Happy Travels: Key West
OUR TRAVEL GUIDE (updated April 2026) for online readers of all things HappyGuide and friends/family. Kelli Darlin and I (Tony McLean Brown) have been coming to Key West since 2018 ... and over almost 10 years, we've seen and done it all! Open to suggestions ... food, drinks, music, activities, and other MUST DOs!
Our first dance was at Hogs Breath performance with Kenny Fradley and Barry Cuda. For the past 30 years ... Kenny our personal ambassador for the KW music, entertainment, Conch hospitality, and sunset cruises. #gratitude #kidcreoleandthecoconuts
This is NOT a commercial travel guide. This is simply a list of stuff we've really enjoyed doing in Key West since 2018. We are 100% confident that this is an incomplete list of KW Top 10/Bubbas Best ... and we apologize for omissions.
To be clear, we wrote this blog so when the zillion of folks who we know talk about coming to KW ... we can just send them the link to this blog. If you actually show up, at least we know ya'll have a GREAT time, meet great people, and see a ton of beautiful views.
CLICK HERE - 1 PAGE PDF
Kelli Darlin & Tony McLean Brown's Key West Travel Guide
If you are prefer to "watch" a video instead of read this ever-growing travel blog, here's our Key West highlights reel. Strap in ... let's go to work. #margaritaville #hemmingway #jimmybuffett
KELLI DARLIN & TMB's TOP 3 RECOMMENDATIONS
If you are planning to come to Key West, there are three things you need to know:
Duval Crawl is Unachievable Worthy Goal - Kelli and I have been thrown out of every bar from Mallory Square/Hogs Breath to Southern Most Mansion. If you google it, that's 1.1 mile of bars, watering holes, and excellent music. Try as we might, we've never made it end-to-end stopping in each drinking establishment along the way. You can walk it, use a rickshaw, rental bike, or uber ... none of it helps. Just too many bars in too short a distance to cover in one night. BTW, Rickshaw Kim can get you in 5 mins and take you anywhere! His number is 305-850-8946 and his Venemo is @kambar-zhumabekuly ... tip him well and tell him Kelli sent you.
Sandbars are a 100% Must DO! - If you go to Beale Street and don't see Grace Land, if you go to 6th Street and don't see a Long Horn Bull, if you come to Key West and don't get to a sandbar, then you have missed 50%+ of the experience. Let's face it ... Key West Beaches are not like Mrtyle Beach or St. Pete. They are too small, too rocky, and often too full of sea weed to compare to our Nation's best beaches. BUT, the local sand bars are pretty damn special and stack up to some of the best in the Caribean.
Art & History Matters - Don't come to Key West without reading Hemmingway's "Old Man in the Sea." We actually shame any/all of our guest who don't have the 2 hours to read this small treasure. Hemmingway house takes 30 minutes, Key West Arts & Historical Society has stuff all month long, and for the most ambitionous (and rich - it's pricey) tourists ... take the float plan to Dry Torgugas. There's tons of art stores and gallaries for folks with a propensity for shopping.
HERE'S OUR TOP PICKS
From sunsets to sandbars, here is how to enjoy the island like Kelli Darlin & Tony McLean Brown. It's full of salty air, good vibes, great bartenders, and delicious food.
Please note: Sh!t is expensive ... only thing that is cheap are $5 neon tshirts size XXLL from 2005 with a logo of a palm tree and squashed turtle. #cussinbackinstylewhew
Best Performers
While we would like to be helpful in finding these folks during your stay, IG is OK ... but often inaccurate. Bars websites are OK, but change without notices. UPSIDE: you might go to WillieT's to see Nick per IG, but Kari is playing ... she got a last minute call. Don't hate the players, love the game.
Nick Brownell - "Nick the Dick" is his stage name. You have been warned, but it's a good time. If you can catch "Honkey Tonk Tuesday" or "RawDawgs", it's a special opportunity for locals and visitors. If you happen to see Nick sing with his wife Kara, you can say "thank you" to Kelli. His wife is 100 times better singer then him. Again, he's a self-proclaimed dick. FYI - He's plays at a dive bar in PoonTang Bay on Lake Michigan during some summer weeks ... it's an OH- -IO thing. His IG account is mostly reliable. Take him a big cash tip, and ask him to play "What's Up" by Four Non Blondes ... it's his favorite request! Tell him Kelli sent you.
Kari & Jack Wolf - WolfLove or separately, you will be happy to enjoy their music. Great performers and entertainers. Rev T and Kelli Darlin were in their wedding. They give it 100% at every show ... and live stream on the regular. Take them a $20 tip, and ask them to play your favorite song in life ... I promise you, even if they don't know it, they will give it an honest try! Tell them Kelli sent you.
Tony Baltimore - "Let's All Go Insane" pretty much sums it up. Great alternative to Wagon Wheel, Take Me Home, Sweet Caroline, and Free Bird. Kelli was in his That Girl's Got Eyes music video. Give him a $20 tip and ask him to play "Come Together" by the Beatles. Tell him Kelli sent you.
Aaron Hudgins - Let's be clear, if he's drinking Jaeger ... strap in. It's gonna get rowdy and most assuredly hard-core country. His name is pronounce, "AA Ron" and his crowd favorite is "Feel Like My Brother." Give him a tip and tell him Kelli sent you. #longstory Check out his orginal tune "June" by Aaron Hudgins .
Harrison & Rochi Turner - Now this is high praise ... Harrison has the worst social media in the Keys. The only way you can find him is by sheer chance and intervention from the gods. Rochi has one of the best voices in town ... but her song menu is about two decades behind most 60+ year old tourists. This is embarrassing ... his name is really Turner Harrison ... and I'm terrible with remembering folks with two first names and apparently two last names! Here's their individual IG accounts: Rochi Harrison Turner Harrison
Reggae Lou and the Kind Budz - It might be that we love his dreads, but a multi-year Iggies winner ... hands down best island vibe and love for all. #chillAF
Supporting Folks - While the frontmen/women are key to show, we've come to love so many supporting band members: Hiram (drums), David (drums), Martin (fiddle), Drake (bass), Henry (bass), Clair (bass), Prince (bass), Steve (steel guitar), and so many others ... THANK YOU!
Music Venues
Halo - nice to get above the street. Cool, small, easy to get drinks, and music is always very good. People watching is from a bird's eye view. Music is always just one person with a guitar ... and everyone who plays here is a true professional. The bartender's name is Maria ... as calm when they're slammed as when the place just opens up. #REALPRO
Hogs Breath - great bartenders and nice mix of local and visiting bands. No doubt a true pillar of Duval's scene. Gets hammered with the Cruise Ships dock ... and folks keep coming back for the rest of their lives. Music is good ... drinks are better. Mark is one of the best bartenders on the island. Tell him Kelli sent you ... he's great.
Willie T's - small, crowded, old, dirty, loud, rowdy, sometimes hard to get to bar, but maybe the most consistent good time in Key West. This is why 80% of the tourists come to Key West ... this is what folks from Ohio were visualizing when they dreamt "Springbreak meets Mid-life Crisis!"
Bali Bar - buried inside of The Key West Hotel, their slogan is "Come hide with us!" The music is more sophisticated or nuanced. Once you make it through the jungle entrance, it's chill by design and Tikki covered bar is extremely comfortable. During the day, feel free to relax in their pool while sippin' on your favorite drink. If Rich (the owner) or his son are in town, tell them Kelli sent you. #greatpeople
Capt. Tony's Saloon - First off ... the Tshirts are awesome. Secondly, you gotta try to toss a quarter in the big grouper's mouth just above the side-walk: Jason, Logan, Adam, Julia, Ali, Kelli, Jack, Maggie, and I've done it. There's a 100% winning technique. DM us.
On the Water
Commotion on the Ocean - you gotta do it once ... try to get on Kenny Fradley's Fury Sunset boat cruise ... ask the sales person when buying your ticket for his boat. He's the best trumpet player in Florida Keys (played on U2 album) and the open air is ideal for his contribution. Drinks are free and bottomless ... next day ya'll question your decision making. #enjoytheride
Snipes & Marvin Sandbars - again, it takes a bit of effort, but it's well worth it. Spend 4 hours with your feet in white sand, waist deep in clear water, and take in 360 degrees of beautiful. If you are adventerous, call Shelby at Sugarloaf Marina and rent a pontoon boat with a sun deck and two slides! It's the shortest trip by water to Marvin/Snipes ... and they are open 365 days a year.
If you are not comfortable renting/piloting one of Shelby's rental boats, call Capt. Jerry Harbin (828)238-3971 at Sugarloaf Adventures. He will take you to on a ride the flats, creeks, canals, sandbars, and ocean. You'll might get a gander at light houses, sharks, dolphins, baracudas, pelicans, and crocidilles ... at least that's what his business card says! #goodguy4sure
Loo Key Snorkling - it's a bit of a chore to get there from Key West, but go if you can get there. In 25 years, it might not exits. Science is real ... global warming is real ... and it's killing the coral reefs. Listen to us ... if you have teen-agers ... do this.
The Paddle Hut at Geiger Key - Embark on a serene kayak tour, at The Paddle Hut at Geiger Key, nestled in the tranquil waters of Florida Keys. You can kill two migratory birds with one stone (it's a joke folks) ... have lunch at Geiger Key Fish Camp.
Best Places to See Sunset
Mallory Square (FREE) - everyone should watch sunset here at least once in your life. Take in the sounds, street performers, and historical reflections. It's busy, chaotic, then amazingly peaceful.
Key West Lighthouse ($$$$$+) - it's expensive and exclusive, but rent the lighthouse for a private event. If you got more than 4 people, it's really not that bad. 360 degree view of Key West and the highest angle of attack on the island. Plus you get wine & cheese for sh!ts and giggles ... in private.
Elevate Skye Bar ($$$) - IF there is NOT a cruise ship docked at Mallory Square, this is the best view of sunset. Get up there early to get a seat/standing spot ... and order your drinks early (or you will miss sunset standing in line). The place will be empty about 15 mins after sunset, so stay a bit and watch the colors in the clouds.
Tikki Boats - If the crowds are too big or you just want a more intimate experience, then you will be thrilled with this sunset vantage point. It's a slow ride from the dock (next to Mac's Place) to Atlantic, but it's pretty special. Take your own food and music, you get a qualifed captain who will make your trip and sunset optics ideal.
Best Place to See a Show
Key West Theater - Kelly Norman (she's Nick Norman's better half)and her staff do it all. Local talent, national talent, tribute bands, bingo, charity events. One thing for sure ... if they are putting it on, then it's gonna be worth putting your eyeballs on it. Don't forget to look for shows in the Backstage Listening Room ... intimate setting for great entertainment. We like the upstairs tables with private bar and bathrooms.
Here is some video evidence of great shows of shows at the Key West Theater: Tony Baltimore Key West Follies, Carol King/James Taylor tribute and Kari Wolf
Waterfront Playhouse - We love this place. It's a tiny place, not a bad seat, but the quality of the show is big-time. This is NOT amatuer community theatre. It's serious performances put on by local/national professionals that will stand up to what you see in Miami, Washington DC, Boston, Seattle ... ask us how we know. Say hi to Patrick ... he runs the show. (literally and figuratively). Tell him Kelli sent you, and he'll give you the best seats in the house. #aintbadseats
Aqua - we like La te Da and we've survived 801, but if you are looking for the drag show that's "just right" ... this is the place. Highly recommend shots before, during, and by then after ... why not? If you are offended by cross-walks being painted rainbow, you are in the wrong town cowboy. Please note: you are gonna need $1 bills.
Comedy Key West - when you are tired of standing in a crowded bar screaming to your lover 2"s away, this is an excellent alternative. Nationally-known comedians come through and the local talent hammers hard on silliness of the island inhabitants. BUT, if you care anything at all about Jimmy Buffet, the Burgers & Buffet Show is worth the time. It's more music and Buffet history lesson then one-liner jokes. We enjoyed ourselves and the cheese burgers were good!
Best Bars for "Just a Drink"
22&Co ($$$) - Best Gay Bar in Key West! Who knew? We met Jenn in 2018 ... and have been fans/friends ever since.
The Saint ($$$$$) - This hotel bar offers a great list of "Seven Deadly Sins" drinks. Bartenders are truly experts in mixology.
Shotz & Giggles ($$) - Get the "tall" Mermaid Drink. This place will be 95% locals ... think bartenders that are off the clock. Do NOT pee between the cars outside, they are cop cars.
The Roost ($$$$) - Back in the day, we loved this place because of Anette and Blondie. It's our buddy Steve Hanes last stop any night he's out and about. Deviled eggs are ... not like the ones you got on Sunday's cover-dish ... but we eat'em.
Sky Bar at the Mansion - We knew Michael from the Playboy Party during Fantasy Fest ... he looked exactly like Hugh Hefner. Once he built the Sky Bar, it gave the entire pool areas an upgrade. We love it up there, and the view is great ... just know you are gonna need shade.
Fancy Restaurants
Bel Mar ($$$$) - Food is excellent and service is perfect. Ask for Hanrow's section. Tell him Kelli sent you ... he's a kind soul. If you can, sit near a window and enjoy the view of the marina/harbor. We use this place for any business meetings where we need to talk and impress our guests.
Louie's Back Yard ($$$$) - Upstairs is first come first served with a tapas menu. While you don't get a direct sunset view, the colors in the sky and water is museum worthy. Best service in Key West ... just the best. If you are lucky enough to get Blondie as your host, tell her Kelli sent you. She's the best!
Lola's ($$$$$ holy shit) - but you MUST have a reservation and it is BYOB. Reservations are difficult to get because there are only a few tables. The chef will make your meal across the room and bring it to your table. Fantastic, but we told you it's not cheap.
Breakfast Spots
Blue Heaven for Sunday Brunch ($$$) - During busy season, arrive early and be prepared to wait for a table. Food is awesome, but the music is always great. If you can catch Cayman playing with Kenny ... you can thank me later. They are season professionals with a long-standing career on the Rock.
Hot Tin Roof ($$$) - if you can sit outside, the view of Sunset Key and Fire Island is just beautiful. Food is good enough ... but the location is fantastic. But pay attention, it's a perfect place for BREAKFAST. It's calm, quite, and service is solid. You really do want to get a table outside.
Riviera Coffee & Sandwich Shop ($) - the breakfast sandwich and cuban coffee are as good as it can get.
Too Drunk - Gotta Eat
Mr. Z's ($$) - cheese steak is the best and look for Julia's photo. Sometimes there is a long line, PRO TIP: a big cash tip will get you to the front of the line. Who don't love free-enterprise? The folks on the grill and in front of the pizza oven work harder than rented mules.
Super Dogs ($)- not sure we'd recommend if you are sober, but this cart sits right outside The Bull on Duval Street. We don't have memories of most of our visits, but the next day ... we are glad we stopped!
Angelina's Pizza ($) - watch out ... it's hot. The owner has a podcast SIT WITH KIT that's pretty good. ALSO, pls note: The Durtbags play at Durty Harry's which is in the same complex. David Baron is the drummer and for a big tip, he will get the band to play "Inner Sandman" by Metallica. It's a classic from the 90s and the crow will love it! Tell them Kelli sent you.
Water View Dining
Salute's ($$) - sit and watch pick up beach volleyball. On Sunday nights during high season, listen to local acts performing on beach pavilion. Food is good, but service can be slow during busy times. Sit back and just enjoy the views.
Latitudes ($$$$$) - must have reservations and take the water-taxi. It's a pain-in-the-ass to get a reservation. You gotta call and be persistent with the host.
Geiger Key ($$) - best backwater fishcamp below MM50. It's off the Rock, but worth the drive or Uber. Justin who runs the place is a friendly as they come, and you will most assuredly see some remarkable wildlife.
Casa Marina Toes in the Sand Dinner ($$$$) - If you have a family or close group of friends, this is a MUST DO. You sit on the beach (thus the name) and enjoy a true Caribbean island setting. If you are lucky, they'll have music. If you go at sunset, add that to the scoreboard.
Bar Food
Mary Ellen's ($$) - best tomato soup and cheese sandwich. Drunk spelling bee and vibrator races don't disappoint if you happen to be in town.
Willie T's ($$) - it's been around for a long while. Kelli like the southwest egg roles. Not sure about Health Dept. rating, but again ... it's bar food.
Best Key Lime Pie
Blue Heaven - Not even close, this is the place to get the best "all-around" key lime pie in USA's southernmost town.
Cafe Sole - it's not that big. it's not that tangy. BUT the graham cracker crust is perfect.
Kickin Back Food Mart - this place is awesome ... you can buy underwear, floaties, and the best bite sized key lime pies you ever tasted. Now you gotta get to Cudjoe Key ... but that's on you. While you can't get the bite sized pies online, you can get the "mini" version. We've sent them to folks all across 'Merica just to make them envious. If you want be be a real ass, send them the chocolate dipped key lime bars in the middle of February.
Best Sloppy Joe
Sloppy Joe's ($$) - it's 100% tourists, but why not? Go ahead and order the sloppy joe and prepare for wearing the slop. Music is lively, and bartenders are very capable. If you happen to be in town on a Sunday night, check out Rolando Rojas for the best Latin Music show of your visit. Tip him good and ask for "Red Red Wine." Tell him Kelli sent you!
Tonio's Seafood Shack & Tikki Bar ($$)- we like it ... a lot. It's off the Rock by a lot. Like MM24. BUT it's a local vibe and the sloppy joes are very sloppy.
Best Cuban
Sandie,s Cafe - it's on White Street and is connected to a laundry mat. If you don't speak Cuban, you better bring your A1 translator ... OR go with "Cuban Mix and coke."
Riviera Coffee & Sandwich Shop - it's on Flagler Ave next to the new Timmy Tuxedo's. Can't go wrong with Cuban coffee, cuban sandwich, or their breakfast sandwich.
Meal Before a Show
El Meson De Pepe's Restaurant & Bar ($$$) - sitting next to Mallory Square and beside Waterfront Playhouse, this place has the best Mojito's in Key West. We think you should order #66 ... but need to check next time we visit. Now this is important, if you want an authentic dining experience with Latin food and music, check out our buddy Rolando Rojas ... he's as legit as it gets in Key West! Give him a big tip and tell him Kelli sent you ... request "Red Red Wine" ... we know it's nutty.
La te Da's ($$$) - Randy Robert's show is hands-down best show in Keys. Might as well eat downstairs to remove stress of being early. Food is great. Service is great. Pool side tables are good vibe.
The Grand Cafe ($$$) - Best duck on Duval Street. The people watching is front row with white table cloths ... right in the heart Key West main walking traffic.
Restaurants off the Rock
The Docks - all the locals get pissed because Stock Island is in the Key West zip code. Personally, don't care ... but you are gonna have to leave the Rock to eat at The Docks. Well worth the trip. Bartenders are as awesome as the sunset over the marina. Sits next to a fish store if you are into that cooking thing.
South of 7 - this is the closest sit down proper place to eat to Sugarbush, so we go on the regular. Spencer & Billy are at the bar ... they serve Australian Vodka ... and they are great guys.
My New Joint - can't take kids to this place. Music starts at 6pm. Ray and Anna are as nice of folks you'll meet in the Keys. Gets loud at times, but all you gotta do is drink more. Kelli like the bar seats cause she can sit criss-cross apple sauce.
Key West Blue Crabs (Food Truck) -if you love Maryland Blue Crabs ... well you can have the same goodness here in the Keys! Tell Stacy that Kelli sent you! We've ordered them several times and the JUMBOs are perfect! Here's a video evidence: How to Eat Blue Crabs
Best Places to Stay
Southern Most Beach Resort ($$$$) - it's on the "slower" side of town, but the views are awesome. There is a sandy beach next door if you get tired of sitting by the pool. For best all-around experience ... request Room 8201: overlooks pool/music, little sandy beach (used to be clothing-optional), and water. It's right above the Spa and the Pool Bar is immediately available. #HashMarks
Ocean Key Resort & Spa ($$$$) - best "sunset" rooms in Key West. Sits next to Sunset Pier ... great music and boat watching. Sits next to Mallory Square which is a MUST SEE during your visit. Pay attention: request a west-side Deluxe Oceanfront with balcony. If possible, you want to see Sunset Key from your room. Guess why?
Casa Marina ($$$$$) - it's the fanciest place on the "rock." A Flagler hotel that's been renovated and offers upscale option. If you have a client, boss, or persnickety relative ... put them here. If they b!tch ... it ain't on you ...it's as fancy as we got.
The Key West Hotel ($$$$) - pay attention, this boutique hotel is on Duval Street next to Key West Woman's Club and the Red Barn Theater. The only water view you get is the pool. However, it's a NO car hotel ... wake up, coffee, and walk around town. Rich, the owner, is a great guy who works hard to provide an AWESOME experience to his guests.
FISHING GUIDES
Captain Chris: Big Kahuna Charters - is a life-long friend of Jimmy Buffet. Don't believe us ... ask him! He's got the pics and stories to prove it. He took Uncle Leonard out and after docking ... we took all the fish to Mangrove Mama's for lunch. Couldn't ask for a better day in the back country. Call him at 305-304-5498 ... tell him Kelli sent you. You probably want to see his nakid picture standing behind a grouper ... classic old school.
Captain Timmy Carlile: The Outcast Charters - Far an away, the most well-know fishing guide out of Sugarloaf Marina. He's been at it since a young boy. Call him at 305-304-4834. Tell him Kelli sent you. If there are fish out there, you will catch 'em. Great guy with great history.
Captain Jamie : I Wanna Iguana Hunt - He also does efoil boards and eco-tours. Great guy ... pilot, captain, and great dad. You'll have a good time. We took our catch back to Geiger Key Fish Camp and had them cook 'em up. Taste like chicken. Call him at 573-257-0727 and tell him Kelli sent you.
Family Fun Activities
There is a ton to do in Keys for entertainment. For an overview of a typical "Summer Camp", there are the nigh points:
Butterfly Conservatory - For years, we talked sh!t about folks walking around with the butterfly stickers on their shirts/hats (you get them at the end of your tour). Who comes to KW and spends time looking at butterflies? WE DO! ... as often as we can. Just amazing! It's our #1 recommendation to folks of all ages/interest. You will thank us later ... go!
Hemmingway House - slow down ... listen to us ... do NOT take this tour until AFTER you have read "Old Man in the Sea." Do NOT take this tour self-guided. Pay the extra ... get the guide ... and pay attention. There is a big difference between knowledge and understanding. Be prepared for comparing/contrasting Cardi B and Hemmingway over lunch.
Sky Dive Key West - these folks jump 365 days a year ... weather permitting. It's a unique opportunity to parachute with a 360 degree few of water. People travel from all over the world to check this off their bucket list. We've watched over a dozen of our friends and family ... 100% are THRILLED they did it. We ain't ... we're pilots ... and we do everything possible to stay in the plane.
Sunset Sports Jet Ski Tour - We generally book the early bird special out of Cow Key. It's a smaller group with easy access to the Gulf of Mexico (old school) and Atlantic Ocean. This matters most on days with rough waters and/or strong winds. On most days, you enjoy a complete trip around the "Rock" with a guided tour from some dude who just makes shit up. You'll see stuff from a water-view ... and it's fun riding in the "washing machine" turbulence in front of Mallory Square.
Couch Trains - this is a fun way to get an "overview" of what's available to do in Key West. Think double-decker buses in London. We've done it a few times, and the information is always unique to the tour guide/comedian conductor driving the train. Some might suggest they just make sh!t up ... which is sorta funny, too.
FITNESS
Peak Performance Pilates & Fitness - Larysa Kolosoka (aka Larissa in hillbilly speak) is all about your well being: salsa dancing, Pilates, boot camps, and just about all things sweaty and good for you!
Mile 0 CrossFit - Kelli and I have grinded it out in this legit box. It's hot, heavy, safe, and fun. Coaches are qualified and facility is clean enough to sweat. Probably shouldn't eat of the floor ... we sweat like pigs.
Mata Yoga Key West - if you are looking for hot yoga in the only tropical climate in the 48 United States ... get down dog with your self. The garden hose shower afterwards is awesome, but you need to understand that water is piped in from Miami.
Pickleball - the courts are on Higgs Beach next to Salute's and Casa Marina. They are either empty or crowded AF. It'll take a minute to figure out the rules ... who plays who on what court, but always friendly competition. Watch out for the octatrienes with knee braces, they'll show no mercy.
Key West Golf Club - look ... it's the same as folks looking for long sandy beaches. If you are looking for a wide-selection of beautiful links and manicured puttin' greens, Key West ain't for you boss. However, if you can play the 5th hole a bit before sunset, it's as beautiful as Cypress Point, Pebble Beach. Heard it here ... go find you Bermuda Shorts and Pink Polo. FUN FACT: many local musicians tee off at 7am ... possibly with blood shot eyes and whiskey sweats. Key-West-Golf-Club-Scorecard-web
Worth Making the Trip to Put Your Eyeballs On
Fantasy Fest - it's not for everyone, but it's a week long Halloween party for adults who want to forget they are grown-ups. It's held the last week in October with strict "pasty" rules ... for the love of all things good in the Universe, do NOT bring kids under 18. Zombie Bike Ride is always a crowd favorite. #fatdudeswithtittiesout
Overseas Highway (Miami to Key West) - You need to do this ONE time ... everyone should. It's the most beautiful drive over blue water that's truly spectacular. Now, after you've done it once ... the romance might wear off. The traffic is slow, the idiots from Miami drivers pass at 100mph to sit in the line with everyone else at 35mph, the key deer are cute ... but are you shittin me? ... and if you get a convertible, the top will stay up most of the drive. Keys sun is hot as hell.
WetStock - for 21 years running, this springtime floating music festival is held near Picnic Island (sandbar). The lineup always includes some of the best local bands in the Keys. It's a great day of music that brings all types of folks together. #powerofmusic
Pole Vault in Paradise - held in January every year on Higgs Beach, this competition brings in the best pole vaulter from around the world, USA, and Florida.
New Year's Eve Red Shoe Drop - CNN and other main street media usually show up to compare/contrast Key West with New York, LA, Sydney, and Paris. It's crowed but safe as can be. It's work putting your eyeballs on it once.
Non-Profits to Support
Key West Arts & Historical Society - we are big fans of their museum. Go find our brick ... send us a pick ... and we'll donate $ in your honor! The art work from "Old Man in the Sea" is one of a kind. You won't be disappointed by any exhibit. Check out the gear by Diane Nyad who swam from Cuba to Key West.
Wesley House Family Services - good people and great cause. If you are in town for their Valentines Gala or Xmas Bike ride ... you will walk away with a smile on your face.
Plant a Million Corals - Dr. Vaughn is a globally-recognized expert in coral restoration. A statue of him has been placed down-under at the Great Barrier Reef. Check out their factory/laboratory to learn more.
Jose Wejebe Foundation - "Making Fishing Dream Come True" for children with life threatening illness, disable veterans, and women in need of a great time on the water!
Shopping
Nu Shuz - all kinds of stylish, off-color, and island clothing. Tell them Kelli sent you ... the dude with the tin beer can hat is a good guy. We like the energy. If you happen to need a coat, this is the spot.
Mel Fishers - Larissa work here ... and will hook you up with an Atocha Coin. Tell her Kelli sent you and she'll give you an excellent deal! Also, ask her about signing up for her next fitness class.
Assortment Inc. - it's just men's clothing. I've bought clothes for weddings, non-profit galas, work, and special events. Ever need matching tie, belt, socks, and handkerchief ... they can hook you right up!
NEW YORK, NEW YORK - NOVEMBER 13: <> at Cipriani South Street on November 13, 2025 in New York City. (Photo by Slaven Vlasic/Getty Images for CARE)
Bikini Village - Here's the down low ... if you go in there and spend $$$$$, then stop and remember ... somebody is about to walk around prodimately nakid. Money well spent in my book. If you go in and buy a cheap string bikini that falls apart in one wearing, then somebody is about to walk around prodimately nakid. #oldschoolwinwin
ALTERNATIVE STUFF
Garden of Eden - located on top of the Bull on Duval Street, this place is uniquely "clothing optional" all day and night long. We've Pooh Beared it ... we've stripped down to less clothes than when we were born. Nobody even noticed I was there ... imagine that?
801 and Bourbon Street Pub - These bars are across the street from each other. Good fun for enlightened folks with inclusive mindsets. Oddly, they don't allow women in the VIP pool/bars. The drag show upstairs ain't for the faint of heart. Also, if your sons are from an elephant state, it will most likely make them want to kiss boys and wear dresses. You've been warned. #biggerproblems
Don's Place - Pay attention, this bar is open from 7am to 4am. Why the hell do they close for 3 hours? ... I'm thinking OPEN 24/7 has a nice ring to it. Police just off the night shift are there for Breakfast Beers #englishvibe
Sorry You Missed It ...
We've had the pleasure to enjoy so many things about Key West that no longer exists in it's original form. Evolve or die ... so that's what this might town does. Thanks for all the memories of people/places gone by:
Anna Sweet Gallery - There's art and then there is Anna's sweet photography. With her unique resin and adornments, her photos were truly special.
Smokin Tuna Saloon - Caffine Carl & the Buzz was the house band. Erin, Ed, Emi, and so many other awesome bartenders. Honky Tonk Tuesday ... classic.
Rock House - Never figured out how this place could have three stages in it? BUT it was without a doubt the best place to watch a Duval Parade.
Little Jazz Room - this was our Wednesday night date spot. Music was always good, and the crowd was so calm. Wasn't a bad seat in the house.
Oriole Club - permanently shut down, this place opened up after the "normal" bars closed. Attended by off-duty bartenders and rando ner-do-wells. GONE ... after stabbings, alleged drug usage, and random fornications/fellatios by some well-fed tourists. That's what we heard ...
Pride Crosswalk - Clearly a top priority of the Sunshine State ... and while ignoring pot holes all over Monroe County ... the DOT proudly (thus PRIDE) and bravely irradicated the city of the extremely dangerous rainbow colored paint stripes. #OneHumanFamily
Old Town Mechanical Bull - we love Kaya complex and have enjoyed music out back. However, it was pretty special to witness the cultural clash of Conch & Cowboys. Mel & Dewayne bought it and moved it to their bar Scratch Ankle Fillin' Station in Asheville, NC.
Just In Case ...
Medical - Advanced Urgent Care of the Florida Keys (Dr. Wagner) I've had to go to Urgent Care twice since 2018. Both times ... Dr. Wags has had to fix an infected cut (spider bite? yard work?) that needed attention. He's a nice guy, good talker, and is very serious about providing EXCELLENT care.
Auto Repair - Pitstop Tire Service (Junior) has worked on three of our cars over the years. Oil changes, flat tires, and some body work. They normally come to our house for auto service. If you see him out at Marvin on a Sunday, you are gonna want to try his grilling skills.
Nails - Nailtini (Beth) has been our GOTO spot for medi-pedi & waxing. It's a unique setting and the walk-up traffic can be entertaining. Fancy drinks are on the house, but remember ... it takes a while for the paint dries!
Haircut/Shave - World of Blendz (Marc Blendz)
Body Painting - Air Brush Hero (Avi)
Tony McLean Brown
A Western NC hillbilly through and through, Tony McLean Brown was born in the small town of Enka-Candler outside of Asheville. His parents re-named him when he was 3 years old to Tony (a nickname provided by his grandfather) McLean (middle name of his Uncle Michael) while retaining his legal surname Brown.
Throughout his career, Tony McLean Brown worked as a farmer, computer programmer, and management consultant – in his adventurous years – author, song-writer, bass player, poet, pilot, mountaineer, certified scuba diver, and competitor in professional bull riding, NASCAR late model racing, Toughman boxing, Crossfit Open, Ironman, pole vaulting, marathon and ultra-marathon running, as well as parenting.
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Hey my name is Logie and key west is an amazing place to visit! My favorite part about key west was jumping out of the pane and having the biggest adrenaline rush of my life! The view doesn’t get much better from up there!
My daughter and I returned from KW this spring break and had an awesome time!!! We read the book The Old Man and the Sea and visited Hemmingway house. Highly recommend! Also went to the Randy Moore show and even my 17 year old daughter enjoyed it! Sand bars are a must 100% do! Butterflies were also a treat!! Seafood is spectacular!!! See you spring break 2027!!
Randy Roberts at La Te Da’s … Randy Moore sells Fords in Mooresville. Glad ya’ll got tanned in time for Prom!
Thanks for coming down to #sugarbushkw … had a blast with you girls. Come back soon!
Logie – so great to have you down to #sugarbush … thx for iguana meet!
Love you both!!! Love Key West!!!! IT IS A WHOLE vibe….Hope to be there soon….love Candy and David….
Dave & Candy … it’s been too long! Need ya’ll to get down out of that cold Tennessee rain/snow/sleet/hell. Miss ya’ll
Candy & David – enjoyed all your trips to KW! Y’all are the best
Love this list!! Tried many of these spots when we came years ago! Need to come back and hopefully you guys are around!
Glad you made the trip … the photos were awesome! Pretty soon we’ll get your kids skydiving at #skydivekeywest
Go Cougars! Pun intended-ish
We came to Key West as a family after the holiday. Went Jet Skiing around the island and it was amazing. My other favorite memory was the assortment of Diners, Drive-Ins and Drives “joints” with delicious local food twists such as local seafood reubens! The entire vibe of the island is a unique orientation of so many historic and tourist spots. Looking forward to coming back now that my crew is all over 21:)
Can’t wait for you and the boys to come back down! Had a blast jet skiing around the ROCK!
Let’s agree the Over 21 experience is very different than the Under 21 activities. Not sure the boys would be totally cool with parental oversight. But ya’ll will figure it out. #nothinggoodeverhappensaftermidnight
Love the Glenn Family… that was a beautiful day on Jet Ski’s!
Great recommendations. Tony and Kelli are great friends and know the meaning of a fun (legendary) night on the town. Look forward to trying it all out next time we are in the Keys
@boo we had such a great time with you and Ben at Louis Backyard. Blondie asked about ya’ll … we told her the experience was simply perfect! #GoPack
K & T, what an awesome ‘blog’ of pics, tales and more! So fun reading and seeing! I have two stories on my two adventures in KW. 1981 and 1992. Neither are repeatable unless using a nom de guerre. I guess what happens in the Keys, stays! Saw Charley the other day out walking with L. He said they often stroll down Puritan Road saying there’s Billy’s house and there’s Tony’s. Miss you, brother!! BW.❤️
Billy – next gen Key West experiences … bring your nieces and nephews! It’s as much fun … you just take naps and are in bed by 10pm. COME ON down. Best to all wonderful folks up north!
Boo – great time at Louis Backyard… thanks for sharing your time!
Only Tony Brown (and the beauty of Key West) could convince me to skydive! Tony and Kelli have the best recommendations and are basically local celebrities. Can’t go wrong with any of their ideas.
Ana! We are so proud of you and your courage to take the jump! As pilots, there’s no way in hell we are gonna jump out of a perfectly functioning airplane. You are NUTS to do that! Awesome video tho … Hope you and the boys can make it back down before the nuptials.
Ana – so excited for you and Daniel! Honeymoon in Keys?! Cya in Fall!
These are all great places to visit when you are in key west! I have been down multiple times and love every second of it and keep planning on going down every year! A lot of fun and a great place to go visit!
@adam – dude … you gotta get back down! Auqua ladies are asking about you … said they’d buy you a Bud Light.
These cats are spot-on! I’ll always cherish the memories of enjoying the best fried chicken with them on the boat in the ocean. Their recommendations are always spot-on, and they always make for a fantastic time!
DIONS chickin can’t be beat. Thanks for making the trip … one of the best shows we have seen at Key West Theater. Ya’ll rocked it. Come on back ya hear!
Well researched. Determined. Spot on. Kelli & Tony have done the hard work for you.
Thx Bruce – will make necessary typo repairs … and always open to your suggestions!
I can’t wait to get back down there. Sounds like there are so many places to go! The live music was outstanding!
Next time … BRING Tracy! We’ll trace your steps from last visit!
This is absolutely fantastic! Can’t wait to get back down there and get thrown out of some bars together!
We’re not as good as we once were … but we got try in our hearts. Love ya’ll
What a great list of local information for anyone visiting Key West! I appreciate the insights and hope to be back soon. It is great keeping up with you guys here. Let me know if you ever come back to Nashville!
Hold that thought! @aaron hudgins is always looking to fly back up to KBNA for his music!
We had the best time with Tony and Kelli! They took us and our twin boys out on the boat, had lunch, found a remote beach, saw a bunch of sharks and all around had the best time!
We’ve been to many of the places on this list over the years and they are spot on with their recommendations. Key West is a magical place!
We can’t wait to get back!
Love having Julie & the boys down … what a day on the water. Tell Julie I want a job with her https://www.runninginaskirt.com/ … Key West Section!
Sounds like we need a blog trip/collab just to be sure we get some good pics! Total write-off!
Key West is a true fun in the sun holiday…jet ski around Key West, washing board side, great fun. Many places to enjoy the Sunset party, Mallory Square, Snipes sand barge trip…the Butterflies Museum. Playhouse always have neat plays…Sky Dive over the keys, what a rush…many places to enjoy delicious food. Key West should be on your vacation Bucket List…
Ya’ll get back down here ASAP! Uncle Leo needs a tan after the long winter. Every time we pass the Sunshine RV Park … we think about the years of fun ya’ll had in the Keys!
Mandy and I look forward to the stories we create with the Tony and Kelli Key West experience!
Go Pack!
What happens on the Rock … goes back around the globe. Bring your dancing shoes and dress!
Great recommendations! I’m sharing this with my friend that lives in KW to see how it measures up with his experience. It’s been a minute since I’ve visited, so it’s definitely time to go back!
Best story ever … boat shuttle from airport. That’s good livin’ my friend!
From a born and raised local Kelli and Tony are dialed in! I will be reaching out to y’all next date night for recommendations. Thank you Tony and Kelli for all you do!
Gratitude for all you and your family have done as the true spirit of the Keys!
There’s just something special about Key West and you don’t wanna miss it! My husband and I visited Key West a few years ago and had a sensational time. It’s such a cool vibe. Toni and Kelly know all the places to go for a vacation or quick getaway. Now you stop working so much because nobody ever sit on their death bed. I wish I could go back to the office. Get yourself down to Key West y’all!
Thank you Jennifer! Love you! Toni “with an i” and Kelly “with a y” … bring the kids!