Key West and the Keys –
Dining, cocktails, nightlife, hotels, great pitstops (Key Largo, Islamorada, Key West)
I absolutely love Key West. I’ve found that people either love it or hate it. But often, those that hate it didn’t know where to go/ weren’t in the right places or the right part of town (or didn’t go with the right person). I also find that people who live in Florida and have never been to Key West often have misperceptions of it. So I’ll describe it to help you decide if it is somewhere you want to visit. I definitely recommend it – especially if you take a day or two to make your way down thru the Keys and stop along the way, maybe spending a night or two in other Keys and just one night in 'Key Weird', as my friend who lives there calls it.
Key West is a historical place and you can feel the history as you walk the streets – the big, old banyan trees, the hanging moss, the architecture, cottages, and historic buildings. If you are into history then there is plenty to see here not only just walking the streets but by visiting the library, the Mel Fisher Museum, the Hemingway House, the B & B’s.
The Mallory Square end of town is the bustling, touristy, lively section. Bars full of people at night (less crowded by day), live music and bands, people filling the sidewalks – street hawkers and performers – this is “downtown Key West on a Saturday night”. However, on weeknights and off season (summer) it is fun and lively but not packed. It is really fun to bar-hop here as there are so many different places – and my favorites are listed below. You can find whatever you like - a soft guitarist playing James Taylor or a classic rock band jamming Rolling Stones.
Even if you aren’t into nightlife and not going there to party – you would still enjoy Key West. It IS a party town and very fun at night, but you can absolutely come down, check into a quaint hotel or B&B, and relax by the pool, do some shopping (cool stores abound!), go sightseeing (ride the Conch tour train or do a walking tour, or grab a pedicab or rent a bike or scooter – lots of ways to get around), enjoy fabulous dining, take in a sunset cruise, visit museums and art galleries. I tell people that the thing to know about Key West is that it is a COLORFUL town, meaning it has all sorts of things to enjoy – a wide variety of types of places, types of people, types of entertainment. From a snorkeling or glass bottom boat excursion to a mimosa brunch, to a ghost tour or a wine tasting – there really is something for everyone.
I should add that there really isn’t much for kids. Other than the pool at your hotel, and going out on a boat ride or renting a bike, children’s attractions don’t really exist here. It is more for adults and couples than it is for families, and you don’t want to walk around at night on Duval Street (the bar scene) with your young child in tow. If you do take kids, go during the week.
My favorite thing to plan for people is a weekend in the Keys, so depending on what you like and what you are looking for, feel free to use my inexpensive Concierge Service to ensure a great time in the Keys or Key West, whether it be for one night or 3 nights. And now, here are some of “P’s Picks” – my favorite places in the Keys and Key West!
Let’s start in Miami and work our way down. If you have time before heading into the Keys, visit Vizcaya (amazing historic mansion on the water) near the entrance to Key Biscayne. The rooms and the grounds are breathtaking.
Vizcaya Museum and Gardens
3251 South Miami Avenue, Miami, Florida 33129 305-250-9133
Or go out onto Key Biscayne and experience the beautiful, uncrowded beaches of Virginia Key. If you want a cold beer and don’t mind a place that’s a bit rough around the edges, head out past VA Key beach area and follow the road toward the water tower and on around to Jimbo’s – home of discarded vehicles and boats, roosters and lizards, old codgers and cronies, a Bocci Ball court, and cold beer sold out of a barrel. You can take your own food and drink – they don’t care. Jimbo’s is quite a place – unlike anywhere you’ve been before, trust me. If you have nice shoes and clothes on, change into old stuff. An online search of “Jimbo’s Miami” will give you the whole skinny on this quirky, notorious landmark. The Rusty Pelican at the beginning of Key Biscayne is a fabulous restaurant and bar on the water.
NOTE: I list and describe the best places to go for this and that. This does not substitute for a map or itinerary. If you want details and directions, you can research these places online or use my inexpensive Concierge Service and I’ll layout out your trip and pitstops for you with details. Enjoy this site – and your travels!
After heading south from Florida City and starting down into the Keys, take Card Sound Road south instead of the main drag (US1). Card Sound Road is a rural, less crowded drive and will lead you past Alabama Jacks…a Keys landmark. Just a dive bar with cold beer and good drinks, they also boast the best conch fritters (corn meal based with bits of jalapeno – yummy!) and often have live music. I never go to Key West without this pitstop – on Card Sound Rd (alternate to US1 when you first enter the Keys).
Card Sound spits you back out onto the main highway after 30 minutes or so but just before US1 on your left is the little street that leads you to Shipwrecks. What a neat little plays that epitomizes a Keys bar. On the water, with tables inside and out, and a rough-around-the-edges-salty-dog feel. The coconut onion rings are to die for and the bartenders are fun and friendly. Cheers to them!
Once at US1, you’ll continue south into Key Largo. Look for Snappers around MM 94 on Oceanside – and grab a cup of tomato based Conch chowder. Order the “stress relief” – a bag of little sardine-like fish that you toss off the dock and feed to the huge Tarpon circling in the water. (Don’t do what my city-kid friend Ned did one time, and lie on the dock dangling the fish from your fingers – the Tarpon almost took his finger along with the sardine). On bayside I like to stop for a drink and/or a bite at Snooks – lovely view of the water and sunset, good food, good service, casual but nice place. On weekends there is usually a singer-guitarist playing laid back tunes.
Snooks 99470 Overseas Hwy, Key Largo, FL 33037 (305) 453-3799
As you head down through the middle keys, you go thru Tavernier and into Islamorada. Be watching for the Rain Barrel artisan village on your right (bayside) – an artisan’s village that you can stroll through. You’ll see all sorts of artistic and craft items, metal sculptures, paintings, wind chimes, you name it. Neat little café in there also – worth a visit!
The Rain Barrel Artisans' Village, 86700 Overseas Hwy. Islamorada, FL 33036
Great places for a drink or a bite as you travel through the Keys
While still in Key Largo you may want to dine at the Ballyhoo “Old Florida” Restaurant. Yummy local fare, reasonable prices, and just all around good. 97800 Overseas Hwy, Key Largo 33037; (MM 97.8 in the median), (305) 852-0822
A bit further south is Lorelei– LOVE IT! Wooden ‘boathouse’ type place, rustic, salty-dog-type place, Old Florida, water all around you. GREAT sunset party and the best burgers and rumrunners! Definitely casual!
MM 82, Islamorada, Bayside – Look for the Big Mermaid – you can’t miss it! 305-664-2692
Just a couple blocks further south and you are at Morada Bay. Upscale and lovely but could you stop in shorts and a t-shirt? Yes as long as the t-shirt isn’t worn out or stained. Morada Bay is also a great place to be at sunset and they have a little beach lit with tiki torches – very cool. If you can be there on a full moon for their full moon party (reggae band on the sand!) – it’s highly recommended! Nice food, good place to dine, and if you want to get romantic in the Keys, this stop is a must. If you happen to be there when it’s a full moon, they throw quite a party!
81590 Overseas Hwy, Islamorada, FL 33036 (305) 664-0604
Now you are on the road again, bound for Key West and headed into Marathon. At the southern end of Marathon is the 7 Mile Grill (west end of the 7-mile bridge, an amazing bridge to drive over). The 7-mile Grill is a local’s favorite and you will love the food, for breakfast or lunch or an early dinner. Fish sandwiches, burgers, omelettes – just good stuff and inexpensive. Have a beer and a bite and then head across that gorgeous water under that long bridge – you’re now an hour from Key West!
1240 Overseas Highway, MM 47.5 Bayside
Marathon, Florida Keys 33050 (305) 743-4481
Where to stay
Key Largo - Stone Ledge Inn & Popp's Motel - small, cute, clean, affordable, and on the water. 'Nuff said!
Tavernier - Coconut Palm Inn - Bayside at MM 91.5 with hammocks, grills, a beach, kayaks, tiki hut, and comfortable, tropical rooms (a few of which are pet friendly! Yay~!) I'm happy to coordinate an island style wedding at this property for you - just ask!
Phone: 800.765.5397 Tell them Priscilla sent you.
For an upscale resort try Hawk's Cay - oh my! On Duck Key (middle Keys) - for pampering yourself and having a tropical getaway. (866) 347-2675
Key West Best Places
When you cross that last little bridge and turn right on the road into downtown Key West, you just feel great. It’s such a neat place to be! The water comes right up to the sidewalk and it is a pretty, aqua blue. Be patient with the parking situation and if you’re renting a car, choose a small one – you’ll be glad you did.
Where to drink
They call it “a last little piece of Old Key West” – and indeed, it feels old, and there aren’t any bars like it left. This rustic old relic pours a mean drink and yeah, the bartenders can be a little mean (to tourists anyway) too but I don’t mind – it’s all part of the places charm! If you like unpretentious, ultra-casual places – you’ve found it!
Schooner’s Wharf, 202 William Street, Key West, FL 33040
Sloppy Joe’s is just plain fun and if you don’t think so, you don’t like loud, lively bars. Always a band or duo playing on stage, and buckets of beer or yummy cocktails. To me, a Duval crawl (Duval is the main street where a lot of the bars, restaurants and shops are) wouldn’t be complete without at least one drink at Sloppy’s. Mind you this is also the place for “bar food” like wings, chicken fingers, burgers and such. Watch out you could end up on the Sloppy Cam for all the world to see.
201 Duval St. Key West, Florida 305-296-2388
Also the Lazy Gecko right next door is fun for dancing to bands and DJ's
Rick’s Tree Bar
This bar is actually part of a multi-bar property that includes an upstairs bar, downstairs bar, indoor and outdoor bars including Durty Harry’s. All are rockin’ most nights and the Tree Bar is busy during the day too. And yes, there is a tree in the middle of the place. Ask for the drink specials – they usually have some good ones.
Rick’s & Durty Harrys, 208 Duval St, Key West, FL 33040 (305) 292-1421
Ah-h-hhh…Virgilio’s. If there’s one bar I frequent more than others in Key West, it’s this one – so I guess it’s my favorite. Small dance floor and bar on one “enclosed” side, and an open air, funky bar on the other side with a gorgeous big tree growing up through the middle of it. Virgilio’s gets great live music – blues bands, jazz, disco and dance – I’m never disappointed. And as a martini lover, I admire their ability to make great martinis of all kinds. Especially their Espresso martini does it for me (I get it with a splash of milk or cream) and I love how they give you the little carafe on the side, sitting in its own little bowl of ice, to refill your martini glass when it gets low…priceless! No food, just drinks – but good ones! Note it’s tucked away down the alley not so easy to spot – you have to be watching for the small sign.
524 Duval St, Key West, FL 33040 (305) 296-8118
Crowd is young, and yes this is touristy place, but it makes my list due to a tradition that I first learned from the Milian gang but which I now do with anyone I’m in town with…which is, every time you pass Fat Tuesday, you must go in and do a jello shot. There have actually been times when I’m up and down Duval 4 or 5 times in a day or evening and actually TURN AROUND to avoid passing Tuesday and having to do ONE MORE SHOT. ! The frozen drinks are good and you have to admit, if you wanna get f***d up, the Octane is gonna do it for you!
305 Duval St, Key West, FL 33040 (305) 296-9373
Why don’t we get drunk, and s***w!
A page on Key West wouldn’t be complete without mentioning the Green Parrot and The Bull – two Bar’s bars that are always a pitstop when spending a day or night bar-hopping.
The Bull & Whistle
You can’t miss the big black bull’s head with red eyes sticking out the side of the building. Nor can you miss the outdoor balcolny that runs around the side and front of the place and usually contains a full lot of turistos who are getting sloshed and people watching from a safe vantage point. If you go ALL the way upstairs you are at the clothing optional rooftop bar. If you’re only there to gawk and not taking anything off, you are tolerated (for a limited time) but not so welcome. So “if you go up THERE then you must DARE to BARE” – I wrote that! Good stiff drinks at decent prices for Key West, and good live music – usually rock bands – on weekends.
224 Duval St, Key West, FL 33040 (305) 296-4565
The Green Parrot
Nothingpretentious, upscale, or all that endearing about this place except that it has history, a past, and a reputation for people getting rowdy. Locals by day – a mixture of tourists and locals by night – this regular bar that doesn’t sell food is a drinker’s delight. The people watching is great, the bartenders are tough but can tell some good stories if you get them warmed up to you, and you’ll see a variety of entertainment in this place – both scheduled and unscheduled! Cold beer, a fun time – what more could you ask for?
601 Whitehead St, Key West, FL 33040 (305) 294-6133
Ohand I suppose I need to say that Jimmy Bufett has a Margartiville Bar there – oh-so-touristo but also quite fun when the crowd gets going right along with the live music. Remember, sometimes it's OK to be a tourist. Love the nachos.
500 Duval Street, Key West - (305) 292-1435
Upscale Drinking can be done at Martin's - a sophisticated restaurant-lounge with great martinis and other cocktails and nice wines. Liked the vibe and I was able to "chill" even though there are loads of people walking by. 917 Duval Street Key West, FL 33040-7407
Where to dine
Now I have to admit something else…that I DRINK more than I EAT when I’m in Key West. So my list of ‘places to dine’ is a little short. There are many good restaurants – avoid the pricey hotel ones – no need. Lots of good food at the smaller, mom and pop places – don’t be afraid of them. And don’t be afraid to step OFF DUVAL to explore. Side street businesses work a bit harder to provide good food and service and can often be very rewarding – for less money.
I first got turned onto this strange, eclectic eatery when I stayed at the Key West Youth Hostel in 1995 and asked the guy working there where HE went to eat. What a great discovery! Now if you are a germaphobe-clean freak you won’t like this place due to the chickens, peeps, and cats roaming around. They come walk under your chair while you’re dining. But for me, having grown up on a farm, this is a normal thing so no worries here. The food is delightful and it’s a breakfast – brunch – lunch spot. This is also – despite having moved here from Baltimore – my first time having CRAB CAKE EGG BENEDICT. Damn! that’s good stuff! This rambling wooden house with dining tables in the backyard is located well off the beaten path, but worth the bike ride.
729 Thomas St, Key West, FL 33040 (305) 296-8666
I love friends. And I love Friends! This place has been a Key West favorite for locals and visitors for a long time – and it warrants it. No matter which meal of the day you eat there, the food is consistently very good. The servers on the floor and in the bar are friendly - something I admire and require! Two Friends Patio Restaurant boasts a full bar with good bloody marys and the weekend Karaoke nights. It’s a large, covered but open-air dining room and it just has a great feel to it. Enjoy! (I recently was there with my friend's large "pre-wedding" group for dining, drinks, and revelry, and they did a FANTASTIC job! Managers Jeff and Scott and waitress Brenn - I thank you!)
512 Front St, Key West, FL 33040 (305) 296-3124
La Te Da
I like the bar here but the food is very good also, albeit pricey. Great place for an appetizer and nice martini or glass of vino, or dessert and coffee. This is an upscale but still Keysy restaurant-bar property that also has hotel rooms. It boasts a diverse menu with snapper, shrimp, lamb – and prime rib night on Wednesdays. Just a “nice-nice” place.
1125 Duval St, Key West - (305) 296-6706
This place has its own conch farm! For seafood, friendly bar and wait staff, and nightly entertainment -- as well as a great mix of locals and tourists alike - drop by this friendly bar and restaurant - open to the water like a big pavilion. I predict if you go once, you'll go back again!
631 Greene St Key West, Florida 33040
A & B Lobster House
I love seafood and more and more lately, fish dishes of all types (I used to be very limited but as I age, I like more kinds of fishes. Remember folks – it pays to try things you didn’t like years ago because our tastebuds definitely change over time). When I’m in Key West and want to treat myself, I go to A&B Lobster House by the Marina and I get shrimp, lobster, fish – the bisques and salads are great, too. Good bloodies, good wine list – good service. I like watching the boats go by.
700 Front St # 101, Key West, FL 33040 (305) 294-5880
DJ's Clam Shack
I lived in Baltimore for 5 years so I'm picky about my seafood. This place is a GREAT find. Blink and you'll miss it. 4 stools and carry-out. Delicious lobster roll, fried clams, crab cake sandwich. Thank you for knowing what to do with seafood!
629 Duval St. Old Key West (downtown) 305-294-0102
Camille's for breakfast on the other end of town from the tourist area is great too! Diner-style
And Martin's mentioned above for drinks has nice European fair and flair!
917 Duval St.
Other things to see and do...
Don’t miss the Mel Fisher Museum (all that GOLD – it’s stunning) and the Hemingway House – two great local attractions. And the Ferry Ride to the Dry Tortugas is pretty cool too. Smattered around Duval St. you will see white huts (booths) where you can get info on these and all Key West attractions (including the famous Conch Tour Train).
FURY CATAMARANS - Fury Water Adventures docked at the Westin Key West Resort and Marina, 245 Front Street Key West, FL 33040 1-877-994-8898 • (305) 294-8899 (They did a great job on a Rehearsal Night party before a friend's wedding. Cheers, Mates!)
KEY WEST overnight
Olivia by Duvall
Quaint, cute, cost effective. It’s nothing fancy but it is friendly. Rooms are small but so is the price compared to the majority of Key West accommodations. This place is clean and located walking distance to all of downtown’s shopping and nightlife. But on the quiet end of Duval, which is what you usually want.
511 Olivia St. Key West, FL 33040 (305) 296-5169
The Mermaid & The Alligator
This is a Bed ‘N Breakfast with nice furnishings and a neat “old island” vibe. The place is surrounded by beautiful lush tropical foliage and has a nice porch to relax on. It’s located in the heart of Old Town so you can walk to most everything and here’s my favorite part – they give you a complimentary glass of wine each evening. Dip in the pool, enjoy the charm of this neat place. Not too pricey but not cheap either.
729 Truman Ave, Key West, FL 33040 (800) 773-1894
Almond Tree Inn
This is another charming and affordable place to stay in Key West. With 22 rooms – a clean and manicured property. A nice pool and charming décor makes this a cute and unpretentious place to stay. Free parking and a fitness center round out the amenities. Check it out for a night – you’ll like it.
512 Truman Avenue - Key West, FL 33040 305-296-5415
Old Town Manor
I’ve stayed here and truly enjoyed it. I love the grounds – a lovely, lush courtyard and garden (and yes, they do weddings here!) and a cozy kitchen and lobby – living room area. A wraparound porch to sit and sip and watch the passersby, clean, nicely appointed rooms, friendly staff (Runi rules!) – I highly recommend a stay here. Rates are good and never inflated. Location is central. An all-around nice place to stay when in Key Weird. You can have the whole place for a wedding - just ask me!
511 Eaton Street, Key West, FL 33040 (305) 292-2170
I should mention that Key West has all the usual chain hotels and motels so if you’re not into the B & B thing or the Mom & Pop Inn thing, you can find your favorite chain. I personally like to stay in places I haven’t stayed in before, finding that each one has its own feel and its own charm and there are things I love (or don’t) about each place. I don’t know ‘bout you but when I travel, especially to Key West, I don’t spend a lot of time at my hotel. Clean and cute and affordable is what I look for. Wherever you stay, enjoy the laid-back, Bahamian-Caribbean, tropical-drinks-in-paradise feeling of Key West!
I also have to mention the best 5-day party in the U.S. -- Fantasy Fest every October. Can you say "Costumes"? (and lack of costumes ; )