Destin, FL > Sailing Charters
05/11/2021 ~ 05/16/2021
Talk to us
We are currently closed.
Please call us during normal business hours or book online 24/7.

We are open 7am - 7pm
CST Monday-Sunday
4 Hour Private Daytime Sailing Adventure
$525
Duration4 Hrs.

Destin Sailing Charters

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

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

1 rating
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!...

New to TripShock

from
$320
Destin Sailing Cruise Aboard The Daniel Webster Clements

Destin Sailing Cruise Aboard The Daniel Webster Clements

243 ratings
Duration1.5 Hrs.
SPECIAL OFFER
Set sail aboard one of the very last schooners in the Destin Harbor, the Daniel Webster Clements! Enjoy aquamarine and...
It was an awesome cruise around the Destin harbor. Crew was excellent and they were very friendly and took time to chat with everyone on board. The cruise was very relaxing. Our excursion had about 25 ppl ... it was perfect and not at all crowded. We were offered a variety of drinks throughout the cruise. They took a photo as we boarded and we had the option to buy at end . It was reasonably priced so we bought it! We were able to see many dolphin. We will definitely do this again!
So glad I booked this sailboat excursion. It was absolutely wonderful. The Captain & his assistant Bailey were amazing!! The amount of time on the water was perfect & the music and drinks made it very enjoyable.Seeing the beautiful dolphins was the highlight of our cruise!! Definitely coming back in the summer with the kiddos.
I had a wonderful time on the schooner excursion. I enjoyed hearing about the history of the schooner and watching the crew working with the sails, etc. It was an authentic experience. The men on the ship did their jobs, but also are very personable with the passengers. I have recommended it to several people already.
from
$30
2 Hour Destin Fireworks Sailing Charter (for up to 6 passengers)

2 Hour Destin Fireworks Sailing Charter (for up to 6 passengers)

New to TripShock
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!...

New to TripShock

from
$400
Discover Destin Private 3 Hour Swim & Sail

Discover Destin Private 3 Hour Swim & Sail

27 ratings
Duration3 Hrs.
Experience Destin like never before. Get up close and personal with everything the exciting Emerald Coast has to offer...
The three hour private sail is exactly what we needed to end our vacation. The captain, JD, was very personable and laid back. The sail was relaxing with beautiful views of the aqua blue gulf waters along with dolphins. We sailed and snorkeled which were our main goals. JD let our daughter steer the boat! We wish we could've booked the evening sail also. Will book again when we go back. Thanks JD!
Since I was little I have wanted to go sailing. Captain JD & Vitamin Sea Sailing made that dream come true today. My sister and I had a blast! We saw dolphins and a shark and enjoyed the relaxation of being on the water, riding the waves, and the refreshing gulf breeze. JD is an awesome Captain, super fun, knowledgeable, attended to our needs, and is an overall caring and wholehearted person. He is super chill and made the experience of booking, preparing for the sailing adventure, finding the marina, and more seamless, so my sister and I could just truly enjoy the experience. So grateful for Captain JD & Vitamin Sea sailing :)
We sailed with the Dolphins! This was one of the best sailing trips we have experienced. The Vitamin Sea is very comfortable and Captain JD is super fun. It is a must do when visiting Destin!
from
$375
Private Sailing Adventure (6 Person) Departing from the Destin Harbor

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

44 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...
So fun! We had a great time and Captain Max was great!
Great trip with our great captain Max!
Our trip was awesome. The service level provided exceeded our expectations. We would certainly recommend this to anyone wanting to enjoy Destin. Thank you for making our trip memorable.
from
$275
Destin Sunset Sailing Cruise Aboard The Daniel Webster Clements

Destin Sunset Sailing Cruise Aboard The Daniel Webster Clements

13 ratings
Duration2 Hrs.
SPECIAL OFFER
Set sail aboard one of the very last schooners in the Destin Harbor, the Daniel Webster Clements! Enjoy aquamarine and...
Loved the cruise! We enjoyed the music selection the Captain Taylor and crew chose. That can be a problem sometimes and we were presently surprised with this aspect. The crew was personable able and responsive. They told stories and shared knowledge. We saw some dolphins jumping in the waves which was wonderful. We'd recommend to anyone.
LOVED IT! The crew was very friendly and courteous. Thanks for the great time!
What a beautiful sunset cruise! The crew was excellent in watching and attending to every detail, especially safety. Two of our party are prone to seasickness, but the captain steered clear anytime waves became an issue. Our whole party of six loved sailing on the beautiful boat under its gorgeous sails!
from
$42
6 Passenger Private Catamaran Sailing Charter in Choctawhatchee Bay

6 Passenger Private Catamaran Sailing Charter in Choctawhatchee Bay

76 ratings
Sail away and enjoy the area's stunning emerald green waters. Customizable...
When Trip, fiancé, was younger, he passionately loved to sail his tiny Hobie cat sail boat on the Chesapeake Bay in Mathews County. I surprised him today with a catamaran sail boat cruise on the Choctaw Hatchee Bay near Destin, Florida, hoping to fill his brain with awesome memories. Captain Karl and his wife Dorothy did not disappoint! The sail was incredible and you can tell they are extremely experienced and so Daggone friendly. We had the time of our lives and they made it extremely romantic for us right down to the perfect music. We would highly recommend these to love birds (captain Karl and his wife). ♥️♥️. Go get ya some! You will not be disappointed with their beautiful boat and wonderful charm.
Had an excellent time on the Catamaran Bay cruise at sunset. Captain & crew were engaging and well equipped for an enjoyable time in the bay.
It was an amazing trip. The captain called to change the time to make sure we got to see the sunset. He also wanted to make sure we didn't have any questions. I got this for my anniversary and it was the most beautiful and peaceful sail. We got to take the most amazing pictures. The only downfall is the weather was a bit chilly but I brought a blanket so no big deal. Thanks again it was wonderful.
from
$250
Destin Dolphin & Sailing Charter (for up to 6 passengers)

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

New to TripShock
Duration3 Hrs.
Climb aboard your very own Destin Dolphin & Sailing Charter and enjoy a day out on the sapphire-blue waters of Destin,...

New to TripShock

from
$425
Discover Destin Private 2 Hour Swim & Sail

Discover Destin Private 2 Hour Swim & Sail

4 ratings
Duration2 Hrs.
Experience Destin like never before. Get up close and personal with everything the exciting Emerald Coast has to offer...
I booked the private 2 hour tour with Captain JD. The sailing tour of the harbor was relaxing and unhurried, perfect for my 85 year old mother. Highly recommend for families, couples any age. Txs again
We enjoyed this private sailing charter. So cool to be in a sail boat. Relaxing and captain JD was awesome.
from
$300
Private Sunset Sailing Cruise from Destin

Private Sunset Sailing Cruise from Destin

14 ratings
Duration2 Hrs.
Don't miss a stunning cotton candy sunset on the water in Destin, Florida. ...
Excellent cruise with a great family! Thank you!
They were awesome! It was a beautiful sail and they were very attentive and informative.
Tracy and Lad are the nicest and most accommodating people! They are very knowledgeable about the area as well! They answered all the questions I had about the area. We took the sunset cruise and the sky that night definitely did not disappoint! Everything about the cruise was perfect! I would definitely recommend and would do it again on future visits!
from
$325
4 Hour Private Daytime Sailing Adventure
Spend a half day among the wind and the waves in the heart of Destin, Florida. This 4-Hour Private Daytime Sailing...
Swim & Sail Aboard the Daniel Webster Clements
The Daniel Webster Clements is a great way to start the day in Destin, Florida! This is a 3 hour excursion where you can...
Private Destin Dolphin, Sailing & Snorkel Charter (for up to 6 guests)
Don't miss an exciting day on the water in Destin, Florida. Set sail on a 35 foot catamaran cruise and enjoy the fresh...