A vacay or staycay in the Upper Florida Keys offers endless fun and relaxation. To help you balance high-octane activities with rejuvenating kick-back experiences during your visit to Key Largo and Islamorada, we assembled a short list of must-do eat, play and wind-down options. ‘Course, they only scratch the surface of things to do in these hot spots, but since we’re pretty positive you’ll already be planning your next trip to the area even before you leave, just pick up where you left off once you’re back.

Key Largo

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• To frolick and explore in the water (actually, under water), head to John Pennekamp Coral Reef State Park, the country’s first underwater state park, which encompasses a stretch of the Atlantic Ocean. It’s got a portion of the only living coral reef in the continental U.S. and the plant and marine life you can see here is incredible. Explore the coral reefs (their formations will blow you away), seagrass beds and mangrove swamps and prepare for a ton of Insta likes. GOAT!

Kayaking, canoeing, glass bottom boat touring, snorkeling and diving are just some of the activities you’ll want to take part in here. Tap into the two companies below to get going—they’re both standouts among the many excellent options available to you.

• Key Largo Princess offers 2-hour, glass bottom tours of the reef and its wildlife (at 10 am, 1 pm and 4 pm, daily) aboard the V. Key Largo Princess, a luxurious 75-foot motor yacht that can hold 140 passengers. Plan on relaxing on the sun deck or inside in the cabin as you sip a cocktail or another drink from their full-service snack bar. Large windows give you the perfect view of live and formerly alive sealife as the guide points out everything from sea plumes to tropical fish of all sizes.

• With their intimate, private, once-daily 4-5-hr. scuba diving and snorkeling charter trips (for groups of up to 6 people, 4 divers max—e.g., 4 divers and two non-divers, 6 snorkelers and non-swimming watchers, etc.), Lucky Fish Scuba gives an up-close purview of the underwater lifestyle of zillions of colorful creatures. Comfort is this company’s thing: They take you out on a 29’ World Cat with cushioned seats, retractable sunshades and other amenities (they’ll even snap underwater pics of you and hand them over). And they provide you with everything from snacks, water and sunscreen to towels and snorkeling equipment.

Just promise to report back on your sightings, be they orange sea stars, seahorses, multicolored sponges or anything else equally spectacular (there will probably be too many to mention but post grams of your faves.)

One thing you’ll def see (and won’t forget) is the famous The Christ of the Abyss underwater statue on the Key Largo Dry Rocks. TBH, snorkeling in Key Largo is said to be as good as scuba when it comes to what you can see—that’s how clear these waters are and how accessible the sea life is.

Eat:

• Keep your strength up and your taste buds happy with a Keys-style meal of the freshest of the fresh seafood (it’s all locally caught), at The Fish House, a multi-award-winning restaurant (and seafood market). Their homemade chowder is an excellent way to launch your meal, but good luck figuring out what mouthwatering fish to follow it up with. Whatever you choose, you can get it smoked, seared or sauteed in any number of styles (Bobby Flay and Guy Fieri have touted the Matecumbe-style prep on their Food Network appearances). And if you prefer turf over surf, well, the menu hardly disappoints—how ‘bout a Chicken Breast & Back Back Ribs combo dish?

And don’t forget the ultimate Key Largo meal chaser: a wedge of Key Lime pie—Florida Living Magazine named The Fish House’s version the best in all of Florida. Su-weet!

• Key Largo Conch House Restaurant and Coffee Bar, a family-owned operation, has been featured on numerous food shows and serves land-based and water-based dishes for breakfast, lunch and dinner. For breakfast, the Conch House Omelet with diced sauteed conch and the Cracked Conch Eggs Benedict sound irresistible—or maybe the Key Lime Pancakes are the way to go. For dinner, try house specialties like the Conch House Sampler appetizer and Mahi & Avocado entrée. Decadent too much? We don’t think so…

Wind Down:

• Watch the day make a disappearing act in spectacular fashion at Snook’s Bayside Restaurant & Tiki Bar’s daily Sunset Celebration (they mark the ‘sink’ with a blaring horn; who knew there could be that many colors in a darkish sky?). Each and every seat at the Bar Ledge or patio provides an unobstructed view over the water while a misting system helps you keep your cool—that and their delicious Key Lime Martini (not to mention other great drinks). Come for lunch, Happy Hour or dinner and chill to the tunes of live music every evening. The menu’s always changing, but the land and water-based dishes are always super fresh and flavor packed.

 

• In and around your meals, get liquid the original way—with mead. Keys’ Meads Meadery gives you the chance to experience creative takes on the very first alcoholic beverage to have ever been discovered. Mead is made by fermenting honey (BTW, in ancient times, a wedding dowry had to include a month’s worth of mead. …and now you know how the term ‘honeymoon’ was born). Channel your inner Viking (marriage not required) and head over to this cool spot for a taste of up to 10 meads.

Islamorada

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• Don’t let Capt. Skip Bradeen’s thick New York accent fool you—he’s been offshore fishing in the Islamorada waters for over half a century and few, if any, bring his level of expertise to the sport. He’s a total rock star! He and his boat—a 50-ft. Carolina Sport Fisherman named New Blue Chip Too (which is also the name of the business)—will take you and up to five others out for a half day or full day of fishing. With the aid of the finest electronic fish-finding equipment around, the Capt. will lead you directly to your dream catch. You’ll do the fishing under his foolproof guidance and have a boatload of fun in the process.

Eat:

• It’ll be amore at first sight (or taste…or both) at Ciao Hound, an Italian kitchen and bar that serves dinner dishes made with locally sourced ingredients and plays Rat Pack-era music (think: Frank Sinatra, Dean Martin). Come for favorites like Sweet Pan-Seared Florida Shrimp with Cream Polenta and Garlic-Rosemary-Basted Tuscan Sirloin Steak. Just know that even after you’ve scraped the last morsel off your plate (guests seem to have a no-crumb-left-behind policy) and sipped the last drop of your Limoncello Sunrise or Loaded Bloody Mary, you won’t want to say ‘Ciao’ to this spot. Not unless you mean ‘hello.’

 

• Just reading the menu of E.A.T Eatery and Taproom, a burger hot spot, will make your mouth water. Their burgers (many of which are the signature foods of various U.S. states) brim with meats smoked on-site, scratch-made condiments, and unbeatable flavor. The burgers have garnered raves and awards from all corners—in 2020, their Inside-Out Juicy Lucy Burger was voted #1 Best Burger in Palm Beach County and from 2015-2019, The Nancy Pants With Cheese burger was named a Top 101 Burger in America. Non-meat eaters can get their fill (deliciously) with the menu’s salad and veggie dip offerings. The Adult Milkshakes (try the Nutella Banana Bread Ale) make for perfect pairings with pretty much anything you order.

Wind Down:

• If you’re on the hunt for a nighttime entertainment spot where a beautiful view comes with equally stunning food, search no more. At the luxe Postcard Inn’s Raw Bar you’ll sit outdoors at the edge of oh-so-blue Atlantic Ocean around a glowing rock firepit or table while sipping a frozen rum runner (or other awesome concoction), munching on seafood and listening to live music. Beats, eats (the hearty, delicious kind like snow crab legs, fresh fish sandwiches and fish tacos) and a view you won’t believe—it doesn’t get much better than this. Keep your seat through sunset—it’s beyond beautiful and you’ll get a complimentary Sunset Shot.

 

• You know what the phrase ‘hog heaven’ means? It describes a state of total happiness, and there couldn’t be a more perfect name for this Sports Bar & Grill, a late-night spot housed in a weathered wood structure right on the water. It’s got its own private beach and a biker bar vibe that makes everyone feel welcome. (Hog Heaven stays open until midnight during the week and until 2 a.m. on weekends, but given how great this place is you may want to start hanging out here as early as 11 a.m., when it opens.)

 

Dine (try the Ultimate Hog Heaven BBQ Sampler or Hog Burger) and drink (does a Hog-O-Rita sound ‘bout right?), inside or out. It’s all GOOD (the seafood, too)! One thing’s for sure though—wherever you choose to sit, you won’t want to stay there once the live DJ starts spinning or the live bands start playing. Dancing away the night—or wee hours of the morning—is a given here.