Since the Scots settled Sarasota in the 1880s, this slice of semitropical paradise has lured the rich and famous. Romanov Prince Mikhail Cantacuzène and his wife, Julia, granddaughter of President Ulysses S. Grant, moved here after the Russian Revolution. Stephen King, Dick Vitale and Katherine Harris are among the prominent personalities who call it home today.
Whether you gravitate to the outdoors (the city boasts more than 50 miles of waterfront property), the arts (every medium is represented here) or sporting events (such as the Modern Pentathlon World Cup), there are ample reasons to visit Sarasota.
Day 1
Evening
Kick off your weekend with happy hour (4 to 6:30 p.m.) at The Table Creekside. Though only a few yards from one of Sarasota’s most heavily traveled thoroughfares (U.S. 41), this spot offers the same intimate ambience you’d find at your best friend’s lake house. Whether you choose to dine indoors or alfresco, you can look out on Phillippi Creek, its surrounding neighborhoods, and the local gondolier (sì, he sings and wears a striped boat-neck shirt). Everything costs a mere five dollars, which can spur indecision and overindulgence. Avoid those tortures by ordering a bojito (basil, vodka, club soda, simple syrup, and lime), the bacon jam flatbread (topped with manchego and fontina cheeses and sautéed Vidalia onions), Chilean sea bass fritters (served with Key lime aioli), or spinach fondue (ask to swap the pita wedges with yucca mozzarella rolls). Then promptly remove the menu from sight.
Photo via Owen’s Fish Camp
For nightlife, visit Burns Court. This neighborhood of mostly stucco buildings, which date back to 1924, houses nearly 50 small businesses in its roughly 12 square blocks. On the second Friday of the month, (many of) the boutiques, art galleries, and salons keep extended hours and serve refreshments. End the evening at Owen’s Fish Camp. Don’t fret if you overhear the hostess announce an epically long wait (you’re likely too full to enjoy this heavy Southern fare anyway), for the real fun happens in the backyard of this cracker-style bungalow. Grab a beer, a jar of spicy boiled peanuts, and a seat at a picnic table, bar stool, settee or tire swing. Then unwind while local bluegrass groups perform tunes like “Wagon Wheel,” “Country Roads,” and “Landside” beneath strings of globe lights. If you get a little restless—play a round or two of corn hole, or roast s’mores over a fire pit.
Day 2
Morning
Avoid the crowds milling about downtown for the weekly farmer’s market. Duck into Lolita Tartine in the nearby Rosemary District for a basket of mini croissants and a cup of café au lait, and enjoy your petit déjeuner in peace.
Next, head over to Lido Key for a guided kayak tour of Sarasota’s mangrove tunnels and local wildlife, including sea birds, manatees, dolphins and rays.
Afternoon
Migrate two miles north to City Island, where you can dry off and refuel at New Pass Grill & Bait Shop, a restaurant that’s ramshackle in appearance but beloved for its juicy burgers and crispy onion rings. (Note: if your idea of vacation does not involve completely throwing nutrition to the wind, opt for the sesame ahi tuna at Café L’Europe on St. Armands Circle instead.)
Just down the street, you’ll find Mote Marine Laboratory & Aquarium, which includes manatee, shark, sea turtle, Florida bay and coral reef exhibits, as well as windows into Mote’s animal hospitals and sea horse conservation laboratory.
