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Love Stories Of Sarasota Returns!

a woman wearing a red hat

Celebrate Valentine’s Week with your sweetheart on the Love Stories Of Sarasota trolley tour, back for a second smashing year!

Guests will enjoy complimentary chocolates and champagne at the Trolley Depot while browsing through our Vintage Sarasota gift shop full of fun old-time treasures.

After taking a quick “love quiz,” guests will board the trolley to listen to love songs performed by Richard Caldwell and Lilian Moore and hear stories of famous Sarasota couples as portrayed by actress and tour guide Kathryn Chesley. During the tour Kathryn plays 8 different characters including Mable Ringling, Vernona Burns, and Marie Selby.

Love Stories of Sarasota runs from 7:30-9:00 PM on Thursday February 13, Friday February 14, and Sunday February 16.

Tickets are $35 per person, or Couples for $60. Ages 21+. Limited availability, so book now!

While waiting to board, visitors can also enjoy Discover Sarasota Tours’ Vintage Sarasota gift shop, with many featured items from local artists, and The ChillMobile, our NEW vintage ice cream truck.

Book online at or call 941-260-9818.



Discover Sarasota Tours offers 18 entertaining, interactive and informative air-conditioned trolley tours about the most interesting people, intriguing places, and amazing stories that have shaped Sarasota’s rich cultural past.

All tours depart from our charming Trolley Cottage (behind the Breakfast House off Fruitville in downtown Sarasota). The Trolley Cottage features ample FREE shaded parking, a fun Vintage Sarasota gift shop, and The ChillMobile, a vintage ice cream truck.