Sarasota: Trolley holiday music tour with caroling & lights

Summary

Holiday songs, Sarasota lights, and a trolley full of laughter

You’ll board an air-conditioned trolley in Sarasota for a 75-minute ride filled with live holiday music, stories from your local guide, and glowing downtown lights. Sip wine or soft drinks before departure and join in caroling down Main Street—moments you’ll remember long after the last note fades.

What’s the experience like?

We climbed onto Dolly the Trolley just as dusk was settling over Sarasota — you could already hear the performers warming up somewhere behind the gift shop, their voices drifting out with the smell of cinnamon from someone’s cup. Our guide, who actually goes by “Christmas Carol” (I thought that was a joke at first), waved us in with a grin and a sparkly scarf. Kids were clutching their soft drinks like prizes; grownups had little cups of wine or beer. The whole thing felt like stepping into one of those old Christmas movies, but with palm trees outside instead of snow.

As we rolled down Main Street, the lights started popping on — not all at once, more like a slow reveal. Carol (the guide) led us in singing “Jingle Bells,” and I’ll admit I mumbled through half the words. The Trolley Troubadours joined in for harmonies that made even my dad try to sing along (he’s usually not much for public singing). At one point, we passed Marie Selby Botanical Gardens all lit up; someone behind me whispered it looked like fairyland. There was this moment when everyone went quiet for a story about Christmas in Sarasota — something about oranges and old parades — and you could almost feel the history tucked between the songs.

I didn’t expect to laugh so much. Blitzen and Vixen (yes, those were our drivers’ names for the night) kept making little jokes over the speaker — mostly about getting lost if we didn’t sing loud enough. There were families in matching sweaters, couples holding hands, even a teenager who pretended not to care but ended up belting out “Feliz Navidad.” The air-conditioning hummed quietly while outside you could see people waving from sidewalks or porches. It wasn’t perfect harmony every time, but honestly that made it better.

The ride ended too soon for me. We spilled back out into the warm Florida night with cheeks sore from smiling. I still think about that last song echoing after we stepped off — kind of stuck in my head all week, you know?

Step-by-step itinerary

Day 1 — Holiday Trolley Tour in Sarasota

• The Trolley tours holiday light displays in downtown Sarasota.
• Performers share Christmas stories and musical numbers.
• Performers share Christmas stories and musical numbers.
• Performers share Christmas stories and musical numbers at Marie Selby Botanical Gardens.

Top questions

Is there alcohol included on the Sarasota trolley holiday tour?

Yes, complimentary beer or wine is available for guests 21+ before boarding.

Are children allowed on this Christmas Carol Trolley tour?

Yes, children aged 2–11 are welcome but need their own paid ticket.

How long does the holiday music & lights tour last?

The trolley tour lasts approximately 75 minutes.

Is there air conditioning on Dolly The Trolley?

Yes, the trolley is air-conditioned for comfort during your ride.

Does this tour include stops at Marie Selby Botanical Gardens?

You will pass by Marie Selby Botanical Gardens to see its holiday lights from the trolley.

Are non-alcoholic drinks available before boarding?

Yes, soft drinks are offered for kids and anyone who prefers them before boarding.

Can I bring my service animal on this Sarasota holiday trolley tour?

Yes, service animals are allowed on board.

Is parking provided at the starting point?

Free parking is available at the departure location.

What’s included

Your evening includes free parking at departure, complimentary beer or wine for adults (and soft drinks for kids) before boarding Dolly The Trolley, an air-conditioned ride through downtown Sarasota’s holiday light displays with live caroling and stories from professional performers—all guided by locals who know how to make everyone feel part of the show.