Feature

Summer Staycation: Sarasota Style

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By Ryan G. Van Cleave | June 2022


There’s no doubt about it—COVID brought a slew of new people to the sunny shores of Florida for good reason. This is a wonderful place to live, after all. But that means a lot of people are summering here for the first time in a “live where you vacation” environment. What can a grizzled old Florida veteran like me tell them (or other grizzled old Florida veterans who yearn for something new) about how to live it up staycation style? 

I’ve grouped the following options into four categories to help. Let’s start with the easy stuff and go from there. Ready?


Manatee Level: A.K.A. The Great Outdoors

Bike the Legacy Trail
This dog-friendly, multi-use trail is open year-around (6 a.m. to sunset) and takes you from the historic Venice Train Depot and all the way up to Payne Park in downtown Sarasota. If that’s too much walking (more than 15 miles!), bring a bike or rent one at Pedego, Siesta Key Bike & Kayak, Voltaire Cycles, or Bicycles International. Whether you’re biking, skating, or walking, take advantage of the regular drinking fountains and frequent shaded stopping points.

Parasail over Anna Maria
Working with a company like YOLO, you can fly single, double, or triple as you soar 400 feet above the Gulf of Mexico. Being up that high and seeing the dolphins, stingrays, and waves below? It’s breathtaking.

Geocache at Myakka River State Park
If you’re into sightseeing, the unspoiled wetlands are magnificent and rich with foliage and creatures of all types. But if you like geocaching—using GPS technology to find hidden “treasures”—this is the mother lode. With hundreds of places to find loot, you’ll want to give yourself plenty of time to roam and explore.

Lounge at Beer Can Island
A sandy stretch of beach that wraps around the northern tip of Longboat Key, this small island (also known as Greer Island) was created in the 1930s during the Intracoastal Waterway dredging. Low waves, little wind, and lots of manatees make this one of the best beaches around for relaxing, birding, or looking for shells or sand dollars. There’s no public bathroom, though, so keep that in mind.


Flamingo Level A.K.A. Destination Spots

Say “Cheese!” at Clyde Butcher’s Venice Gallery and Studio
Enjoy the stunning (mostly black and white) nature photos taken by an internationally known artist who’s sometimes called “the next Ansel Adams.” See his gallery, the darkroom, and plenty of amazing work created by this master photographer. Be sure to check out the images from Clyde’s visit to Salvador Dalí’s homeland as well as his dramatic work focusing on the Everglades. 237 Warfield Avenue, Venice

Enjoy the Wonders at the Marietta Museum of Art & Whimsy
It might have limited hours (1-4pm Tuesdays through Saturdays), but it’s well worth the stop. Founded in 2006 by Marietta Lee, the bright, colorful site is home to cool sculptures and truly whimsical artwork. Don’t miss the seashell/crystal/bead/pearl/marble archway! 2121 N Tamiami Tr, Sarasota

Rev Your Engine at Sarasota Classic Car Museum
Travel back through the history of the automobile in the second-oldest continuously operating antique car museum in the US. The History of Porsche and Ferrari exhibit has been extended through 2022, so that’s a real treat. For extra automotive fun, pop by next door to Vintage Motors and see what’s for sale there. Just don’t buy the 1955 Jaguar XK140SE Drophead Coupe—I’m saving up for it myself. 5500 North Tamiami Trail, Sarasota

Bargain Hunt at Red Barn Flea Market
This flea market has been in operation since 1981. With 80,000 square feet of shopping space featuring 500+ shops and booths, you’re likely to find something to buy, whether it’s fresh produce, vintage clothes and goods, hip shoes, or knick-knacks. If you get the munchies, fuel up at either of the two food courts. 1701 1st Street, Bradenton


Gator Level a.k.a. Food and Drinks

Sample Local Suds at Motorworks Brewing
Since 2014, this dog and family friendly venue has been producing first-rate beers. Make sure to try Pulp Friction (a grapefruit IPA), Gronkzilla Red IPA, or the Midnight Espresso Coffee Porter.
1014 9th Street West, Bradenton

Snack Away at the Donut Experiment
This isn’t your grandma’s donut shop! Here, each person gets an order sheet with three vital questions: icing flavor, topping, and drizzle. Then the magic happens. Watch the delicious treats be made before your eyes, or put in your order, walk along the pier, and come back a half hour later to get piping hot made-to-order donuts.
210C Pine Avenue, Anna Maria Island

Gnosh at Cha Cha Coconuts
After a day of shopping or hanging out at the beach, the carefree island atmosphere here is hard to beat. The grouper tacos are dynamite, but don’t miss the honey mustard sauce or the guava sauce—some of the best around! With outdoor seating and live music, and coconut cups you can keep, this is a fun, fun place. 
417 St. Armand’s Circle, Sarasota

Dine on the Rails at Bob’s Train
It’s a little tricky to find, but Bob’s Train is well worth finding. Taken together, four 85-foot railroad cars make up a restaurant that offers tasty, eclectic American food. The various cars from different periods also serve as a museum of sorts for local history, circus history, military history, and sports memorabilia. Of particular note is John and Mable Ringling’s second custom-built railway car, an all-steel unit built for them in 1916. The top item on the menu? The homemade potato chips that come with every sandwich. 2211 Fruitville Road, Sarasota


Panther Level a.k.a. Nightlife

Dive Wine & Spirits
While this could’ve easily fit in the previous category, it’s got such a vibe that it just belongs here. During the day, it’s a liquor shop with all you’d ever want for your drink-making needs. At night, there’s a cozy bar serving up well-crafted drinks. Try the tiki cocktails, but honestly, master drink technician James Dennis won’t treat you wrong no matter what you order. 2881 Clark Road #19/20/21, Sarasota

The Ugly Grouper
Let’s be clear, the grouper options here are tremendous, as are the Ugly Cheese Logs and Ugly Chicken Chunks. Being 100% outdoors, it can get hot however, so dress accordingly. Live music’s also on tap every day, weather permitting. No reservations, though, so plan to wait a bit! This place can be busy because the food is that good. 5704 Marina Drive, Holmes Beach

The Gator Club
Whether you want a vast selection of spirits or live music five nights a week, this fits the bill. If you want something more, pick your night for burlesque shows, karaoke, adult bingo, or more.
1490 Main Street, Sarasota

Haunted Sarasota Trolley Tour
For a different spin on the idea of nightlife, take a 90-minute ride on an air-conditioned trolley through downtown Sarasota to learn about its most haunted landmarks, spooky areas, and supernatural places. With a complimentary drink (wine or beer from the Trolley Cottage Tiki Bar) and a macabre costumed guide to recount tales of horror, murder, and the unexplained? It’s a night to be remembered. 1826 4th Street, Sarasota

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