Sailing Charters

Fort Walton Beach-Okaloosa Island

Florida

Featured Sailing Charters in Fort Walton Beach-Okaloosa Island

Fort Walton Beach-Okaloosa Island has developed into a popular destination for Southern travelers over the years. When you visit Fort Walton Beach, you'll find tours, activities, and attractions that can appeal to almost anyone. Top things to do in Fort Walton Beach-Okaloosa Island include boat tours, deep-sea fishing, and dolphin cruises.

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

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

Spider Crab Charters

Upgrade your dolphin experience on this Destin Sailing & Dolphin Adventure departing from Fort Walton Beach, Florida. Soak up the sun as you sail along in a Stiletto 27 Special Edition cruiser. On this tour, you will take in the sights and the sounds of the Emerald Coast with the chance to see dolphins, sea turtles, shark, manatee, or tons of other marine wildlife. This Destin Sailing & Dolphin Adventure is a great way to get outside and on the water! Perfect for any occasion, book your charter today!

Destin Sailing & Dolphin Adventure

Upgrade your dolphin experience on this Destin Sailing & Dolphin Adventure departing from Fort Walton Beach, Florida....

Destin Sailing Adventures

Enjoy an early morning sail at the most peaceful time of day with this Destin Sunrise Sail. Enjoy a wonderful start to your day from the best possible perspective, from a catamaran. Sail across the Choctawhatchee Bay, as the sun rises over the world, for a spectacular view like no other. Bring your favorite coffee, meditation book, or yoga mat to enliven your morning routine with this private sailing charter. The sunrise sail departs about 30 minutes before dawn. Be one of the first boats on the water just after the sun rises, book yours today!

Destin Sunrise Sail

Enjoy an early morning sail at the most peaceful time of day with this Destin Sunrise Sail. Enjoy a wonderful start to...

Close the day in an extraordinary way with this Destin Sailing Sunset Sail departing from Fort Walton Beach, Florida. Get out on the water and see a sunset from a catamaran. You will end your day with a whole new appreciation for the world around you. Sit back, relax, and just kick your shoes off for a little while as you take in the beauty of the Destin Harbor and Choctawhatchee Bay. Don't miss out, book your charter today!

Destin Sailing Sunset Sail

Close the day in an extraordinary way with this Destin Sailing Sunset Sail departing from Fort Walton Beach, Florida....

Other than the drive from 30A, we had a great time with Kip and his cat.

Great sunset sail

I can’t say enough great things about this boat ride. The sailboat/Catamaran was amazing. If you haven’t been on one, do it! It was so serene and peaceful out! We even got to see dolphins. Kip and Elizabeth were amazing too! Definitely would recommend! I went with a group of girlfriends and had so many good picture ops! It would also be great for a couple to take a romantic sail ride around the bay! A++++

GREAT ENDING TO OUR TRIP!

Captain and mate were very friendly . Weather was perfect. Got to see dolphins

Sunset cruise

If you are looking for the perfect place to propose or to celebrate a special anniversary, then look no further. Sail atop the gorgeous water with your significant other and enjoy this peaceful and magical outing. The natural beauty of the landscape around you is the perfect backdrop to pop the big question. Spend quality time with your other half without any distractions as you celebrate your love. Create memories to take with you for the rest of your life, book your Proposal or Anniversary Sail today!

Proposal OR Anniversary Sail

If you are looking for the perfect place to propose or to celebrate a special anniversary, then look no further. Sail...

Join in on a catamaran cruise to remember on this Santa Rosa Island Sailing Adventure. Glide through the Santa Rosa Sound and tour the Spoil Islands, created from dredging the "Narrows" for the Intracoastal Waterway. Get the chance to gaze up at the sea birds and look for other wildlife that inhabit the area. Sail, swim, relax, and snack as you cruise atop the water with family and friends. Win the day, book your Santa Rosa Sailing Charter now!

Santa Rosa Island Sailing Adventure

Join in on a catamaran cruise to remember on this Santa Rosa Island Sailing Adventure. Glide through the Santa Rosa...

Get out on the water for an adventure and experience some of the best spots that Destin and the Choctawhatchee Bay have to offer. On this Destin Sailing & Snorkel Adventure, you will have the opportunity to see some amazing ocean life like sea horses, dolphins, stingrays, crabs, fish, and more. This experience will take you to see the unknown underwater world of sea life large and small. Book your tickets today!

Destin Sailing & Snorkel Adventure

Get out on the water for an adventure and experience some of the best spots that Destin and the Choctawhatchee Bay have...

Me & my family had so much fun! It was our very first time on a sailboat & it was very relaxing! Captain Kip was very nice & did  good making sure we had a good time!

Had a Blast!

Loved everything about the trip, Kip and Elizabeth made it fun. The goal of the trip was to relax and see lots of marine life, and goal accomplished! We sailed next to a large pod of manatees, without disturbing them, so we got to witness them in their natural behavior. It was really a meaningful and a wonderful surprise! We also saw much more snorkeling than we thought we would and Kip knew the good spots! Will definitely seek out this team again on our next trip.

More than we expected

Crab Island is THE spot everyone wants to see when visiting Destin, Florida! Close your eyes and imagine traveling over a beautifully engineered bridge with the most clear blues and greens beneath you. On this Crab Island Destin Sailing Adventure, you will be front and center to the magic. Cruise around, relax, enjoy lunch, and a float. Discover the beauty of the Emerald Coast as you soak up the sun. Book your Crab Island Destin Sailing Adventure today!

Crab Island Destin Sailing Adventure

Crab Island is THE spot everyone wants to see when visiting Destin, Florida! Close your eyes and imagine traveling over...

Destin

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!

Excellent

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

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.

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

Climb aboard an authentic sailing cutter for an experience to remember on this Private Sunset Sailing Cruise 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. Take in the sky as it erupts in color as you witness the breathtaking sunset. 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 Sunset Sailing Cruise

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

Cat. Matt was great and we enjoyed every minute of it!  We will certainly do it again.

Climb aboard an authentic sailing cutter for an experience to remember on this Private Swim and sail adventure 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 Swim & Sail Adventure

Climb aboard an authentic sailing cutter for an experience to remember on this Private Swim and sail adventure in...

Hop aboard your very own 2 Hour Destin Day Sail and enjoy some time out on the aquamarine waters of Destin, Florida. Cruise around on a Stiletto 30-foot catamaran and see the area like never before with the wind steering your path. Take in the sights of marine life and maybe even see a dolphin or two. Enjoy the sounds of the sea birds and feel the wind in your hair. Perfect for families, celebrations, or romantic engagements. Don't miss out, book your sailing charter today!

2 Hour Destin Day Sail

Hop aboard your very own 2 Hour Destin Day Sail and enjoy some time out on the aquamarine waters of Destin, Florida....

Our cruise was fantastic.  Booked a private cruise so we could enjoy the quiet and did we ever.  Captain Bill was superb—knowledgeable, informative and yet let us have our time.  We will definitely be booking with him again!

Catamaran daytime cruise

The captain is very experienced.  Our family of 4 had a very relaxing and enjoyable trip!

Great day of sailing!

We had a great time with Capt Bill and Southern Country Charters. Sailed around Destin/Ft Walton Bay, saw dolphins and seabirds. Was a wonderful time.

Sail cruise

Plan an activity everyone is sure to enjoy as you end your day the right way on this Destin Harbor Fireworks Sail. Watch the explosions in the sky as you say goodbye to another beautiful beach day on a Stiletto 27 Special Edition cruiser/racer. Glide across the water and admire the colors dancing in the sky. Your family and friends will have a blast, don't miss out, book yours today!

Destin Harbor Fireworks Sail

Plan an activity everyone is sure to enjoy as you end your day the right way on this Destin Harbor Fireworks Sail. Watch...

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

Vitamin Sea Sailing Charters

Don't miss a stunning cotton candy sunset on the water in Destin, Florida. 
Set sail on a 35 foot catamaran cruise and enjoy the fresh salt air around you as you watch the sun disappear into the endless horizon. Let your captain take your worries away as you relax, enjoy the sunset, and watch dolphins play in the surf! Don't miss a gorgeous way to say goodbye to the day on this Private Sunset Sailing Cruise from Destin!

Private Destin Sunset Sailing Cruise

Don't miss a stunning cotton candy sunset on the water in Destin, Florida. ...

We had a great time on the Sailing Moby.  Would definitely recommend and do again.

Good times!

My 12 and 15-year-old sons and I unanimously agree that our sunset Sailing Moby excursion was our favorite Destin activity. Tracy and Ladd were so welcoming and accommodating, and their boat is lovely. This activity was worth every penny!

Favorite Destin Activity!

Had a great time!  Beautiful ride!
Skipper and First Mate were great!

Wonderful!

Sailing Moby Adventures

Explore the Emerald Coast in style on 45-foot Beneteau Sailboat in Destin, Florida. Enjoy an authentic sailing experience from the deck aboard your own private sailing yacht. Sit back and feel the warm Destin breeze, see dolphins play in the water, and unwind as you sip on your favorite beverage. Don't miss out on the beautiful sights of the Destin Harbor, book your Destin Gulf Sailing Adventure today!

Destin Gulf Sailing Adventure

Explore the Emerald Coast in style on 45-foot Beneteau Sailboat in Destin, Florida. Enjoy an authentic sailing...

My family had the pleasure of spending a summer morning sailing with Chris and Matt. They were incredibly hospitable, knowledgeable and engaging. Highly recommend East Pass Sailing!

First Class!

Captain Chris and Matt were excellent. The boat was perfect. They have great knowledge of the area and a very experienced sailors. My two sons and I had a blast and would like to charter the boat for a couple of days the next time.

Sailing with sons

This was everything we expected it to be. Dakota and Christian were amazing and very professional! We definitely will be booking again!

Excellent experience

East Pass Sailing Company

Experience Destin like never before. Get up close and personal with everything the exciting Emerald Coast has to offer with this Discover Destin Sail. Set out on this 30' Stiletto catamaran and soak up the rays and the sights around you as you cruise at your own pace. There are so many intriguing places to visit along the coastal beaches, places that cannot be reached by car. Nestled in these hidden treasures are places to explore and get an up-close look at fascinating aquatic life. Experience the amazing marine life and beautiful water. Don't miss the boat! Book today!

Discover Destin Private 2 Hour Sail

Experience Destin like never before. Get up close and personal with everything the exciting Emerald Coast has to offer...

JD was the best. We had so much fun seeing Jellyfish and swimming around. It was a beautiful way to take in the coast. Highly recommend. He even takes some pictures of your group and shares them with you after!

So much fun!

So glad we booked this excursion!  Captain JD was funny and fabulous.  The sailing was excellent and we saw sharks, dolphins and a sea turtle.  The whole family loved it and I would rebook and recommend to others!

Fabulous Sailing

Relaxing ride along the gulf. Dolphin sitings were AMAZING!! J.D. was extremely informational & let us enjoy the ride!!

Dolphin Extravaganza

Set sail on this Gulf Sunset Sailing Cruise in Destin, Florida. Relax on the top deck of this 45-foot Beneteau Sailing Yacht as you feel the Gulf breeze in your hair. Cruise the emerald water of the Gulf Coast as you take in the natural beauty around. Keep an eye out for the playful dolphins swimming beneath the water and jumping above the waves. Witness the sun set beyond the horizon as the sky erupts in an array of colors. Create lifelong memories with family and friends and experience a sunset like never before! Book your Destin Gulf Sunset Sailing Cruise today!

Destin Gulf Sunset Sailing Cruise

Set sail on this Gulf Sunset Sailing Cruise in Destin, Florida. Relax on the top deck of this 45-foot Beneteau Sailing...

Beautiful evening!
Captain Matt and Captain Matt were very professional as a team. The gentleman were very friendly and enjoyable. Destin history including the panhandle would have been interesting to learn.