Name: Private Catamaran Sailing Charter from Choctawhatchee Bay
Brand: TripShock
SKU: 1606
Price: 270 USD
Availability: InStock
Rating: 4.8421 (133 reviews)

Private Charters

Sailing

Sailing Charters

Are you ready to sail away and enjoy the stunning waters around the Emerald Coast? If so, then here is your chance to get out on the Intracoastal Waterway and Choctawhatchee Bay and cruise by those mesmerizing emeralds and aquamarines. This customizable chartered trip allows you to choose between dolphin watching, a leisurely sail, or a picturesque sunset cruise. Whatever trip you choose, the salty air and warm breezes are sure to melt away your worries. Book your charter today!

Private Catamaran Sailing Charter from Choctawhatchee Bay

How to Redeem: Show the confirmation details from your mobile device for entry. Please have a valid ID with you to confirm your order if needed.
Parking: Free parking is available at 100 Old Ferry Rd Shalimar, FL 32579. 
Departure Details: This charter departs from Two George's Marina located at 100 Old Ferry Rd Shalimar, FL 32579. Please arrive at least 30 minutes before departure to receive a safety briefing. Boat departs on time. Please call to confirm departure details at least 24 hours prior to arrival. Reservations booked less than 24 hours prior to arrival are not guaranteed until confirmed by the vendor. Customers may depart as early as 8:00AM and as late as 6:00PM (seasonal). The time chosen is a request, the captain will call to confirm specific times. Expect a call from Capt Karl to discuss any details or questions you may have. If you have not heard from the captain and it is 6 hours before your departure time, kindly give him a call at 850-830-3427.
Gratuities: Although not required, it is appreciated and encouraged to tip your captain. 20% is the standard.

100 Old Ferry Rd

133 Reviews of Private Catamaran Sailing Charter from Choctawhatchee Bay - TripShock!

Private Catamaran Sailing Charter from Choctawhatchee Bay

Customer must cancel 24 hours prior to the arrival date in order to receive a full refund. Cancellations received less than 24 hours prior to the arrival date will not be eligible for a refund. No shows will not be refunded.

Cancel or Reschedule 24 hours prior to arrival for FREE

Are you ready to sail away and enjoy the stunning waters around the Emerald Coast? If so, then here is your chance to...

We had us a great time out cruising around the bay. Got to see dolphins along with great views. 

Worth the money and drive out.

Sailing!

The whole experience was amazing!!  Captain Karl and Doddy are very friendly people and made sure all of us had a great experience.

A "must do" for local and visitors alike

Wonderful evening on the sailboat. Capt. Carl and his first mate, Dody were amazing. He called prior to the cruise to confirm our reservation and move the time around so that we got the most out of our sunset cruise. Enjoyed every minute of it. Would definitely do it again.

Fabulous Time

We had a wonderful time with captain Carl and Dodie. They were very hospitable and made our trip great. We would recommend this to our friends and family!

Sailing the bay

Omg! It was the best one yet! The husband and wife was literally amazing all around and the boat was B*E*A*U*T*I*F*U*L!! I highly recommend them!

Sunset Cruise

The trip was great. The captain was fun and very knowledgeable. I’d rent through them again.

Sailing trip was great

Captain Karl and his wife (first mate) Dorothy were nothing short of amazing! As soon as we got onto the catamaran, they had seats/ cushions laid out on the front of the boat for us! Super considerate and accommodating to make the experience over the top. Completely worth it and I consider it a must have!! Very sweet people.

Amazing experience! Would do it again all over!

Captain and his wife are so kind! It is a great experience to have a private sailing experience. It was our first time going sailing and we enjoyed the ride. It was a record hot day, but while sailing the breeze felt great!

Fantastic Experience!

Great adventure for the whole family!  The Captain and his first mate are well experienced and we enjoyed getting to know them…good people!!

Capt’n Karl & Dodie

We had a very relaxing 3 hour sail.  Felt welcome and comfortable on the boat.  Carl and Dodi were great hosts.  Enjoyed the time with our family. Highly recommend!

Relaxing afternoon sailing the bay!

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Say adios to another beautiful day as you hop aboard this Sunset Dolphin Cruise. Let your experienced captain guide you as you watch the sunset shimmer on the water. Take in the sights and sounds of the evening as you cruise the Harbor, Bay, or let the captain decide where he thinks provides the best view! Sit back and relax with this private dolphin watching experience. Book yours now!

Sunset Dolphin Cruise (for up to 6 guests)

Say adios to another beautiful day as you hop aboard this Sunset Dolphin Cruise. Let your experienced captain guide you...

What a wonderful experience!!  Saw lots of dolphins!!  Chip was an excellent captain!!  Highly recommend doing the private boat tour, get closer to the water and I believe see so much more!

Sunset dolphin excursion

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Whether you are looking to learn a new water activity or simply want to relax and escape from the stress of everyday life, this charter is for you! Let your captain plan the perfect day on the water. This trip is perfect for a family with young kids who only want a short excursion or for those looking for a little more time out on the water. You can choose to cruise or choose two activities ranging from wakeboarding, kneeboarding, or tubing. This is your chance to get out on the water for a day of fun. Book your charter now!

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Chip was great, he took us tubing in a place where there was no traffic ensuring our safety. Told us about sites and history of places we passed on the way. Will definitely be doing again next year.

Awesome Time

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Get out on the water for the perfect sunset view of Destin Harbor. Grab those nearest and dearest and experience a surreal way to end your day. Float around and see the sights, watch the boats go in and out of the harbor, and relax knowing your experienced captain has your back! Watch dolphins frolicking, hear the hustle and bustle of HarborWalk Village, and even stop by one of the area's delicious restaurants for a quick bite to go or a beer. It's your cruise, do what you like! Book your Destin Harbor Private Sunset Cruise today!

Destin Harbor Private Sunset Cruise

Get out on the water for the perfect sunset view of Destin Harbor. Grab those nearest and dearest and experience a...

By far Capt Barry exceeded our expectations, highly recommended him to anyone as he went above and beyond for us during our trip. His business is Executive Saltwater Charters.

Boat trip sight seeing

Executive Saltwater Charters

My wife and I celebrated our anniversary with a sunset cruise ran by Executive Saltwater Charters. It was an amazing experience. Captain Barry and Connor were great. Everything about the experience was top class. Thanks again to Captain Barry and Connor for making it such a memorable experience.

Wonderful experience

Enjoy a private sunset cruise to make lasting memories during the season. This cruise is perfect for a small family gathering or even a nice romantic evening out on the water. A certified captain will guide you through the Choctawhatchee Bay while the sun is setting over HarborWalk Village on the Destin Harbor. Book your Private Pontoon Dolphin Sunset Cruise from Fort Walton Beach for up to 6 guests today!

Private Pontoon Dolphin Sunset Cruise from Fort Walton Beach

Enjoy a private sunset cruise to make lasting memories during the season. This cruise is perfect for a small family...

Excellent trip with Derek.  Up close encounter with the dolphins.  Bluetooth connection allowed us to play our own music which was great.  Beautiful sunset too!

Wonderful experience. Great friendly knowledgeable captain (Derek).

Captain Derek was so accommodating and great fun on our trip! He had great stories to share about our surroundings. We had such a pleasant ride and enjoyed a beautiful sunset and dolphin sighting in the bay! We were also able to take our small pup on this boat charter which not many other charters allowed. Would definitely charter with Power Up Watersports again and will definitely request Derek to captain for us! Definitely a memorable experience!

Awesome excursion!

Power Up Watersports

Destin

Join your captain on this Private Destin Sunset Cruise and catch the sun fading into the horizon. Hop aboard the Key Cat, a 26-foot power catamaran for a twilight cruise to remember. Ease into the sunset in search of dolphins and other marine life. Perfect for families, couples, or celebrations of any kind, this is a great option for smaller groups. Don't miss your chance to see the sun sink in a glorious display, book your Private Destin Sunset Cruise today!

Private Destin Sunset Cruise

Join your captain on this Private Destin Sunset Cruise and catch the sun fading into the horizon. Hop aboard the Key...

Chandler was great, we saw dolphins performing, mansions on the harbor and a spectacular sunset. Highly recommend!

Great Time

We booked a small, private cruise to watch the sunset and hopefully see dolphins.  We might have caught a glimpse of a couple of dolphin fins, but the cruise around was excellent.  Captain Chandler was knowledgeable and friendly.  We did not know we could go prepared to get in the water.  there were only 4 of us plus the captain, and we would all recommend it.

Amazing Cruise around the Harbor

This is well worth the money!  I promise that you won't regret this!!

Best Sunset Cruise Ever!!

Destin Aquatic Adventures

Immerse yourself in the captivating beauty of Crab Island with a licensed captain leading the way. Relax and unwind on a 15-foot lily pad, surrounded by water toys that add to the excitement. Feel the rhythm of your favorite tunes resonating through the air as the complimentary Bluetooth speaker sets the perfect atmosphere. Prepare to be amazed as you navigate through Destin Harbor, East Pass, Crab Island, and Choctawhatchee Bay, all while enjoying a small dolphin tour that brings you face-to-face with these magnificent creatures in their natural habitat. Take an all-inclusive journey where the star of the show is the enchanting Crab Island, leaving you with memories that will last a lifetime. Book today!

Private Crab Island Charter with Xtreme H20

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Had such a good time we booked another slot out. Highly recommend!

Awesome!

We loved our Captain TaYlor he is the best. The pontoon was nice just wish the speakers was louder other then that we had fun.

We went to crab island with captain. John. He was outstanding!

Crab Island

Xtreme H20

Hop aboard the famous pink pontoon for a memorable experience cruising through the water of Destin, Florida as you witness a stunning Florida sunset. Your captain will take you and your family to Destin Harbor or to the spoil islands of the Santa Rosa Sound, where wild dolphins are frequently spotted. Enjoy the excitement of seeing dolphins in their natural habitat. Don't miss your chance to see the spectacular colors dance in the clouds as another summer day ends. Book your Destin Dolphin Sunset Cruise now!

Destin Dolphin Sunset Cruise

Hop aboard the famous pink pontoon for a memorable experience cruising through the water of Destin, Florida as you...

Had a great time!! Beautiful night for a cruise and we saw dolphins! Would highly recommend

Sunset cruise

We had a wonderful trip around the harbor. We got to see a couple of dolphins and got some great family photos in front of the lights at Harbor Walk. 
Jennie and Michael did a great job getting us in and out of the boat with our Parents which needed some extra assistance. 
Would definitely recommend them.

Jennie Lou service was excellent

What a great experience!  Michael, the captain of our pontoon, and his “first mate” Jennifer, took such good care of our entire family during our recent Dolphin Sunset Cruise.  They were knowledgeable, kind and oh-so friendly.  It actually felt as if we were touring the area with friends.  We had a wonderful time.

So much fun!

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Captain Brandon was very professional and friendly. Highly recommend this trip to anyone visiting Destin.

Great excursion

Always a nice , relaxing day on the sandbar , my captain John Rayfield was the best highly recommended..

Destin for R&R

Tiki Cruising with Josh

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If you are looking for a uniquely Destin experience, then this is the perfect activity. This Sunset Tiki Tour is ideal for those looking for a laid-back cruise like no other. Bring your favorite snacks and beverages and relax as you take a cruise through the aquamarine waters of Destin Harbor. So climb aboard and take a seat at the tiki bar that floats and witness a breathtaking sunset to remember. Book your Destin Harbor Sunset Tiki Cruise today!

Harbor Sunset Tour by The Original Cruisin’ Tikis

If you are looking for a uniquely Destin experience, then this is the perfect activity. This Sunset Tiki Tour is ideal...

We had a fabulous time. CAPTAIN BRIAN was very nice and took us to find the dolphins. Sunset was amazing on this evening.  I Cn't wait to make it back for day trip. Highly recommend this cruise.

Good company that takes care of their customers. Our booking got canceled because of bad weather and they were prompt to call us and let us know. 
Thank y’all!

5 Stars

Our captain was Brandon and he was great. 
 The sunset was gorgeous and the dolphins beautiful.

Tiki boats

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!

6 Passenger Private Day Time Sailing Cruise

Climb aboard an authentic sailing cutter for an experience to remember on this Private Sailing Tour in Destin, Florida....

James and Matthew were awesome and we had a wonderful 3 hour afternoon cruise. They took us out into the Gulf waters and the swells were lovely. It was all very enjoyable and I highly recommend them! The boat was beautiful!

Lovely afternoon sail

A true sailing experience.     Very different from pontoon boat.    Sailed into gulf.   Got splashed by water.     Different from any other experience.

Excellent

Captain James was great. We loved the 2 hour sunset sail. Parking in the Destin harbor was definitely not easy and cost $20.

Good

Fair Winds Sailing Co

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!

Private Destin Catamaran Sunset Cruise

If you are looking for a beautiful way to end your day, this Destin Sunset Cruise is the perfect match for you! This...

Captain Bill was great and made us feel right at home. Our trip was relaxing and beautiful - the best sunset activity before dinner!

My friends and I had a wonderful time on the sunset cruise. We especially enjoyed lounging on the bean bag chairs on the trampoline part of the catamaran. Captain Bill was very friendly and accommodating. We were even able to see several dolphins which made our night! Definitely recommend!

Even before the cruise Captain Bill communicated with us to help us be prepared.  Our cruise was comfortable and he was friendly and very knowledgeable about the area.  The dolphins were putting on a show for sunset and Captain Bill stuck with them.  We had a great time and would highly recommend!!!

PERFECT!!!

Southern Country Sailing

Experience a full range of fun in Destin, Florida with a Crab Island and Dolphin Adventure. Cruise to spot playful dolphins, stingrays, crabs, turtles, and more! Anchor up at Crab Island for some sun-soaked excitement in the emerald-green water. This captained pontoon boat comes fully equipped with ice chests, paddleboards, kayaks, a Bluetooth speaker, and more, ensuring you and your family and friends can enjoy everything Destin has to offer. Book today!

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FunDestin Adventures

Relax in luxury and enjoy an epic day of carefree cruising around Destin, Florida aboard your very own captained pontoon boat charter. Experience the bustling Destin Harbor and enjoy ample, comfortable seating as well as dual-decks, expert navigation, and so much more! Cool off with a splash using the onboard slide or hang out on the lily pad and chill to the max in the water. The sky's the limit with this Private Chartered Pontoon with Slide for up to 6 Guests. Book yours today!

Private Chartered Pontoon with Slide for up to 6 Guests

Relax in luxury and enjoy an epic day of carefree cruising around Destin, Florida aboard your very own captained pontoon...

Was amazing!!!! Can’t wait to do it again!!

We had the most fantastic time!!! The entire crew was absolutely wonderful and Captain Jesse made sure everyone had a super great time! Would HIGHLY recommend Destin Pontoon Charters!!!

We had a great day at Crab Island.  Jeff was an awesome captain.  My family of 6 had a really nice day on the water.  It was by far the best day of our Florida vacation.

Awesome Day!

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Wonderful time,  we made sure to book around high tide and the water was beautiful. Our guide Luke was the best

Our Captain did a fantastic job of giving us the experience we hoped for! Next time we are in Destin we will book our excursions through Tripshock

District Sales Manager

Destin Parasailing

Discover the relaxing beauty of an Emerald Coast sunset while sailing along on the gentle breeze. This Private Gulf of Mexico Sunset Sail offers guests a breathtakingly beautiful cruise around Destin and is the perfect way to spend your vacation. Cruise the waters of the Choctawhatchee Bay, Destin Harbor and Gulf and relax as you cast the what-ifs away. Witness dolphins jumping near and far and an unbeatable cotton candy sky as you enjoy this unique way to spend time with the love of your life or with your crew. A sunset sail on the waters off Destin is something you'll never forget. So, hop on the catamaran and sail off into the sunset today with this Private Gulf of Mexico Sunset Sail!!

Private Gulf of Mexico Sunset Sail

Discover the relaxing beauty of an Emerald Coast sunset while sailing along on the gentle breeze. This Private Gulf of...

JD was awesome and the sail was our favorite part of vacation! JD went above and beyond to make sure we had a great time and took us all around to see lots of dolphins playing, he even let the kids help drive the boat which they loved! Sunset was beautiful, we will definitely book again!  Thanks, from OHIO!

Sunset sail

JD was so great and went above and beyond for our trip. HIGHLY recommend!!!

Great Trip

We really enjoyed our sunset cruise! Beautiful

Beautiful sun set cruise

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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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We purchased VIP seating to see Noah and Heather Wills Maximum Magic Show at the Theater at the Harbor Walk. It DID NOT DISAPPOINT. We sat three feet from the stage and his “magic” was incredible!!! We laughed and were in awe. He engaged the audience and has an huge personality that is captivating. Our favorite trick was the Grand Finale. I’m still stumped. Lol.

Maximum Magic was AWESOME!!

Captain Bill was everything she more. Gave us local  insights both land and sea and tracked fish dolphins for us. We had an incredible time. We WILL travel with him again when we come back

Dolphin Trip

If you are looking for a relaxing day on the water where you can throw your worries to the wind, then this is the activity for you. This Private Captained Cruise is the perfect way to get out on the water and have some fun with your crew. Hang out, swim, float around, and just relax. Jump aboard and let the fun begin on this good time on the water. Book your Private & Captained Cruise for up to 6 guests today!

Private & Captained Pontoon Cruise for up to 6 guests

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Trent was a great captain. Very knowledgeable and friendly and took us to all of the great spots.

It was really nice and Trent was the coolest we even got to see dolphins I would highly recommend the platoon with a captain

We had a great time on our two hour bout tour with Captain Billy. He made it a lot of fun for my 7 year old son. We got to cruise around and see dolphins, a shark, other marine life, and check out crab island. We can’t wait to come back and try the banana boat rides.

Enjoyed our excellent boat tour!

Mobile Sports Banana Boat Rides

Cast your worries aside and immerse yourself in all-day fun with this All-Inclusive Captained Pontoon Charter. Paddleboard and explore to your heart's content or just relax in luxury as you experience beautiful Destin Harbor from the lower deck of the pontoon. Make a splash in the gorgeous water around you, swim around, or lounge on an inflatable. Regardless of what you choose on this all-inclusive day, you will enjoy yourself as you soak up the warm Florida sun! Reserve this charter today!

All-Inclusive Captained Pontoon Charter in Destin

Cast your worries aside and immerse yourself in all-day fun with this All-Inclusive Captained Pontoon Charter....

We celebrated my daughter’s bachelorette party on the pontoon boat at Crab Island.  We had a great time.  The captain and mate made sure we had everything we needed. Can’t wait to go back to Destin and charter other day in the
Pontoon at Crab Island

Pontoon boat trip

Absolutely Awesome!

Best experience in destin

Florida

Featured Fort Walton Beach-Okaloosa Island Activities

- Activity: 6 Passenger Private Catamaran Sailing Charter in Choctawhatchee Bay
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- Children: None


We loved it so much, It was beautiful Sunset

- Activity: Private Catamaran Sailing Charter in the Choctawhatchee Bay
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The Trip Was Surreal

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Great Music and Beautiful Dolphins 

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Private Catamaran Sailing Charter from Choctawhatchee Bay

Private Catamaran Sailing Charter from Choctawhatchee Bay

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