Happy Travels: Key West
Kelli Darlin and I have been coming to Key West since 2018 ... and over almost 10 years, we've seen and done it all! Our first dance was at Hogs Breath performance with Kenny Fradley and Barry Cuda. For the past 30 years ... Kenny has been true ambassador for the KW music, entertainment, counch hospitality, and sunset cruise good times. #gratitude
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 they actually show up, at least we know they'll have a GREAT time, meet great people, and see a ton of beautiful views.
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
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 Places to Stay
Southern Most Beach Resort ($$$$) - it's on the "slower" side of town, but the views are awesome. There is a sandy beach next door if you get tired of sitting by the pool. For best all-around experience ... request Room 8201: overlooks pool/music, little sandy beach (used to be clothing-optional), and water. It's right above the Spa and the Pool Bar is immediately available. #HashMarks
Ocean Reef Resort ($$$$) - best "sunset" rooms in Key West. Sits next to Sunset Pier ... great music and boat watching. Sits next to Mallory Square which is a MUST SEE during your visit. Pay attention: request a west-side Deluxe Oceanfront with balcony. If possible, you want to see Sunset Key from your room. Guess why?
Casa Marina ($$$$$) - it's the fanciest place on the "rock." A Flagler hotel that's been renovated and offers upscale option. If you have a client, boss, or persnickety relative ... put them here. If they b!tch ... it ain't on you ...it's as fancy as we got.
The Key West Hotel ($$$$) - 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.
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 thank you. She's 100 times better then him. Again, he's a self-proclaimed dick. FYI - He's plays at 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.
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
Music Venues
The Alamo - formerly Smokin Tuna with a face lift. Food is good enough. Bathrooms are clean enough. Acoustics are good enough. If you like a singer/band ... go see them at The Alamo ... you will like the vibe. TIme to enjoy the memories of the Tuna and make new ones at the Alamo.
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.
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.
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!" Don't blame us if their schedule is out of date ... #lameAF
Bali Bar - buried inside of The Key West Hotel, their slogan is "Come hide with us!" The music is more sophisticated or nuanced. You probably ain't gonna hear "Take Me Home," but you might hear a unique rendition of "Freebird" played by a piano man. 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.
On the Water
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.
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.
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.
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.
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.
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)
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.
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 under-cover cop cars. Ask me how I know.
The Roost ($$$$) - Back in the day, we loved this place because of Anette and Blondie. It's our buddy Steve Hanes last stop any night he's out and about. Deviled eggs are ... not like the ones you got on Sunday's cover-dish ... but we eat'em.
Fancy Restaurants
Bel Mar ($$$$) - Food is excellent and service is perfect. Ask for Hanrow's section. If you can, sit near a window and enjoy the view of the marina/harbor. We use this place for any business meetings where we need to talk and impress our guests.
Louie's Back Yard ($$$$) - Upstairs is first come first served with a tapas menu. While you don't get a direct sunset view, the colors in the sky and water is museum worthy. Best service in Key West ... just the best.
Lola's ($$$$$ holy shit) - but you MUST have a reservation and it is BYOB. Reservations are difficult to get because there are only a few tables. The chef will make your meal across the room and bring it to your table. Fantastic, but we told you it's not cheap.
Breakfast Spots
Blue Heaven for Sunday Brunch ($$$) - 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 ($$$) - if you can sit outside, the view of Sunset Key and Fire Island is just beautiful. Food is good enough ... but the location is fantastic.
Riviera Coffee & Sandwich Shop ($) - the breakfast sandwich and cuban coffee are as good as it can get.
Too Drunk - Gotta Eat
Mr. Z's ($$) - 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 ($)- not sure we'd recommend if you are sober, but this cart sits right outside The Bull on Duval Street. We don't have memories of most of our visits, but the next day ... we are glad we stopped!
Pizza Place at Rick's ($) - watch out ... it's hot. The owner has a podcast 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.
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.
Family Fun Activities
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.
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.
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. #fatdudeswithtittiesout
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.
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.
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!
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!