Now that there’s a chill in the autumn air, if you’re like me, you may be thinking about planning a winter vacation to a warmer climate.

Come October or November, that’s exactly what I do so I have something to look forward to when the snowy weather approaches in months like January, February or March.

For the past few years, my boyfriend and I have selected different spots in Florida to visit. We look for towns that have cultural and outdoor activities, good restaurants, nice lodging, soft sandy beaches and plenty of sunshine. Last year, we vacationed in Sarasota for the first time and thoroughly enjoyed our stay.

Sarasota Bay (as seen from the Marie Selby Botanical Gardens)

Sarasota Bay (as seen from the Marie Selby Botanical Gardens)

Sarasota ranks as a top best place to retire

We always toy with the idea of finding places to retire. Sarasota, on the southwest coast of Florida, ranks #2 in U.S. News 2019 Rankings of Best Places to Retire and #18 in its Best Places to Live Rankings. As U.S. News states: “Warm temperatures year-round, award-winning beaches and a thriving arts and cultural scene have made Sarasota a go-to place for retirees and families.”

In terms of its beaches, Siesta Key beach is “widely regarded as one of the best beaches in the world.” Both Travelocity and Doctor Beach awarded Siesta Key as “Best Beach in 2017.”

What to do in Sarasota: Some of my favorites

With an abundance of fun things to do in and around Sarasota County, it was challenging to pick and choose what to add to our schedule, especially since our visit was a short one. Here are five of my favorites:

1) Soak in the sun on Sarasota’s beautiful beaches

The six islands that line the gulf coast of Sarasota provide plenty of beautiful beaches to soak in the sun by day and watch picturesque sunsets at dusk. There’s Longboat Key, Lido Key, Siesta Key, Casey Key, Manasota Key, and Venice.

We stayed in the city in a renovated bungalow in Gillespie Park, a quaint area that is being gentrified. Most of the beaches were a short driving distance away.

One afternoon, we drove north over the bay bridge to Longboat Key, which is 12 miles long. It’s a quiet residential section with high-rises, golf courses and magnificent beachfront homes to ooh and ah over. Many of the beaches are private, but if you drive closer to the end of the island, you’ll find a public stretch for a nice walk.

Birdwatching is a popular pastime at Longboat Key beach

Bird watching is a popular pastime at Longboat Key beach

With just one strip mall with a few shops and a restaurant or two, the island has little in the way of commercial property  The Lazy Lobster is a popular place to dine and I’ve heard it has superb lobster dishes. Unfortunately, it was closed for lunch when we were there in early January.

For our second beach adventure we drove a bit further (about 20 minutes) to Venice, which was worth the ride. We had brunch at the Upper Crust Café & Bakery in the historic downtown. After filling up on delicious pastries and omelets, we drove to Venice’s Caspersen Beach for some exercise. The beach has hiking paths as well as boardwalks and a pier for bird watching.

2) See sensational horticulture at Marie Selby Botanical Gardens

The city is home to the Marie Selby Botanical Gardens, which has been described as “a tropical urban oasis featuring unparalleled horticulture displays.”

What to do in Sarasota: A mindful moment in nature at Marie Selby Botanical Gardens

A mindful moment in nature at Marie Selby Botanical Gardens

Even if you’re not a gardener, the bayfront setting will win you over as will the scenery at every turn – from the orchids to the rainforest, the epiphytes plants that grow attached to the trees to the meditation garden. It is an awesome place to relax surrounded by nature’s beauty. I highly suggest taking a guided tour to learn more about the horticulture and educational programs.

Selby Gardens recently announced a great new exhibit for 2020 featuring Salvador Dali: Gardens of the Mind, a collaboration with The Dali Museum in St. Petersburg, Florida. Open from February 9 to June 20, 2020, Selby Gardens will present Dali-themed lectures, performances, special tours, and other exhibit programs. It makes me want to book a trip to Sarasota right now!

3) Wander the grounds and gardens at The Ringling

As you travel around Sarasota, you’ll notice that there are quite a few streets and buildings with Ringling in their name. That’s because John Ringling, from the famous “Greatest Show on Earth,” and his wife, Mable, used to house the circus and live in Sarasota during the winter months. Since they had no children, when they died, they left The Ringling estate to Florida. Dating back to the early 1900s, it encompasses 66 acres of waterfront property.

What To Do in Sarasota: John Ringling's original train is on display at The Ringling Circus Museum

John Ringling’s original train on display at The Ringling Circus Museum

Currently governed by Florida State University, the estate includes: The John and Mable Ringling Museum of Art, with rotating exhibitions from around the world; a Circus Museum (Do go on a guided tour, it’s so much fun to learn about the Ringling Bros and Barnum & Bailey Circus); Ca’d’zan, the Ringling’s 56-room mansion; the historic Asolo Theater featuring a full schedule of films and performances; and an Education Center that offers extensive art and cultural programs.

The Bayfront Gardens are equally impressive, with Mable’s Rose Garden filled with 1200 rose plants; Mable’s Secret Garden where she, John and his sister Ida are buried; The Dwarf Garden with stone statues that John Ringling originally had brought from Italy; and The Estate’s Trees, filled with the largest collection of Banyan among other exotic trees.

There’s a formal restaurant for dining and casual outlets around the venue to grab a snack. And if you want to bring home a souvenir, it’s fun to browse through The Ringling shop.

4) Visit Sarasota’s vibrant downtown district

You won’t want to miss the vibrant downtown district. I recommend visiting the area on a Saturday, when there’s a Farmers Market from 9:00 a.m. to 2:00 p.m. It’s bustling with local fruit and vegetable stands, prepared foods vendors, and local artisans.

farmer's market in downtown Sarasota

The Saturday farmer’s market in downtown Sarasota

The downtown is filled with hip and cool restaurants and coffee shops – most with outdoor seating for alfresco dining. During our stay, we enjoyed happy hour at Boca Sarasota, a farm-to-table bistro known for its signature cocktails and yummy bar food. We also sampled lattes and breakfast sweets at the award-winning Pastry Art Bakery Café. The raisin bran muffins were so good, so good, so good.

Beyond the food scene, I encourage you to pop into some of the unique boutiques that line the downtown streets. Many are located between Main Street, Lemon Street and Orange Avenue.

What To Do in Sarasota: Unique boutiques and bistros line downtown Sarasota streets

Unique boutiques and bistros line downtown Sarasota streets

5) Indulge in the lap of luxury at St. Armands Circle

For indulgent high-end shopping and fine dining, St Armands Circle is the place to go. The upscale shopping center offers a wide selection of luxury fashion emporiums and fine dining.

Speaking of fine dining, there are so many restaurants to choose from that we went back to the Circle multiple nights, feasting on a fantastic coastal menu at Shore the first night and going with Greek cuisine the next at Blu Kouzina. Our moussaka and stuffed veggie entrees were such large portions that we brought home leftovers for the next day’s lunch.

Crab lobster salad at Shore restaurant is a work of art

Crab lobster salad at Shore restaurant is a work of art

A new four-level, 480 car garage recently opened at 57 N. Adams Drive providing much-needed additional parking: Another reason to return now that we don’t have to hunt for a parking spot.

Ready to book your winter vacation to sunny Sarasota?

After writing and reminiscing about my favorite things to do in this fabulous part of Florida, I’m eager to go back. Another draw in 2020: The new Sarasota Art Museum opens on December 15, 2019, which promises to be a “stunning” contemporary art museum.


  • Sarasota is an easy hour or so drive from the Tampa International Airport. In addition, there are seasonal direct flights into the Sarasota Bradenton Airport beginning in December or January. (Check dates with airlines such as Frontier or American Airlines.)

What’s appealing to the over-50 luxury traveler?

  • According to Visit Sarasota, the official tourism information bureau, about 60 percent of the population is 50+, making this part of Florida an attractive destination for retirees and snowbirds.
  • There is a wide variety of arts and cultural offerings and a vibrant and growing food scene in and around Sarasota County and downtown Sarasota.
  • January to April brings an influx of travelers to Sarasota, so book your stay early. There are plenty of places to stay ranging from budget to luxury properties. The good news is that last year several new hotels opened, and a great deal of business and residential development is going on in and around the downtown area, too.
  • The Visit Sarasota website provides timely information about arts and cultural offerings, places to stay, and beaches for planning your trip.

Take note 

When possible, make reservations in advance for dinner at restaurants that offer them. During peak season, the book up quickly even on weeknights.

If you are visiting off-season, be sure to call restaurants and attractions ahead of time to find out hours.

All photo credits (except for lead photo): Judy Freeman

Disclosure: The author received a complimentary Official Sarasota County VIP Pass to visit cultural venues during her stay. Regardless, she only recommends products or services that she endorses for her readers.

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