Sarasota’s Top Unique Restaurants

Sarasota is known for its diverse restaurants and fine cuisine. But what about a little whimsy to add to the mix? Sarasota Events Calendar culled some of the most interesting, unique places to dine, and came up with this list. To start, how about taking your kids on a restored, old-fashioned train for food and fun?

Bob’s Train is a restaurant located in four restored Pullman train cars. The menu features classic American fare, such as burgers, hot dogs, and milkshakes. Bob’s Train Restaurant is housed in four restored Pullman train cars, which were originally built in the early 1900s. Bob Horne, the owner of Bob’s Train Restaurant, has a passion for trains and circuses. He purchased the train cars in 2004 and began the process of restoring them. The restoration took several years, but Bob was determined to create a restaurant that would be both unique and enjoyable for his customers.

The restaurant opened its doors in 2007 and the train cars are decorated with circus memorabilia, and the staff is friendly and welcoming. The food is good, but the atmosphere is the real draw. Bob’s Train Restaurant is a fun and quirky place to eat, and it’s a great place to learn about the history of trains and circuses.

Here are some additional fun facts about the history of Bob’s Train Restaurant:

  • Bob Horne is a lifelong train enthusiast. He began collecting train memorabilia as a child, and he eventually amassed a large collection.
  • In 2004, Bob purchased four Pullman train cars that were originally built in the early 1900s. The cars were in disrepair, but Bob was determined to restore them.
  • The restoration of the train cars took several years. Bob worked on the cars himself, and he enlisted the help of friends and family.
  • Bob Horne is a passionate advocate for the preservation of train history. He is a member of the Sarasota Historical Society, and he has spoken at several events about the importance of preserving train history. Here is a short Youtube video highlighting Bob’s Train Restaurant.
    Bob’s Train Restaurant is a great spot to take kids.

    Cafe Barbosso is one of  Sarasota Events Calendar’s favorite, unique hot spots to go for excellent Italian food while simultaneously enjoying the sounds of a LIVE 17th piece jazz band, or watching local artists create paintings on easels while you dine.

    Cafe BarBosso motto is, “Eat, Laugh & Love or Else.” It is known for its classic Italian dishes with a modern twist, prepared by Chef Joe DiMaggio Jr., the former personal chef to numerous Hollywood A-listers and rock stars.
    The restaurant has a casual atmosphere with outdoor seating and – as stated above – live music
    from The Sarasota Jazz Project – a 17-piece big band that was founded in 2007 by George McLain.Sarasota Jazz Project is a high energy 17 piece jazz ensemble comprised of some of the finest musicians on the West Coast of Florida. These talented all-stars play both original compositions and standard tunes, creatively arranged in a unique contemporary Big Band style.

    For a great evening, dine outdoors at Cafe Barbosso on Friday or Saturday to listen to the live tunes, or take out food and tailgate in the parking lot with friends. Either way, it’s a dining experience found nowhere else!

    Here is a Youtube video of the jazz band playing outdoors at Cafe Barbosso.

    Sarasota Jazz Project, a 17-piece band of professional musicians, performs LIVE at Cafe Barbosso on the weekends.

Shoogie Boogies:  The name, alone, brings a smile to your face and beckons you to make a reservation. It’s also a restaurant that is a bit of a hidden gem, serving American cuisine with a creative twist. The menu features dishes like the “Shoo-Fly” burger, which is made with a beef patty topped with bacon, peanut butter, and banana. The atmosphere is fun and funky, and you have options in which to dine.

There are actually three separate areas in which to dine:  Garden Room at Shoogie Boogies  is a fabulous place to hold a special event and perhaps the most intimate and charming setting to be found anywhere else. The Garden Cottage includes a children’s photography studio, gallery, gift shop & cafe serving tea. The Courtyard is outdoors (weather permitting). All rooms are truly whimsical with luscious plants, twinkling lights and candles.

Florida Studio Theatre (FST) in the heart of downtown Sarasota is one of the major cultural resources in the Gulf Coast region, bringing the best in contemporary plays, musicals, and comedy to the Sarasota community since 1973. A professional regional theatre with the largest subscription base in the state, FST serves more than 230,000 live attendees each year across its six core is on our top list of places to go for cabaret, plays, shows and music. What makes it even more special is the fact that they have two separate restaurants in which to choose, one – a  full-service restaurant located in the Hegner Theatre Wing of Florida Studio Theatre and a Parisienne-style dinner theater located in the Goldstein Cabaret.

Green Room Cafe & Bar is a full-service restaurant located in the Hegner Theatre Wing of FST. The menu features American cuisine with a focus on fresh, seasonal ingredients. The restaurant also has a full bar with a wide selection of wines, beers, and cocktails.

The Goldstein Cabaret is a Parisienne-style dinner theater sits 100 guests and is open one hour prior to shows and features American cuisine with a focus on comfort food. The restaurant also has a full bar with a wide selection of wines, beers, and cocktails. Built in 1991, the Goldstein Cabaret has been home to such past original music revues as Friends in Low Places, Outlaws and Angels, Guitar Girls, Blue Suede Shoes, Piano Men, and more.

Florida Studio Theatre has two restaurants at two of their five sites in downtown, Sarasota.

Both restaurants offer indoor and outdoor seating, and they are open before and after performances at FST. They are also both popular spots for locals and tourists alike.

Andrea Martone

Andrea Martone is a former Arts & Entertainment Editor for the Sarasota Observer Newspaper Group, as well as a former Editor-in-Chief of a Long Island (New York) newspaper chain. She moved to Sarasota 14 years ago after working as an executive in NYC in public relations and marketing. She currently is a Public relations & marketing consultant and President of Insightful PR. She lives and breathes all things art, culture, music food and wine and is proud to be the Executive Editor of Sarasota Events Calendar.

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