Destin Itinerary: 5 Day Vacation in Destin, Florida


February 8th, 2019


Destin Florida

Mix two parts water with one part sugar white sand. Sprinkle in a generous helping of sunshine, a dash of southern hospitality, and a splash of adventure and you’ve got yourself the perfect recipe for fun on the Emerald Coast! Florida's Emerald Coast offers 24 miles of sugar-white sand beaches situated along the Gulf of Mexico, with Destin, Florida situated squarely in the center, offering the closest proximity to the famed 100 fathom curve, which provides anglers with the unique ability to quickly reach every depth of fishable water for all Gulf species. The sand, sugar-white in appearance and made of pure Appalachian quartz, gives the waters here their trademark emerald-green color as it reflects sunlight through the surf. 

Visit Destin Florida, aptly referred to as both the 'Crown Jewel of the Emerald Coast' and the 'World's Luckiest Fishing Village', for spectacular beaches that are continually voted among the top in the country, and some of the best fishing in the world. The expansive waters of the Choctawhatchee Bay extend the beauty inland, providing endless opportunities for fun in the sun. But the fun doesn't stop there. Destin has plenty of things to do to to keep both beach-goers and land-lovers entertained. Here is a sample five-day Destin itinerary of the best that the Emerald Coast has to offer... 

destin itinerary

Things to Do: A Sample Five-Day Destin Itinerary

Photo of Destin beach

Day One-Hit the beach! A visit to Destin, Florida wouldn't be complete without a visit to its world-renowned beaches as the starting point of a good itinerary. Spend the day laying on the sugar white sand or frolicking in the crystal-clear emerald green surf. You're sure to work up an appetite, so hit up one of the area's many restaurants for some tasty fare. We like The Edge Seafood Restaurant on the Destin Harbor for fresh, local seafood harvested just offshore each day. For those looking for things to do to keep the little ones entertained, The Edge, recently voted Best Outdoor Dining in Destin, has fish feeders lining their dock and underwater lights that attract fish at night-lots of fun for the kiddos! Or, pay a visit to Fudpucker's Beachside Bar & Grill (conveniently located across the street from Henderson Beach State Park, one of the area's loveliest beaches) for great food and live alligator feeding. You can even get your picture taken holding one, and nothing says "Florida" quite like getting your picture taken holding an alligator!

destin florida attractions itinerary fun

Day Two-Pay a visit to the Destin History & Fishing Museum for a look into Destin's rich fishing history, which dates back to the 1800s when New England fisherman Captain Leonard Destin settled in the area and pioneered the fishing industry. Afterwards, take the 2-minute drive on over to Calhoun Avenue to Dewey Destin's Seafood Restaurant for some fresh, local seafood from the descendant of Captain Destin himself. After lunch, rent a jet ski (or two) and ride around, taking in the breathtaking views of the area by water. Be on the lookout for playful dolphins  and other marine animals that call our Florida waters home! When you return from your ride, grab a fruity drink, snack, or cocktail from one of the vendors along the Destin Harbor Boardwalk and take a stroll. You'll see the charter boats coming in with their catches and enjoy the hustle and bustle on the docks.

waverunner dolphin tours destin fl

Day Three- Destin has been named one of the Top 10 Places in the world to live and boat by Boating Magazine, and boating is a must for the perfect travel itinerary. Visitors can rent all manner of recreational watercraft, including fishing boats, pontoon boats, power boats, sailboats, and jet skis to explore the Emerald Coast. You'll want to rent or charter a boat, or take the Crab Island Shuttle Boat, to check out Crab Island, an underwater sandbar and popular gathering spot for boaters. Click here to see available boats. And if you're in the mood to be entertained, check out the Crab Island Adventure Tour, a fun-filled captained boat excursion that includes an inflatable water park, snorkeling, shelling, kayaking, paddleboarding AND a stop at Crab Island to check out the festivities.



Day Four-You may need a break from the sun for a day, and what better way to spend the day than to hit up the local shops. Destin has a huge variety of local boutiques, an expansive outdoor retail shopping mall, and even a giant outlet center at Silver Sands Outlets . Stock up on souvenirs from your trip to commemorate your epic vacation! Plan to finish up your shopping extravaganza with the shops at HarborWalk Village, and grab dinner from one of the many restaurants (The Edge Seafood Restaurant is our favorite due to its panoramic water views) while you're there. Sunset views on the Harbor are breathtaking sights to see, and on Thursdays between Memorial Day and Labor Day you can even watch an air show featuring vintage WWII airplanes and a spectacular fireworks show after dark. Bring it up a notch and take a sunset cruise, with the most amazing views from the water.

red snapper fishing report september destin fl

Day FiveGo fishing! No trip to The World's Luckiest Fishing Village is complete without a fishing trip!  The small community of Destin Florida is situated along the closest access point to the 100-fathom curve in the Gulf of Mexico, boasting the closest deep water access in the Northern Gulf and the largest and most elaborately equipped charter fishing fleet in Florida. Where fishermen in most coastal towns must travel 30 or more miles offshore for deep sea fishing, Destin fishermen can fish for species such as red snapper, grouper, amberjack, and triggerfish all within just a few miles of the beach. Spend a few hours, or the day, experiencing the bounty of the Gulf. When you return, you can even take your catch to one of the local restaurants along the Harbor and they will cook it for you! Lucky, indeed!


When To Go

Destin is typically a summer destination. Families enjoy coming to the beach during spring, summer, and fall breaks, but it's a little-known secret that fall (September-October) is the best time to come, when the crowds have thinned but the weather-and water-are still warm. October is also known for the Destin Fishing Rodeo and, of course, its amazing sunsets, so if you plan on visiting during this time of year, make sure to add these activities to your Destin itinerary as well. For other seasonal events, check out this website for a list of Destin events and things to do.


Climate in Destin, Florida

Expect temperatures in the upper 70s-low 80s in April/May and again in October. June-September mid to high 80s with high humidity.  Winter brings highs in the low 60s.


Getting There & Around

Destin Florida is typically a drive-in destination, meaning the majority of visitors live within driving distance and come by car, but if you are going to fly, the closest airport is Northwest Florida Regional Airport (VPS). The easiest way to get around is by car, but plan to pay to park ($5-10) in most public parking areas, especially in the Destin Harbor District. Uber and Lyft are also popular transportation methods.



  • Support local businesses (restaurants, boutiques, art galleries, etc). They are the heart and soul of the Destin community.
  • Pay attention to the flag system at the beach. GREEN: LOW HAZARD - Calm Condition, Exercise Caution
    YELLOW: MEDIUM HAZARD - Moderate Surf and/or Moderate Currents, RED: HIGH HAZARD - High Surf and/or Strong Currents, DOUBLE RED: WATER CLOSED TO PUBLIC, PURPLE: Marine Pests Present.
  • Plan ahead. Many popular activities such as fishing charters , Crab Island excursions, boat rentals and sunset cruises book up quickly.


  • Call the Gulf of Mexico "the ocean". This is a dead giveaway that you are a tourist. Locals simply refer to the body of water as "the Gulf".
  • Forget sun protection (shades, sun screen, and a hat).  The sun is strong from all directions, even off the water's reflection. A bad sunburn will ruin even the best planned vacation.
  • Watch the local weather forecast. The Destin weather forecast is unreliable at best. Due to the city's high humidity and proximity to the Gulf, it is not unusual for the forecast to call for rain every single day. Don't panic. It is unlikely to rain out your entire vacation, despite what the weatherman says.

Fun Facts about Destin, Florida

  • Destin is known to have some of the softest, whitest sand in the world. This is because the sand particles come from quartz found in the Appalachian Mountains that travel to the Gulf of Mexico by way of the Apalachicola River. Of course, this process began some 20,000 years ago, but it continues today. These perfectly oval grains of sand literally squeak under your feet when you walk on them.
  • Florida's Department of Environmental Protection estimates that more than 80 percent of Florida's Emerald Coast's 4.5 million yearly visitors travel to the region to visit Destin, however, the full time resident population consists of only about 12,000 people.
  • Although Leonard Destin is credited with founding Destin Florida, Native American Indians had discovered and been living in the area since the 7th century because of the area’s natural resources that included an abundance of seafood.
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