Table for One: A Guide to Solo Travel in Sarasota

Sometimes we travel alone, be it for work or for fun. Maybe the boss sent you out for a conference, maybe it’s research, maybe you need time to think and get away. For whatever reason, traveling alone is always different than traveling with others because you get to do whatever you want to do. No need to consider what the little ones need or what the significant other is begging for. It’s your time to be selfish and do whatever it is that makes you happy. That, however, is different for every person. Whether you want to mingle with the locals and chit-chat the day away or keep to yourself and take a break from the world, there’s a great way to spend a day – or days - alone in Sarasota.

Morning: Start Your Solo Day in Sarasota

With warm, sunshiny mornings like we have year-round in Sarasota, it’s a waste of a morning to not start with fresh, salty air on your skin. Enjoy the bountiful nature alone with a stroll down the beach (look towards the water and watch for dolphins and diving birds or look down and look for shells; here, neither is rude and no eye contact is necessary) or over the Ringling Bridge (those headphones and a purposeful gait tell others you’re not in the mood to chat and that’s okay). For a little mingling with your aerobics, a class at Fly Dance Fitness will get your blood pumping and your smile growing. Any potential embarrassment that comes from dancing in front of people disappears when no one knows you, and all that’s left is pure joy. 

We all have to eat, and breakfast is the most important meal of the day. Even if you’re alone, you don’t want to be cranky with yourself. Mind to yourself and grab a quick cup of joe and something for on the go from downtown’s Five-O Donut Co. The quirky shop adds a taste of local flavor without the need to sit and tête-à-tête. Across the street is Payne Park, where you can sit in solitude and anonymity, reading your book, finishing that presentation, or surfing the net in silence. If you’re alone but wouldn’t mind a little morning visit with a stranger-turned-friend, C’est La Vie on Main Street tends to attract  the friendly, loquacious crowd, where your new vacation acquaintance awaits. In-the-know residents dine here regularly at the outdoor tables and catch up on the latest local news over crepes and cappuccinos.

Midday: Explore Sarasota on Your Own

The world is your oyster and often the hardest part is deciding which oyster to shuck. The positive and negative about Sarasota is that it isn’t just one thing- it’s an eclectic mix of nature, culture, small town, and downtown.

Outdoor Adventures & Sarasota Bay

If nature tops your to-do list, Myakka River State Park is a must-see. This massive park boasts trails, boating, animal spotting, and activities for any age or desire. A lone adventurer can meander the paths for hours on end, never seeing another human, but spotting birds, reptiles, and mammals galore. Say hello to an armadillo, tell your woes to the gator (from a safe distance), or practice that conference speech on the deer.

It’s truly a shame to come to the home of the #1 Beach in America and not visit the water. Hop on Le Barge Tropical Cruise and you’ll get the ultimate tour of Sarasota Bay aboard the notorious boat, complete with bedazzled mermaid and live palm tree. With the close proximity and flowing drinks, guests on Le Barge tend to become quite friendly, quite quickly. It’s a great opportunity to ask the crew and fellow passengers about the city, the Bay, neighborhoods, architecture, and marine life. For a quieter angle to the water, throw in a few casts with the help of CB’s Saltwater Outfitters. From the beach or a bridge, cast on out and see what bites. It’s an unspoken rule of thumb that you don’t interrupt someone as he/she fishes, so unless you want company, you’re excused from getting it. If you do change your mind, though, and want to trade tips with the angler nearby, you’ve got an in for an easy conversation.

Museums, Gardens & Culture

Visiting the Ringling Art Museum is a must-do on anyone’s trip to Sarasota. Between the architecture, the extensive collection of art curated by John and Mable Ringling, the contemporary exhibits, the grounds, the circus museum, and the Ca’ d’Zan, there is something for everyone. Solitary visitors can traverse the grounds and the exhibits at their own pace, while docent-led tours offer insight and company for social butterflies.

Want someone to talk to and to learn a little something, something? The Sarasota Historical Society offers tours that tell of time gone by and how Sarasota became the outstanding place it is today, and Siesta Key Rum’s tours not only explain the formation of this intoxicating elixir, but offers plenty of samples. Both are guaranteed to spark a convo and ignite new friendships.

Don’t want to talk? No problem. Sarasota County is home to over 60 golf courses, including TPC Prestancia and University Park Country Club. Grab a club and swing in solitude.

Where to Eat Alone in Sarasota

Eating alone can be tricky. Some people don’t mind it, some dread it. If you’re on the latter team, there’s a combo that never fails – pop into downtown’s Bookstore1 Sarasota, grab the latest from your favorite author, and walk over to Brick’s Smoked Meats. With a book in one hand and a pulled pork sandwich in the other, it’s midday bliss. Stick around for another chapter and order their S’Mores for the perfect ending. The Selby House Café at Selby Gardens also offers solitary dining; order and enjoy on the grounds overlooking the Bay or under a banyan tree with anoles and butterflies as your company. When you’re finished, a stroll through the Gardens provides a peaceful reprieve from, well, everything. Social diners will find their match at tropical destinations - O’Leary’s Tiki Bar in downtown Sarasota and Daiquiri Deck on Siesta Key. The friendly crowd is always welcoming to newcomers, but be prepared to spend longer than you planned -  it’s always a party that’s just getting started.

Evening: Dinner, Comedy & Live Theatre

The standard evening involves something to eat and something to do. With a name like Arts & Central, it’s only appropriate that it’s the go-to dinner location for locals who want a lively, creative dining experience. I could sit outside with their Dirty Rotten Fruit Basket and Smoked Old Fashioned and people watch the Rosemary District all night. Follow up with a visit to McCurdy’s Comedy Theatre and Humor Institute, only a few blocks away. Laughter is universal, and you’re never alone when you’re sharing a joke. Care to keep to yourself for the night? No problem. Head to Boca and eat at the bar (bonus points if you bring your book from lunch) for outstanding food with minimal interruptions. Known for their artisan cocktails and creative, fresh menu, Boca will satisfy your cravings for good cuisine both now and later – grab a few things from their in-house market to store in your hotel room for late-night binges. Follow up with some culture at the West Coast Black Theatre Troupe or Urbanite Theatre, both downtown and both bursting with local talent. Don’t expect to see shows like you see at home at either of these establishments – this is Sarasota theatre at its best, and you won’t regret it. Sitting alone is no problem as you’ll be so engrossed in the show to realize whether anyone else is there or not.

Where to Stay as a Solo Traveler in Sarasota

“…to sleep, perchance to dream.” Whoever or whatever is keeping you away from the elusive sleep back at home isn’t here. No honeydo lists, no dogs begging to be let out, no waking toddlers, no morning commute to dread missing. A big bed that someone else will make and a dark room await and, with them, the promising potential of a good night’s sleep. For a place that has everything - pool, rooftop, gym, restaurant, walkable neighborhood - Aloft Sarasota  fits the bill. The location is fantastic and the amenities you want are there, without ever needing to leave. This is your time and don’t feel bad being selfish with it. Across the street is the Ritz-Carlton Sarasota, which offers a bit more activity with the same privacy. Take a trolley to their Members Beach Club to wade and bask away from the public beach crowds, enjoy a rub down at their spa, or head to their golf club for an exclusive round. Action Jacksons will find their crowd at the new Westin Sarasota, where 19^th story The Roof Bar + Eats is the current obsession with locals looking for a night out. The views of the city and Bay are stunning, be them seen from the bar or adjacent swimming pool. The hotel itself is located within walking distance to myriad restaurants, the Sarasota Bayfront, and downtown Sarasota, where all the action is. Then again, it’s your vacation, so you are the action.