. We did many fun things during our Destin trip, but I quizzed my three girls on the way back and they all agreed this trip was the best part of it. It did not hurt that we had a dolphin escort back to harbor.
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$330
Destin Dolphin, Sailing & Snorkeling Charter (for up to 6 passengers)

Destin Dolphin, Sailing & Snorkeling Charter (for up to 6 passengers)

4 ratings
Duration3 Hrs.
Climb aboard your very own Destin Dolphin, Sailing & Snorkeling Charter and enjoy a day out on the sapphire-blue waters...
My family was looking for a nice day on a private catamaran dolphins watching and snorkeling. We were lucky to find Capt. Bill and https://southerncountrysailing.com It was a perfect afternoon. Capt. Bill knew right where to see a lot of dolphins and take us snorkeling. My teenage boys and nine year old girl all said, “sailing, dolphin watching and snorkeling was their favorite part of the vacation”. We’ll be back to go fishing next time!
Captain was very nice! He took us where we wanted to go. Great with kids! Had a wonderful experience!
Our Captain was fantastic and his boat was exactly what we wanted…I highly recommend this particular captain and vessel. Great family experience with one of the best !
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$400
Discover Destin Private 2 Hour Swim & Sail

Discover Destin Private 2 Hour Swim & Sail

12 ratings
Duration2 Hrs.
Experience Destin like never before. Get up close and personal with everything the exciting Emerald Coast has to offer...
Captain JD showed us a great time! Kids had fun snorkeling catching fish and crabs in their nets. Loved seeing the dolphins too. Thanks for an awesome family experience!!
Captain J.D. was a perfect host! The boat was really nice and comfortable We took the two hour trip which was a great intro. Got to see dolphins closeup and snorkeling too Definitely will do it again !
Humor. Knowledge. Southern hospitality. He made our family forget about the craziness of this new normal (covid). On the sea, private trip masks left in bags all we needed was Dolphins...wait that's right captain JD summoned not one but 4, and two kept us company. Will recommend this trip!
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$325
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