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Orlando Walking Tours

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Orlando Tours

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Shared Premium Distillery Tour in Orlando

“Kristin was fantastic and knowledgeable.”

— P1755DYkristind

Escape to the Moonshine Distillery and Tasting Room at the Orlando Vineland Premium Outlets for a one-hour tropical adventure. Enjoy a guided tasting of SIX …More

Likely to Sell Out
Likely to Sell Out
5.0 (1)

Shared Premium Distillery Tour in Orlando

Escape to the Moonshine Distillery and Tasting Room at the Orlando Vineland Premium Outlets for a one-hour tropical adventure. Enjoy a guided tasting of SIX...

1 hour • Free Cancellation
5.0 (1)
from
$95
Happy Hour Downtown Pub Crawl

Take the time to sip and enjoy history in award winning Downtown Winter Haven's happy hour hot spots! Many of these establishments have won several …More

5.0 (1)

Happy Hour Downtown Pub Crawl

Take the time to sip and enjoy history in award winning Downtown Winter Haven's happy hour hot spots! Many of these establishments have won several...

3 hours • Free Cancellation
5.0 (1)
from
$139
Orlando : Private Custom Walking Tour with A Guide (Private Tour)

Orlando can sometimes feel busy and confusing for newcomers. Take the mystery out of your visit by exploring with a local on a private walking …More

5.0 (1)

Orlando : Private Custom Walking Tour with A Guide (Private Tour)

Orlando can sometimes feel busy and confusing for newcomers. Take the mystery out of your visit by exploring with a local on a private walking...

2 to 8 hours • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$47
Orlando Self-Guided Historic App/GPS Audio Walking Tour

Every year, millions of people come to Central Florida to visit the world-famous theme parks and they think they have seen “Orlando”. But truth be …More

5.0 (1)

Orlando Self-Guided Historic App/GPS Audio Walking Tour

Every year, millions of people come to Central Florida to visit the world-famous theme parks and they think they have seen “Orlando”. But truth be...

60 to 90 minutes • Free Cancellation
5.0 (1)
from
$10
Enchantment and Elation: A Private Disney Springs Christmas

Enjoy a private, exclusive tour with your own local guide. Enchantment and Elation: A Disney Springs Christmas Journey” invites you to a world where the …More

5.0 (1)

Enchantment and Elation: A Private Disney Springs Christmas

Enjoy a private, exclusive tour with your own local guide. Enchantment and Elation: A Disney Springs Christmas Journey” invites you to a world where the...

2 hours • Free Cancellation
5.0 (1)
from
$292
Orlando Area 5 Day Self Guided Disney Save Tour & More

Discover Central Florida like a local—without breaking the bank! These self guided tours are your ultimate adventure hub, designed to turn any Disney-area vacation into …More

5.0 (1)

Orlando Area 5 Day Self Guided Disney Save Tour & More

Discover Central Florida like a local—without breaking the bank! These self guided tours are your ultimate adventure hub, designed to turn any Disney-area vacation into...

5 days
5.0 (1)
from
$15
Orlando Ghost Tour: Ominous Otherworld Ghosts & Hauntings

Step into the shadowy streets of Orlando on our enthralling walking ghost tour, where history and hauntings come alive! Guided by a seasoned local expert …More

4.4 (48)

Orlando Ghost Tour: Ominous Otherworld Ghosts & Hauntings

Step into the shadowy streets of Orlando on our enthralling walking ghost tour, where history and hauntings come alive! Guided by a seasoned local expert...

1 hour • Free Cancellation
4.4 (48)
from
$26
Flavors of Winter Park Foodie Walking Tour

Take a bite out of the best of Winter Park and stroll down Park Avenue on our unique Flavors of Winter Park Foodie Walking Tour! …More

4.6 (45)

Flavors of Winter Park Foodie Walking Tour

Take a bite out of the best of Winter Park and stroll down Park Avenue on our unique Flavors of Winter Park Foodie Walking Tour!...

2 hours 30 minutes • Free Cancellation
4.6 (45)
from
$67
Sanford Ghost Tour

Dare to explore the haunted heart of Historic Downtown Sanford on a Historical Ghost Walking Tour like no other! Step into the shadows of Sanford’s …More

4.5 (15)

Sanford Ghost Tour

Dare to explore the haunted heart of Historic Downtown Sanford on a Historical Ghost Walking Tour like no other! Step into the shadows of Sanford’s...

1 hour 30 minutes • Free Cancellation
4.5 (15)
from
$29
Winter Haven Guided Brunch Tour

Experience what Downtown Winter Haven has to offer. Guests will enjoy brunch items from our local award-winning restaurants while visiting historic locations. …More

4.3 (10)

Winter Haven Guided Brunch Tour

Experience what Downtown Winter Haven has to offer. Guests will enjoy brunch items from our local award-winning restaurants while visiting historic locations....

3 hours • Free Cancellation
4.3 (10)
from
$127
Flavors of Winter Haven Food Tour

Explore award-winning Winter Haven's local restaurants that offer food from around the world all within walking distance. …More

4.7 (10)

Flavors of Winter Haven Food Tour

Explore award-winning Winter Haven's local restaurants that offer food from around the world all within walking distance....

3 hours • Free Cancellation
4.7 (10)
from
$140
Orlando Haunts Boos and Booze Haunted Pub Crawl

If you want to spice up your work week or vacation with some spooky spirited fun, join us for our Haunted Pub Crawl! Experience up …More

4.6 (9)

Orlando Haunts Boos and Booze Haunted Pub Crawl

If you want to spice up your work week or vacation with some spooky spirited fun, join us for our Haunted Pub Crawl! Experience up...

2 hours • Free Cancellation
4.6 (9)
from
$29
Snow, Ice & Lights - Holiday Celebrations Orlando Style

It's beginning to look a lot like Christmas! This very 'cool' tour will take you to three locations in Orlando that celebrate the holiday season …More

4.7 (3)

Snow, Ice & Lights - Holiday Celebrations Orlando Style

It's beginning to look a lot like Christmas! This very 'cool' tour will take you to three locations in Orlando that celebrate the holiday season...

6 hours • Hotel pickup offered
4.7 (3)
from
$119
Savor Orlando Culinary Gems in Mills 50 Food Tour

Discover the vibrant flavors of Orlando’s Mills 50 District on a guided food tour that showcases a mix of inventive street eats and cultural comfort …More

4.5 (2)

Savor Orlando Culinary Gems in Mills 50 Food Tour

Discover the vibrant flavors of Orlando’s Mills 50 District on a guided food tour that showcases a mix of inventive street eats and cultural comfort...

2 hours • Free Cancellation
4.5 (2)
from
$85
Self-Guided Walking Audio Tour around Lake Eola in Orlando

Take a self-guided GPS audio walk along the most beautiful path in Orlando around Lake Eola. This tour along the paved path around this iconic …More

4.0 (1)

Self-Guided Walking Audio Tour around Lake Eola in Orlando

Take a self-guided GPS audio walk along the most beautiful path in Orlando around Lake Eola. This tour along the paved path around this iconic...

1 to 2 hours
4.0 (1)
from
$8
Awesome Scavenger Hunt: Lake Eola's Art Scene & Scenery

Let’s Roam takes the lead in app-led adventure hunts! Embark on a thrilling journey to iconic landmarks and secret spots, where you’ll conquer trivia and …More

3.7 (6)

Awesome Scavenger Hunt: Lake Eola's Art Scene & Scenery

Let’s Roam takes the lead in app-led adventure hunts! Embark on a thrilling journey to iconic landmarks and secret spots, where you’ll conquer trivia and...

2 hours
3.7 (6)
from
$12
An Epic Scavenger Hunt: Feel the Adventure Breeze at WinterPark

Let’s Roam is the #1 app-led adventure hunt company. Explore the best landmarks and hidden gems, answering trivia questions and tackling challenges along the way. …More

3.3 (3)

An Epic Scavenger Hunt: Feel the Adventure Breeze at WinterPark

Let’s Roam is the #1 app-led adventure hunt company. Explore the best landmarks and hidden gems, answering trivia questions and tackling challenges along the way....

2 hours
3.3 (3)
from
$12
Haunted Orlando: Downtown Ghost Hunt Escape Game

You are the Gatekeeper between the living and the dead, and you left the gate open. Souls have escaped into downtown Orlando. Hunt them down …More

3.0 (4)

Haunted Orlando: Downtown Ghost Hunt Escape Game

You are the Gatekeeper between the living and the dead, and you left the gate open. Souls have escaped into downtown Orlando. Hunt them down...

45 to 75 minutes • Free Cancellation
3.0 (4)
from
$7
Gastro Secrets of Winter Park - Foodie Walking Tour
What’s included
  • 10% discount for your next Original Orlando Tours adventure (valid for 30 days).
  • Demonstrations and presentations during each visit.
  • Sample selection of delicious food and beverage items at each tour stop.
  • 10% discount all day on purchases and meals after the tour given by each tour stop location.

Take a bite out of the secret side of Winter Park and venture off Park Avenue on our unique Gastro Secrets of Winter Park Foodie …More

3.0 (1)

Gastro Secrets of Winter Park - Foodie Walking Tour

Take a bite out of the secret side of Winter Park and venture off Park Avenue on our unique Gastro Secrets of Winter Park Foodie...

2 hours • Free Cancellation
3.0 (1)
from
$72
Orlando Murder Mystery: Self-Guided Detective Walk

The streets of Orlando hold clues to a chilling murder. Can you piece together what happened on this self-guided walking quest? Your smartphone delivers clues, …More

Orlando Murder Mystery: Self-Guided Detective Walk

The streets of Orlando hold clues to a chilling murder. Can you piece together what happened on this self-guided walking quest? Your smartphone delivers clues,...

1 hour 30 minutes • Free Cancellation
from
$6

Frequently Asked Questions

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

Recent tour reviews
Seeing Winter Park Through a Whole New Lens - Wonderful Guide and Wonderful Tastings!
New York City
Flavors of Winter Park Foodie Walking Tour
olteech, Sep 2026
Seeing Winter Park Through a Whole New Lens - Wonderful Guide and Wonderful Tastings!
What a wonderful way to experience Winter Park! Although I’ve visited Winter Park many times over the years, our guide, Michael, shared so much interesting information that I now feel like I see the area through a completely different lens. He was knowledgeable, engaging, and so attentive to everyone’s needs and comfort throughout the entire tour.All of the tastings were delicious, but there were a few highlights that really stood out. The olive oil store did an amazing job of not only educating us, but feeding us, too! At BoVine, we had such a great time chatting with Joanne, the owner, while sampling their wonderful sangria. Later in the tour, we visited her Vintage Vault store and had another opportunity to spend some time with her. What an absolute delight!Everything about the tour was enjoyable, and Michael made the experience even more special. I’m already looking forward to returning to BoVine for dinner—and I would happily take another tour with Michael. Highly recommend!
Read more
History with paranormal
New York City
Sanford Ghost Tour
419caitlinm, Aug 2026
History with paranormal
Great time learning about Sanford history with some ghost stories. Not your usual stories, for sure. Best for history buffs with an interest in the paranormal!
Read more
ORLANDO GHOST TOUR
New York City
Orlando Ghost Tour: Ominous Otherworld Ghosts & Hauntings
viancasully, Aug 2026
ORLANDO GHOST TOUR
⭐⭐⭐⭐⭐Rodger was amazing! He made the entire tour such a great experience and was friendly, helpful, and professional throughout. We had an awesome time and I 100% recommend booking a tour with him!
Read more
Ghost tour was very interesting!
New York City
Orlando Ghost Tour: Ominous Otherworld Ghosts & Hauntings
anyssas2026, Aug 2026
Ghost tour was very interesting!
Roger was an amazing tour guy, very enthusiastic and very knowledgeable!! Absolutely recommend!
Read more
One of the best tours
New York City
Savor Orlando Culinary Gems in Mills 50 Food Tour
B5627MHchristinaa, Aug 2026
One of the best tours
Tracy was so much fun and knowledgeable! Not only would I recommend this tour but anytime I’m in Orlando I will be booking another tour with her. Food and drinks were fantastic and shown some local hidden gems. Highly recommend
Read more
Great experience!
New York City
Shared Premium Distillery Tour in Orlando
P1755DYkristind, Jul 2026
Great experience!
Kristin was fantastic and knowledgeable. Will be back on our next vacation!
Read more
Was great!! We had a wonderful time. It was fantastically interactive love how the updated the app to assign roles
New York City
Awesome Scavenger Hunt: Lake Eola’s Art Scene & Scenery
Camglee, Jul 2026
Was great!! We had a wonderful time. It was fantastically interactive love how the updated the app to assign roles
Was great!! We had a wonderful time. It was fantastically interactive love how the updated the app to assign roles
Read more
Roger was amazing!
New York City
Orlando Haunts Boos and Booze Haunted Pub Crawl
N7708BVemmab, May 2026
Roger was amazing!
Roger was amazing! Such a friendly and knowledgeable guy! Would do again!
Read more
Ever so popular Park Avenue
New York City
Flavors of Winter Park Foodie Walking Tour
takanew2026, Apr 2026
Ever so popular Park Avenue
Olive oil & wine stores were excellent. Restaurants' samplings were fun. We had 14 people in our group with 2 tour guides with kind hearts. It's hard to find parking spots on Saturdays. Arrive early and wear good walking shoes.
Read more
Stellar by all accounts!
New York City
Orlando : Private Custom Walking Tour with A Guide (Private Tour)
Jay_D, Mar 2026
Stellar by all accounts!
Roger was awesome. He has a ton of knowledge about the area, super chill and it made for a most excellent day. We learned so much about the area…there’s way more to Orlando than theme parks…that’s for sure.He was familiar with the property we were staying at and picked us up promptly on time. His demeanor was chill and inviting, we thoroughly enjoyed our day with him.
Read more
Nice feel of the joy of the season
New York City
Enchantment and Elation: A Private Disney Springs Christmas
carlottacH2300MO, Dec 2025
Nice feel of the joy of the season
The joyous ambiance and shimmering waters for our cherished memories. Amazing decorations and the twinkling lights. What a memorable tour.
Read more
Amazing Christmassy Tour of Gingerbread, Ice and Snow in Sunny Orlando!
New York City
Snow, Ice & Lights – Holiday Celebrations Orlando Style
ALWO24, Dec 2025
Amazing Christmassy Tour of Gingerbread, Ice and Snow in Sunny Orlando!
We have just returned home (UK) from a 12 day break to Orlando, we do not do the parks, but for the past 10 years have relied on Cool Destinations for our sightseeing and repeat trips to various locations we link in Florida.This year was the first time we have been able to book the Gingerbread, Ice and Snowfall tour with Cool Destinations and we can honestly say it did not disappoint.First of all Ishmael (our tour guide for a second tour this holiday) took us to a couple of the most amazing Disney Hotels to look at their Christmas trees and Gingerbread houses, followed by a trip to the Gaylords Palm resport to experience the Ice Sculptures, which were truly amazing. The evening was topped by a visit to Celebration where we were able to watch snow fall at 6pm and again at 7pm before leaving the area to return to our hotel.Ishmael made this tour extra special for us, he knows the areas so well and is able to give great commentary along the way which is always great to learn a bit more about the areas we are visiting, as well as hints and tips about things to look out for.We had Ishmael take us on another tour a few days earlier and he greeted us for this tour like long lost friends, so completley genuine and a lovely guy. We would look forward to seeing him again in the future next time we come back to Orlando.I cannot recommend this tour enough if you are visiting Orlando during the festive holiday period.Well done Cool Destinations and thank you to Ishmael for looking after us so well.
Read more
Fun time for all
New York City
Snow, Ice & Lights – Holiday Celebrations Orlando Style
Nicola_H, Dec 2025
Fun time for all
It was a great experience and very festive. The tour guide was great and super knowledgable. Pick up and drop off was exactly as described
Read more
Winter Haven Brunch Tour
New York City
Winter Haven Guided Brunch Tour
James_A, Nov 2025
Winter Haven Brunch Tour
Amada was wonderful, great stories and conversations! Food was delicious and Winter Haven is quaint. Very easy to walk around ( my husband and I both use canes ).
Read more
Fun time with the application
New York City
Orlando Area 5 Day Self Guided Disney Save Tour & More
J_J, Oct 2025
Fun time with the application
Was a really good experience from all the locations was easy to identify and made a great time for us
Read more
Totally worth it
New York City
Orlando Haunts Boos and Booze Haunted Pub Crawl
anthonyoM1392IP, Aug 2025
Totally worth it
Had a great tour with Trent. He was very knowledgeable and easy to talk to. Even with the rain, I didn't want the event to end.
Read more
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