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Holly Jolly Trolley Tours In December

a young boy wearing a costume

Discover Sarasota Tours brings back the Holly Jolly Trolley daytime tour with cocoa, carols & Christmas stories of Sarasota.

Perfect for families, this tour hosted by guide Jenny Jingle, will visit city spots with Christmas story connections, hear about our Sarasota traditions during the holidays & a sing along to favorite Christmas songs.

Includes FREE cocoa at the Trolley Cottage while you browse the holiday gift shop before the tour!

Holly Jolly Trolley Tours will run Wednesdays, December 16 and 23 at 11 AM, and Sunday, December 20 at 1 PM. $34.99 for adults and children 12+ | $18.99 for children 6-11 + tax and fees. Book online at:

Discover Sarasota Tours Gift Certificates make terrific gifts! Buy $100 in Gift Certificates and get $20 off with code XMAS through December.

All tours depart from DST’s charming Trolley Cottage (behind the Breakfast House, off Fruitville in downtown Sarasota). The Trolley Cottage features ample FREE parking, a fun Vintage Sarasota gift shop, and The ChillMobile, a vintage ice cream truck. To accommodate COVID-19 requirements, DST staff and guests will have their temperatures checked when they arrive. All guests must wear masks.


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Discover Sarasota Tours offers 14 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.