How (and Where) to Have a Grown-Up Fall Break

Sep 6, 2019

Long favored as a hot spot for families, The Beaches of Fort Myers & Sanibel is quickly picking up grown-up cred as well. An impressive new brew trail and burgeoning restaurant scene (Uzbek kebabs with your tropical getaway, anyone?) now round out the area's big draws: laid-back coastal vibe, copious nature preserves, vibrant artisan culture and, of course, some of the world's most beautiful stretches of shoreline.

If other getaways are all about “woo!” here’s a spot that's simply about “wow.” So pack your carry-on bags (flip-flops may well be the only shoes you'll need) and grab your favorite travel partner—then use these tips for a gloriously grown-up escape.

Start at the end

...of the day, that is. Whatever's on the docket, you'll want to plan your entire day around sunset. The event is so spectacular here that, as daylight wanes, you'll want to be well-positioned on the waterfront, preferably drink in hand and toes in the sand. If you're lucky, you'll catch the legendary green flash—a fleeting splash of color just as the sun slips into the Gulf of Mexico.

It's hard to go wrong with just about any west-facing vantage point in the area, but one clear favorite is Captiva's Mucky Duck (so much so that the pub's website publishes sunset times and images from a beach cam, so you can monitor the situation for yourself). Park yourself at a picnic table there, order up a local brew—the Last Laugh IPA is a current crowd-pleaser—and prepare for greatness.  

Other ideal vantage points include the Fort Myers Beach Pier and Turner Beach, but wherever you decide to sunset-spectate, linger by the water for a while, then look up. There's incredible star-gazing, especially away from the mainland. In fact, Sanibel Island is so serious about starry nights that a local ordinance requires all outdoor lights to face down to limit light pollution.


Savor some grown-up grub

The sun may be down, but the night is young. In a place that offers more spectacular seafood than you can shake a fishing pole at, you've got some serious eating to do. 

As for how that bounty is prepared—and what accompanies it on the menu—you'll find amazing variety and creativity, especially with a food scene on the rise.

Despite the name, the Original Shrimp Dock Bar & Grill is a new addition to the dining scene on Fort Myers Beach. Set in an old shrimp packing facility, the restaurant serves up generous amounts of "pink gold," aka Gulf shrimp. (You'll find around 20 shrimp-adorned menu items, including a decadent white pizza with ricotta, Gulf shrimp and scallops.) The 600-square-foot waterfront patio is one new aspect of Yucatan Waterfront Bar & Grill on Matlacha, but the cracked conch remains the go-to on the updated menu. For an old reliable, try the unassumingly named fish stew (shrimp, scallops and more in a tomato saffron broth with Pernod aioli) at Sweet Melissa's Cafe on Sanibel—though you may be tempted by the seared scallops with pork belly and fig and bourbon jus, or the espresso-chili crusted tuna.

Of course, your options are not limited to seafood spots, or for that matter, Gulf cuisine. Case in point: Silk Road, a new favorite in Fort Myers, where you'll find Uzbek blinchik (savory crepes that could pass for egg rolls, until you bite into them), kebabs (if you're wracked with indecision, try the lulya, a blend of beef and lamb) and palov (similar to pilaf, but way more gussied-up than any version you've likely tried). To enter a different world altogether, go down the rabbit hole at the Wonderland-themed—but still romantic—Mad Hatter Restaurant on Captiva, where the water views alone are worth the trip. The menu changes often, but if dayboat scallops are on it, run, don't walk, there. For dessert, find a spot that serves Queenie’s ice cream, and ask for the Key Lime Pie flavor—like a palate-cleansing sorbet, but yummier.


Get your brew on

In the span of a few years, this area of Southwest Florida has gone from a drought of local drafts to a microbrewery mecca—more than a dozen brewers call the region home (with a rum distillery thrown in for good measure). 

It's hard to pick a bad brew among the bunch, but local favorites include Fort Myers Brewing Company (the first in the region, and home to the famed High 5 IPA), Bury Me Brewing (try the Hell-bound Honey Brown) and Millennial Brewing Co.'s fun 6,300-square-foot downtown Fort Myers location (try the Tactical Penguin). 

For a guided, open-air brew tour, catch a ride on the Pedal Pub in Cape Coral. Whether you show up with your own group or join one, everyone pedals the party bike through downtown from Big Blue Brewing to Big Storm Brewing Co. Come prepared with your beverage of choice or load up during the stop at Craft No. 3.


Join the in crowd on the Outer Islands

Those in the know venture off the mainland for quick day or overnight trips to the region’s outer islands. With 100 islands dotting Estero Bay, Pine Island Sound and Charlotte Harbor, the biggest challenge might be fitting everything in.Rent a boat, call a water taxi or book an island-hopping tour to maximize your island time. The sands of North Captiva Island are a seashell hunter’s treasure trove. Enjoy Cabbage Key's old Florida feel (and we do mean old; the Cabbage Key Inn and Restaurant is actually built on a Calusa Indian shell mound). Take a couple bucks to tape on the wall at the Dollar Bill Bar, then climb the island's water tower for a panoramic view. To really go off the grid, dock at Cayo Costa State Park, a barrier island with 9 miles of undeveloped beach, plus campsites and primitive cabins for anyone who's in no rush to get back to civilization.


Don't miss Downtown

Much as you'll love the sleepy vibe of the outer islands, the Fort Myers River District—a hub of festivals, art events, concerts, shops, bars and restaurants—makes for a nice contrast.If jamming is your jam, time your trip to the Music Walk every third Friday of the month, when musicians line the streets to give your night an eclectic soundtrack.

Visual art gets its day, too. The first Friday of each month, to be exact, as you'll find during the Art Walk, when First Street closes to traffic and local galleries stay open late. One can't-miss that stuns by night: the Jim Sanborn light sculpture Caloosahatchee Manuscripts in front of the Sidney & Berne Davis Art Center. 


Think outside the gym

There's something to be said for lazy days by the gulf (we'll get to that soon), but with an abundance of parks and preserves in the region, getting a workout in the wilderness is easy and fun.

Rent a tandem kayak (if either of you is a control freak, that person should ride in back) and paddle through mangroves for a few of the 190 miles of the Great Calusa Blueway. You can take a guided tour from the likes of Tarpon Bay Explorers, or venture out on your own (though a manatee may show up as your third wheel).Back on terra firma, you'll find bountiful bike-friendliness: Sanibel has 25 miles of bike paths (some within the 6,400-acre J.N. "Ding" Darling National Wildlife Refuge), Cape Coral has 90 miles, and you can even ride on the hard-pack sand of Fort Myers Beach. For wheels, stop by one of the local rental shops on Fort Myers Beach.


Get your groove on

80+ musicians. 20+ venues. 10 days. Zero admission fees (at least for the majority of the shows). That's the Island Hopper Songwriter Fest (Sept. 20-29) by the numbers—but the fun you'll have? Infinite. This year's genre-spanning lineup includes everyone from Gone West (lead singer: multiple Grammy-winner Colbie Caillat) to country superstar Rodney Atkins.

A number of the venues are so intimate, you'll find yourself interacting with the performers (but that same intimacy means you should show up early for the shows you know you don't want to miss—as seating's limited). And look for deals at the local hotels, where discounts go up to 30% during the festival.


Have a shell of a time

If Sally sells seashells by the seashore, then she probably has a shell shop on Sanibel Island. And while you'll be drawn to the boutiques across the island that feature shell-bedecked art and tchotchkes, you can pull in a pretty good haul yourself directly from the sand.Thanks to Gulf and Caribbean currents, the east-west beaches of Sanibel and Captiva islands are shell central, blanketed in bivalves that arrive in pristine condition. And once you start identifying alphabet cones, lightning whelks, lace murices and dwarf arrow tritons, you'll soon be doing the "Sanibel Stoop" (walking with your head parallel to your waist) in pursuit of them. For the best luck, arrive at low tide, when you may be able to walk farther out to sand bars and shallow pools (awesome shelling grounds). The Blind Pass strait between Sanibel and Captiva is a particularly rich spot.

After shelling to your heart's content, you'll find plenty of great spots to just laze on the beach, especially if you're willing to go the extra mile. The beaches of Boca Grande on the south end of Gasparilla Island are uncongested and come with historic lighthouses. A quick trolley ride from Fort Myers Beach takes you to Lovers Key State Park, an undeveloped barrier island with 2 miles of beachfront bliss (and a popular wedding spot, so bring your finest flip-flops if you'd like to crash the party). If you prefer your beach to be out the front door of wherever you're staying, you'll find plenty of beachfront resorts and cottages to choose from.


Expect the unexpected—in a good way

It could be the Bubble Scouts waiters in boy scout uniforms serving you a gigantic slice of orange crunch cake at the Bubble Room on Captiva, or the Crayola-colored cottages lining Matlacha's main street, or the 28-foot-tall "Big John" statue greeting visitors to Cape Coral.

In a place where golf carts can outnumber cars, the ocean brings daily treasure ashore, and you’re more likely to find a mom-and-pop shop than a chain store, just about everything has a cute little quirk (much like the person you're vacationing with). 


Ready to go? Find more inspiration on The Beaches of Fort Myers & Sanibel Instagram or request a visitor's guide to start planning your grown-up getaway.

Camille Guzman contributed to this story.

Related Offers Related Offers & More

More Great Deals & Tips

** Advertisement