15 Fun Things to Do in Sarasota Florida

Some of my favorite things to do in Sarasota Florida include some of the best beaches in the world, a walkable downtown with abundant culture, cool museums, phenomenal state parks, and luscious #USGulfCoast weather.

This article focuses on the southern end of Sarasota County, including Osprey FL and Venice FL, and on natural attractions. Even lifelong Sarasota visitors and residents will learn about a couple off the beaten path places to include on future Southwest Florida explorations.

Thank you to Visit Sarasota for hosting McCool Travel.

15 Fun Things to Do in Sarasota Florida

1. Fun Places to Stay in Sarasota

The latest Sarasota hotel I stayed and absolutely adored is Art Ovation Hotel. It has a magnificent downtown Sarasota spot, near the Opera House and Main Street shops and restaurants. The creative, artsy theme will keep your interest. Make sure to try Sarasota’s newest restaurant, Tzeva, featuring healthy Mediterranean cuisine.

Art Ovation Hotel Sarasota ukulele
enjoy in-room use at Art Ovation Hotel

Golden Host Resort is an old Florida themed motel on Tamiami Trail between downtown Sarasota and the airport. The highlight is Bahi Hut which is Florida’s oldest tiki bar and the third oldest in the US.

Another recent Sarasota hotel where I stayed, and loved, is the Home2Suites across from the Sarasota airport control tower and next to the USF campus. I would definitely stay here again. Love the spacious and quiet rooms, suites (full size refrigerator, dishes, dishwasher), and convenient location. It is ideal for multi-night stays. There is also a Hilton Garden Inn right behind the Home2Suites.

When looking for a place to stay in the southern portion of Sarasota county, consider Casey Key Resorts in Osprey FL. It was formerly called Bentley’s Boutique Hotel. All ground floor rooms have a patio and all upper floor rooms have a balcony.

Check out my video tour of a Casey Key Resorts room.

This convenient south Sarasota hotel offers free breakfast and is located less than a mile from to Oscar Scherer State Park and close to Venice Beach and Siesta Key. The pool area is the centerpiece, with a tiki bar, beach area, and common space.

pool area at Casey Key Resorts Sarasota
pool area at Casey Key Resort Sarasota

2. Sarasota Bayfront

A short stroll from Sarasota Farmers Market is Sarasota Bayfront Park featuring some amazing oak and banyan trees. It is a wonderful area to walk around. Walk through Five Points Park between Whole Foods and the Sarasota Bayfront Park for another nice tree scene and read some local history on the park plaques.

magnificent oak tree at Sarasota Waterfront
magnificent oak tree at Sarasota Bayfront Park

Look for cool street art as you walk around Sarasota.

public art at Sarasota Waterfront
public art at Sarasota Waterfront

3. Sarasota Farmers Market

Since 1979, Saturday mornings are all about the Sarasota Farmers Market. Give yourself a vitamin C jolt with a fresh squeezed orange juice for $1 a cup. There are dozens of local vendors with fresh produce, citrus fruit, crafts, prepared foods, and more. This is the place to see and be seen!

every Saturday morning is the amazing Sarasota Farmers market
every Saturday morning is the amazing Sarasota Farmers market

4. Mad Moe’s Pub & Grill

After being in Florida for about a month, my car was definitely in need of a bath. Why do I tell you this? Well, the second time I went to Mad Moe’s (for consecutive lunches, yep!), a sparkling, new, shiny, pristine Rolls Royce parked next to us.

The juxtaposition was interesting and cool because Mad Moe’s is definitely a locals place and not upscale. But it shows that everyone likes Moe’s! The Cuban sandwich is amazing. Fish tacos are fantastic. Sit at the walk up bar for the best of both worlds—great people watching spot, interact with the bartenders, and enjoy some great food and drink.

Cuban sandwich at Mad Moes in Osprey Florida
Cuban sandwich at Mad Moes in Osprey Florida

5. Venice Fishing Pier

The 700 foot Venice Fishing Pier seemingly spills out from Sharky’s on the Pier, which is the only waterfront restaurant in Venice FL. The pier is a cool place any time of the day but especially at sunset, when you have very long shadows.

Venice Fishing Pier Sarasota FL
long shadows at sunset on Venice Fishing Pier in Sarasota county FL

6. Venice Beach Florida

If nothing else, I will always remember Venice Beach FL for the place I captured a sunset photo with a heart reflection. How wonderful is that?

heart sunset in Venice Beach Florida
heart sunset in Venice Beach Florida

But Venice Beach itself is quite lovely. A wide stretch of sugar sand allows plenty of room. Which is great because it is a popular place to be at sunset.

Venice Beach FL sunset
Venice Beach FL sunset

7. Caspersen Beach

Most people come to Caspersen Beach to find shark teeth. I loved seeing the “regular” beach sand here, so different than the typical #USGulfCoast sugar sand. Huh? Why? Inquiring minds want to know.

Caspersen Beach is promoted as the natural beach—and I do not mean clothing wise. Hmmm, or maybe that IS what they mean.

No, I am pretty sure they mean because the sand is darker. Caspersen Beach also has hiking trails and boardwalks to see wildlife and birds. Ah, that is the natural element!

Caspersen Beach Sarasota FL
Caspersen Beach Sarasota FL

And finding shark teeth at Caspersen Beach is one of my favorite Cool US Gulf Coast activities.

8. Cafe Venice

Once I saw Bloody Margarita on the Cafe Venice menu, I had to try it. Honestly I do not remember what made it bloody but I believe it was some Malbec.

bloody margarita (with Malbec) at Cafe Venice Florida
bloody margarita (with Malbec) at Cafe Venice Florida

Like most places along the Florida Gulf Coast, fresh fish is the thing to order and snapper and grouper were the right choices during my visit. A caprese salad with a generous portion of pesto started things off right.

9. Best Places to Watch Sunset in Sarasota

Siesta Key beach often is honored with the best beach designation but you should visit for more than just the soft, white sugar sand. Arrive about an hour before sunset and let your ears guide you to one of the most interesting daily spectacles you will find anywhere in the world. On my last visit, hundreds of people gathered around the Siesta Key drum circle, complete with dancers, drummers, funness for all types and ages, and, yes, a little funky odor.

Siesta Key FL sunset drum circle
Siesta Key FL sunset drum circle

Check out this video of the Siesta Key sunset celebration drum circle.

One enterprising young lady pulled a wagon full of Girl Scout cookies for sale. Absolutely brilliant. But the star of the show is the sunset so make sure you see it. It is real and it is magnificent.

Siesta Key beach sunset
Siesta Key beach sunset

Siesta Key is a Favorite Gulf Coast Spring Break Destination.

Besides Venice Beach (see above) and Siesta Key, another fabulous spot to see sunset in Sarasota is at Centennial Park, just north of Van Wetzel. Here you will find more than enough free and convenient parking, plenty of benches, bathrooms, and an ADA compliant area.

spectacular Sarasota sunset
spectacular Sarasota sunset at Centennial Park

10. Siesta Key Oyster Bar

Come to Siesta Key Oyster Bar for the oysters, stay for the paella. OK, also come to this popular Gulf Coast beach bar for drinks, as SKOB makes a killer Dark & Stormy. They also carry a great selection of Florida craft beers. And make sure you have at least one dollar bill for each person in your party. You will find out why when you visit!

Siesta Key Oyster Bar near Sarasota FL
Siesta Key Oyster Bar near Sarasota FL
paella at Siesta Key Oyster Bar
paella at Siesta Key Oyster Bar

11. The Original First Watch Restaurant

You may have dined at a First Watch Restaurant or several dozen but have you been to the FIRST First Watch? Well, my friends, this is it, the original First Watch. Ta da! Bonus is that this First Watch location offers waterfront seating. I know, what could be better than al fresco breakfast. The answer is NOTHING so y’all have to go here.

original First Watch Restaurant Osprey FL Sarasota
have breakfast at the original First Watch Restaurant in Osprey FL Sarasota

Some other great places to eat in downtown Sarasota include SoFresh (also with locations in Lakewood Ranch and five in Tampa), Circo (taco and bourbon bar), and 99 Bottles—all across the street from Whole Foods. There is free parking in the garage in front of Whole Foods.

Some classic Sarasota places I want to try include Cafe Baci, Alpine Steakhouse, Owen’s Fish Camp, Phillippi Creek Oyster Bar, and Antojitos La Michoacana. Let me know if you have tried these places or have any other favorite Sarasota restaurants.

12. Oscar Scherer State Park

As one of the last remaining Florida scrub habitats in southwest Florida, Oscar Scherer State Park is a natural wonder, fun hidden gem, and valuable environment. A popular Sunday morning Florida scrub jay hike led by Ranger Tony led to many sightings of the endangered bird (the only bird found exclusively in Florida) but also a few bald eagles and other migrating birds.

The park has many other hiking trails, a very popular campground (reserve well in advance), and a robust itinerary of talks, walks, and events.

Florida scrub habitat at Oscar Scherer State Park
Florida scrub habitat at Oscar Scherer State Park

Later, Tony led us on a fun kayak tour along South Creek, educating us on more habitat features. I saw great blue herons and other wading birds, wonderful oaks, and YES a gator! For a fun experience, sign up for one of the guided night paddle events.

kayaking Oscar Scherer State Park
kayaking South Creek Sarasota Oscar Scherer State Park

For more information, see 8 Great Things to Do in Oscar Scherer State Park

13. Legacy Trail

Nearly a quarter of a million people use the 14 mile Legacy Trail every year and there are currently discussions to extend it another 30 miles. Yippee! My rental bicycle from Venice Bikes and Trikes were delivered to the Oscar Scherer State Park trailhead. After my kayaking liquid road trip, I biked the Legacy Trail and then locked up the bike when I finished. They picked them back up later. So convenient.

Legacy Trail in Sarasota FL
Legacy Trail in Sarasota FL

I love that Legacy Trail passes through natural areas, has access points and trailheads at several parks in Sarasota county, and crosses over water.

bike riding Legacy Trail in Sarasota
bike riding Legacy Trail in Sarasota

14. Historic Spanish Point

The Historic Spanish Point area was settled in 1867 by the Webb family from New York state, told of this section of higher ground land on Little Sarasota Bay by a Spanish merchant. The Webbs thus named it Spanish Point in honor of him. In 1885 Webb’s Winter Resort was the first tourist resort in this area and northerners flocked here to escape the winter cold. Now 30 acres of lush gardens, historic buildings, and archaeological sites.

McCool Travel tip: In the historic homestead, pay attention to the original wood floors. I will definitely one day include it in my Cool Floorida Spots article, along with the Dade County Pine floor at Museum of the Everglades and a few other secrets. Please let me know about other fun and cool Florida floors!

Historic Spanish Point in Osprey FL Sarasota
Historic Spanish Point in Osprey FL Sarasota
oaks at Historic Spanish Point Sarasota
beautiful #USGulfCoast oak trees at Historic Spanish Point Sarasota

15. Baltimore Orioles Spring Training Site

Starting mid-February, Sarasota rolls out the banners to welcome Baltimore Orioles fans to Spring Training practices and games. “Home” games are played at Ed Smith Stadium, about 5 miles from I-75 and less than 1 mile from downtown Sarasota.

Home of the Orioles banner for Spring Training

Where is Sarasota FL?

Sarasota is located midway between Tampa and Fort Myers Beach. Go south from Anna Maria Island and north from Punta Gorda to visit Sarasota. It is about a two hour day trip from Tampa and about the same time to drive between Orlando and Sarasota.

Day Trips Near Sarasota FL

Located between Tampa and Naples, Sarasota is a magnificent Southwest Florida Gulf Coast destination. Captiva Island, Anna Maria Island, Punta Gorda, Lake Placid, and Indian Rocks Beach are easy day trips from Sarasota. Plan your Southwest Florida US Gulf Coast getaways with these guides:

Other Places to Visit in Sarasota

There are many other amazing and cool things to do in Sarasota and I just scratched the surface here. Hopefully it provides you an idea of the variety of funness to experience there. On future trips, I hope to explore some of the following Sarasota attractions and discover even more.

If your favorite Sarasota beach, place to eat, or secret place is not listed, please let me know.

Other places on my wish list of places to visit in Sarasota include:

  • Marie Selby Botanical Gardens
  • Myakka State Park
  • The Ringling Museum
  • Ca’ d’Zan
  • Lido Key, St. Armands Circle, and Longboat Key
  • Big Cat Habitat
  • Mote Marine Laboratory
  • Jungle Gardens
  • Many Sarasota Restaurants (Tell Me More!) …
  • Owens’ Fish Camp, Selva Grill, Walt’s Fish Market, Mirna’s Cuban, Yoder’s Restaurant and Amish Village, and Indigenous Restaurant

What are your favorite things to do in Sarasota, Florida?

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