Go Back in Time with These Vintage-Style Things to Do and Restaurants in Sarasota

Do you ever wish you could go back in time and enjoy the simpler days? When you visit Sarasota, you can!

There are tons of fun vintage-style things to do in Sarasota, as well as historic sites to see near Siesta Key, and they are all located within a short drive of our Siesta Key condo rentals.

Vintage Inspired Things to do
in Sarasota

Sarasota Classic Car Museum

The Sarasota Classic Car Museum is the ultimate destination for anyone who wants to take a trip back through time. This historic establishment has been recognized as the country’s second-oldest continuously operating antique car museum! This museum has been in business since the early 1950s and is a favorite destination for locals and visitors alike. They have all the brands and models you could think of, including American and European brands, exotic cars, and unique classics. Some museum exhibits rotate, so you can always expect to see something new every time you come!

Sarasota Tours

One of the best things about Sarasota is that you don’t have to drive everywhere to see the city. What better way to explore Sarasota than with a trolley tour? Discover Sarasota Tours offers both year-round and seasonal tours that will not only teach you about the most fascinating parts of Sarasota but will actually drive you right through them! You can opt for the classic City Sightseeing Tour or choose an excursion that’s a bit more unique, such as Circus Secrets of Sarasota or the Amish Experience Tour. No matter what you choose, you’re sure to be impressed!

Unconditional Surrender Statue

Everyone is familiar with the famous “V-J Day in Times Square” photo (taken by photographer Alfred Eisenstaedt) that depicts a soldier kissing a nurse in the middle of Times Square on the day that World War II ended. It’s perhaps one of the most famous depictions of vintage America. There is a beautiful statue of the classic moment right here in Sarasota! The Unconditional Surrender Statue stands 25 feet tall and is made out of Styrofoam. Local artist Seward Johnson is the talent behind the statue. Be sure to get your photo taken with it when you’re in town!

Siesta Key Restaurants With
Vintage Flair

Waffle Stop

Start your day off right, head out of your Siesta Key rentals and enjoy breakfast at Waffle Stop. What makes this establishment vintage, you might ask? Well, “The King” Elvis Presley himself once dined here! Come inside and see some incredible pictures of the musical talent. At the same time, you enjoy delicious menu options, including eggs, French toast, biscuits, country-fried steak, and tons of other classic American favorites. Everything is prepared fresh as you order it, making for the most mouthwatering meal you could hope for. If you want to copy Elvis, try to eat three eggs, three pieces of bacon, two pieces of toast, pan-fried potatoes, and three glasses of milk!

Bob’s Train

Bob’s Train is another amazing eatery in the Sarasota area. Nothing quite says “vintage” like enjoying a meal onboard a locomotive! This restaurant is situated inside four actual train cars, providing a totally unique atmosphere for your family meal. You can rest assured that the food is just as excellent as the location! Try a specialty sandwich like the Grilled Brie and Berry, get a mouthwatering Mushroom Burger or An Almost “Chicago” Dog, or come in for Sunday brunch to get a custom omelet or another egg dish.

Station 400

Station 400 offers an awesome old-school vibe with classic dishes for breakfast and lunch, so you can get some delectable dishes throughout the day! They have a convenient location in downtown Sarasota that’s just moments away from all the best attractions in the area. Every dish on the menu is made with delicious, fresh, local ingredients, and the chefs here are as creative as possible. From mini doughnuts to unique varieties of pancakes to all kinds of egg preparations, you’re sure to find something mouthwatering.

Yoder’s Amish Restaurant

If you’re searching for a simple but absolutely delicious meal, be sure to make a trip to Yoder’s Amish Restaurant. They offer every meal of the day and prepare every dish with love and care, and they’ve been doing so since 1975. Breakfast options run the gamut from eggs and cornmeal to Mom’s Homemade Sweet Roll. For lunch and dinner, come in to try the meatloaf, chicken salad, roasted turkey breast, Alaskan cod, and more. Everything is reasonably priced and sure to leave you satisfied.

Der Dutchman

Finally, Der Dutchman has all kinds of delicious offerings, whether it’s breakfast, lunch, dinner, and dessert, all made fresh in-house. Sit down for a hot and savory meal or grab a quick pastry to go to get your day started. They also have a convenient carryout menu and a family-style carryout menu, so you can enjoy delicious food all from the comfort of your Siesta Key rentals. From sandwiches to roast beef to seafood and everything in between, you’re sure to find something amazing to enjoy.

Speakeasy Bar

There’s no better way to take a step back in time than enjoying a delicious drink in a speak-easy. Be sure to make a trip to Rudolph’s for some of the most unique concoctions and the most beautiful décor and atmosphere. The bar and lounge area feature a distinctive mid-century modern flair that is sure to impress, whether you want a casual night with your friends or a romantic date night with your sweetheart. 

Rudolph’s offers unique specialties that you won’t find anywhere else alongside classic beverages with a new twist. Although Rudolph’s is located with The Modern hotel, it definitely has a vintage flair!

Shop Vintage

You don’t have to stop your vintage adventure with food and drinks. You can go shopping around the Siesta Key area, too! Rosemary Indie Market is an incredibly monthly market that takes place downtown, offering all kinds of amazing foods and wares from local artists, entertainers, designers, and more. This is a family- and pet-friendly event with free admission and parking, so it’s perfectly accessible for anyone. They only have 28 vendor booths, so the whole experience is incredibly intimate. 

Another fantastic shopping destination is The Bazaar on Apricot and Lime. More than 30 local vendors gathered to sell their clothing, jewelry, furniture, home décor, and more. This indoor indie market not only has amazing wares, but they also have live music throughout the afternoon, as well as tons of terrific classes that you can participate in! Best of all, if you find that you really enjoy The Bazaar on Apricot and Lime, you can also purchase from them online once you get home!