• What makes Key West awesome:  Wonderful weather, fabulous food, and happy people
  • Why we went:  Short break from the Chicago winter, catch up on our Vitamin D intake, and take advantage of a phenomenal 40% off airfare flash sale on Southwest Airlines
  • When we went:  February 1-5, 2013
  • Weather:  65-75⁰F – perfect in the sun, little chilly in the shade, but still 64⁰F warmer than Chicago that weekend!
  • Food & Drink:  Seafood, Cuban food, lots of frozen drinks and mojitos
  • Activities:   Hit up the Bars and Restaurants of Duval Street, see the Southernmost Point in the US, and experience the Sunset Celebration at Mallory Square
  • Accommodations:   Hotels were quite expensive (i.e. we found nothing halfway decent close to Duval Street for less than $250/night when booking a month in advance).  Therefore, we decided to split our time between the Silver Palm Inn and the Marriott Beachside Resort, thanks to our Marriott points.
  • Here’s a map of where we stayed, ate, drank, and enjoyed the laid back island life…


View Key West in a larger map

Delve into the Details…

After our short layover, once we boarded the plane from Tampa to Key West, we knew we were in for a real escape from our humdrum reality.  There was a total party atmosphere on the plane with drinks flowing in full force, even though the flight was just an hour long.

Just a few short hours before, we were freezing on the jet bridge in 1⁰F temperatures, watching our breath as we exhaled waiting to board the plane.  Stepping off the plane into warm, sun-soaked air was instantly invigorating.

We leisurely sauntered across the taxiway to baggage claim, just happy to feel the sun on our faces.  I have never seen an airport filled with so many smiling faces, even while everyone was waiting (kind of a long time) for their bags!

All these smiles made us think that Key West should officially dethrone Disney World as the happiest place on earth…or maybe just Florida…for adults.

That’s a lot of caveats, but point being that it was such a wonderful change of pace being surrounded by people that were truly loving life.  The smiles and laughs were contagious.

Another observation we had while waiting is that the key (no pun intended) demographic of Key West is the over 55 set.  We estimate they made up a solid 65-70% of the people on the island while we were there.  Making up the difference were groups of friends in their 20s and 30s, couples, and people with very young children, but it was quite rare to see a family with older children.

This makes sense because there’s really not a whole lot of “attractions” or things for kids to on the island outside of beach/pool time and maybe some water sports.  We saw this as a positive feature because this trip’s purpose for us was purely a short getaway to somewhere new to eat, drink, and be merry.  Key West definitely fit the bill.


Food & Drinks

Speaking of eating and drinking….we were most excited to try Cuban food as close to its homeland as possible in the US.  We were also really looking forward to noshing on tasty seafood straight from the Ocean/Gulf.  We asked around and got some fantastic recommendations we’d like to share with you.

Here are our favorites (all of the places we visited are on the map above):

Best Cuban SandwichSandy’s

Pictures speak louder than words…you simply must have this sandwich if you go to Key West!  You should also try their Cuban coffee.


Best Cuban RestaurantEl Siboney

Adorable little family run Cuban restaurant.  It was a tremendous value for the amount of food (read:  humongous portions!).  They don’t take reservations, so I’d recommend getting there early so you don’t have to wait.

IMG_2395 IMG_2396

Best SeafoodHogfish

Definitely far from the heart of things, but it’s worth the trip for their seafood.  Their fish tacos are amazing.  The Keys is one of the few places you can get a hogfish, so this is a must try for those looking for local varieties of fish they can’t get at home.


Best MojitoEl Meson de Pepe

These strong mojitos were the perfect way to kick off our trip.  Bonus – it’s right on Mallory Square, so pull up to the bar early, have some mojitos, and watch the performers get set up for the Sunset Celebration.


Honorable Mention – Key Lime Pie & Frozen Drinks

It’d be a bit of a sin to NOT have a Key Lime Pie and at least one frozen drink while in Key West.  We won’t claim any favorites in this category since our choices were just ok, but worth mentioning that you should try them if you visit!

IMG_2425 IMG_2465


Truth be told, there’s not a lot of “must do’s” in Key West, which is fantastic in our opinion.  Most of the action revolves around Duval Street, which is packed with restaurants, bars, and kitschy shops.  The Southernmost Point in the US is at one end of Duval, while the Sunset Celebration at Mallory Square is on the other end.

During the day, there is pretty much always a line to get your picture taken by the Southernmost point, so if you’re not a fan of lines, go early.


The Sunset Celebration starts before dusk with street performers lining the square, vying for the biggest crowd.


Leaving the Rat Race is what we’re about to do!

Jan was the lucky (unlucky?) one pulled out of the crowd for one of the performances.  We assume he was picked to assist because he looked young with his Asian genes.  The performer was slightly thrown off when Jan revealed is true age!  The busker wanted to show off that he was 55 and doing handstand push ups, which were quite impressive, regardless of Jan’s performance doing 15 regular push ups!


Lesson Learned:  Don’t stand too close to the performers if you don’t want to be chosen!

Here are some other pics from the Sunset Celebration…


If you want a bird’s eye view of the island, make your way up to the 7th floor of the Crowne Plaza – it’s the tallest building in Key West and gives sweeping views of the shoreline and island.  It’s an alternative spot to catch the sunset.


OK, maybe there are a few other things to do, but we chose to skip them.  The highlights are:

  • Ernest Hemingway’s House
  • Truman Little White House
  • Fort Jefferson
  • Butterfly Sanctuary
  • Aquarium


We found Key West a little bit strange because it’s like there was an unspoken bedtime for the older folks when those in their early 20s took over the bars and clubs after 11pm.  Being somewhere in between we could hang either way, but when we attempted to go to a club at approximately 11:05pm, we lasted about 5 minutes before retreating to a more chill bar.


Sloppy Joe’s was more our scene…especially when Pat Dailey was performing

Another fun activity we did was go to a drag show at 801 Bourbon Bar.  There are shows at 9 and 11pm every night.  It was very entertaining.  This place is also home to the “ruby slipper drop” that happens on NYE every year.




Due to the cost of hotels close to Duval street (see above), we ended up paying for two nights at the Silver Palms Inn and using points for two nights at the Marriott Beachside Resort.  Generally we don’t like switching places in such a short stay, but it was a good way to see both the crazy and chill sides of the island.


Our view of the sea and pool from the Marriott

I would recommend looking into apartment/house rentals if you’re staying for a longer period of time and/or with more people.

Another money saving option would be to go during low season, which is August to October for the best deals.  Of course that is smack dab in the middle of hurricane season, but we found out that it is extremely rare for hurricanes to hit Key West.



If you stay close to Duval, most of the main attractions, restaurants, and bars are well within walking distance.  However, a popular way to get around the island is by bike.  Bike rentals run around $15 per day, with discounts for multi-day rentals, and are available for rental all over town.  I truly enjoyed seeing some of the “mature adults” riding around on bikes with childlike grins on their faces.

Another unique mode of transportation is by electric cars that are kind of like golf carts on steroids.  We’ve never seen anything quite like them.

Taxis aren’t too expensive when using the meter; however taxis from the airport are a flat rate per person depending on your destination.  If you are headed close to Duval Street, it’s $8 per person, which isn’t bad when compared to most places, but felt like a bit of a rip off considering it’s about a five minute drive.


The airport rate will get ya!

If your hotel offers an airport shuttle, definitely take advantage!  The Marriott did have a shuttle, so we only encountered this taxi loophole once.



If you’re looking for an island getaway without leaving the US, then consider Key West.  No passport or currency exchange needed, but you feel worlds away from home!


What are your favorite spots in Key West?  We were only there for a few days so we know we didn’t hit all of the gems of this beautiful island!