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Top Florida Trolley Tours

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Florida Tours

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Key West Ghosts and Gravestones Trolley Tour

Join your gravedigger guide aboard the Trolley of the Doomed for a journey through Key West's darker side! Take an evening trolley ride down the …More

Key West, USA
4.4 (1,376)

Key West Ghosts and Gravestones Trolley Tour

Join your gravedigger guide aboard the Trolley of the Doomed for a journey through Key West's darker side! Take an evening trolley ride down the...

1 hour • Free Cancellation
4.4 (1,376)
from
$40
Miami to Key West Day Trip with Trolley Tour

Our best Key West day trip features a scenic Overseas Highway tour and 6 hours in unique Key West plus fun hop-on hop-off trolley rides …More

Special Offer
Special Offer
Miami, USA
4.6 (3,259)

Miami to Key West Day Trip with Trolley Tour

Our best Key West day trip features a scenic Overseas Highway tour and 6 hours in unique Key West plus fun hop-on hop-off trolley rides...

6 hours in Key West (approx.) • Hotel pickup offered • Free Cancellation
4.6 (3,259)
$169
$129
Key West Hop-On Hop-Off Trolley Tour

The has been a classic Key West attraction for decades, mixing entertaining and educational touring with fun and convenient city transportation. …More

Key West, USA
4.6 (1,732)

Key West Hop-On Hop-Off Trolley Tour

The has been a classic Key West attraction for decades, mixing entertaining and educational touring with fun and convenient city transportation....

1 hour 30 minutes • Free Cancellation
4.6 (1,732)
from
$56
City Sightseeing Trolley Tour of Sarasota

Sarasota's BEST City Sightseeing Tour, a wonderful way to learn where to eat, shop and visit, and about Sarasota's interesting past, whether you are a …More

Likely to Sell Out
Likely to Sell Out
Sarasota, USA
4.9 (1,012)

City Sightseeing Trolley Tour of Sarasota

Sarasota's BEST City Sightseeing Tour, a wonderful way to learn where to eat, shop and visit, and about Sarasota's interesting past, whether you are a...

1 hour 30 minutes • Free Cancellation
4.9 (1,012)
from
$86
St. Augustine Hop-On Hop-Off Trolley Tour

Sit back as the talented Old Town Trolley conductors share the history, attractions and sights of America's oldest city. Founded by Pedro Menendez de Aviles …More

St Augustine, USA
4.6 (3,996)

St. Augustine Hop-On Hop-Off Trolley Tour

Sit back as the talented Old Town Trolley conductors share the history, attractions and sights of America's oldest city. Founded by Pedro Menendez de Aviles...

1 hour 30 minutes • Free Cancellation
4.6 (3,996)
from
$40
1 Hour Historical Tour of Saint Augustine Florida & FREE Parking

Please support small businesses and consider booking us directly, just use a web search to find us: Pineapple Ride and Tour ***Nights Of Lights Tours …More

St Augustine, USA
4.9 (229)

1 Hour Historical Tour of Saint Augustine Florida & FREE Parking

Please support small businesses and consider booking us directly, just use a web search to find us: Pineapple Ride and Tour ***Nights Of Lights Tours...

1 hour • Free Cancellation
4.9 (229)
from
$48
Amish Experience Trolley Tour: Bridges to Understanding

Visit the only place in the world that the Amish and Mennonite communities come to vacation en masse and learn about their culture with your …More

Likely to Sell Out
Likely to Sell Out
Sarasota, USA
4.9 (224)

Amish Experience Trolley Tour: Bridges to Understanding

Visit the only place in the world that the Amish and Mennonite communities come to vacation en masse and learn about their culture with your...

1 hour 45 minutes • Free Cancellation
4.9 (224)
from
$80
Marco Island Safari Truck Tour

Climb up into the Safari truck, fasten your seatbelt and get ready for the Around the Island Safari Truck Tour! Your tour guide driver will …More

Likely to Sell Out
Likely to Sell Out
Naples, USA
5.0 (126)

Marco Island Safari Truck Tour

Climb up into the Safari truck, fasten your seatbelt and get ready for the Around the Island Safari Truck Tour! Your tour guide driver will...

80 to 90 minutes • Free Cancellation
5.0 (126)
from
$45
Key West Shore Excursion: Hop-On Hop-Off Trolley Tour

When you arrive in port in Key West, take an independent, hop-on hop-off trolley tour shore excursion for the best way to explore the island. …More

Key West, USA
4.4 (83)

Key West Shore Excursion: Hop-On Hop-Off Trolley Tour

When you arrive in port in Key West, take an independent, hop-on hop-off trolley tour shore excursion for the best way to explore the island....

1 hour 30 minutes • Free Cancellation
4.4 (83)
from
$56
Haunted Sarasota Trolley: Ghost Stories, Mysteries, Spooky Fun

Step aboard the trolley for a thrilling and historical musical journey through Sarasota’s eerie past with Lady Melody & Mystery Spirits! Hear stories about famous …More

Likely to Sell Out
Likely to Sell Out
Sarasota, USA
4.7 (82)

Haunted Sarasota Trolley: Ghost Stories, Mysteries, Spooky Fun

Step aboard the trolley for a thrilling and historical musical journey through Sarasota’s eerie past with Lady Melody & Mystery Spirits! Hear stories about famous...

1 hour 30 minutes • Free Cancellation
4.7 (82)
from
$92
Sarasota Architecture Tour

Sarasota is home to an amazing architectural legacy. On this 105-minute air-conditioned tour, guests will visit some outstanding examples of architecture and design, with tours …More

Likely to Sell Out
Likely to Sell Out
Sarasota, USA
4.9 (43)

Sarasota Architecture Tour

Sarasota is home to an amazing architectural legacy. On this 105-minute air-conditioned tour, guests will visit some outstanding examples of architecture and design, with tours...

1 hour 30 minutes • Free Cancellation
4.9 (43)
from
$80
Guided Tour of Naples on a Vintage Trolley (Hop on - Hop off)

Join us for a fascinating tour of the Naples area in one of our vintage trolleys. Hop-on/Hop-off all day and explore all Naples Florida has …More

Naples, USA
4.6 (110)

Guided Tour of Naples on a Vintage Trolley (Hop on - Hop off)

Join us for a fascinating tour of the Naples area in one of our vintage trolleys. Hop-on/Hop-off all day and explore all Naples Florida has...

2 hours • Free Cancellation
4.6 (110)
from
$45
Murder Mystery Trolley: Who Killed The Circus Queen?

Fun, interactive murder mystery theater on the trolley! Someone has murdered the Circus Queen...and suspects abound among the circus folk on board. Everyone seems to …More

Likely to Sell Out
Likely to Sell Out
Sarasota, USA
4.9 (98)

Murder Mystery Trolley: Who Killed The Circus Queen?

Fun, interactive murder mystery theater on the trolley! Someone has murdered the Circus Queen...and suspects abound among the circus folk on board. Everyone seems to...

1 hour 30 minutes • Free Cancellation
4.9 (98)
from
$92
Tampa City Trolley Tour - THE ULTIMATE ALL-IN-ONE TOUR

• FREE authentic original Tampa Cuban sandwich tasting at the iconic Flan Factory in historic Ybor City, included with your ticket • Tampa’s only open-air …More

Tampa, USA
4.9 (58)

Tampa City Trolley Tour - THE ULTIMATE ALL-IN-ONE TOUR

• FREE authentic original Tampa Cuban sandwich tasting at the iconic Flan Factory in historic Ybor City, included with your ticket • Tampa’s only open-air...

90 to 120 minutes • Free Cancellation
4.9 (58)
from
$30
Amelia Island Trolley Exploration

You won't find a better tour on Amelia Island! Step aboard our classic trolley and experience the stories that made Amelia Island unlike anywhere else …More

Jacksonville, USA
5.0 (18)

Amelia Island Trolley Exploration

You won't find a better tour on Amelia Island! Step aboard our classic trolley and experience the stories that made Amelia Island unlike anywhere else...

1 hour 30 minutes • Free Cancellation
5.0 (18)
from
$48
Party Bike through St. Pete with Bar+Mural Stops on Trolley Pub

Experience the vibrant spirit of Downtown St. Petersburg like never before with our Mixer Tour. Jump aboard this unique, mobile pub and join a lively …More

St Petersburg, USA
4.8 (90)

Party Bike through St. Pete with Bar+Mural Stops on Trolley Pub

Experience the vibrant spirit of Downtown St. Petersburg like never before with our Mixer Tour. Jump aboard this unique, mobile pub and join a lively...

2 hours • Free Cancellation
4.8 (90)
from
$39
Party Bike Pub Crawl of Downtown Pensacola

You and your crew pick the bars. We pedal you there. Climb aboard a 15-passenger pedal trolley and spend two hours bar-hopping through the heart …More

Pensacola, USA
4.7 (92)

Party Bike Pub Crawl of Downtown Pensacola

You and your crew pick the bars. We pedal you there. Climb aboard a 15-passenger pedal trolley and spend two hours bar-hopping through the heart...

2 hours • Free Cancellation
4.7 (92)
from
$45
Flamingo Bus Miami Tours | Miami's Only Open-Air Trolley!

Discover Miami's Only Open-Air Trolley Tour! Live American Tour Guide delivering 2-hours of fun Miami sightseeing! See Miami Beach Art Deco District, Wynwood Walls, Miami …More

Miami, USA
5.0 (110)

Flamingo Bus Miami Tours | Miami's Only Open-Air Trolley!

Discover Miami's Only Open-Air Trolley Tour! Live American Tour Guide delivering 2-hours of fun Miami sightseeing! See Miami Beach Art Deco District, Wynwood Walls, Miami...

2 hours
5.0 (110)
from
$69
St Petersburg Ultimate (ALL-IN-ONE) City Trolley Tour

• FREE admission to the St. Petersburg Museum of History • FREE tastings at the award-winning St. Pete Distillery • Complimentary onboard refreshments including ice-cold …More

St Petersburg, USA
4.6 (38)

St Petersburg Ultimate (ALL-IN-ONE) City Trolley Tour

• FREE admission to the St. Petersburg Museum of History • FREE tastings at the award-winning St. Pete Distillery • Complimentary onboard refreshments including ice-cold...

90 to 120 minutes • Free Cancellation
4.6 (38)
from
$30
Psychic Sundays Tour

Get in touch with Sarasota’s metaphysical community on this interesting 90 minute “energy” tour. Learn why Sarasota is considered a psychic and spiritual energy center, …More

Sarasota, USA
4.9 (28)

Psychic Sundays Tour

Get in touch with Sarasota’s metaphysical community on this interesting 90 minute “energy” tour. Learn why Sarasota is considered a psychic and spiritual energy center,...

2 hours • Free Cancellation
4.9 (28)
from
$86

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
Would do tour again
New York City
St. Augustine Hop-On Hop-Off Trolley Tour
carlagL4995TT, Sep 2026
Would do tour again
Very convenient and educational. Everyone is very friendly and helpful.
Read more
Fantastic Tampa Tour
New York City
Tampa City Trolley Tour – THE ULTIMATE ALL-IN-ONE TOUR
Kimberly_M, Sep 2026
Fantastic Tampa Tour
Had a great time touring Tampa with Sully! Amazing tour. Our guide was friendly, knowledgeable, and made the whole experience so much fun. Highly recommend this tour—we had a great time!
Read more
Convinced and fun
New York City
St. Augustine Hop-On Hop-Off Trolley Tour
sharongO9083VJ, Sep 2026
Convinced and fun
We really enjoyed the hop on hop off trolley. We were able to park the car and leave it in garage for the day.
Read more
Experience Key West!
New York City
Key West Hop-On Hop-Off Trolley Tour
F4734QEpatriciap, Sep 2026
Experience Key West!
It was a great way to see the city if you only have a day. The drivers were very informative with city history. If there were tourists who needed assistance getting on and off the Trolley the drivers were very caring and helpful. The ease of getting off at an attraction and getting on again was great. Would take the tour again.
Read more
I had a wonderful...
New York City
Tampa City Trolley Tour – THE ULTIMATE ALL-IN-ONE TOUR
Jeliasko_N, Sep 2026
I had a wonderful...
I had a wonderful experience on the trolley tour around Tampa and Ybor City. Our guide, Sully, was fantastic! He was very knowledgeable about the history of the area and shared interesting stories that made the tour even more enjoyable. He was also very friendly, generous with his time, and made everyone feel welcome. Highly recommended if you want to learn about Tampa and Ybor City while having a great time!
Read more
Fernandina Beach Trolley Tour
New York City
Amelia Island Trolley Exploration
626kathyo, Sep 2026
Fernandina Beach Trolley Tour
Great tour, worth the price. The guide kept it interesting and we enjoyed the history lessons. A fun place to visit!
Read more
Easy way to see Key West...
New York City
Key West Hop-On Hop-Off Trolley Tour
Samantha_C, Sep 2026
Easy way to see Key West...
Easy way to see Key West from a cruise ship. Just a less than 10 min walk from the cruise dock. Great way to see the island in an efficient way.
Read more
So fun and interesting
New York City
Key West Ghosts and Gravestones Trolley Tour
mommyritzbitz, Sep 2026
So fun and interesting
Absolutely loved this. Our tour guide - Scarlett Morgan and driver Howard were fantastic. She was so animated and was great at story telling. I love ghost stories and I think it gives the town and lore more depth. Loved all the locations and stories. Highly recommend for an hour well spent. :)
Read more
Fun and informative
New York City
Key West Ghosts and Gravestones Trolley Tour
DanBobbi, Sep 2026
Fun and informative
Tour was excellent. Guide was great. September 23 2026 8:30 PM Dan & Bobbi R. New Hampshire
Read more
A+ tour
New York City
Marco Island Safari Truck Tour
danonymousdvm, Sep 2026
A+ tour
Great tour . Very funny and friendly guide.
Read more
Definitely worth the time and money
New York City
Amelia Island Trolley Exploration
Shari23061, Sep 2026
Definitely worth the time and money
Great stories! Mary and Amy gave a great tour.
Read more
Glenn knows Marco Island...
New York City
Marco Island Safari Truck Tour
Randall_S, Sep 2026
Glenn knows Marco Island...
Glenn knows Marco Island and its history, from the beginning to what famous people live where now. The best part was seeing examples of the wildlife that aren’t found most places.
Read more
Great tour - recommend
New York City
Flamingo Bus Miami Tours | Miami’s Only Open-Air Trolley!
Tourist20853963969, Sep 2026
Great tour - recommend
We went on this tour for my adult daughter’s birthday. We live in South Florida and did the tour just for fun. It was a great tour with Alex. I learned a lot of interesting things about the area. The tour was thorough and just right at two hours.
Read more
Easiest way around
New York City
Key West Shore Excursion: Hop-On Hop-Off Trolley Tour
Indiana2021, Sep 2026
Easiest way around
Easiest way to travel around the island. Good for the entire day. See a place you want to get off at, jump off, then get back on later. Just keep your receipt or sticker. Just needs to keep going much later into the night. Good guided tour.
Read more
Very interesting stories...
New York City
St Petersburg Ultimate (ALL-IN-ONE) City Trolley Tour
Jane_D, Sep 2026
Very interesting stories...
Very interesting stories about St Petersburg. We went through many different areas of the town and heard about how they were started. We went past many art galleries and saw many murals. I felt like we really saw and got to know the city. We really enjoyed the tour.
Read more
Wonderful tour and tour guide
New York City
St Petersburg Ultimate (ALL-IN-ONE) City Trolley Tour
H7624FQmerediths, Sep 2026
Wonderful tour and tour guide
Wonderful tour of St Petersburg! We had a nice stop at a distillery, too. Great way to learn about the city . Only problem were a bunch of old ladies. Talking so loud that you could not hear the audio. I had to move up front to hear the audio!
Read more
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