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Key West Private Tours & Local Tour Guides
Discover Things to Do and Plan a Trip to Key West, United States of America (USA) with a Local Guide
Popular Key West Private Tours
Insta Photo Tour in Key West.
Key West
3 hours
Get ready to walk the town and get those bucket list photos. We will start in the Seaport and make our way to the Southernmost Point and back. It maybe 1 mile from the Atlantic Ocean to the Gulf of Mexico along Duval street, but we will make our way in a zig zag fashion so you can get the picture spots you want to capture while in Key West. Hemingway House, USCG Ingham, Key West Cemetery, Custom House, Little White House, Key West Lighthouse, Mallory Square, and many other spots.
FROM$325/ per group
Whiskeyrick W.
5.00 / 5
(1 reviews)
Sip N Stroll with history, laughs, tales, hidden gems
Key West
1 hour 30 min
Happy Hour tour!! Ok EVERY hour in Key West is Happy Hour. This is your tour. It is designed as a historic sip n stroll to discuss what happened in key places in town and go into more detail and depth. With that typed many folks just want faster and funnier so we can keep moving and going to different spots. The famous watering holes are there. I can take you to the ones that are nearby and have unique stories as well. We can also mix in items from my other tours if you wish.
FROM$235/ per group
Whiskeyrick W.
5.00 / 5
(1 reviews)
WTF: Wild stories,Twisted tales,Freaky things..GHOST tour
Key West
1 hour 30 min
Cayo Hueso which is Spanish for "Island of Bones" is the original name of Key West. Yes ghosts and spirits of been part of this city going back to 2000BC when the Indians first inhabited this area. Piracy, disease, natural disasters, tragic stories will all be shared on this tour. We will talk about a dead bride and perhaps the most haunted doll in the world. This and much more awaits as we take a dark and creepy walking tour of old town.
FROM$300/ per group
Whiskeyrick W.
5.00 / 5
(1 reviews)
Welcome to Key West -- history and tips
Key West
1 hour 30 min
What a way to start your stay in Key West... a walking tour that will cover the Old Town area from the Atlantic Ocean to the Gulf of Mexico. Understand the history and how the island grew as the seaport became prosperous and needed more space. Get an overview on today and an idea where things are to do and places to eat (sorry with so many GREAT places to dine and everybody having very different tastes I prefer to give tailored recommendations on my tour vice trip advisor top places). WELCOME
FROM$275/ per group
Whiskeyrick W.
5.00 / 5
(1 reviews)
New Key West Private Tours
Key Lime Experience
Key West
1 hour 50 min
Key lime pie was created in the Keys ... hear the story and visit those places where it came together. We will try a few types of pie, ice cream, and candy. For those over 21 we can add an adult beverage or two into the mix. We will walk about a mile in just under 2 hours trying various types and learning the history and flavors.
FROM$95/ per person
Whiskeyrick W.
5.00 / 5
(1 reviews)
Historic Seaport Stroll
Key West
1 hour 30 min
The Spanish founded Key West in 1513 while the Indians have been in the keys since 2000BC. The natural harbor would provide shelter during storms while the fresh water well would enable survival when ships stopped for resupply. As commerce increased in the 1800's the city became a very wealthy town. Turtle harvesting, cigar making, sponge farming, and of course fishing would sustain this seaport until tourism today. This tour will share all that and more.
FROM$275/ per group
Whiskeyrick W.
5.00 / 5
(1 reviews)
Key West Tour Reviews
D
David K.
5 / 5
Feb 24, 2025
“Whiskey Rick doesn't diappoint”
Our hour long custom tour of Key West was made amazing by Whiskey Rick. He shared Jimmy Buffett, Hemingway, island history, and architecture into the tour as we walked around. Very knowledgeable and full of fun stories! He is also very funny while professional. Gave many recommendations for restaurants and other places to explore. Knows many of the local musicians and who he recommends for the rest of the week. Very easy to customize to our group. I would highly recommend Whiskey Rick! Dkell
Whiskeyrick W.
Glad you enjoyed!! Had fun with you and your group. Great to share history, legends, and lore of Key West along with personazlied recomendations. Thank you!!
Key West Private Tour Guide
Whether it’s your first time to Key West or you are back to discover more, a good tour guide can make all the difference. Enjoy the best of what Key West has to offer, without all the fuss of planning everything by yourself!
You can pick your favorite itinerary from the Key West tours offered by our local guides, but feel free to ask for customizations based on your preferences. We want to help travelers get the most out of their trips, and we believe a good tour with a local guide is the best way to ensure that.
There is so much to see and do in Key West, and the best way to get the most out of your time there is to have a local expert with you. GoWithGuide is committed to delivering unforgettable tour experiences, so let us help you create your next favorite memory.
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