A Day in Downtown Sarasota

From breakfast spots to nightlife destinations, how to spend a day downtown

With the winter holidays approaching, many Sarasota residents will soon be looking for places to entertain out-of-town guests. Maybe you’re one of those visitors yourself, or perhaps you’re among the thousands of new residents arriving in Sarasota-Manatee, wondering what the area’s largest downtown has to offer.

Downtown Sarasota’s attractions may not have the name recognition of tourist destinations like our world-famous Siesta Beach or the John and Mable Ringling Museum of Art. Yet you’ll find an impressive array of restaurants and bars, as well as performing arts venues and late-night locales.

To get you started, we’ve assembled an 18-hour day in downtown Sarasota. Note: for this list, we’re not including the nearby Rosemary District or North Trail, two neighborhoods that could warrant their own separate days.

8 a.m.: Start off with the most important meal of the day and a dose of Old Florida charm at The Breakfast House (1817 Fruitville Road; 941-366-6860.) Recently celebrating its 10th anniversary, the breakfast and lunch spot is housed in a Floridian bungalow, as are its neighbors like German restaurant and beer garden Siegfried’s. The cottage provides a cozy setting for classic breakfast fare like their much-loved pancakes or Guinness-steeped corned beef hash and eggs. Breakfast House’s laid-back pace is part of its charm, but if you’re looking for something quicker, try Michelle’s Brown Bag Cafe on Main Street, whose tomato, mozzarella and basil bagel egg sandwich is my go-to breakfast in a hurry.

9:30 a.m.: Heading onto downtown Sarasota’s Main Street, there’s no better place to immerse yourself first than Pastry Art (1512 Main St.; 941-955-7545; pastryartbakerycafe.com). The cafe’s sidewalk tables along Main Street’s busiest intersection offer a prime people-watching spot. If you’re still hungry, it offers pastries and other breakfast bites, as well as many of the same sandwiches served at sister business Main Bar Sandwich Shop, one of downtown’s oldest and most beloved restaurants. A large coffee here is truly large, too, and less than $3. If you’re a coffee aficionado who cares more about quality than quantity, try O&A Coffee & Supply, the artisan coffee cart regularly found at the intersection of Main Street and Indian Place that also recently opened a storefront location.

11 a.m.: If you — like me — could spend a whole day combing through a bookstore’s shelves, A. Parker’s Books (1488 Main St., 941-366-2898; aparkers.com) is your refuge. The nearly 40-year-old store specializes in “scholarly, rare and antiquarian books,” including several first-editions. Yet there’s something for everyone in its vast collection, including vintage paperbacks and new-ish releases such as Amy Poehler’s “Yes Please.” Bookworms should also visit Bookstore1Sarasota, which sells new releases and has hosted events with Sarasota area resident Stephen King and other nationally renowned authors. And check out a historical marker in Five Points Park dedicated to Sarasota literary luminary John D. MacDonald.

12:30 p.m.: For a lunch spot that’s hip, healthy and delicious, check out the vegetable-centric restaurant Lila (1576 Main St.; 941-296-1042; lilasrq.com.) The menu is primarily vegetarian or vegan, but even meat-eaters should be won over with dishes like the deceptively simple macro bowl: a meld of chickpeas, kale, avocado and more over a tahini-turmeric dressing that’s teeming with flavor. Lila encourages customization, too, with add-ons including pork or vegan chorizo, a farm egg and more. A favorite lunch dish of mine is their mushroom burger, paired with a side of their addictive sweet potato steak fries. Not able to make it for lunch? No problem, as the restaurant also offers a great breakfast and dinner menu.

2 p.m.: Now it’s time to take a break from Main Street and head down to catch an afternoon matinee at Burns Court Cinemas (506 Burns Court; 941-955-3456; filmsociety.org.) Don’t let its humble, three-screen settings fool you: Burns Court is one of the most impressively programmed movie theaters in all of Florida, showing a wide array of international and arthouse films, including each year’s Oscar contenders. The theater has also recently started screening Netflix movies like “The Irishman” and “Marriage Story,” offering the chance to see these acclaimed films on the big screen as well as the comfort of your home. If you have time before or after the movie, take a walk around the artsy Burns Court neighborhood that gives the theater its name.

4 p.m.: The ideal day in Florida should at some point include sitting waterside while sipping a drink. In downtown Sarasota, that’s O’Leary’s Tiki Bar & Grill (5 Bayfront Drive; 941-953-7505; olearystikibar.com.) The casual spot — think drinks served in a plastic cup, picnic table seating and laid-back live music — sits on the sand overlooking Sarasota Bay, offering a prime spot to watch the sunset and maybe even catch a glimpse of dolphins. Palm trees and a thatched-roof tiki bar only help contribute to the tropical vibe. If you’re looking for somewhere slightly more upscale, there’s Marina Jack nearby. Wherever you choose, make sure to take a walk through Bayfront Park.

5:30 p.m.: There’s no shortage of good happy hours in downtown Sarasota, but not many offer drinks as inventive as those at Made Restaurant (1990 Main St.; 941-953-2900; maderestaurant.com.) Local cocktail craftsman Spencer Taliaferro helped design the rotating drink menu, with past concoctions including a margarita “umami” served over a mescal, mango, mint and sea salt-infused ice pop. You also have a standout selection of bar bites at Made (an acronym for Modern American Delicious Eats), which earned a spot on the Travel Channel show “Food Paradise” for its takes on comfort food classics. Favorites include the Pork on Pork on Pork mac-and-cheese (bacon, chorizo and pork shoulder with gruyere and parmesan) and cheesy tots.

6:30 p.m.: There’s arguably no more acclaimed downtown Sarasota restaurant than Indigenous (239 S. Links Ave.; 941-706-4740; indigenoussarasota.com). Chef Steve Phelps has been a semifinalist multiple times in the James Beard Awards, the culinary world’s version of the Oscars, and Vogue Magazine is among the national publications that have highlighted the restaurant. As its name implies, Indigenous puts an emphasis on sourcing ingredients from native Florida, particularly sustainable seafood from local fishermen, with its indoor and outdoor seating bungalow backdrop offering additional Florida flavor. After dinner, take a walk around the surrounding Towles Court artist neighborhood.

8 p.m.: After dinner, catch a show at one of several performing arts venues in the heart of downtown Sarasota. You’re most likely to find something to see at Florida Studio Theatre (1241 N. Palm Ave.; 941-366-9000; floridastudiotheatre.org), which features multiple productions of plays, musicals, cabaret programs and improv in one of its five theaters most days of the week. You’ll also find operas and other performances at Sarasota Opera House, housed in a historic building that hosted an Elvis Presley concert and premiere of the Sarasota-shot Best Picture Oscar winner “The Greatest Show on Earth” in the 1950s. And if you’re looking for something edgier, try the black-box Urbanite Theatre, which tends to host more contemporary and daring plays.

9:30 p.m.: Downtown Sarasota’s slew of rooftop bars offer multiple vantage points to look down on all the ground you’ve covered. In terms of the view, there’s no beating The Westin Sarasota (100 Marina View Drive; 941-217-4777) and its 19th-floor The Roof Bar and Eats, which offers a panoramic vista of downtown and Sarasota Bay. The view is gorgeous any time of day, but it turns into a hip hangout spot by night, with chic music and fire pits during colder weather. Art Ovation Hotel’s eighth-story Perspective Rooftop Pool Bar across the street is another popular late-night locale. And though Sage’s fourth-floor rooftop bar can’t compare to them height-wise, it’s housed in the visually striking and historic Sarasota Times building, and features the most creative cocktails out of the three.

11 p.m.: Pangea Alchemy Lab (1564 Main St.; 941-870-5555; pangealounge.com) sports a fun speakeasy-style setup: there’s no front entrance, with customers instead coming in through a back door in the alley. Yet as its name suggests, the bar’s real appeal is its inventive craft cocktails, overseen by owner and mixologist Brad Coburn. Drinks range from takes on classic cocktails like the Sazerac to boozy cereals made with milk and alcohol, with a sleek and dimly lit interior to sip them in. Pangea also offers upscale late-night bar bites like duck spring rolls and rabbit tacos courtesy of next-door restaurant Melange, another one of downtown Sarasota’s hippest spots that’s owned by Coburn’s partner Lan Bradeen.

12:30 a.m.: We’ll end our day at one of downtown Sarasota’s most historic establishments, as well as one of its most popular late-night spots: The Gator Club (1490 Main St.; 941-366-5969; thegatorclub.com.) Over its hundred-year history, this two-story brick building has been a Prohibition-era bar, a filming location for the Woody Harrelson movie “Palmetto” and supposedly even a brothel. Nowadays, it’s a neighborhood watering hole that offers two floors of entertainment by nighttime. The ground level has a stage that regularly hosts live music, while upstairs features a DJ spinning hits as well as a pool table. Gator Club closes at 2 a.m., and so does this trip downtown.

By Jimmy Geurts
Entertainment reporter