A local’s guide to visiting the famous Siesta Key Beach and much more.
September 2, 2019
Sarasota, Florida is best known for its beautiful beaches including, namely, Siesta Key Beach. Siesta and its powdery cool sugar sand was named #1 Best Beach in America by Dr. Beach first in 2011 and again in 2017. It also received a similar accolade, #1 Beach in America by TripAdvisor Travelers' Choice™ awards for both 2015 and 2017. But there’s more to experience here in this Florida paradise including curious, crowd-drawing events, tasty culinary adventures, a rich arts scene, and a community filled with even richer people (both from a personality sense and the quite literal sense). There are serious opportunities to mansion gawk in case that’s your thing.
As a former 10-year local and a returning visitor, here’s a collection of places to see and explore in and around this beautiful coastal city.
First, a few geographical notes. Sarasota is a mid-sized city located an hour south of Tampa. To get there you’ll most likely fly into the Tampa International Airport. It’s by far the largest regional airport in the region though it is worth noting that SRQ, the Sarasota-Bradenton International Airport, now has eight airlines serving passengers. It’s probably going to cost more, but it might be a wash when you factor in transportation from Tampa such as a rental car, shuttle, or ride share option.
Sarasota itself is protected by three barrier islands—Long Boat Key, St. Armands, and Siesta Key. Generally speaking, most tourists stay on one of these three keys. But those willing to stay inland around downtown or outer Sarasota may experience a bit of a savings on a hotel or vacation rental, and the drive time out to the keys can be as little as 10 minutes or maybe closer to 20 to 30 depending on how far east you are.
things to see, taste, and experience
With so many options, here’s a categorical breakdown of the area’s most popular sites and surroundings to better plan your visit.
The John and Mable Ringling Museum of Art — Situated on waterfront property purchased by John and Mable Ringing in 1912 during the height of his circus-era success, the museum is now home to a distinguished art and cultural collection. Other highlights at The Ringling include the interactive circus museum featuring a 44,000-piece Howard Bros. Circus miniatures model, the 55-room Venetian Gothic style Ca’D’Zan mansion that was once the home of John Ringling and his wife, and the Historic Asolo Theatre which was founded in Asolo, Italy in 1798 and brought to Sarasota in the early 1950s and then later restored in 2006.
Marietta Museum of Art and Whimsy — One of the most curious and eclectic galleries I’ve ever entered. Donation-based and closed for most of the summer.
Sarasota Opera — A highly praised, internationally-respected institution performing within the gorgeous and historic Sarasota Opera House.
Sarasota Ballet — An internationally recognized full residential ballet company offering a diverse repertoire of choreography and performances.
Sarasota Cuban Ballet — World-class ballet training and performances in the tradition of the Cuban method.
Sarasota Contemporary Dance — Formerly Fuzion Dance Artists, they perform high-energy, modern dance interpretations and performances throughout the community.
West Coast Black Theatre Troupe — A professional theatre promoting and celebrating the African-American experience.
Florida Studio Theatre — A contemporary theatre presenting plays, cabarets, children’s theatre, and improv opportunities to the public.
Asolo Repertory Theatre — An adored local professional theatre company delivering contemporary and classic works along with musical theatre.
The Players Centre for the Performing Arts — Sarasota’s community theatre, delivering impressive classes, workshops, and shows in an intimate setting.
Towles Court Artist Colony — A neighborhood of artists’ studios and galleries featuring regular art walks and other fun events.
Sarasota Orchestra — This 80-member orchestra performs over 100 times a year and is one of the oldest in Florida.
The Perlman Music Program — Public concerts and events showing off their dedication to music training for the top talented string players of today.
Jazz Club of Sarasota — Over 90 local performances a year + Monday jazz cabarets + an annual festival.
McCurdy’s Comedy Theatre and Humor Institute — Dedicated to all things stand-up comedy, come here to see internationally-known acts and rising talent.
The Van Wezel Performing Arts Hall — The leading performance hall in the area, go here to see concerts, comedy shows, ballets, speaker series, and Broadway-style shows, among so much more.
area Festivals And events
Chalk Festival Avenida De Colores — Annual chalk festival with international artists, music, classes + huge, spectacular 3-D pavement illusions.
St. Barbara Greek Festival — This annual Glendi is a fun, multi-day event of traditional Greek food and dance.
Thunder by the Bay — An annual festival celebrating all things music and motorcycle.
Cortez Fishing Festival — A two-day waterfront commercial fishing fest with an Old Florida vibe and plenty of friend mullet.
Whiskey Obsession — Dubbed as the largest world whiskey festival in the US, this four-day event offers classes, tastings, bartender activities, and a street party in the heart of downtown.
Shark’s Tooth Festival — Fossils, artists, live music, food, and games in nearby Venice, Florida.
Sarasota Film Festival — A springtime film festival celebrating the art of cinema through red carpet events and parties with screenings at various local theaters along with other community events.
De Soto Grand Parade — A colorful and raucous parade celebrating Spanish explorer Hernando de Soto’s landing near the Manatee River in 1539.
Circus Sarasota — If you really want to experience what Sarasota’s circus legacy is all about, this is a must-see event worthy of planning a trip around. For around a month and usually in February and/or March, incredible international artists join to perform under a one-ring red and white Big Top.
Sailor Circus Academy — America’s oldest youth circus presenting several performances throughout the year.
Siesta Key Crystal Classic — A popular competition and festival since its arrival in 2010, this event features some of the best sand sculptors from around the world.
Savor Sarasota — A summertime culinary festival featuring culinary deals at some of the best dining spots around town.
The Marie Selby Botanical Gardens — Fascinating gardens—butterfly, bamboo, children’s rainforest, among others—along with a tropical conservatory, a historic mansion, and several other exhibits to visit on site.
Sarasota Children’s Garden — A whimsical garden and interactive play space with plenty of unforgettable sculptures for kids to climb on.
Payne Park Circus Playground — A circus-themed playground at the entrance to Payne Park. A skate park and walking/biking trails are also popular things to do right alongside.
Bayfront Park — Stroll along beautiful, waterfront pathways under Banyan trees. Take a picnic. Let your kids play in the children’s fountain. Watch the boats float in and out of the Bay. And last but not least, grab a drink at O’Leary’s.
Myakka State Park — Bicycle (or drive) along the tranquil meandering roads under the shady oaks and Spanish moss. Hike to the famous Deep Hole site saturated alligators. Stay in a rustic cabin. Camp. Take a boat tour. Fish. Geocache. Go birding. Explore the wildlife (and spiders).
Oscar Scherer State Park — Hiking, canoeing and kayaking, fishing, and bird watching are among the popular activities here at this quiet state park.
Kayaking + Paddle Boarding — Take a tour through mangrove tunnels, stand up on the still waters of Sarasota Bay, or get a core workout in out in the Gulf.
Parasailing — See Siesta Key Beach from whole new heights. There are multiple companies in town, and reservations are usually required.
MOTE Aquarium — Up-close views of manatees, sharks, and sea turtles, a stingray touch tank, and other cool exhibits like jellyfish and fossils make this a must-see destination for adults and kids alike.
Sarasota National Cemetery — Even if you don’t have a relative resting here, the grounds and public art installations including a photojournalism exhibition are well worth a visit.
Siesta Key Rum Distillery Tasting Room — Visit the tasting room and tour the distillery where this award-winning rum is made.
Break that fast:
Toasted Mango Cafe — A fun and friendly diner with fast service and absolutely delicious food to satisfy any craving.
Morton’s Market — Excellent coffees and teas, pastries, and every other baked dessert or treat you can imagine. Plus, grab and go meals for later. Perfect for vacationers who don’t want to cook.
Sun Garden Cafe — Walt’s Way Waffle w/bacon and pecans cooked inside… Need I say more? Outdoor + indoor dining right in Siesta Key Village.
The Breakfast House — A cozy, local favorite reminiscent of a New England cafe. Soak in the sun while starting your day on their porch or outdoor patio.
Sophisticated (and perhaps boozy) vacation/staycation lunch:
State Street Eating House — Fun, unexpected food and drink combinations to satisfy your inner foodie.
The Cottage — Seasonally-inspired dishes. One of my all-time favorites in town, their house-made plantain chips and paired sauces are worth the visit alone.
Walt’s Fish Market — Fresh fish market and restaurant. Hang out under their outdoor tiki for some of the best seafood in town.
Shore — A mid-century, al-fresco eatery with rooftop dining and a very hipster (albeit pricey) beach-inspired boutique below.
Michael’s On East — Upscale, white tablecloth dining with impeccable service and delicious everything.
Other lunchy fun:
Bangkok — Traditional Thai dishes that are both so yummy and well-priced that you’ll come back again and again.
Pho Cali — The best Vietnamese noodle house in Sarasota, no question. Take it from a local and get there before the noon lunch rush.
C’est La Vie — Croissants, french pastries, paninis, and salads. If that weren’t enough, their crepes are beyond excellent. Patio dining options right on Main.
Pacific Rim — Great sushi and excellent martinis in a dim and swanky dining space near Southgate.
Surf Shack — Fantastic tacos under @$5 each with open-air dining right on St. Armand’s Circle. Perfect for sipping margaritas and people-watching.
Cafe Epicure — Delicious eats like wood-fired pizza and a sleek atmosphere make this place one of the more popular indoor/outdoor dining spots downtown.
Happy hours/evenings out:
Social Eatery & Bar — Youthful, sophisticated dining and drinks with an outdoor dining and lounge area that is second to none.
Libby’s — Recently renovated local favorite with amazing everything. Moody Blue Kettle Chips and dreamy vegan options like Woodfired Cauliflower Steak.
Owens Fish Camp — Top-rated on Yelp, the incredible seafood plates and old Florida charm draw in a steady and loyal crowd. Make sure you’re willing to wait if you go at prime dining hours. Located in the historic Burns Court neighborhood, supposedly the Banyan tree out front was given to developer Owen Burns by Thomas Edison. Edison is famous, among other things, obviously, for transplanting a cutting of the world’s largest Banyan tree in India to his part-time home he shared with Henry Ford and their families in Fort Myers now known as the Edison Ford Winter Estates.
Phillippi Creek Oyster Bar — A full-on tourist draw but with absolutely some of the best seafood in town to back it up. Bring the kiddos. They’ll love climbing on the gator statue out front.
Siesta Key Oyster Bar — Known as SKOB locally, this place is definitely a Siesta Key favorite among locals and tourists alike. Dollar bills adorn the wood shack interior. The atmosphere is approachable, the food is better than you expect, and everyone seems blissfully buzzed.
Selva Grill — I love this place. Love, love, love. You can get great happy hour drinks and snacks in a low-lit bar, and/or you can head into the restaurant for a lovely dinner of Latin Fusion awesomeness.
Ophelia’s on the Bay — This waterfront dining spot has long held a strong reputation as one of Sarasota’s must-visit restaurants. A cringe-worthy check is to be expected but so is the inventive and memorable food.
JPAN — Fresh, high-quality, and inventive sushi options with two locations in Sarasota.
Blase Cafe — Locals adore this artsy, intimate martini bar and restaurant on Siesta Key. Opening soon is a sister location in Southside Village. Best news ever.
We just want drinks:
O’Leary’s Tiki Bar & Grill — Waterfront tiki bar with live music, beach-inspired cocktails, and a fun mixture of locals, liveaboards (literally, they live on their boats), and tourists. Dress down and get ready to sip rum with your feet in the sand.
Lido Beach Resort Tiki Bar — Situated directly on the white powdery calm of Lido Beach, this tiki bar is part of the swanky Lido Beach Resort but is also open to the public. Buy the $12ish rum runner and sneak a dip in one of their two pools or hot tubs. Shhh. Local secret number one.
Bahi Hut Lounge — The fourth-oldest tiki bar in the US, this ‘50s vintage dive bar is one you’d probably never go in unless you were taken or told. It’s part of the Golden Host Resort, an old Florida motel in northern Sarasota. Best Mai Tai ever. Sip slowly as there’s a two Mai Tai limit.
Jack Dusty — Probably some of the most expensive drinks in all of Sarasota, the craft concoctions + swanky atmosphere at The Ritz-Carlton Sarasota are well worth the hefty price tag. Some of their curiously named drinks include Smoked Painkiller, Swallow the Anchor, and Cat O’ Nine Nails.
Pangea Alchemy Lab — I’ve never been to this popular late-night spot, but I’ve heard amazing things. And their happy hour is later than most (6pm to 8pm) with numerous well-priced options that might just lessen the pain of your vacation overspending.
Here’s my favorite spots and recommendations to get the most out of your visit to Sarasota’s best beaches.
Siesta Key Beach
First and foremost, if you’ve never been to Siesta Key Beach and you’ll be visiting on a Sunday evening, one of the coolest experiences to be had is venturing out to the public beach at sunset for the crazy fun that is the Siesta Beach drum circle. Imagine fire jugglers, hula dance artists, wolf costumes, glowy everything—all to a free-flowing, rhythmic drum pulse as the sun sinks into the Gulf.
If that’s a no-go in your schedule, my second favorite beach experience at Siesta is parking somewhere around beach access #3 to #5 and then walking south all the way to what’s known as the point of rocks on the lower end of what becomes Crescent Beach. This walk is about four miles roundtrip, and it’s a lot less miserable if you hit it as early as you can—both for ease of parking and not sweating to death.
For all other general beach hanging, aim for arriving before 10:00 AM during peak season unless you LOVE parking frustrations. I personally prefer going even earlier than that. Even better, get there around 4:00/5:00 PM when everyone’s leaving for the day and stay until dusk.
A more approachable and easier access alternative to the more well-known Siesta Key, local’s love this quieter cousin located just about 10 minutes from downtown Sarasota. Depending on where you park, you’re within walking distance of the famous (and pricey) St. Armand’s Circle shopping district where you can pop in and out of boutiques featuring surf wear, local art, curiously brazen hot sauces, and about a thousand different varieties of ice cream and fudge.
Local’s tip: Score a spot in the lesser-known but locally-wise parking lot between the Lido Beach Resort and the public beach parking. You’ll be steps from the sand, and you can slip into the nearby resort for one of their amazing Rum Runners which you can carry directly onto the beach!