(The VMO is way off topic today, hope you don’t mind. In fact, a little serendipity is good for the soul. I’ll be back to law firm topics next week…with a post on law firm business cards: part II. Meanwhile if you’re curious, I hope you read and enjoy this post about Key West, Florida.)
January 2014: This post has been so popular I decided it needed updating. I’ve been told that it has helped a lot when people are planning a trip to KW. I’ve added a few more spots and a couple of corrections. I’ll also add here that a local friend of mine has a really great blog, which reviews restaurants and other big events in the Florida Keys. You should check it out @ www.FloridaKeysGirl.com. If you are planning a summer get-away to Key West, do so by all means, it’s my favorite time of the year. For more specific insight, read Rick Skwiot’s entertaining and informative article “A Hot Town for Adult Pleasures.” (It’s really not what you think! Summer camp for adults, it is!)
Key West, Florida | Close to Perfect, Far From Normal
“Anyone will tell you Key West is a little kooky – and darn proud of it. In the words of one local: ‘It’s like they shook the United States and all the nuts fell to the bottom.’ The town’s funky, laid-back vibe has long attracted artists, renegades and free spirits. Part of that independent streak is rooted in its physical geography: barely connected to the USA, Key West is closer to Cuba than to the rest of the States. [ed. that is Cuba is closer than the nearest Wal-mart!] There’s only one road in, and it’s not on the way to anywhere. In other words, it’s an easy place to do your own thing.
Because of its handy proximity to absolutely nothing, it’s been immune to corporate interference. Chickens and six-toed cats have their run of the island. Bikes are the favored means of transportation. And few people work nine to five.”
–Lonely Planet (travel website)
I live in Key West, year round. I know, I know… how does a small town girl from Pennsylvania possibly endure the absence of changing seasons? Fact is, our seasons do change: from hurricane season to mosquito season, from lobster season to mango season, from dry season to rainy season, and of course, the most famous season of all…. tourist season (referred to by locals as simply “season”).
Every year I get a dozen or so requests for info about the Conch Republic—Southernmost City/Mile Marker Zero/Cayo Hueso (Bone Island)—from friends, colleagues and family. So, in the winter “holiday season” spirit, I thought maybe others planning a trip this way might find helpful suggestions from this list of the things I LIKE to do in Key West. These are by no means comprehensive, nor will they be to the likings of everyone. And, there is way too much to do and see in KW to list them all here.
TIP: For another perspective on the oddities and characters that live in Key Weird far from normal, read this book! Key West Story by Rick Swkiot is available on Amazon and other great books stores, including Apple iTunes. Read it before or bring it along. It’s great Key West beach reading!
My suggestion for a four-day Key West agenda:
Day one: Play, Eat, Rest, Play, Sleep.
Day two: Play, Eat, Rest, Play, Sleep.
Day three: Play, Eat, Rest, Play, Sleep.
Day four: Play, Eat, Rest, Play, Sleep.
If you’re planning a longer stay, rinse and repeat:
Play, Eat, Rest, Play, Sleep…
(Disclosures: (1) I am in no way affiliated with any of these businesses nor am I getting any perks for recommending them. (2) Your experience may vary. Inconsistencies are bound to happen where humans, weather, and other Key West oddities are involved.)
Since this post went live in 2011, many people have contacted the VMO asking what is the best month/time to be in Key West. Although I think anytime is a good time, if its your vacation, you’ll probably want to avoid a few months when the weather is really iffy. That would be December and January. The “winter” months can deliver a few days or weeks of cold, rainy weather. It will most definitely be a mix of sun and clouds with only a few full-sun days. (Right now the temps are in the low 60’s but the sun is shining and hot.) If you don’t like steaming hot, avoid August, September and October. However, those three months have some of the most fabulous displays of color and great events and street festivals. The Poinciana trees, vibrant orange, light up the town and people here really get into Halloween in October, which culminates with Fantasy Fest. (Book hotels now.)
My favorite months are May and November. The water temps are a little cooler than the summer, but usually doable. Flowers are blooming and the sweltering heat is limited. But I really like June and July too. The water is perfect. June can be rainy. July can be stormy. Both can be hot, hot, hot, but the past few years they’ve been really nice. Feb, March, April are popular months. Usually good weather, lots of stuff going on downtown, but restaurants are crowded, beaches full, flights expensive, and hotels at a premium. Rental houses are precious and should be booked in advance if you want to be here in the spring. Snowbirds are all in town, but generally leave by mid-April and sometimes you can get a good deal on a monthly summer rental. Hope that helps!
#! RENT A BIKE.
Driving a car in Key West is a pain in the…neck. Parking is either impossible or expensive—getting towed is a hassle. So, rent a bike. It is super easy and cheap and most of the places you want to go are close by, the island is only eight square miles!
If you rent a bike, there are only three things to remember: (1) keep a street map with you at all times because the streets in Old Town are catawampus; (2) obey the traffic laws—one way streets are, well…one way and stop signs and red lights mean stop; and, (3) Yes, you can get a ticket for riding a bike while intoxicated—don’t drink and ride! If you opt to rent a moped, beware: They are dangerous in Key West.
Update: I’ve since become the owner of a scooter. It was a opportunity I couldn’t pass on. I didn’t think I’d use it, but since it was such a great deal why not. Ha! Now, I love my scooter. It’s fun. However, I know the streets of KW. I know where the pot holes are and how visitors on bikes and in cars aren’t looking out for you. I drive VERY VERY cautiously and never after I’ve had an adult beverage. I still think scooters are an okay choice for visitors, but be careful and obey the street rules. If you need to get around the island and don’t want to get exercise, its a perfect solution.
PLAY: ON THE WATER
“It’s like… an Island… mon,” a grungy street musician said to a guy sitting next to him on a Duval Street sidewalk one evening as I was passing.
He’s right! Incredible, beautiful, bountiful, gin clear, aqua waters surround Key West and make getting out on the water a priority, IMHO.
Private boat charters are great if you have a group of 4-6 people. The City Marina has a bunch of them. Easy Day Charters is highly recommended.
#1 Yankee Freedom $$$$
The Dry Tortugas are stunning. It’s a full day trip, out and back, but worth the time and every penny. Family friendly. (Dramamine suggested for anyone with the potential for motion sickness, as the straits can get a little choppy in the winter months.)
The beach and snorkeling at Fort Jefferson are pretty awesome—giant Tarpon, Barracuda, fantastic coral forests, and tons of colorful tropical fish. Swimming around the old brick fort wall is like swimming in an aquarium, seriously! Lunch is included and the crew is very accommodating. Walk around the old Fort and the attached sandbar beaches. It will probably be the highlight of your trip to sofla—even if you don’t swim! You can also catch a seaplane to Fort Jeff, if you want to splurge!
#2 Snorkel boat to Sand Key or Dry Rocks $
Fury or Sunset $25-35 half-day trip (Internet discount)
If you don’t want to spend a whole day on the water going to the Dry Tortugas, or pay for a private charter, a group snorkel trip to Sand Key or Dry Rocks is a decent way to see some fantastic tropical fish. It’s lots of fun and a low maintenance outing as they provide snorkel gear and instruction. The boat has a snack bar, soft drinks and adult beverages. It’s a group thing and sometimes you’ll be bumping into other snorkelers from the boat in the water, but the reasonable price tag makes it a deal.
#3 Kayaking or Paddle Boarding $
Lazy Dog Outfitters
Hurricane Hole on Stock Island, a short cab ride or bike ride from downtown, will set you up for a fantastic ½ day of paddling. Guided tours or hourly rentals will take you to mangroves, mansions and more. It is great exercise and a nice way to see the eco system of the Florida Keys, see the flats fishermen in action, and snag some derelict lobster bobs from the mangroves for an authentic KW souvenir! After your work out you can “rest” at the Hurricane Hole bar or “eat” at the restaurant—it will not disappoint. Try a fried snapper or grouper sandwich. They have icy cold beer, local color, and cool breezes. Seriously, I like this place for authentic KW atmosphere and food. Sometimes they have live music, but the real attraction for me is the mix of boat fuel, fried fish, and beer. It makes me return time and time again.
EAT: ON THE TOWN
Key West prices can be high in “season,” food quality mediocre, and service so-so, however, over the course of a few days you should be able to procure some really great meals that you cannot get elsewhere in the contiguous 50 states. These are some of my favorites.
#1 El Siboney – Catherine Street. Very casual. $$
Cuban food. Nothing fancy, but totally addicting. Of all the Cuban restaurants in Key West and Miami, El Siboney remains my fav! Expect a waiting line for a table at dinnertime, especially during “season.” If you don’t want to wait, try lunch. Or, sit at the counter for dinner, which can be much more entertaining. Great service. Great food. Smashed garlic chicken or shrimp enchilado, an ice-cold Presidenté beer or home-made Sangria makes a fine, and filling, meal after a day of biking, beaching, snorkeling or kayaking.
#2 Five Brothers Grocery – Corner of Southard and Grinnell $
A queue of locals and snowbirds wait every morning for their fix of café-con-leche. And, there’s a reason for that: it’s worth the wait. A great way to start your day. While you’re there, order a Cuban Mix—all the way—or the Grouper fish sandwich to take on the boat or to the beach for lunch. (You can also call ahead and pick up in 20 minutes.) If you’re feeling a little fuzzy after a night of too many fruity rum drinks, Five Brothers’ cheese bread and café con-leche is an amazing remedy!
#2B Coffee Plantation – Caroline Street
Free Internet access with purchase. Great coffee, lovely ambiance, close to the old seaport, shopping. Pastries! Morning-evening…a real local establishment! Lots of books, newspapers, friendly conversation, and unique gifts too.
#3.1 Azur – Flemming and Grinnell $$$ or $$$$
My first dining experience at Azur was about 9 years ago for a wine dinner. The sommelier was excellent and the food remarkably paired. Subsequently it remains my favorite distinctive restaurant! Perfect for brunch, lunch, small plates, or dinner, it is located beyond the high traffic tourist area but close enough to walk. And while there is no view of the water or tourist foot traffic, the interior is comfortable upscale and the patio is tropical and pet friendly. The wait staff is above average, typically attentive, and the menu is creative but never pretentious. The owner/chef is usually around and checks in with his guests. A locals’ favorite.
#3.2 Santiago’s Bodega – 207 Petronia $$$
This tapas-style eating establishment often comes up in local conversation as a favorite, but until earlier this month, I had avoided it because I heard it was hard to get a table. Pick up the phone, make a reservation…NOW. My new favorite. We sat at the bar. Our server was awesome, food wonderful, great wine list and the atmosphere was upbeat. Having been to many tapas bars in the past, I expected the dishes to be small. Not so here. Yes, they are small plates compared to an entree, but two or three items could feed a family of four! There were two of us and we tried six. Took a lot home. Try the greek hot cheese dish, saganaki. It’s amazing. I loved the lamb meatballs too. Everything is good.
#4 Café Sole – $$$$ Francis and Southard
I go here for the hogfish (snapper), when it is in “season,” (see I told you we have seasons!) but I always leave thinking the side dishes (vegetable concoctions) are the main event. They are always awesome, wholesome, and tasty without a lot of salt—just butter, butter, butter. Lots of KW restaurants do a good hogfish, but Café Sole is always my first choice. I always order sans sauce or on the side. A true Key-West-garden ambiance, they will accommodate groups or a romantic table for two. Call for reservations. I just like this place. Very French. (If you’re looking for more French cuisine, try also La Crêperie in Bahama Village at Petronia and Thomas. An authentic French bistro and a top spot for breakfast or lunch—expect to wait for a table during “season.”)
#5 Hogfish Grill – $$
Speaking of hogfish, this establishment on a funky Stock Island pier lined with live-aboards and art studios is really my all time Key West favorite. You’ll need to cab out there if you don’t have a car. Everything on the menu is great, yes, including the hogfish tacos, which are outstanding. Take a stroll around the pier and you’re sure to feel the spirit of old Key West.
Off the radar, Mo’s serves Haitian French Creole food from a spot that New Yorkers’ might call a whole in the wall joint—only a few tables, a counter and a take out business. Fuggetit! Not a hole in the wall, it is clean, hospitable, and delicious—oxtail is amazing. The ambience is special and the open kitchen will make you feel like you’re at home and mom is cooking up her most delicious secret recipes. I’m not sure where you’re going to get more authentic Haitian/Creole cooking in the U.S. (except maybe in Miami), so if you’re adventurous and want some ethnic food, this is the spot. No view.
#7 Origami. Simonton and Duval. $$$$
I like their sushi, a lot. Nothing especially Key West about this place except for all the locals who frequent it, but if you’re looking for sushi, it is my favorite. Cute open garden courtyard setting in the heart of Duval Square. Plenty of parking for your bike (or your car, if you must).
#7 The Restaurant Store and Cole’s Peace Artisan Bakery. $$
Eaton Street, just beyond the Eaton/White intersection in Old Town you’ll find this homegrown establishment has a wonderful, healthful collection of sandwiches and a nice, but small, selection of wine. Their bread is amazing. You can also grab a loaf if you’re in Fausto’s Food Palace (the ONLY, and thus the best, full service grocery store in Old Town). There are a few outdoor tables, but no view. Get your sandwich and a bottle of wine to go (keep it in the brown bag), then head over to Mallory square, sit on the seawall, and watch the boats go by, or ride to Higg’s Beach, grab a picnic table, and watch some volley ball.
#8 Turtle Kraals $$ or $$$ Old Seaport
The only reason I add this is because if you’re at the old seaport, have to eat, and don’t want to spend a lot of money, Turtle Kraals is a good-enough option. Family dining and the proportions will satisfy. Great views of the harbor from most tables. They also serve a good and hearty breakfast. Another notable breakfast stop at the Old Seaport is Harpoon Harry’s—expect a wait on weekends. One of the few places that makes grits!
#9 Salute on the Beach $$-$$$
One of the few on the beach restaurants, under new ownership for the past year or so, the food is great again. (Same ownership as Blue Heaven/see below) The view is unbeatable. Lots to take in; always something going on. One of the few places I’ll buy a margarita. Chill in the afternoon with a cold drink, lunch or dinner, this is the spot. Plenty of beach to rest on (Higgs Beach), a couple volley ball nets, tennis across the street and shallow water for swimming. Sometimes the snorkeling around the pier is pretty good. After lunch, visit the East Martello Tower gardens next door.
#10 Latitudes $$$$$
A list of nine feels incomplete. So here’s number 10, Latitudes on Sunset Key. Romantic, beautiful, delicious, an ultimate Key West indulgence. Great for celebrating a special occasion (without the kids). Lunch is lovely, dinner is amazing. Only accessible by ferry, it’s a five minute ride to Sunset Key. This is a Westin property. If you’re doing dinner, find out what time the sun sets and plan accordingly. It’s a lovely spot for watching the changing sky. I’d add that for me, just that short ferry ride takes you away from the urban environment of downtown Key West. There’s a little beach there for people who use the spa or dine at the restaurant. Service is attentive and everything feels luxe.
REST: ON THE BEACH
As far as I’m concerned there is only one beach in Key West—Ft. Zach. Beautiful water, great view of the channel, delicious shade trees, grills, clean bathrooms, snack bar, and some of the nicest snorkel spots right off the beach. You can rent snorkel gear, chairs, umbrellas, and even kayaks from the concession.
Getting in and out of the water in bare feet is not for sissies. Remember, this isn’t the Bahamas—it’s Cayo Hueso-Bone Island. Some say named for the skeletons that once littered the shores, I say because of all the coral, which when dry is essentially bone! Ft. Zach beach is mostly coral bed, but it’s worth it! Bring water-shoes or footwear if you don’t have tough feet. This beach is family oriented. Best of all, radios are RARE.
Some other things to note about Ft. Zach:
- The road into the beach from the gate is a bit of walk, especially on a hot day (no shade). If you don’t have a bike (or a car), you may want to plan for a cab.
- The old Fort tour is pretty interesting.
- Migrant birds pass through Ft. Zach and there can be some terrific sightings at certain times of the year.
- In the summer months you’ll see spectacular fish that aren’t always there when the water is cooler during “tourist season,” but there are always plenty colorful tropical fish like Parrot Fish, Sergeant Majors, Yellow Tail, and Blue Tang. Certain times of the year you might see loggerhead turtles and lobster, juvenile barracuda and fantastic schools of Tarpon. Occasional sightings of manatee and dolphin.
#2 Bahia Honda $$
The most BEAUTIFUL beach in all of the Keys, traditional soft, white sandy tropical beach (although in some “seasons” sea weed on the shore), Bahia Honda is a state park and worth the 45-minute drive up the Keys and price of admission, approx. $10, if you’re looking for something special. Luscious sand bars, kayak rentals, hiking, and picnic tables (take that sandwich from Five Brothers!). Make sure to walk the old railroad bridge—a fantastic backdrop for photos. This is the only beach in the Keys where you can take a LONG, ROMANTIC walk. It’s big.
SLEEP: ON A BED
I have never been a hotel guest in Key West, but I’ve put plenty of visitors in them. You will be spending very little time in your room so what’s the difference, right? However, if you’re looking for something extra special, here are three good ones.
The Gardens Hotel $$$$$ (in season)
The garden at the Gardens is special. Add to that an interesting local staff, 5 star services, concierge, large pool, tropical bar, wine tastings, grand piano, a pet tortoise, and jazz on Sundays and you get a perfect combo resort/guest house feel. Centrally located. Traditional. Extravagant. Highly recommended.
The Casa Marina $$$$$ (in season)
Private beach with imported soft white sand! Great onsite dining choices, both indoor and outdoor, this is the closest thing to an all in one resort on the island. Fantastic pool and a slew of planned activities for kids and grown ups. Plus: public tennis across the street. A friend brought his two young daughters for a weekend get-away and they never left the resort! They loved it! Free bikes, plenty of parking, the “Casa” is a historic landmark now being managed by Marriot, under the Waldorf Astoria brand, so you can use your Marriot points! It is close to downtown but still quiet and peaceful. When you walk on this property you feel like you’ve arrived.
PET FRIENDLY. Cozy, clean, charming accommodations with location, location, location. (Off “season” rates here are a bargain.) Decent outdoor space with a serviceable pool, but the beauty is that you are just two blocks off Duval Street and you can easily walk or bike everywhere and yet still feels away from it all. I have friends from Miami who come here three times every year and they love it.
Southernmost Hotel. $$$$
One of the few hotels where you can get a room on the beach. It’s a public beach, but it’s sandy and friendly. Nice cafe. Close to everything downtown. Some of the rooms are expensive, but the amenities are nice.
Best Western Hibiscus. $$$
When my daughter got married in Key West last year, a number of our guests stayed here. The price is reasonable and the location is perfect. A couple blocks from the beach, a block off Duval, close to several restaurants. The pool area in the central courtyard is nice. The rooms were clean and staff was friendly. This is a Best Western Plus. Expect more and pay more than the BW Ambassador, which is out on the Atlantic.
PLAY: ON THE LAND (Family Friendly Attractions)
Home of the Key West Garden Club, I am always amazed and delighted at the variety and beauty of our plant life on Key West.
Small, but special and unique.
Educational for all ages and entertaining. Includes a large aquarium display. Make sure to watch the 25-minute video presentation. (FREE ADMISSION)
Located on Stock Island, these lovely gardens will give you a 360 degree look at the indigenous plant life of our island city. Birds and butterflies too. Highly recommend this.
Small by most standards, but interesting all the same.
but I’ve never been inside! Okay, so I finally did this. Went on a weekend that offered free admission, only to learn that its always free if you have a Monroe County id (local). It was crowded so we didn’t do the guided tour. Lots of cool photos and writings. If you are interested in the writer’s life, check it out. Beautiful gardens.
Beautiful grounds. Quiet and relaxing. Off Mallory Square.
Flamingo Crossing. 1105 Duval Street. Allegedly the best ice cream anywhere, if you can get past the attitude…think Soup Nazi (Seinfeld episode). Tourists rave, locals crave.
Ghost Tour. Hahaha. Never thought I’d do this, but when my “kids” visited over the holiday they wanted to do it. (My kids are in their late 20s and early 30s.) I totally enjoyed this. The guide was funny and full of knowledge. The one we took went around downtown to the hot spots and all the way out to East Martello Tower where Robert the Doll is encased in plexiglass. They give you ghost meters and everything. It was worth the $30. Ghosts and Graveyards.
PLAY: ON THE TOWN
Some people come to Key West specifically for the Duval Street bar crawl. Not my scene, but it can’t be denied a little attention especially in “season.” All the bars on Duval Street are pretty typical: loud music, generous pours, and lots of tourists. These are the more noteworthy, though dubious, establishments.
Virgilio’s (in the back of Trattoria):
Quaint garden bar with an always interesting mix of locals and visitors. Live music every evening, hit or miss on quality. Only decent place to dance on Duval St. if you’re over 40. Your experience may vary.
Schooner Warf Bar: Old Seaport. Legendary atmosphere, view of the marina, live music, and the fish and chips are good. The bar is interesting. Go there to experience an authentic outdoor Key West bar (dogs welcome if leashed) and buy a t-shirt, which are pretty nice. At the foot of William Street on the Historic Harbor Walk, Schooner Warf Bar really is…”A Last Little Piece of Old Key West.”
Margaritaville: As a long time visitor to Key West, I never went to Jimmy Buffet’s original Margartiaville until last year when my daughter visited. I have to say it was surprisingly fun! The Margaritas were very yummy. The bar tender was attentive, told great stories, and even snapped our photo. The food wasn’t bad either. Live music most afternoons and evenings. (Actually very family friendly during the daytime and they have a fun, but gimmicky, gift shop.)
Green Parrot: Live music, crowded bar, historic late nightspot. Lots of serendipity. Locals and tourists. A classic and not to be missed if only to say “been there, done that.” This is one of the only nightclub venues I will go out of my way to go to. If you’re here and the Red Elvises are playing it’s an
obsolete absolute no brainer. GO!
Irish Kevin’s: There is no other place in the U.S. like Irish Kevin’s, but then, that’s a good thing. What you’ll find is a loud, live, solo singer/songwriter musician belting out a repertoire of drinking songs, thus attracting extremely drunken youth. With all the weddings in Key West, this is the in-place for pre and post-wedding drinking parties. Are you seeing a theme here? Step in side for a minute, look around, shake your head, and move on.
Cowboy Bills: Country music and bull riding.
Never been, but heard it’s a hoot if you want to holler! Went here, finally, with a friend from out of town. We had a blast. The live music was really great. Lots of C&W dancing. Went another time and it was so so. All depends on the band. Sexy Bull Ride night is Wednesday. It’s a hoot. After being shut down for a few months, CBB reopened and so I can’t comment on the latest version, but I’ve heard it’s the same.
Captain Tony’s: Claims to be the original site where Hemingway hung out in the day. There’s a big tree in the middle and usually live music.
LaTeDa: Duval Street. The Sunday afternoon tea dance is fun. Older crowd. Nice bar.
There’s a couple new establishments on Duval that I haven’t tried but have heard about. There’s a Jazz club and a wine bar you might want to check out.
Aqua: Drag show and night club. This place is fun. They put on a truly hilarious and classy show. Dance music later. Recommend it. On busy weekend nights, you may want to reserve a table up front. You won’t be disappointed.
There are a number of artsy things to do in the city and a really great movie theater, The Tropic, right downtown on Eaton Street for that occasionally rainy day. Recently, a group of artist-types held a short-poetry contest and the winners will have their poems placed in the sidewalks around old town. The first installments are in front of Captain Tony’s and St. Paul’s Cathedral on Duval. (A friend of mine has his there!) As they get more money they’ll add the others, but for now, don’t forget to look down to the sidewalk. It’s fun.
A few other Key West classics include: Sunset Celebration at Mallory Square, (or Ft. Zach beach if you’re not interested in crowds), Blue Heaven (key lime pie with real meringue
or so I am told as I’ve NEVER eaten there!) is really good if you don’t mind waiting for a table. I love their grilled cheese sandwich. Out of town guests love the lobster Benedict and so I’ve been there for breakfast frequently in the past two years. Tip: be there when they open at 8 for breakfast and you won’t have to wait. Bloody Mary’s are pretty darn good. B.O.’s Fish Wagon on Caroline (Conch Fritters), and Southernmost Point—got to take a photo there! Most tourists go to Sloppy Joe’s and/or Hog’s Breath Saloon. Both are pretty typical KW bars. Lot’s of tourists. Food marginal.
Tennis? Bayview Park on Truman. Pick up a game. The locals are friendly and it is some of the best tennis anywhere. Early morning or evenings are best.
That’s a wrap! See you in Key West!