KEY WEST, A City Without an Attitude

Key West, Florida is one of those binary destinations that needs to be experienced to see where one “fits”.  You either love it or hate it…there seems to be no gray area.

I discovered Key West (a.k.a. The Conch Republic) roughly 25 years ago as a result of attending a conference at the Navy Base. I had been out of the country on Navy business and had looked forward to a long weekend at home in RI but got orders to report directly to Key West to attend a special security conference. I called my wife (whom I had not seen in several weeks) and asked if she’d like to meet me in Key West..and of course the answer was “Yes” (It was mid-February after all). So off we went into uncharted territory..and have never looked back.

We had booked accommodations at the Pier House (One Duval Street) which is still an wonderful hospitality destination on the Gulf of Mexico end of Duval Street in the heart of Old Town Key West. We had both arrived late in the evening and I was due at my conference at 7am (the Navy likes to get things going early).  The front desk advised the hotel’s restaurant did not open for breakfast until after 7am but noted there were a few small,  places along Duval Street that opened very early for fishermen or local tradesmen.

So here we were headed up Duval Street at 5:30am looking for breakfast.  It was a balmy low seventies and the city was reasonably quiet except for the sound of rushing water a block or two ahead. As we approached,  I saw water streaming out of an open door and noted the sign “Sloppy Joes” over the establishment. Inside, I could see chairs piled on top of well worn tables and an older chap washing debris out the door using a fire hose.  “Hey, my kinda place” I thought to myself as we jumped over the swirling water on the sidewalk.

In the next block we spotted “Shorty’s Diner” (I think that was the name, but it unfortunately is now long gone.) and headed in.  We had just entered a time warp to the 1940’s and a central casting crew of cooks and waitresses working on a Hollywood set of every stereotypical diner ever built…only this was the real thing.  There was even a picture of Harry Truman up over the cash register on the faded lime green and yellow wall over the stainless steel prep counters.  What’s not to like?  Our steaming hot coffee and plates of eggs over-easy, bacon, toast and hash browns were in front of us in less than two minutes and life was good again.   The people watching was terrific (as you might expect at 5:30 in the morning). The resident wino was at one end of the counter trying to shake off the cobwebs with a droopy cigarette, a cop was seated nearby working on a coffee and piece of pie and a couple of truck drivers were busy chatting up a storm with one of the waitresses.  The smell of brewing coffee, cigarette smoke and bacon grease permeated everything…and I was totally relaxed, glad to be “home” in America.

That visit to Key West in the mid eighties turned out to be the first of what has turned-out to be an annual trek that has enabled my wife and I to totally enjoy a corner of the universe that is totally unique in so many ways.   We have discovered the best way to really enjoy the sights and sounds of Key West is to wander down the side streets and alley-ways which constantly seem to blend a host of cultures and lifestyles. The part I enjoy the most is the ability of these cultures, styles and sub-cultures  to live together with considerable tolerance. Even the Key West Police seem to understand the unique values that thrive in a somewhat open society and are flexible in their dealings with the public.

The best way to see Key West on an initial visit is to take a Conch Train or a Trolley Tour. The Conch Train is an open-air, guided tour that makes occasional stops along the route and takes you literally around the entire island and gives you a good sense of what’s around and where things are.  The Trolley Tour follows a somewhat similar path but has windows and protection from the elements if the weather is funky.  We have taken both and found them to be worth the investment.

The main drag (pun intended) is Duval Street which runs from the Gulf of Mexico to the Atlantic Ocean in roughly a mile and a half.  To many visitors (mostly cruise ship passengers), this is the center of the Key West Universe and these folks believe it reflects all of Key West. Totally not true. The Gulf end of Duval is packed with tee shirt shops and honky tonk bars while the other end of Duval caters to art galleries and more laid-back restaurants. One has to get off Duval to capture the essence of Key West. That isn’t to say Duval is totally without redemption, because it does have a good mix of eating venues and shops, it’s just that once off Duval, one tends to get a broader picture of the cultural nuances that make the place so wonderful.

At least once during a visit to Key West, you absolutely MUST attend a sunset “viewing” at the Mallory Docks down near the Gulf of Mexico end of Duval Street. This is a daily, and memorable (free) experience that challenges a single description because it varies from day to day.  For starters, it is an opportunity for Key West residents and guests to rate the “quality” of the sunset. Who would ever think to do that except the residents of the Conch Republic?  In reality, it’s simply an opportunity to hold a party..and even that term would be a stretch.  It’s on open-air party,  carnival,  flea market, and social event that draws hundreds of folks every evening to watch the sun sink silently into the Gulf of Mexico.  One can watch magicians doing  tricks, sword swallowers doing their thing, pigs walking on tight-ropes, craftsmen making jewelry, artists painting portraits, straw weavers making hats,  vendors selling food and drink…the list goes on….until the minute or two before the sun actually sets and things grow quiet, with total concentration on watching the sunset and the round of applause as a gauge of the “quality” of the day’s final view of the sun.  You could go every day and find a new experience…but I typically manage to only go once during a visit for my sunset fix.

What follows are snippets of reviews of places (mostly places to eat and stay) I have collected over the years.  Many have appeared in Trip Advisor while others were written as part of a semi-blog to friends and colleagues.

Places to Stay:

Navy Lodge, Sigbee Point

“Best Value in the Conch Republic”

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5 of 5 stars Reviewed for Trip Advisor March 3, 2013.    Last visited January 2020

Note: This property is restricted for use by active duty and retired military and DOD (Check for specifics).
My wife and I discovered Key West in the mid-80’s while I attended a military conference and we have returned every year since. We have stayed at a cross section of better hotels all over Key West and have rented multi-bedroom houses to accommodate friends and family.   About five years ago, a retired National Guard Adjutant General chided me for never checking out the Navy Lodge at Sigbee Point. He shamed me into it and we have never looked back. Thanks General. It’s the only way to go; especially now that the Navy Lodge has installed a reliable and free Internet access that had been my nemesis from our very first visit.
About five years ago, the Lodge underwent a major “refreshment” and thanks to a terrific staff, they have kept the place almost like new. The rooms are located on two floors (downside – no elevator) but are roomy and squeaky clean with one or two beds, flat screen TV, a comfy chair, a work/dining table and chairs and two very large dressers. An adjacent kitchenette includes an apartment sized fridge, a two-burner electric cooktop, stainless sink, a good sized microwave, a coffeepot and loads of kitchen cabinets and drawers fully equipped with pots, pans, silverware, glassware and dishes for four. Daily housekeeping service is also included.
Sigbee is primarily a military housing, dependent’s school and recreation area (with a huge RV Park) and as such is protected by Navy security personnel who take their job very seriously ( ID checks, strict speed enforcement, etc.). Although it’s a hike to Old Town (a rental car is a necessity), Sigbee is extremely quiet in comparison to almost every place in Key West where the incessant, high pitched drone of chainsaw-engine motor bikes and scooters will drive you nuts (even at the high end hotels).
A word of caution: rooms book up quickly during the high season, so plan on reserving a room at the sixty day mark (the earliest date you can make them) or risk loosing out.
If you want the action and high energy level of Old Town Key West, this is not the place to stay. But for $99.00 a night, you can’t find a better rate on the entire Island….and the folks are just plain nice. Do it!

Lighthouse Court, Whitehead Street

“Great location. Downhill From There”
2 of 5 stars Reviewed for Trip Advisor April 15, 2014     (Note: New ownership and name in 2020)

Every hotel or inn has a room next to the ice machine or the elevator that everyone complains about..and perhaps it is Room 1A at the Lighthouse Court that is the hub of my utch. After driving in circles for a while, we managed to find an offsite parking space and lugged our bags roughly three blocks to the front desk where our greeting was warm and cordial. (40 rooms and roughly nine parking spaces for guests. Hmmmm?). We were directed to room 1A, in a two-guest-room cottage nestled at the rear of the property (thankfully well away from the traffic and Hemingway House crowds on Whitehead Street at the front of the property). Ah, now to unpack…but wait..there’s no luggage rack…OK, use the bed…but wait, there’s no closet…just some hooks on the wall over the dinky little bureau. Oh dear. Maybe if we put the suitcases on the little bench next to the door, that will work? At least if we turn sideways we can slide along the walls to access the bed. Tiny, you say??? Well, time to check on emails..but wait..there’s no desk..and that’s not a problem because the WiFi signal is barely intermittent at best. Time to visit the front desk. All smiles and a wonderful tap dance. The desk clerk even suggested I could rig a tray on a luggage rack to double as a desk. But wait..there’s no luggage rack. Oh dear. Would I like an upgrade to a larger room? Oh, at the higher rate, of course. Bait and …. whatever? Maybe it was because I booked online (not with TripAdvisor) and prepaid for my “discounted” rate that worked out to $350/night. But wait..the hotel’s rate card shows I paid the full rack rate. “Sorry, there’s nothing we can do” – so sayeth the desk clerk. Ah, hang in there Skip, it’s only four days.
So then I discovered the best WiFi location (and charging plug) was in the “Mojito Bar” next to the pool. That made for great people watching because hotel management had posted a sign by the front of the hotel advertising “Public Rest Room” for anyone waiting in line to visit the Hemingway House across the street. The queue was a steady stream of interesting folks to use the facilities. Nothing like some peace and quiet?
“Breakfast” was another interesting experience. Bagels, yogurt and occasionally some fruit. Oh yum. Thank goodness Blue Heaven (restaurant) and a Crepe place were around the corner. Even the coffee was only lukewarm. Ah, delicious.
As we packed our bags after four nights, I reminded myself that my wife and I had made a couple of excursions (including a transatlantic) on the Queen Mary in a beautiful stateroom (larger than the cubby at the Lighthouse) that included three VERY complete meals and extraordinary levels of service for about $310/night.
Sadly, as I brought all my concerns to the property manager, all she could do was express her “deepest concerns” and wished I had contacted management earlier. I pointed out I viewed her front desk staff as her direct representatives and they appeared totally disinterested in dealing with my concerns.
Bottomline: Would I stay there again? – probably not, but certainly not in the cubby that barely passed as a “room”.

Garden’s Hotel, 526 Angela Street
“Over the Top”
(First posted 2005)
Fourth visit to this Key West charmer. Nervous at first due to new ownership, but our concerns were dashed immediately on arrival. A glass of bubbly at the reception desk and music from the grand piano in the sitting room convinced us that things had not changed. Here’s a small (but not inexpensive) gem in the heart of Old Key West. The rooms have been freshened and the gardens (out of a picture book) have been thinned (the right way). Sorry, no chrome and gaudy, but that’s why folks stay here.
(Updated 2015)
     The Gardens consists of roughly a city block of buildings and gardens crafted from an old, tropical estate by hospitality experts with taste and vision. The “Main House” (lobby, wine bar, reception room and sometime breakfast dining area is a focal point of the property that open to the rear on a small pool and series of smaller buildings that have the best rooms on the property.  Each  large and spacious room is tastefully decorated in period furniture and includes bathrooms to die for. (Note: The only rooms I would not recommend are those over the reception area in the “Main House”. The late week crowds who enjoy the after-dinner piano bar in the breakfast/ reception area tend to get a tad noisy as the evening progresses. Fair warning.) The out-buildings are separated by a series of decades-old tropical gardens that makes one totally relaxed. A comfy and informal pool-side bar tends to the focal point of afternoon and evening conversations and is the locus of Sunday jazz performances featuring small groups of local and nationally recognized musicians.
  The Gardens is  one of the more expensive places to stay in Key West, but if a truly delightful, laid-back experience in a relaxing, up-scale environment is your preference, this is the place for you.  No on-site restaurant, but there are loads of places to eat nearby. One block off Duval in the heart of Old Town Key West.  Parking is at a premium and reservations may be tight, so plan ahead (especially during the high season).
Hyatt Beach House Resort  5051 Overseas Highway (At the northernmost  spot on Key West)
(Modified from a Trip Advisor posting March 2015).      Last visited Feb 2019.
Although the inexpensive options at the Navy Base are my first choice, those properties are often booked well in advance and are tough to get. This year we planned to include our two adult sons as our guests and this required two bedrooms. The Navy housing units were only available for the second half of our ten day winter visit. We locked in the Navy quarters for the second half and for the first half we opted for the Hyatt Beach House Resort at the northernmost tip of Key West. We knew it was several miles from the “action” of Duval Street (and the incessant drone of chainsaw-engined motorscooters) but welcomed the break. We needed two bedrooms and a kitchen and Hyatt delivered in spades. Spiffy clean and quiet (mostly). Guests who plan to visit throughout the island or the lower keys definitely need a rental car or a good pair of legs for a bike. (The hotel has a shuttle service of sorts but charges a fee for its use). The property has a beach (one of the few in Key West to offer such an amenity, but it’s not what I would classify as “resort quality” simply because of its size).
The property itself calls itself a “Resort” and that is also a stretch. We loved our stay, but only needed a homebase for our day trips and did not anticipate using the so-called “resort” options. We were delighted at the pre-paid rate we enjoyed (through a popular on-line booking service) until we received a $76.00 “resort fee” as we checked out. Ouch! Why not bundle it into the rate and avoid upsetting guests with the fine-print “gotcha”?
Would we stay there again? Probably..but I’d have a “chat” with management about their so-called “resort fees” before I booked things. Great property – silly “gotchas”.
(2016 update)  Went back for a five night visit and were of mixed emotions.  The room/suite was well appointed (as before) but was not as clean and well maintained as I had hoped. Heavy black dust on the floor and mildew in the shower and a malfunctioning sliding door (repaired within minutes of reporting it).  Considering the cost, next time we might consider renting a house for the same investment.
2018 Update:  Following the 2017 hurricane, management managed to repair and update the property and re-staffed key positions. Had a delightful visit.
Other Options to Consider:  If you plan to stay in Key West for more than a week and are not married to a list of amenities like daily housekeeping, room service,  concierge, etc,  seriously consider renting a house. I don’t recommend this for your first visit to the Conch Republic, but having gone this route over a half dozen times, I can highly recommend it. First and foremost, identify your specific needs. Do you need a pool, a gourmet kitchen (we did – we are foodies), a quiet neighborhood, parking, multiple bedrooms, etc.? Have a rough budget in mind and then track down an experienced rental agent to walk you through the offerings. Most professional rental agencies will attempt to match your needs with your budget and coordinate the rest. Do an online search for “Key West Rentals” (or similar) and you will get a sense of what the range of  options is available. This is where a knowledge of the island will be useful. (Example: There are new, and attractive rental properties in or adjacent to neighborhoods that might make one uncomfortable..but you should know about those areas beforehand or a slick rental agent may try to ease you into a place you may not enjoy.).  Rental prices may appear high but should be compared to the rates at a better hotel in the area to have a better perspective.)

Places to Eat

Margaritaville, 500 Duval

Reviewed for Trip Advisor February 2012. Last visited Feb 2020.

It started over twenty years ago on our first night in Paradise (Key West) and has been a first-night requirement every year since. Margaritaville is not just a place, it’s a destination. It’s the original one…and reflects almost everything I complain about in restaurants..and yet I keep coming back with a smile. Our needs are simple: My wife needs a top-shelf margarita while I prefer a “bottom-shelf” version because I will soon not know the difference. These will keep us occupied as we wait for our “Cheeseburgers in Paradise” (which are always cooked perfectly and totally delicious). Gotta have a couple more margaritas to wash everything down. A big slice of Key Lime pie (if there’s any room) tops things off.
Margaritaville is noisy (both inside and out) with boisterous customers at the bar, on the balcony and at the tables. The Harley’s with no mufflers that cruise by the open front of the building somehow always need to rev their engines as they pass and the sing-alongs with the Jimmy Buffet tunes are of course a requirement. But hey, this is Key West, and I’ll leave my attitude home on the shelf.

Last visited 2020

Sarabeth’s, Simonton Street
If you dine anywhere in Key West (breakfast, lunch or dinner) make it Sarabeth’s for at least one meal. It’s situated in an 1800’s, Old Town ark of a house that most recently had been a Synagogue. David Case had managed the original Sarabeth’s in New York for over two decades and then transplanted himself to Key West where the southern version was born. Thank goodness.
Over the years, we have eaten practically everything on the menu and have been totally delighted every time. Simplicity is the rule, with delicious offerings of meat loaf, fried chicken (Sundays), soups, yummy salads, sandwiches and a full array of main courses in the dinner menu that include loads of fresh fish.
Our server, Nicolas (a long time employee David brought from NY) started today’s breakfast with coffee and a four-flowers juice followed by a Farmer’s omelet (for me) and a cheddar cheese omelet for my wife. Freshly baked bread was toasted to perfection and rounded out our meal.
Our host, David Case, as usual, was a bundle of energy, acting as the consummate host, making sure every one of his guests was comfortable and pleased…and it’s not an act. It is his attention to detail that has made Sarabeth’s a “Must” destination for us at least once during our repeat visits to the Keys.
If the weather cooperates, try to sit outside on the patio where you can enjoy the people watching just outside the white picket fence. Even inside, next to the patio is a good alternative – the huge windows overlooking the patio are usually open. The main dining room is an option if Mother Nature rumbles outside..but try the outdoor seating if at all possible.

Update: In mid-2013 David Case sold Sarabeth’s to a chap who has adopted the menu and much of the former staff and appears to have maintained the extraordinary levels for food and service we have enjoyed over the past decade or so.

  • Visited Multiple times. Most recent visit 2019.
New York Pasta Garden, 1075 Duval Street
“We Will Be Back”
5 of 5 stars Reviewed February 28, 2012

You’d miss this place if you were not paying attention. It’s tucked in to an office and condo complex between Duval and Simonton Streets with a couple of other interesting restaurants we plan to try later.
“Pasta” is an appropriate name rather than “Pizza Cafe” that showed up on our bill. I’m sure they prepare all sorts of pizza, but no one near us went that route. Everyone appeared to have some variation of pasta that was cooked to perfection. I selected meat lasagna and my wife selected angel-hair pasta for her main course. Both were in the southern Italian style, rich in tomato sauces and garlic seasonings. The lasagna was served in an oval baking dish and had been finished with the cheese topping in the oven (or broiler). Monster proportions. Reasonable wine selections at modest prices. We selected an Antinori Sanat Christina Sangiovese/Merlot/Cab blend that was just perfect with our pasta.
The service was a tad rocky at the start but was soon overcome with enthusiasm by our server.
The weather was equally delightful and allowed a comfortable evening under the trees and stars in the square next to the restaurant.
We will be coming back to try some other dishes.

Blue Heaven, Petronia Street
“A “Must Visit””
5 of 5 stars Reviewed March 20, 2009.  Last visited Feb 2020.

As long-time Key West visitors, Blue Heaven is one of those places that absolutely requires our visit at least once every trip. It’s a hoot and thankfully has changed very little since we first sampled their breakfast fare well over a decade ago. Don’t expect linen table cloths…in fact, expect to compete with several chickens for your table…but that’s part of the charm and ambiance. It’s not unusual to wait for a table (umbrella-covered and outside in the backyard), but you can play ping-pong, listen to a musician strumming under a lean-to, and/or just sip a coffee (or other libation) while people (and chicken) watching at the Tiki Hut bar. The tables are arranged under a canopy of several old trees with a “floor” of brick, stone and hard-packed sand. The breakfast food is “yummy” and we’ve sampled almost everything on it over the years and never been disappointed. It’s open in the evenings, but we have never sampled their dinner menu. It’s a total tourist trap..but nonetheless wonderful. Kick-back and enjoy.

As an aside, it’s not unusual to have an extended wait for a table. Visit the souvenir shop on the premises but then wander next door to Besame Mucho. Here is a gift shop that’s a perfect foil (opposite) for Blue Heaven: a classy snapshot of French and Latin tastes in linens, collectibles, kitchen gadgets, perfumes and all sorts of nice things for the ladies.  For the guys, there are chairs on the porch to people-watch on Petronia Street with a resident cat or two.

2016 Update:  In our many visits to this delightful destination, until this year we had not included an evening meal. Gotta tell you, it’s worth a visit.  The hustle and bustle  of the daytime crowd (and cruise line visitors) is gone, most of the chickens have gone home to roost and a certain Conch Republic charm settles in. The meals are generous and well presented and a guest can just sit back, relax and enjoy.

2018 Update:  This visit was a less than memorable one, primarily due to the highly amplified music from the guitar-playing live musician. Unfortunately (for us), we were seated next to the “stage” (a porch shed) and the speakers (really not needed) were cranked up to max volume. As a result, what would have been a fun-filled, brunch conversation turned into a painful silence with no help from management who refused to acknowledge the issue. Hint: Don’t accept a table near the bandstand.

Grand Cafe Key West, 314 Duval Street

People Watching Heaven

The Grand is one of those spots right on Duval that’s a step above the throngs on Duval and just behind a small fence of shrubs that gives a full few of the crowds while maintaining a small degree of privacy.  Lunch was quite good – mine a ham and brie pannini with a Margarita (just OK) while my wife ordered a turkey pannini and a Pinot Grigio.
The folks at a nearby table had the right idea – they ordered a whole bottle of white wine and a couple of sandwich and settled in for a leisurely, mid-afternoon delight of people watching. That looked heavenly in retrospect..wish we’d thought of it.  Service was a bit slow, but hey, it was a Saturday afternoon in the Conch Republic where it was in the mid-80’s.

Visited February 2013

Kennedy Cafe,  924 Kennedy Drive

Reviewed for Trip Advisor Feb 2014

My bad. We started visiting this unassuming, strip mall restaurant four years ago and discovered I have never reported it before…probably because it’s such a closely held secret among locals and visiting foodies like my wife and me.
If linen table cloths and tuxedo wait staff is what you seek, look elsewhere. If delicious (if not eclectic) international food is your cup of tea, this is the place. The menu opens as breakfast with a cross section of “Cubans” (whatever you might enjoy, smooshed between halve of a fresh Cuban roll). This morning’s offering on my plate was a ham, egg and cheese Cuban while my wife enjoyed scrambled eggs and grits. (a rather all-American combo).
The owners are Uzbekis and the menu claims to be “Healthy Mediterranean Cuisine”. I confess I have never tried their Italian specialty dinners, but over the last few years during annual visits, have worked my way through their Middle Eastern delights and loved every bite .
Last night’s shared dinner consisted of a lamb and potato combo wrapped in a pastry shell (not unlike a calzone). Absolutely delicious with a chopped fresh tomato/garlic/onion/dill salad. With that, we enjoyed a combo kebob of lamb, chicken and ground beef served on individual skewers on a bed of mixed rice (with carrots and chick peas). (huge portions)
Our server was Latvian and suggested a Russian beer which went perfectly with the meal.
Again, this is hardly a fancy-schmanzy place but is perfect for those who like to push the envelope in terms of ethnic eating delights. Kennedy Cafe underwent a facelift during the past year and dressed things up a tad…but it still does a huge take-out/delivery pizza and food business. that keeps a constant bustle near the door. Not to worry…it’s clean as a whistle and worth the time to find it. If visiting without wheels, it’s better to grab a cab because it’s located in a semi-commercial area near the north end of the Island, not close to anything.

Last visited: 2020

Banana Cafe, 1215 Duval

My wife’s quiche was totally over the top: Mushrooms, spinach and mushrooms 2+” high.
Mine was a Swiss and Turkey baguette that was delicious as well.

Caution: Unless you really love the hustle and bustle (and clatter) of a bar crowd or street noise at ground level…insist on going upstairs.
Also – why American and British rock music instead of French tunes? Would have made it perfect.

Seven Fish        Olivia Street

(From a TripAdvisor posting)

It’s been almost ten years since our last visit to Seven Fish (it’s tough to get a table so be sure to call well in advance) and it’s almost like a time warp..so little has changed (thankfully). It’s a hole-in-the wall, cement block building in a residential area, down a side street, but the locals all know about it and the foodies have been forewarned to make this a stop if in Key West..
I ordered warm sushi as a starter and was delighted to find it was better than I had imagined. I’d spent time in Japan but never had warm sushi before. Yum. My wife ordered a Seven Fish benchmark; meatloaf and was as she remembered it from our previous visits. It was served on a small plate, atop a bed of mashed potatoes with broccoli and carrots as a garland. I targeted the sea scallops and found these half-dollar round, grilled delights to be superb. A blob of mashed potato was the centerpiece of the presentation (surrounded by the ring of scallops), covered with a puree of peas and greens (I guess – hard to tell in the low light levels). Tasty, in any event.
We then split a nice chunk of rich chocolate brownie topped with a big scoop of vanilla ice cream.
The down side of this otherwise wonderful stop is the poor lighting and the close proximity to other guests. The guest density is to be expected when you have a place as popular as Seven Fishes. The lighting could easily be remedied with the twist of a wrist on the lighting rheostat (I needed a flashlight to read the desert menu and my check). Minor speedbumps in an otherwise wonderful evening.

Revisited February 2012

Note:  2018 update: Seven Fish has relocated to a larger location and is no longer on Olivia St.

Latitudes, Sunset Key

This is our favorite dining venue in Key West..and probably the most expensive…with good reason. Latitudes is located on Sunset Key, a Westin Resort property made up up condos and high-end luxury accommodations accessible only by launch (and reservations) from the Westin Hotel in Key West . It’s the ultimate in upscale, tropical dining in Key West. We have enjoyed lunch and dinner and both exceeded our expectations (which can be rather high).     Reservations are made through the Westin Hotel and include the launch departure time from the Westin Marina. It’s a ten minute ride which drops you off at the Sunset Key pier where you will find Latitudes Restaurant at the head of dock, overlooking a quiet beach and partially exposed bar and cocktail area. Weather permitting, you can request a beach table (literally on the beach with blazing torches for an evening dinner) or in or near the main facility in a more protected setting. I recommend those arrangements be confirmed when making your reservation. In any event, the service is impeccable by extraordinarily well trained staff and a delightful menu consistent with a high-end dining venue.  This is the place to go if you really want to go “over the top” in Key West.   Rather expensive, but highly memorable.

Last visited 2018

Five Brothers  930 Southard, Key West  (or on Ram Rod Key on Rt #1)

Here is a real, local “joint” that doubles between a fast-food place and a convenience store.   It’s well off the beaten path and in a pretty-much residential neighborhood, but totally worth the trek.  We discovered Five Brothers at least twenty years ago (yes, there were five brothers and probably there are a few still around). We had rented a house a block or two away and discovered Five Brothers’  Cuban coffee and sandwiches were mandatory stops at least once a day.  My usual first cup of coffee every day quickly became a Cafe con Leche in my flip flops and tee shirt as the sun rose in the morning as I’d grab a copy of the local paper and a second cup for my wife and head back to the house to wake up and face the day.  Lunch would become a deliciously yummy, Cuban sandwich from the little counter in the back and even tinier kitchen through the little pass-through window from the store.  Sorry, no linen tablecloths or napkins… heck, no tables either. Grab a folding plastic chair on the sidewalk outside or take your yummies home. It’s a blue-collar dynasty with cop cars, ratty pick-up trucks and various old bikes parked outside..but remarkable food inside. They have an interesting (albeit limited) menu but I confess I have only sampled their Cubans and pulled pork sandwiches. It’s worth the trip. They also have an annex further up the Keys on Ram Rod Key on Route #1 that has a larger footprint and a screen porch out back with tables and plenty of parking.  Note: If you spot Oxtail soup on their menu..grab a cup or a bowl. It’s worth writing home about.

Key Plaza Creperie   Key Plaza, Roosevelt Blvd.

Well, Trip Advisor’s reviewers have aced this one. Nothing fancy, but the food is super yum..and the cafe con leche is worth writing home about. We arrived shortly before noon on a Friday and the place was packed (and a bit noisy with a cacophony of languages). A real mix of townies grabbing lunch and curious tourists like us. We were quickly seated at a booth near the door and were trying to figure out where to start on the ranging menu. Hey, it’s a crepe place, so why not try those? Oh brother..about twenty to choose from, including eleven called galettes (crepes made from buckwheat). The menu was much more expansive (and delicious looking too) but we decided on a prosciutto and swiss, a chicken bechamel and an organic buckwheat galette. While we waited, my wife and son started on their cafe con leches and I worked through a traditional black coffee. The raves began with the first sips. Both styles were delish. A chat (later) with John the owner revealed that filtered water and an extra shot of coffee made the difference. We noted that other patrons were equally delighted with their french-press coffee brewed and timed by the guests themselves.
The galettes were served in the traditional square format with an egg topping..and the race was on to see which was the best. Oh sooooo good. It was a draw, Done to perfection and worth every bite. We shared portions and could not select one over the other for taste or consistency..all three were great.
I commended the owner for his vision in finding a real niche in the Key West community. Key Plaza Creperie is located in a shopping mall well away from the “downtown” noise but with loads of parking. The locals have clearly embraced the great coffee and diverse menu for breakfast and lunch.
We will make this place a regular stop and encourage others to also do so.  If you are visiting, the Key Plaza Creperie is a bike, bus or cab ride from “downtown” so plan on using wheels to get there.

  • Last Visited February 2020

Places to Eat Off Island

Geiger Key Marina Smokehouse, Geiger Key (Mile Market 10, Big Coppit Key)

Terrific “Backside of Paradise” that’s worth your trip if you are looking for a break from Key West and the high prices and poor service you might get a fancy place. This is a tee shirt, ball-cap, shorts, beer and BBQ place with varnished picnic tables and loads of fresh shrimp and delicious, smokehouse BBQ and other delicious and reasonably priced food.  Be sure to try their blackened fish sandwich.  Yum.

Right on the waterway and under the approach and departure flight paths to Boca Chica Naval Air Station.  Live music on many evenings.
It’s tough to find (off MM-10 on Big Coppit Key) but you will enjoy the relaxed atmosphere and laid back attitude of Geiger Key.

Updated 2015

Last visited 2020

Little Palm Island,  Little Torch Key  (Mile Marker 21?)

This is one for your bucket list if you crave fine dining in a tropical setting. It truly deserves the international awards it has received for dining excellence.  Only by reservation, it’s a fifteen minute boat ride from the Little Palm Reception Center right off Route #1 and you are greeted dockside by a dining hostess who will escort you to your table. Weather permitting, you will be seated on the porch overlooking the totally private, sandy beach, right on the Atlantic. It’s also not uncommon to see Key deer browsing or grazing next to the porch adjacent to your table.  The menu is not overly ambitious, but features an assortment of delightful tropical dishes (a blend of French and Latin) that will be worth writing home about. Plated and served to perfection, the well trained staff are ever present and available but totally unobtrusive as one might expect at a fine dining venue.  We have only eaten lunch at Little Palm Island (several times) but have reviewed the dinner menu and plan to visit at some time in the future.  Expensive, but highly worth the investment.

Updated 2014, Revisited 2015 and 2017

Note: Little Palm Island was practically destroyed in the hurricane of September 2017 but is being rebuilt with an expected re-opening date of 2019.  Note: It is now reopened but we have not had an opportunity to visit.

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