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Smile n' wave.

Sailing Charter & Tours in Destin, Florida

Smile N' Wave Sailing Adventures Fleet

Now booking charters for our trimaran "Nice Tri"

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Join Captain Pam for a day sailing charter aboard our new Trimaran, Nice Tri. All her day tours offer the ability to swim, snorkel, look for dolphins or watch the sunset on the Gulf of Mexico in Destin, Florida. You can also choose to visit Crab Island. The place Captain Pam likes to snorkel is called the Grass Flats. It is a shallow area where you can disembark the Sailing Trimaran and be waist-deep in water to hunt for treasures. While snorkeling, some things you may find include seashells, hermit crabs, fish, shrimp, and occasional seahorse. Captain Pam allows you to take a hermit crab of your choice to the boat for a race before releasing it.

Snorkeling Tours

Snorkeling Adventures are fun for all ages, but we have a special treat for the older kids and grownups with the conditions right to travel into the Gulf of Mexico. Captain Pam loves to bring you sand dollar hunting. We get sand dollars on the second sandbar, where you can dive from ten to fifteen feet. You can keep two sand dollars per person. Captain Pam suggests a four-hour cruise so you will have plenty of time to explore.

See The Dolphins

The Gulf of Mexico hosts some pretty friendly Aquatic Mammals, like the Tursiops Truncatus or Bottle Nose Dolphin. These happy mammals are some of our best friends, and they love meeting new people. We have thirty-five to fifty local dolphins who love to interact with sailboats and passengers, and we get to see them on seventy-five percent of our cruises. So when we are fortunate enough to interact with them, they will follow as we sail along.

Party on Crab Island

The cool thing about Crab Island is it isn't an island. It's a sandbar on the bayside of the Destin pass where locals and tourists alike come to anchor their boats, party, swim, or walk to one of the floating restaurant shacks to grab a drink or a bite to eat. You are welcome to bring your cooler with drinks and snacks, no glass, please. Crab Island is fun for all ages; it has ice cream boats, shore dash, and Reef Burgers, Captain Pam's favorite. People come worldwide to enjoy this incredible sandbar.

Sailing Tour & Charter Packages

Online Booking available for select charter packages

Swim & Snorkel

Starting at $525

Sunset Sail

Starting at $450

Seasonal Fireworks

Starting at $350

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Pontoon Rentals
Pontoon Boats with Slides
Jet Ski Rentals
Fishing Boat Rentals
Crab Island Shuttle Boat
Crab Island Adventure Tour
Tiki Boat Booze Cruise
Private Charters & Bachelorettes
Waverunner Dolphin Tours
Sunset Cruises
Dolphin Cruises
Fireworks Cruises
Fishing Charters

BOAT RENTALS & RATES

Browse from the largest selection of boat rentals on the emerald coast. compare prices and easily book online or give us a call to reserve your boat today, all boat rentals:.

pontoon rentals
pontoon boats with slides
jet ski rentals
fishing boat rentals

seven children eating popsicles on pontoon boat

ACTIVITY TYPE: Harris Pontoon Boat Rental

LENGTH AND CAPACITY: 24ft (seats 12)

PICK-UP LOCATION: Destin Harbor

FEATURES: Our most popular Crab Island Pontoon Rental! These 24′ pontoon boats feature bimini tops for shade and comfortable seating for up to 12 people (including infants/children), making it ideal for families and groups! Drop anchor at Crab Island, pull up at Norriego Point, or cruise the Bay. Captain available upon request - call to book with a Captain. Located on the Destin Harbor - 5 minutes from Crab Island.

CANCELLATION POLICY: Full refund if cancelled 48 hours prior to start time (click "Book Now" to read full cancellation policy at checkout).

ACTIVITY TYPE: Double Decker Pontoon Boat Rental with 2 Waterslides

LENGTH AND CAPACITY: 24ft (seats 14)

FEATURES: Bring the whole family! With seating for up to 14 passengers (including infants and children), this Double Decker pontoon boat offers plenty of seating in the sun & shade, loud Bluetooth radio, 2 levels that allow you to take in the view, and two amazing waterslides! Must be 25 to rent. Limited availability. Located on the Destin Harbor, 5 minutes from Crab Island.

CANCELLATION POLICY: Full refund if canceled 24 hours prior to start time.

ACTIVITY TYPE: Sweetwater Pontoon Boat Rental

LENGTH: 24ft (seats 12)

PICK-UP LOCATION: Destin (500 yards from Crab Island)

FEATURES: Our best-selling pontoon rental! This 24' Crab Island Pontoon Boat features a bimini top for shade and plush seating for up to 12 people. Spend the day anchored at Crab Island or cruise Destin’s waterways in style. Only 500 yards to Crab Island – ideal for maximizing your rental time. This is the closest rental to Crab Island in Destin and free parking is available onsite. Click here for more info .

CANCELLATION POLICY: Full refund if canceled 48 hours prior to start time (click "Book Now" to read full cancellation policy at checkout).

ACTIVITY TYPE: Standard Pontoon Boat Rental

LENGTH: Length: 24ft (seats 12)

FEATURES: This pontoon boat features a bimini top for shade and plush seating for up to 12 people making it ideal for bay fishing, snorkeling, or leisurely cruising Destin’s waterways. Located on the Destin Harbor - 7 minutes from Crab Island.

CANCELLATION POLICY: Full refund if canceled 48 hours prior to start time (click "Book Now" to read full cancellation policy at checkout).

ACTIVITY TYPE: 10-Person Pontoon Boat Rental

LENGTH & CAPACITY: 22ft (seats 10)

PICK-UP LOCATION: Okaloosa Island

FEATURES: Our cheapest pontoon boat rental! These 10-person pontoon boats are located on Okaloosa Island (a 15-minute boat ride from Crab Island) and are our least expensive pontoon rental option. All boats are high-quality 2020-2022 models and have the option to add a lily pad or paddleboard at checkout!

CANCELLATION POLICY: Full refund if canceled 24 hours prior to start time (click "Book Now" to read full cancellation policy at checkout).

FEATURES: With seating for up to 14 passengers, this Double Decker pontoon boat offers 2 levels that allow you to take in the view, luxury lounge seating in the sun & shade, loud Bluetooth radio, and a double waterslide! Must be 25 to rent. Limited availability. Located on Okaloosa Island – 15 minutes from Crab Island.

ACTIVITY TYPE: Crest Pontoon Boat Rental

LENGTH AND CAPACITY: 20ft (seats 10)

FEATURES: This 10-person pontoon rental is perfect for smaller groups or families who prefer a slightly smaller pontoon boat. This 20ft pontoon boat still has everything you want (bimini, plush seating, space for coolers and water toys), but is easier to drive for those with less experience or a smaller group! Located on Okaloosa Island - 15 minute boat ride to Crab Island.

ACTIVITY TYPE: Benington Luxury Tritoon Rental with 200HP motor

LENGTH AND CAPACITY: 25ft (seats 15)

PICK-UP LOCATION: 30A ( Cessna Landing Boat Ramp)

FEATURES: These luxury 30A Pontoon Rentals are ideal for guests staying on 30A and in the South Walton area. All boats are new luxury tritoon models with all the bells and whistles, and have a 200HP motor. Upgraded engine gives faster access to Destin waterways and Crab Island. These are the only boat rentals located in the heart of 30A. Why fight traffic when you can get there by boat?

ACTIVITY TYPE: Captained Double Decker Pontoon Boat with Slide & Trampoline - Perfect for Bachelorettes!

LENGTH & CAPACITY: Length: 25ft (seats 11 + Captain)

FEATURES: Captained double-decker with premium stereo system, slide, trampoline, and luxury seating on both levels. A free paddleboard and floating "water couch" are also included for free. This captained outing is perfect for Bachelorettes, girls trips, or families not wanting to drive. Departs from the Destin Harbor – 10 minutes from Crab Island. Captain fee is included in the price. See more info here .

CANCELLATION POLICY: Full refund if canceled 24 hours prior to start time (click "Book Now" to read full cancellation policy at checkout).

ACTIVITY TYPE: Sun Tracker Luxury Tritoon Rental with 200HP motor

LENGTH: 22ft (seats 11)

ACTIVITY TYPE: Yamaha Jet Ski Rental

CAPACITY: Up to 3 passengers (400lbs)

FEATURES: Enjoy these safe, yet fast deluxe Destin, FL jet ski rentals that can seat up to 3 people. These waverunners are located in the heart of the Destin Harbor about 5 minutes to Crab Island. Ski vests and fuel are included in the price of your rental. Click here for jet ski rental rules & requirements . Must be 18 to rent/drive. Waverunner dolphin tours also available .

ACTIVITY TYPE: Captained Pontoon Boat

LENGTH: Length: 24ft (seats 6 + captain)

FEATURES: This captained pontoon boat is just the ticket for your family! On board, you will cruise around Choctawatchee Bay on your way to the Gulf as you scan the clear Destin waters for local marine life. Your skipper will take time to visit Crab Island so you can experience the island life just as the locals do. You are welcome to bring your own cooler stocked with drinks and food. A captain is required for the outing. If you’re interested in having a captained trip to Crab Island and have more than 6 passengers, we offer private charters as well as the Crab Island Shuttle Boat or Crab Island Adventure Tour .

MAKE: 220XT SeaFox Center Console Fishing Boat Rental

LENGTH AND CAPACITY: 22ft (seats 6)

PICK-UP LOCATION: Fort Walton Beach (5 min boat ride from Crab Island)

FEATURES: This 22′ center console with a 200HP Yamaha offers everything you need to spend a day fishing the bay or the gulf, hanging out at Crab Island, or cruising the bay or beaches. Rental includes a T-Top, 7-inch Garmin GPS & Fishfinder, VHF, rear livewell, rocket launchers, BlueTooth radio, plenty of storage, and swim ladder. Holds 6 people. Inshore & Offshore fishing rods are available for an additional $100 charge (8 rods included). Fuel is not included. The renter and driver must be 25 years old and some boating experience is required. Location is a 5-minute boat ride to Crab Island. More info here .

MAKE: 220 Sailfish Center Console Fishing Boat Rental

FEATURES: This 22′ center console with a 200HP Yamaha will get you out to where the fish are biting! Your fishing boat rental includes a T-Top, rocket launchers, 9-inch Garmin GPS & Fishfinder, rear livewell, VHF, BlueTooth stereo, plenty of storage, and a swim ladder. Holds 6 people. Fuel is not included. Inshore & Offshore fishing rods are available for an additional $100 charge (8 rods included). A trolling motor can be included as well for an additional $50. The renter and driver must be 25 years old and some boating experience is required. Location is a 5-minute boat ride to Crab Island.

ACTIVITY TYPE: 10 or 12-person Pontoon Boat Rental

PICK-UP LOCATION: Fort Walton Beach

FEATURES: Our 12-person Fort Walton Beach Pontoon Rentals offer discounted rates from Destin boat rentals and avoid traffic for anyone staying in Fort Walton Beach, Mary Ester, Navarre, or Shalimar! Save big when you rent a boat from one of our Fort Walton Beach locations. Only a 25-minute boat ride to Crab Island through the beautiful Santa Rosa Sound. Options to add a Lily Pad, Paddle Board, or portable basketball hoop to your rental at checkout!

PICK-UP LOCATION: Miramar Beach

FEATURES: With seating for up to 14 passengers, this Double Decker pontoon boat offers 2 levels that allow you to take in the view, luxury lounge seating in the sun & shade, loud Bluetooth radio and a double waterslide! Full-day rentals only at this location. Must be 25 to rent. Located in Miramar Beach - best for families staying in Miramar or 30A.

ACTIVITY TYPE: Double Decker Party Boat with Bar

LENGTH: 30ft (seats 12)

FEATURES: Bring the party with this double-decker pontoon boat with seating for up to 12 passengers. This party boat offers 2 levels that allow you to take in the view, a wet bar area with rotating bar stools, AND a double water slide! Limited availability. Located on the Destin Harbor, 7 minutes from Crab Island .

ACTIVITY TYPE: Yamaha Jet Ski Rental

CAPACITY: Up to 2 passengers

FEATURES: Our cheapest Jet Ski rental! These 2-person jet skis are located in Fort Walton Beach (20-25 minutes from Crab Island) and are our least expensive jet ski rental option. Safety training, life vests, and fuel are included - plus the option to add an action camera at checkout!

PICK UP LOCATION: Okaloosa Island

FEATURES: Rent a jet ski for 1 to 8 hours departing from Okaloosa Island. 2 people max per jet ski and fuel is included! Enjoy discounted Crab Island Jet Ski rentals and get out on the water today!

CAPACITY: Up to 3 passengers (450lbs)

FEATURES: Come check out these Okaloosa Island Jet Ski Rentals. This rental location is perfect for those staying on Okaloosa Island and don't want to drive into Destin. Rent our fast and safe jet skis from 1 to 8 hours - 10 minute jet ski ride to Crab Island.

ACTIVITY TYPE: SeaDoo 130HP Upgraded Jet Ski Rental

PICK-UP LOCATION: 30A ( Cessna Landing Boat Ramp)

FEATURES: These luxury 30A Jet Ski Rentals are ideal for guests staying on 30A and in the South Walton area. High-end 130HP Seadoo jet skis with quick access to Destin waterways and about 20 minutes to Crab Island. These are the only jet ski rentals located in the heart of 30A. Flexible booking times allow you to rent for any time and duration that best fits your schedule.

FEATURES: This 24′ pontoon features a BlueTooth sound system, 10′ bimini top for shade, comfortable seating for 12 people, and an upgraded Yamaha engine. Captain Available upon request – Call to Book with a Captain. Venture to Crab Island for the day or explore the natural beauty of our area while visiting the Gulf Islands National Seashore or Spectre Island in the Santa Rosa Sound. Located on Okaloosa Island - 15 minutes to Crab Island. Click here for more info .

ACTIVITY TYPE: Pontoon Boat Rental

FEATURES: Destin Harbor Pontoon Rental with 10′ bimini top for shade, plush seating for up to 12 people, and quiet 4-stroke engine. Pet-friendly. Located on the Destin Harbor - 1/2 mile from Crab Island.

ACTIVITY TYPE: 12-Person Pontoon Boat Rental

FEATURES: Check out 12-person Crab Island pontoon boat rentals departing from Okaloosa Island. Perfect for anyone staying on Okaloosa Island and wanting to avoid traffic into Destin. Location is only a 15-minute boat ride to Crab Island, features the same quality pontoon boats & equipment, but cheaper than Destin rentals .

LENGTH & CAPACITY: 24ft (seats 12)

FEATURES: Come enjoy discounted Fort Walton Beach pontoon rentals! Head straight to Crab Island or explore dozens of untouched Islands that are perfect for adventuring or enjoying a quieter rental experience away from all the action. Ask the Dock Attendants about Spectre Island at check-in! These 2021-2022 12-person pontoon rentals are some of the cleanest and nicest rentals in Fort Walton Beach and offer discounted rates from Destin rentals.

LENGTH AND CAPACITY: 22ft (seats 10)

FEATURES: These Fort Walton Beach pontoon rentals are perfect for smaller groups or families who are looking for a boat rental away from all the craziness. Perfectly located in the heart of downtown Fort Walton Beach, these 10-person pontoon rentals are some of the cleanest and nicest rentals around and offer discounted rates from Destin rentals. This location is a 5 minute boat ride from dozens of untouched Islands - perfect for enjoying a peaceful day on the water.

CANCELLATION POLICY: Full refund if cancelled 24 hours prior to start time (click "Book Now" to read full cancellation policy at checkout).

ACTIVITY TYPE: Thursday Night Fireworks Pontoon Rental (Every Thursday from Memorial Day - Labor Day)

FEATURES: Rent your own pontoon boat and anchor in the Destin Harbor or Crab Island and watch Destin's full fireworks show from the water. For those who have never seen Destin's famous fireworks show from a boat, it is truly the experience of a lifetime and a local favorite! Pontoon Rentals are available from 6:30pm - 9:30pm on Thursday nights only from Memorial Day through Labor Day.

CAPACITY : Up to 3 passengers (400lbs)

FEATURES: These 2020-2022 jet ski rentals feature seating for up to 3 people or 400lbs. Ski vests and fuel are included in the price of your rental. Closest access to the no-wake zone in Destin. Located In Miramar Beach on the Destin Bay (next to Lulu’s). 20-minute jet ski ride to Crab Island!

ACTIVITY TYPE: Xcursion Pontoon Boat Rental

FEATURES: This 25′ pontoon seats up to 12 people (including infants/children). Each pontoon has a canopy for shade and plenty of space for coolers and water toys. Located in Miramar Beach near the Destin Commons/Crystal Beach, 25 minutes to Crab Island by boat. Free parking on site. More info here .

Destin Vacation Boat Rentals proudly offers the largest variety of boat rentals in Destin, Florida with easy access to the famed Crab Island sandbar . Choose a boat from our award-winning fleet of fishing, pontoon, power, and sail boat rentals and call us at (850) 650-2628 to make your reservation or book online!

A 15% deposit is required to hold a reservation, with the remaining balance due at check-in, unless otherwise specified. Please visit our Frequently Asked Questions (FAQ) page for information on our reservation, cancellation, and weather policies. A full tank of fuel is included unless otherwise specified.

aerial view of crab island in destin florida

We have ALWAYS had a great time on their pontoon boats. We rent one every year to go fishing in the bay. Great staff and very friendly! We will always be returning customers..!!

“Thank you for helping make our sunset cruise/vow renewal perfect! Our captain was accommodating, friendly, and just wonderful. Pastor Eric did a beautiful ceremony. I really appreciate all your help in making our 20th anniversary extra special!”

“We rented a pontoon boat during our 2011 vacation. We had a blast! The boat was very nice. It was the best part of our vacation!"

“This was the best way to spend my bachelorette party and could not have asked for better service. Thank y’all from the Texas chicks!”

“Had a great time at Crab Island, looking for dolphins, and winding up the evening watching the fireworks show! Thanks DVBR!

“We had an awesome time on a jet ski and a pontoon last week that my family rented from you all it was one of the many highlights of our vacation and probably number one for my 2 1/2 year old little boy.”

“Superior service, fantastic boats, and super nice guys. This is how it should be done. We will be back!”

“Gotta love…snorkeling at Crab Island…We had a wonderful time!! Thank you for the lovely service. We will be back next July 4th ).”

The 19′ Cobia we rented was an excellent boat. It was well maintained and had all the options a fishing boat should have. We were especially pleased with the service and professionalism of the staff, who really made us feel like their utmost goal was for us to have an enjoyable experience and we did.

Crab Island Adventure
Snorkel Adventure
Sunrise Sail
Sunset Adventure
Dolphin Adventure
Santa Rosa Islands
Proposal/Anniversary
Fireworks Adventure
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Wind Forecast
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Surf Forecast
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What makes a good sailor?
The Ocean Race

Exclusive Catamaran Sailing Adventures

Come explore the majestic waters of the emerald coast, catamaran sailing in the emerald coast sun..

Are you visiting the Destin, Okaloosa Island, Navarre Beach area and needing a little adventure in your life? This is what you're looking for aboard catamaran Destin Sailing Adventures. The boat is a Stiletto 27 Special Edition Catamaran, designed to provide maximum sailing pleasure and performance over a wide range of wind and sea conditions. Made for adventure and racing, so it offers plenty of excitement and comfort for any occasion. The boat is outfitted with a 20hp motor, so if the wind isn't blowing we can still get out and play! Charter comes with a local captain to take you to all the local spots, while you sit back and relax.

We offer an array of private tours, cruises, and adventures at a reasonable price. The longer you book the more fun you can have and the more money you’ll save. These are private charters, so you won’t be with a huge crowd during these unprecedented Covid 19 times. Just you and the people you bring. Come explore Crab Island, Sunset cruises, Sailing lessons, Dolphin Tour, Snorkeling, Marriage Proposals, Birthdays, sightseeing tours, Anniversary celebrations, and more with us today.

We are dedicated to making sure you have a great time while visiting the Emerald Coast. All trips include up to 6 Guests, Licensed Captain, cooler with ice, bean bag chairs, sound system, and a head (bathroom). Our Captain has 15 years of local experience racing/sailing along the Gulf Coast of Florida and more! Please contact us for special requests.

One of the best catamaran sailing adventures Destin East Pass, Okaloosa Island, Santa Rosa Island, Choctawhatchee Bay has to offer!

Memorial Day

Summer is almost here!

Mins Minutes

Secs Seconds

Jetty East Snorkeling

Usually one of the busiest spots during the summer, so book your trip early to beat the crowds.

Snorkeling with a Manatee.

Early bird got the manatee this day!

Spanish Mack

Up close and personal to a Spanish Mack doing its thing!

Pick up location

Adventure marina, okaloosa island.

1201A Miracle Strip Pkwy SE, Fort Walton Beach, FL 32548, USA

850-217-3448

Open today

05:30 am – 09:00 pm

"A ship is always safe at the shore, but that is not what it is built for."

Albert Einstein

Destin Sailing Adventures

1201B Miracle Strip Pkwy SE, Fort Walton Beach, Florida 32548, United States

Experience Destin in a whole new way.

fair winds sailing co.

Sail along Destin, Florida's Emerald Coast aboard "Selah," a classic 32 foot sailboat. Charter your own specialized adventure with a licensed and experienced sailing captain to create memories that will last a life time. We offer private sailing tours for up to six people that include day time sails, sunset cruises, dolphin tours and more!

A Sailboat With A Story.

Sailing vessel Selah is a beautiful boat with a strong family history and connections to the local area. She is a sea worthy vessel that has sailed all over Florida and the Bahamas, but now take guests out on sailing adventures here in Destin. Her most unique feature is a large bowsprit that is the perfect spot for viewing dolphins and other sea life or taking in the sunset. Whether you are sailing for the first time or are have lots of experience, we offer an excellent opportunity to relax and unwind as we explore the Gulf of Mexico, Choctawhatchee Bay and the Destin Harbor.

Selah is also equipped with plenty of dry storage, a cooler with ice for drinks or snacks you may want to bring along and complimentary bottled water.

Fair Winds Sailing Co prides itself on providing an unforgettable opportunity to experience the joy of sailing and everything Destin has to offer. That's why we want to help you get the most out of your trip. Whether it's taking the whole day to explore the coast, getting the best spot to watch fireworks or planning the perfect evening with your significant other, we can make it happen.

Book Online today! or call 850-502-0664

Guests aboard Selah watch as a dolphin swims along with the boat in Destin, Florida.

Daytime Sails

We'll raise the sails, turn off the motor and head out in to the Gulf of Mexico for a day that's relaxing and exciting. Stand on the bowsprit and watch dolphins swim under your feet as they follow the boat. Lay out on the deck with a cold drink. It's the perfect way to spend an afternoon.

Sunset cruise aboard our sailboat Selah on Choctawhatchee Bay, Destin, Florida.

Sunset Cruises

End the day with a picture perfect cruise on Selah. Watch the sunset over the clear waters of Destin, then cruise through the harbor as Destin lights up the night. It's a great opportunity to share a bottle of wine with friends or to top off a romantic getaway.

A beautiful and initmate wedding ceremony aboard sailboat Selah.

Specialty Excursions

Captain Harbor can customize your sailing trip to make your day with Fair Winds Sailing Co unique and memorable. Book Selah for an engagement shoot or an intimate wedding ceremony. Turn your trip into an all day experience. Ask for a hands-on sailing tutorial. We also offer packages for special events like fireworks cruises, moonlight sails and more.

[email protected]

850 502 0664

Captain Harbor raises the sails on Selah during a trip with Fair Winds Sailing Co.

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Welcome to East Pass Sailing Company

Authentic sailing & family fun in destin, fl, our charters, luxury sailing charters in destin, florida.

Sunset Sail

Looking for something cool to do in Destin Fl? Join us for a private Sunset Sail! This 2 hour cruise is perfect for a romantic date or a family friendly adventure to wrap up a day. All ages welcome on this relaxing evening tour. Want a bottle of champagne on ice, or maybe a Charcuterie board? Let’s go sailing and make a perfect memory on the Best Side of Destin 😉 Add an hour after the sun sets and enjoy the Harbor Lights Cruise.

2 or 3 Hours

Just Sailing

This is our best cruise that focuses on just sailing. A 2 to 4 hour sailing excursion on our fast Beneteau M445 sailing yacht, the Space Dancer, that will satisfy your interest for sailing. Our Coast Guard licensed crew specializes in working the boat with the wind by raising the mainsail as soon as we leave the dock and shutting the engine off right away. Look out for coastal wildlife like Turtles, Pelicans, Herons, and Dolphins! Feel free to jump in on the action - sailing instruction available on request.

2 to 4 Hours

Champagne Brunch Cruise

Why begin your day on land when you can brunch on a boat? Join us for a private champagne brunch experience! Add a Charcuterie Board! Relax on the top deck, feel the gulf breeze, and enjoy a great start to your day.

Sail and Swim

Join us for a 3 to 4 hour Sail and Swim! Cruise down the coastline under sail, then anchor up in the cove and cool off with a swim! Explore the sugar white sandy beaches of Okaloosa Island where the only access is by boat! Plenty of time, there’s no rush! Great for family outings or social events.

3 to 4 Hours

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Sail into paradise with our private sailing yacht charters in Destin, Florida

Why choose us, premier boat tours in destin florida.

Spend a perfect day on the water with an authentic Gulf sailing charter experience. Relax and enjoy the sun and sea. The Destin area has plenty of amazing restaurants and we can arrange a catered meal to enjoy onboard. Feel free also to bring your own food and drinks or beverages of choice.

Space Dancer is a luxurious 45-foot Beneteau sailing yacht with ample space for six passengers to enjoy a private boat tour, dolphin cruise, catered dinner, and fireworks cruise. You'll sail around Destin, Florida in style.

The Emerald Coast is the ideal location for scenic boat tours. Whether it's a daytime dolphin cruise, a fireworks cruise, or a sunset tour, you'll have an amazing time with a picturesque view from every spot on our spacious top deck.

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Destin, florida, frequently asked questions (faqs).

Set Sail on an Unforgettable Adventure!

850.749.2040

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Destin Yachting The Ultimate Yachting Experience in Destin & 30A!

A Miami - Mediteranean Style Charter

with a New Orleans Flare!

Happy Hour is a 63’ Private Yacht that is lightly chartered.

30A & Destin Boarding!

Half day starting at $3,200, 6 hrs starting at $4,000, 8 hrs starting at $4,800, sunset cruise special, vip private chef…check it out, veuve clicquot packages, the yachting lifestyle.

Happy Hour is a luxurious 63' Euro-Yacht.

Unlike other charter yachts in the area, Happy Hour is “lightly” chartered, so she has the feel of a “private yacht”. She also has a shallow draft which alllows her to get into shallow areas like Crab Island and Noriega Point. This allows you to get into the thick of the action rather than just be a spectator from afar.

The Ultimate Yachting Experience!

We love YOU our valued guests and we love getting pics and video from you. This video was made with images and video provided by a few of our charter clients Making Memories! See why Destin Yachting provides Destin’s Ultimate Luxury Yachting Experience!

Tequila on a Boat..It’s Happy Hour!

Tequila on a boat…Nothing better than sand, sun, and summertime on board Happy Hour in Destin!

Checkout a recent client’s video!

Thank you for the Ultimate Compliments! We love YOU too!

"Our trip on Happy Hour was the BEST DAY EVER!!! "

" SOOOOOO MUCH FUN!!!! "

" Happy Hour is absolutely GORGEOUS!!!!! "

" Captain Steve and Lauren were FANTASTIC!!!

Can’t say that to y’all enough!! Hope to see y’all again soon!"

Click below and choose to review

the charter or the Chef Experience!

Yacht Life Photo Gallery

Bam vip rock star private chef service, veuve clicquot bottle service rock star cruise, vip rock stars on board, charter add-on options, make it over the top.

Let us help kick your event up a notch...BAM!

VIP Rock Star Private Chef Experience!

BAM!!! Well maybe not Emeril Lagasse, but you can party like a Superstar and leave the food prep to your own private chefs for the day. Our Chefs, have worked with some of the best restaurants in the area including for famous Chef Emeril Lagasse. Well known on 30A, our latest addition, Chef B from South Louisiana is making quite a stir with our guest!

They will custom tailor cocktails, appetizers, entrees, and desert just for you and your guests.

Private Seaplane Tour

Literally “OVER THE TOP!!!

If you choose one of our longer charters, take “Over the Top” into orbit by adding a private seaplane tour. Let our Concierge Service set up a Special Rendezvous with our Seaplane Service and get a private aerial tour of Destin and the surrounding area. Prices are per hour and are subject to weather and availability.

VIP Rock Star Private Car Service

Want to PARTY HARD Like a Rockstar?

Leave the driving to us!!!

This is your special day so why not let someone else do the driving so EVERYONE can enjoy themselves and Party like a Rock Star! We can arrange for VIP Rock Star Private Car transportation from just about anywhere on the Emerald Coast. Contact us for more information and pricing.

[email protected]

Let's get your party started!

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Pickup is at the Sandestin Marina or a Destin Harbor pickup can be arranged.

Destin yachting/ happy hour yacht charter.

100 Gulf Shore Drive, Unit 508, Destin, Florida 32541, United States

Downloadable Demise Charter & Crewing Agreement

Thanks for choosing Happy Hour! You are going to enjoy one of the most luxurious experiences available in Destin. In addition to letting us know what day and time you want for your Charter, we also need you to complete your purchase online and complete a Charter Agreement which is downloadable here. Every Charter must have a Charter Agreement signed before boarding the vessel. In addition to this agreement, the Captain will require a list of all passengers for the day with their name, city of residence, email and phone number.

2022 HAPPY HOUR Demise Charter & Crewing Agreement (pdf)

Terms and Conditions
Privacy Policy

Complimentary while Boarding

Complementary Vueve Champagne and charcuterie board when you arrive on board!

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CHARTER OPTIONS

Enjoy the beautiful scenery Destin, Florida has to offer with a group or in a romantic setting. We have a variety of charter types so you can be sure to choose the one that’s right for you! Holloway Yacht Charters is committed to providing you and your guests an unparalleled adventure that can only be experienced aboard your own personal yacht. Here in the panhandle and South Florida there are many ways to see the sites and spectacular underwater wonders the area has to offer. Aboard the Propensity you will experience these things in the comfort and luxury of your own private yacht and avoid the one thing the cattle boats and all other high capacity charters have in common… the crowds.

1/2 Day Cruise (4 hours)

Charter includes captain, fuel, soft drinks, & water for up to 12 guests. Alcohol and food can be added.

*Additional Booking Fee May Apply

Full Day Cruise (8 hours)

Our Sunset Cruise includes captain, fuel, soft drinks, & water for up to 12 guests. Alcohol and food can be added.

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5/5 100+ reviews

WHY HOLLOWAY

Heads turn quicker. Hearts beat faster. A lifestyle is expressed instantly in the eloquent lines and luxury of the Princess V72 with the largest engines. Her breathtaking beauty, the exquisitely crafted Oak interior, and stunning Ocean Trac performance have won accolades worldwide and stimulated a legion of home-grown imitators. Yet unduplicated in all aspects of design and completeness, the Princess V72' achieves best in class and measurably exceeds the expectations of the world’s most sophisticated yachts.

A large cockpit with a table and comfortable seating, providing both partially covered and open spaces

Central stereo with satellite music system along with Bluetooth that can be controlled from your phone or tablet

Bow area, containing a sun pad

Swim Platform

Comfortable upper salon, with a table and wrap-around banquet seating

Galley, containing a stove, microwave, refrigerator, and freezer

3 Staterooms with flat screen televisions

3 Heads with showers

OUR LUXURY YACHTS

Our Flagship

Heads turn quicker. Hearts beat faster. The Princess V72's breathtaking beauty, eloquent lines, exquisitely crafted oak interior, and stunning Ocean Trac performance has won accolades worldwide and stimulated a legion of home-grown imitators.

Our Sistership

The Perfect Destin Cruiser. A lifestyle is expressed instantly in the eloquent lines and luxury of the Neptunus 58 Flybridge. Neptunus Yachts are known for their unmatched value, great performance, and exquisite craftsmanship.

Fairline 52

Imagine unwinding in a spacious salon and well-equipped galley, all surrounded by the warmth of high-gloss cherry joinery. This yacht catered to those who craved both the thrill of the open water and the serenity of luxurious comfort.

Crab Island Budget-Friendly Rentals

Explore our fun & affordable boat options.

Fish & Fun Destin

Starting at $250 an hour . Our Sportsman 302 offers a perfect blend of family comforts and angler-driven features at an affordable price. Up to Ten guests.

Boat Rental • Half Day • Full Day • Hourly • Fishing • Snorkeling • Crab Island • Family Fun • Dolphin Watching