Your winter get-away could be Close to Perfect, Far From Normal…

Sunset at Fort Zach Taylor
Sunset at Fort Zach Taylor

Planning a trip to Key West. Look no further! First published in December 2011, (and wildly popular) I’m moving this post about Key West up to the front page again, with 2014 and 2018 addendums. 

(The VMO is 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 @ If you are planning a summer getaway 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!)

Hurricane Irma clean up begins at the Casa Marina beach area.

2018 Update: Long overdue, I’m now taking a few minutes to update this post. On September 11, 2017, #Irma hit our beloved Keys. She was a beast. I’ll not get into the gory details of the traumatic experience, but I am happy to report that Key West (as known by visitors) recovered quickly and is still close to perfect and not normal. Other areas in the Florida Keys fared worse and residents are still fighting insurance companies for funds to repair their homes and businesses, but here in the Southernmost Point, we’re at full capacity. I’ve added a few new observations and recommendations from the local perspective.

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 Cubathan 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)

Fort Zach

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.

For another perspective on the oddities and characters that live in “Key Weird,” read this book! Key West Story by Rick Skwiot is available on Amazon and other great books stores, including Apple iTunes. Read it before or bring it along. It’s a 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. If it’s your vacation, you’ll probably want to avoid a few months when the weather is iffy. The “winter” months – December and January – can deliver a few days or weeks of cold (58-65 (c) degree), rainy weather. You will definitely find a mix of sun and clouds, with only a few full-sun days. (Right now *2014*, 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, great local events, and festivals, including lobster fest. The Poinciana trees are lit in vibrant orange and people here really get into Halloween, which culminates with Fantasy Fest.(Book hotels now.)

My favorite months are April, May, and November. The water temps are okay. Flowers are blooming and the breezes are lovely. Sweltering heat is limited, yet humidity is all year round. As a local, 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 they’ve can also be ideal.

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 a year 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!

Every year is different. In the Florida Keys, every year is REALLY different. This year (2018), we were spared from major hurricanes, while our neighbors to the north were not. :-(. The full moons have been spectacular all year long. Most of the Irma damaged canopy is returning and trees lost during Irma are slowly being replaced. The water temps have been moderate, all year. Spring was nice. Not too much rain, plenty of sun, and cooler temps. While the summer months were exceptionally hot and basically unbearable for anyone hailing from the north, the autumn and winter have been on point. In November, the temps dropped into the low 80s with a few days falling into the 70s and nighttime lows of 64 degrees. December, has provided beautiful crisp (70-75-degree) evenings and warm sunny days. Sunscreen required.


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! Key West welcomed Uber and Lyft drivers last year.

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.

2014 Update: I’ve since become the owner of a scooter. It was an 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 potholes 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.

2018: After four fatal Key West scooter accidents in 2017, I changed my mind. Life is precious. I gave up my scooter. Not to be underplayed, the number of bicycle accidents in KW has ALSO INCREASED. At least five close friends on bikes have been victims of careless drivers and clueless cyclists who do not obey the rules of the road. Slow down. Keep a sharp eye out for dangers and please, don’t ride drunk!

In an effort to reduce downtown traffic and carbon emissions, in 2018, Key West added a new DUVAL LOOP bus. It’s free and frequent. Takes you to several popular stops around Old Town, including the new Truman Waterfront Park. The LOOP makes it totally unnecessary to have a car if you’re staying downtown. Comfortable, convenient, and friendly.


“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.

Boca Grande

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 Chartersis highly recommended. Boca Grande or Marvin Key (on the gulf) are perfect spots for general water fun and sun.

2018: For fishing (or sailing), there’s a new marina on Stock Island at the Perry Hotel that has several excellent charter boat captains that can take you either deep sea or flats fishing. Check it out at

Another sort of campy, but fun, trip to consider, if you aren’t inclined to swim, snorkel, dive, or fish, is the Glass Bottom Boat trip at Zero Duval. I took my four-year-old grandson for the 2-hour trip and he enjoyed it. Great too if you have elderly folks in your party.

#1 Yankee Freedom $$$$

Jellies at Sand Key in the Summer “season”

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 Jeffif you want to splurge!

#2 Snorkel boat to Sand Key or Dry Rocks $$

Fury or Sunset(no clue what the prices are these days)

Sand Key Lighthouse

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 DogOutfitters

Flats Fishing on the Gulf

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 ecosystem 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.

A better choice, though farther from town, is to rent kayaks at Geiger Key Marina. They have great guides and the mangroves are lovely in the surrounding area, as long as the jets aren’t flying out of Boca Chica base. Call ahead.

Lost Lobster Bobs snatched from the Mangroves


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. Some, even affordable. Here are a few 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 enchilada, 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 $$

Five Brothers Grocery Key West

A queue of locals (and snowbirds in season) 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 for sandwiches 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! (Loop stops nearby.)

#2.2 Coffee Plantation – Caroline Street $$$

Locally owned, Tao and Diane serve up a great cuppa. 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. (Loop stops nearby.)

#3.1  Azur – Flemming and Grinnell $$$ or $$$$

Azur Mediterranean Cafe, Key West

My first dining experience at Azur was in 2002 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. (Loop stops nearby.)

#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 saganaki. It’s amazing. I loved the lamb meatballs too. Everything is good. (Loop stops nearby.)

#4 Michael’s $$$ Margaret and Southard

[2019 Update] Sadly, Michael’s has closed after…Celebrating over 20 years as a premier dining establishment in Key West, established and owned by locals Michael and Melanie Wilson, Michael’s serves up delicious food, freshest fish, and hospitality galore. Small bites are available. The ambiance is garden style and sitting at the bar to dine will give you a feel for the real Key West. Locals share stories, gags, and smiles. Everyone gets a warm welcome and you won’t be disappointed. Fantastic wine list. Michael is a creative chef and definitely deserves a spot in my top five for affordable, elegant, yet casual, dining.

#4.2 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 order sans sauce or on the side. A true Key West garden ambiance, the dining area accommodates groups or a romantic table for two. Call for reservations. I just like this place. Very French. (Loop stops nearby.) (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.”) (Loop stops nearby.)

#5 Hogfish Grill – $$

Speaking of hogfish, this establishment on a funky Stock Island pier lined with liveaboards and art studios is really my all-time Key West favorite. You’ll need to cab (or Uber)out there if you don’t have a car. Everything on the menu is great, yes, including the hogfish tacos, which are outstanding. Live local music.Take a stroll around the pier and you’re sure to feel the spirit of old Key West.

#6  MO’s  $$ –1116 White Street

Off the radar, Mo’s serves Haitian French Creole food from a spot that New Yorkers’ might call a hole in the wall joint—only a few tables, a counter, and a take-out business. Fuggetit! Not a hole in the wall, it is hospitable and delicious—oxtail is amazing. The ambiance 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 myfavorite. Cute open garden courtyard setting in the heart of Duval Square. Plenty of parking for your bike (or your car, if you must).

For a more upscale sushi experience, try Ambrosia. Transplanted from its humble roots on Virginia Street to the southern end of Simonton Street in the fancy Reach Hotel district, the food is exotic, delightful, and expensive. Worth it.

#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 fantastic 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 your bike to Higg’s Beach and watch some volleyball.

Old Town Bakery on Eaton Street has great sandwiches too. Locally owned, it is the best bakery in Key West. The cinnamon buns are to die for. Full Stop. Exclamation point.

Directly across the street, BIEN has one of the craziest, best fish sandwiches in the whole world. It deserves its own number, but I’m not going to get carried away here. Just trust me.

#8 Turtle Kraals $$ or $$$ Old Seaport

Old Seaport Key West

The only reason I add this is because if you’re at the Old Seaport (aka The Key West Bight), have to eat, and don’t want to spend a lot of money, Turtle Kraals is a good-enough option. Family dining and proportions will satisfy. Great views of the harbor from most tables. They also serve a good and hearty breakfast.

Another notable breakfast stop in the Old Seaport district is Harpoon Harry’s—expect a wait on weekends. One of the few places that make great grits! Five stars. Possibly my favorite breakfast spot. (The grits at Blue Heaven are good, too.)

#9 Salute on the Beach $$-$$$

If you’re looking for a beach restaurant, Salute on the Beach is one of a handful of choices, 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. Chill in the afternoon with a cold drink (one of the few places I’ll buy a margarita), and enjoy lunch or dinner. This is the spot. Plenty of beach to “rest” on (Higgs Beach), a couple of volleyball nets, tennis and pickleball 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.

Another oceanfront dining option I’ve avoided mentioning in previous versions of this post is Louie’s Backyard in the Casa Marina District. I’m not a fan (expensive, bad service) but lots of tourists like it and locals go there for special occasions because the view is, unarguably, sweet. The upstairs dining (tapas) is best, or so I’ve been told. I add it to this update because…well, I don’t dine out a lot so my expectations are high and they’ve disappointed me a number of times, but I wouldn’t want to exclude a suggestion that others have recommended.

#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 – make reservations. 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.

2018: Still on my BEST list. And, if you don’t want the downtown atmosphere for your overnight accommodations…looking for something more exclusive and relaxing…the cottages on Sunset Key are first class. I stayed there one night to celebrate our friend’s anniversary and it was a lovely experience. Expensive and off the beaten path, but delivers the Carribean-type vacation without the passport and hassle. You can always catch the ferry to the mainland and soak up the chaos, then return to your five-star home away from home.


#1 Fort Zachary Taylor State Park $

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.

2018: Unfortunately, Ft. Zach has SOLD OUT to tourism. The (State) park has become crowded and ruled by a bunch of over-zealous park rangers. It has lost its appeal to locals. The last time I was there I was so sad, (too many portable speakers blaring nasty music). I haven’t returned in months. But, for a day, as a tourist, this is probably the best beach KW has to offer. As a bonus, Key West City has created a Disney-like park leading up to Fort Zach with a splash park for kids, a fitness trail, and lots of greenery – including grass and an amphitheater. From my POV, the whole area has lost its natural charm, but again, for a day, you might like it. Ft. Zach still has lovely water and some decent snorkeling – they can’t take that away!

Baby Egrets

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, snorkeling is at its best. You’ll see spectacular fish that aren’t always there when the water is cooler during “tourist season.” Colorful tropicals like Parrot Fish, Sergeant Majors, Yellow Tail, and Blue Tang hang around the jetties and buoys. Certain times of the year you might see loggerhead turtles, lobsters, juvenile barracuda, and fantastic schools of Tarpon. Occasional sightings of manatee and dolphin.

#2 Bahia Honda $$

Sadly, Bahia Honda Beach DESTROYED by Irma. They reopened the long beach in October 2018. Some of the former beauty is yet to be restored.

The most BEAUTIFUL beach in all of the Keys, traditional soft, white sandy tropical beach (although in some “seasons” seaweed 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 sandbars, 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. Snorkeling is subtle, but we’ve seen some really cool filefish and even a seahorse in the near waters.

RELAX: (new section)

Prana Spa. $$$$

Modest, but oh so sweet. I pampered myself for my 2018 birthday at Prana and I definitely recommend with one positive caveat: You’re not going to get the “hotel” spa atmosphere. Situated in an old Key West house, the spa is clean, fresh, relaxing, with a totally local vibe. No parking. Ride your bikes, take a cab or ride the LOOP. If you book in advance, you can get a couples package. The skin care products are exclusive and luxurious. The massage was awesome. Prices are within the normal range for KW spas.

Mani-Pedi. $$$

My fav salon (and I’ve burnt through a few) is HEADLINES on Duval Square. Color, cut, mani, pedi, facial, waxing, the whole deal is all about you – gals and guys! Best local salon (IMHO) in Key West. Owners Nancy and Daryll will ensure that you are well taken care of. Tell them I sent you. LOVE HEADLINES. The peeps are the best.


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 somegood ones.

If money were not an option…

The Marquesa $$$$$ (at all times)

This centrally located hotel is elegant and generally offers sophisticated and attentive service. Beautiful pool, restaurant, and tropical gardens, you can easily walk to all the great Duval Street bars, restaurants, theaters, and boutiques. If that’s not enough to convince you that this is a great spot, good friends of mine have been guests at the hotel for over 20 years and keep coming back.

The Gardens Hotel $$$$$ (in season)

The garden at the Gardens is special. (Lost some awesome trees to Irma, but in recovery. Still a lovely location.)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.

Southernmost Hotel. $$$$

One of the few hotels where you can get a room on the beach. (Other than the Casa or its sister, the Reach.) It’s a public beach, but it’s sandy and friendly. Nice cafe. Close to downtown. Some of the rooms are expensive, but the amenities are nice.

On a Key West budget: (not cheap but not top of the heap)

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 of 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 the staff was friendly. This is a Best Western Plus. Expect more and pay more than the BW Ambassador, which is out on the Atlantic (just beyond the airport, where airplanes wake you at 5 a.m.).

PLAY: ON THE LAND (Family Friendly Attractions)

West Martello Tower.

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. The gardens took a hit in Irma. Lost a huge, legacy strangler fig tree. But the Garden Club has done an excellent job at reimagining the space left from its demise and it’s definitely worth going.

Butterfly and Nature Conservatory.

Small, but special and unique. The conservatory hosts two flamingos and you can call ahead to schedule a special meet and greet with them. A favorite wedding destination. According to some data, this is the most popular Key West attraction!

Florida Keys Eco-Discovery Center. 

Educational for all ages, and entertaining. Includes a large aquarium display. Make sure to watch the 25-minute video presentation. (FREE ADMISSION) Closed Sundays and Mondays! Say hi to Craig, the director.

Key West Tropical Forest and Botanical Gardens.

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 taking the effort to visit.

Key West Aquarium.  

Small by most standards, but interesting.

Hemingway House

Popular…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. During the cruise ship season, lines for entry can be long.

Truman Little White House.

Beautiful grounds. Quiet and relaxing. Off Mallory Square. Take the tour. The docents are really into it and will share all sorts of interesting history.

DUETO.Pistachio gelato. Amazing. Love their pizza too. Totally Italian.

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 grown “kids” visited over the holiday they wanted to do it. I totally enjoyed this. The guide was funny and knowledgeable, even if the stories were exaggerated. The one we took went around downtown to the hot ghost spots and all the way out to East Martello Tower where Robert the Doll is encased in Plexiglas. They give you ghost meters and everything. It was worth the $30 per person. Ghosts and Graveyards. 


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 (often drunk ones). These are the more noteworthy 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. (The garden bar got damaged during Irma. The big tree that was the central reason to go, hang out and have one of their amazing cocktails, is GONE. But, they fixed it up nice – different but nice – and it’s still one of the best low-key bars, for food, drinks, and dancing.)

Schooner Warf Bar from the Key West Harbor

Schooner Warf Bar: Old Seaport. The legendary atmosphere, view of the marina, live music, and the fish and chips are good enough to keep locals coming back time and again. The bar is interesting. Go there to experience an authentic outdoor Key West bar (dogs welcome if leashed) and buy a t-shirt or two, 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 visitor to Key West, I never went to Jimmy Buffet’s original Margaritaville. But last year when my daughter visited we stopped in for a late lunch. I have to say it was surprisingly fun! The Margaritas were very yummy. The bartender 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 absolute no-brainer. GO! Still my go-to spot. Crazy fun.

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 inside for a minute, look around, shake your head, and move on.

Cowboy Bills:Country music and bull riding. 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. CBB is still cool. Live music and dancing.

Captain Tony’s:The original bar where Hemingway hung out. There’s a big tree in the middle and usually, live music. Tony Tarracino,aka Captain Tony (now deceased), is a Key West legend. He was an American saloonkeeper, boat captain, politician, gambler, and storyteller and a well-known personality in the city. He has been called “arguably the city’s most beloved resident” and “the conscience of Key West.”

LaTeDa:Duval Street. The Sunday afternoon tea dance is fun. Older crowd. Nice bar. Recommend for brunch. Really fun drag show. Local, professional musicians entertain.

There are a couple of new establishments on Duval that I haven’t tried but have heard about. Little Jazz Bar and several wine bars that you might want to check out.

Aqua:Drag show and nightclub. 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.


Sunset at Fort Zach Taylor

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 occasional 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!) 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 Wagonon Caroline (Conch Fritters), and Southernmost Point—got to take a photo there! Most tourists go to Sloppy Joe’sand/or Hog’s Breath Saloon. Both are pretty typical KW bars. Lot’s of tourists. Food marginal.

Some of the gang at Bayview Tennis (women play too!)

Tennis anyone? Bayview Parkon 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!

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  1. says: Florida Keys Girl

    One of my favorite things to do with out of town guests is go to the top of the la concha hotel. It’s seven stories are a “skyscraper” by Key west standards and you get a great 360to degree view of the island.

  2. says: Sandy

    So. I stumbled on this today after a couple of months of rattling around the net in search of straight talk on the Keys. I’m all set to leave Friday week for my first visit. All I can say is….. I freakn love u, gal! Thank u for the insight and the giggles. Hugz!

    1. Thanks for stopping by, Sandy. Now you know the real scoop. In advance, welcome to our little island home. Take care and be well! Stop back and tell us all about your trip–like and dislike!

  3. says: Heather

    We are going to drive from Miami to Key West in December (12-17),2013… we are from Canada…. how is the weather this time of year and are the places you have listed still as good as you say? Loved your article, will print off to take with us.

    1. Heather, you will enjoy it! The weather is unpredictable where rain or wind is concerned, but the air temperatures should be warm – in the 80’s. Only a few times has December had a cold snap for a couple days, and that would be air temps in the 60’s or 70’s. It rarely gets colder than that. December is usually really nice. I’ll be updating this post. Thanks for bringing my attention to it. I also have another one on this topic, so stay tuned…Jayne

  4. says: lara

    looking for direction lol…..i now live in venice florida, but moving to key west for work (medical field), can you give me advice on areas to Stay Away from-as far as a place to live?



    As a fellow local, i love Jayne’s choices, out of so many we enjoy. She reminds me to re-visit a few favorites I’ve neglected, like El Siboney. Thanks, Jayne!

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