Sip N Stroll with history, laughs, tales, hidden gems

Food & Drink

Whiskeyrick W.

Key West
English (Native)
1 hour 30 min
Private tour (only you and your group)
Up to 3 people

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.

Meeting Point

Bearded lady unless another place is chosen

04:00 PM

Bearded Lady

A "Cheers" type establishment where you can enjoy a beverage in A/C as we talk about the history of the area and figure out which places to go next. This bar is a block from MM0, next to the World Famous Green Parrot bar, and nearby a few other fun spots

04:10 PM

Glitter and Drag

The 2nd stop can be a bar that puts glitter in your drinks and/ or the place next door that is famous for it's female impersonator show. We can also skip this place if you would rather focus on another place down the list.

04:20 PM

Old Fashioned on Tap and Grilled Cheese

Yes these go together. This bar that is known to keep you cool due to great AC has a few cocktails on tap and the kitchen makes great grilled cheese and tater tots (recommended stop also late at night if you get hungry).

04:30 PM

Aviation history

This bar was actually in the seaport before it wasn't needed to be an airline headquarters and moved to it's current location. Now home to great food and drink. Across the street is a live music gem and next to that a bar that Bill Murray, the comedian, named after having a great time in Key West. You will have a few options on which place to spend some time (or all of them!!)

04:40 PM

Smoking Tuna

This hidden gem is nearby to Irish Kevin's, Sloppy Joes, and Capt Tony's. All famous bars and we can go those if you wish. Tuna has great live music and being tucked into a side street normally has room for our group. Plus it has some games for people to play in the back area.

04:50 PM

Tons of Laughs

This place is on the ghost tour due to the murder that happened in what was a house and now a bar. With that said it is a place that folks enjoy giggling. Few other watering holes next door and across the street.

05:00 PM

A unique bar with ashes

Yes people have their ashes in the bar at this local. Famous for who drank here back in the day and probably today (who knows who might be in this hidden local). Jimmy Buffet famously got his start here.

05:10 PM

Speakesy

Overlooking the marina this hidden gem has craft cocktails and an intimate environment. Also a deck to smoke a cigar above the boats. Nearby is 2 other bars. One a tiki bar with amazing sunset view. Another some high end spirits if you want to sample or mix. Around the corner another option or two. We will be having fun on this tour and who knows which places you will want to visit and maybe sample some run at the Legal Rum distillery we will pass in order to get to the speakeasy.

05:20 PM

Fish Farm

Located in the heart of the seaport and with a sound studio in view is this very popular eatery with live music and a wide variety of beverages available. This is place to sit and watch the people go by and be watched if you want a table that will enable that.

05:30 PM

Wyland wall

World famous artist for his large sea life murals. Wyland has painted the wall of this now brewery. We can sample some of the beverages they make inside the building or go to a place next door. Yes the Pirate bar known as Schooners is adjacent as is the boathouse.

05:40 PM

Rum and prohibition watering hole

Over by the Atlantic ocean we have a few options. From the Rum bar with many unique spirits to La Te Da next door. These will require a tour that goes towards the Atlantic or getting transportation to visit after the seaport.

Ending Point

Flexible

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Inclusions & Exclusions

What‘s included

Guide to show you around and navigate the island while telling stories

What‘s not included

Beverages for you and guide not included (but very much appreciated by me when you do purchase a beverage for the guide). This is a walking tour and transportation is needed might be extra (city does have a free bus going around the area that we can hop on and off if we wish as part of the tour). Meals and souvenirs also not included in this tour. Group size is recommended at under 3 as with guide getting a table for 4 is usually feasible. The larger the group the harder to find a place and also the longer to have bartenders make drinks.

Important Information

This is a private tour. Happy to adjust start time and location. Reach out as far in advance for as much flexibility as possible. Can design a tour for you and yours. Happy to give recommendations.

I can also potentially meet you in another city or location, but associated costs need to be discussed.

This is your happy hour tour and I can adjust the route and timing. We can not follow the timeline listed if we are stopping and getting drinks. Normally 4 bars are picked around town and a route is designed to enjoy and rest while talking about the others and so much more.

Cancellation Policy

  • Free cancellation - 8 days prior to meeting time
  • 50% Refund - 3 to 7 days prior to meeting time
  • No Refund - Within 2 day(s) prior to meeting time

Frequently Asked Questions

How do we find you and how do we get there

We will coordinate the tour ahead of time and I will help you figure out what is best transportation plan to and from the meeting spot and ending point.

Which place do you think is best

They all are great. The more you share about what your likes and interests are the easier it is to try and pick which locations to focus on, which ones to mention, and which ones to keep moving as we pass. You can't do and see it all, but we will enjoy as much as we can and flex as the winds take us around the island.

We have a large group

Will figure out a plan that will include pre-ordering beverages and going to places that can accommodate larger groups.

$235/ per group

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