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  • FUN Family Holiday Show!

Christmas Carol Trolley: Letters To Santa

From $29.99 - $49.99

Hop onboard Dolly The Trolley to enjoy downtown holiday music and lights tour for the whole family on the Christmas Carol Trolley: Letters To Santa tour. This fun-filled music and light tour features singing cast members: Christmas Carol, Candy Cane, Holly Jolly and Billy Holliday who celebrate the holidays with a Christmas carol sing-along down Main Street, holiday stories, letters to Santa, jokes and trivia, and a charming tour of Sarasota’s downtown neighborhood lights.

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  • December
  • 3-11, 12+
  • 90 minutes

Featured Trolley Tours & Special Events

  • FUN Family Holiday Show!
From $29.99 - $49.99
  • December
  • 3-11, 12+
  • 90 minutes

Christmas Carol Trolley: Letters to Santa

Hop onboard Dolly The Trolley to enjoy downtown holiday music and lights tour for the whole family on the Christmas Carol Trolley: Letters To Santa tour. This fun-filled music and light tour features singing cast members: Christmas Carol, Candy Cane, Holly Jolly and Billy Holliday who celebrate the holidays with a Christmas carol sing-along down Main Street, holiday stories, letters to Santa, jokes and trivia, and a charming tour of Sarasota’s downtown neighborhood lights.

Book Now
Learn More
View All Our Trolley Tours

logo, icon, company nameMost weekday tours run in “Dolly The Trolley,” our new 31-seat trolley. During High Season (November-May), some Specialty Tours may run in “Vanna White,” our 9-passenger high-top van. Both vehicles are enclosed and air-conditioned.

If you book through us directly and need to reschedule, we will be happy to do that for you with a $10 per ticket rebooking fee. We encourage you to book with us directly, as this option is not available on tickets booked through affiliates.

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About Discover Sarasota Tours

Discover Sarasota Tours is a locally-owned tour company offering many entertaining, interactive, and informative air-conditioned trolley or van tours about the most interesting people, intriguing places, and amazing stories that have shaped Sarasota’s rich cultural past.

If you are looking for a fun activity for your next group outing, look no further. Our tours are perfect for groups. Check out our Group Tours page.

Our tours run year-round, but during our hottest months of the summer, we don’t run all tours every day, so please check the calendar. If there is a date not listed when you would like to tour, please email us at [email protected].

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Our Tours Are Great for Groups!

See Group Tour Options

As Featured In

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The Best Sightseeing Trolley Tours In Sarasota

A++++++ tour!

What a joy to spend the time with Kendra, who is such a vivacious tour guide. She knows her stuff and we learned so many interesting things never considered before this tour. She also learned and remembered each and every one of our names on the full bus! (That is amazing!) We were able to meet a delightful Amish photographer who captures daily life of the Amish and Mennonites here. We went with a dear friend who told us about it and it was her 4th time on the tour. That should tell you that perhaps this deserves a 10-star rating! Thank you for having this fabulous opportunity. We look forward to trying another one of the tours! It was a great day!

– Martha M., TripAdvisor (2023)
The Best Thing I Did on Vacation!

This was by far one of my most favorite things that we did on vacation this year! From the tour guide to the bus driver, everyone was very kind and humorous. I learned a lot about the history of Sarasota and its ghostly inhabitants. It was a perfect mix of fun and fright!

– Deaven C., TripAdvisor
Don’t miss this tour

Tour guide Jon Macdonald was both informative and funny. Not least especially for a jaded traveler like me who has been coming to Sarasota for close to 70 years. Can’t wait to take the next one.

– Michael A., TripAdvisor (2023)
Awesome

The Penn Alumni Club really enjoyed the Leading Ladies Trolley Tour on Thursday, January 19, 2023. Our guide Kathryn, who came in character as Rose Wilson, was awesome, so knowledgeable and informative! We received so many nice comments from alumni on the tour about how much they enjoyed learning about Sarasota history and landmarks from our wonderful guide.

– Sharon A., Email
Wonderful city tour

My wife and I have had numerous city tours all around the world. The tour guide on this trolley, Steve, was perhaps the very best one we have ever experienced. His narrative was interesting and his timing was superb for the entire 90 minutes.

– Larry J, TripAdvisor
Amish Explanation

Really a great tour. Our guide, Kendra, was very well schooled in the traditions of the Amish, and her delivery was wonderful.

– Garry S., TripAdvisor
Professionalism, Punctuality, Quality, Value

I can’t wait to do this tour again and to show someone in Sarasota a great time... You will leave the tour with a warm feeling and desire to explore the great city of Sarasota even more!

– Michael P., Google
Made Sarasota Come Alive!

The "overview" tour was packed with insights into the founding of Sarasota and the founders' foibles underneath their aura of riches, including the fabulous architecture. If we knew earlier in our trip how good these tours are we'd have done more!!

– Berkowitz 700, TripAdvisor
One of the best tours

The tour was so informative and fun. We learned a lot about Sarasota that we never knew before and we have been here 14 years. We are going to book more tours in the near future. Jon was an excellent guide.

– Jeff SRQ, TripAdvisor
Circus Secrets

Absolutely fantastic tour today (Circus Secrets) with Bob Collins. The tour was so well-planned, entertaining, informative and Mr. Collins was a kind a gracious host. I plan to come back with neighbors and friends in the near future. Don't miss this one!!

– Ray H, TripAdvisor
Sarasota Secrets

Our goal, after living here for a (very unusual) year, was to learn about the city of Sarasota and find secret historical, cultural, shopping and dining options to enjoy. Our guide Steve delivered that big time and in a VERY entertaining way.

– Cindy & Mick C., Email
A rousing success!

Both the owner of Discover Sarasota, Tammy Hauser, and Jerry Chesley, the art historian, were very knowledgeable and accommodating. A party atmosphere while obtaining knowledge is an absolute winner!

– Jayne K., TripAdvisor
Wonderful!

The tour was really informative, learned alot of history and things I didn't know about the area. The staff were WONDERFUL! From checking in/registering to the tour professionals, they were great, very friendly and knowledgeable.

– Taylor, TripAdvisor
Sarasota Trolley

What a wonderful way to see and learn about Sarasota whether you are visiting or live here it’s worth the trip. The store is adorable and the trolley is comfortable. Our guide and trolley driver made the trip a fun adventure.

– Carol S., TripAdvisor
Fun and informative

Take this tour — as soon as you can — upon arrival to Sarasota. Fun and informative. Pat was our guide and Dori was our driver. They were both gracious and hospitable and Pat’s knowledge of Sarasota is unparalleled. You will get many ideas for fun things to do and tips for great places to eat and drink.

– Nona N., TripAdvisor
Well done, Discover Sarasota!

4 girlfriends who have lived in the area for many years decided to do a Discover Sarasota Leading Ladies Tour on Wednesday, 1/5/2022. We were thoroughly entertained, learned new information, and saw neighborhoods which we normally didn't travel through. Our tour guide was very informative, very knowledgeable, and provided an extremely enjoyable tour. Upon completion of our tour, we all enthusiastically exclaimed we wanted to do another tour soon. Well done, Discover Sarasota!

– Michelle W., Google
An Excellent Tour

Our tour guide, Kendra, made this very interesting tour exceptional. She is probably the most enjoyable tour guide we have had. We knew nothing about the Amish and have learned so much. We also have discrded any preconceived ideas we had and have acquired a great deal of respect for the Amish. We highly recommend this tour.

– Jenniferstravels6, TripAdvisor (2023)