Kristen1206

A January escape to beat the winter blues was just what the doctor ordered. We always travel to the Caribbean but wanted to change it up a bit this time, and I found a great non-stop fare into Key West. My husband and I spent 4 fun-filled nights on the quieter end of Duval. I did the Keys with my parents when I was a kid, then again almost 20 years ago, and finally on a brief cruise ship stop with the kids in 2007 (but that barely counts). My husband’s only experience was on the cruise. So we were really looking forward to exploring somewhere relatively new. And for me, planning is half the fun. So once I secured our flights, I scoured the internet for reviews, recommendations and blogs. We are usually not high season travelers so I was worried that I wouldn’t find any deals. The only thing I like better than a tropical vacation, is finding a good bargain. The Speakeasy Inn went on my short list early on and that is where we stayed. Score! What a gem. But more on that later.

I am also what some might call an obsessive planner. I usually book trips a year in advance (all the more time for anticipation and research) so planning this in October was last minute in my book. As per usual, I made dinner reservations every night based on sunset times, views, menu and rating. But as our departure date drew closer, I made the decision that this was going to be a “fly-by-the-seat-of-our-pants” kind of vacation. This was going to be an adjustment for me, but I was determined to be spontaneous!

Departure day (Sunday) dawned frigid and windy in Maryland, so we were extra jubilant to be getting the hell out and heading south! As we were boarding the plane, a woman was stowing her bags in the overhead bin just as I approached from one direction and a flight attendant from the other. I ducked in to let the FA pass and as I did, Ms. First Class slammed the overhead compartment door shut…on my head. Other passengers looked on in horror. Though my husband, after determining that I wasn’t seriously injured, stifled a laugh I think. The FA rushed back to make sure I was okay while the head slammer looked at me in disgust as if it were my fault. About halfway through the flight, the flight attendant, who had already checked on me twice, came back again to offer free drinks because she felt so bad that 1) it happened at all, and 2) the lady was so rude about it. She came back with two free drinks for each of us. And this was after we had already made our own Bloody Marys. Needless to say I was feeling no pain when we touched down in the Conch Republic.

One of my favorite parts of every vacation is that blast of warm humid air as you step off the plane and onto the tarmac. It was glorious…sunny, 80s and a warm breeze. A quick 5 minute cab ride and we were at our home for the rest of the week. I loved the Speakeasy as soon as we pulled up. The inn itself was simply charming and wonderful. And Barbara and Bobbi were the most gracious hosts. I adored it and will definitely stay here again when we return. The place is a bargain (compared to every other accomodation I researched) and the extra touches made it even more fabulous. First drink free at the Rum Bar and $1 off all others during your stay, great breakfast included, complimentary water bottles (re-stocked daily the room’s kitchenette fridge), chocolates on the pillows and the usual…daily maid service, all toiletries, beach towels and free wifi. And we got the best room in the house with the long wrap around balcony over-looking Duval. And it was in a great location...close enough to stroll to the more happening end of Duval but far enough away that it wasn’t crowded or loud.

After we checked in, we had a quick rum punch at the bar with Bahama Bob then quickly changed and walked the 2-3 blocks to the Southernmost Café for lunch. I had the shrimp tacos and hubby had an awesome looking burger, and his first Key West lager of the trip. The food was good and the view was nice, but the beach it overlooked was crowded and the water murky. Probably not somewhere I would run back to simply because there are so many places which I thought were better. After lunch we decided to stroll down Duval and check things out. We discussed renting bikes or a scooter but the scooter, while it looked like great fun, worried me because KW is a busy place, and I know we would want to partake in some day drinking. But I wasn’t even ready for a bicycle yet. I wanted to take our time wandering down toward Mallory Square and poke in and out of the shops etc.

Oh my, the debauchery of lower Duval is quite entertaining! By the time we made it down to that end, we were parched and popped in for a quick drink at Margaritaville so Mark could catch a bit of the game. Yes it’s cliché, but for one drink it was great. Plus we love JB. I had a yummy orange crush with crushed ice, we had a great bartender and met a fun couple from Chicago. Then we checked out the Mile 0 sign and Hemingway’s House before heading back to inn to get cleaned up for happy hour and dinner and made the walk back down.

We decided on Alonzo’s and enjoyed half-priced drinks and seafood. They make a good mojito here. We sampled peel and eat shrimp (or Key West pinks) as they are called, key lime baked oysters, calamari, and clams. Then we walked around the docks before heading over to Kelly’s (the Caribbean bar & grill owned by Kelly McGillis and her ex). I really like the setting here. And I had a hankering for a margarita. We each had a key lime margarita. So good. As were Kelly’s microbrews (or so Mark told me. I don’t do beer). I also had a good sangria. And, since happy hour was almost over and we were getting hungry again, we tried the beer cheese dip. Thumbs up. Then we stopped into an art gallery along Duval as we made our way home. Mark was admiring one piece in particular. The saleslady swooped in, plucked it from the wall and ushered us into a private room. Oh my. We really weren’t in the market to purchase a piece of art, but now that we were in the midst of a private showing, I figured I may as well ask the price. Now this wasn’t a large painting...maybe 20x30, but it carried a hefty price tag. $5,000. On sale. I will blame my next actions on the adult beverages I had consumed. Something in me decided to play along. I told her it may be too small for above our couch and could we discuss the next size up. I did feel a bit bad for wasting her time, but the gallery was dead and she was the one who started it! We went home after that and were asleep by 9 pm. But not before one of the drag queens tried to get us to come see their show. I would have loved to see it, but Mark wasn’t game.

Monday morning we were roused by a sqwuaking rooster before 6 am. He was loud and long-winded. But I loved him. And his family. We would watch his chick toddle into the road and he would run out after him, wings outstretched to warn traffic, and then herd the little guy back to safety. Papa, Mama, and baby could often be seen strolling down Duval as a family in search of food. Each morning we started with a cup of coffee on the balcony then went down for breakfast. They put on a lovely spread including fresh fruit, fresh baked goods, bagels, breads, crumpets, cereal, yogurt, hard boiled eggs, meats and cheese. But the best part was the fresh squeezed orange juice. We always ate outside and people-watched as we planned our day. Since it was overcast this morning, the plan was to walk Duval again and stop into some of the places we noticed and liked the day before. Since I had taken my tender winter feet and shoved them into flip flops and walked for miles the day before, I had a couple pretty bad blisters. But that wasn’t going to stop me. We shopped and we looked in more galleries (no further incidents; we started telling them that we were appreciators, not collectors). My favorite store was Island Style. Could have spent a fortune in there. We stopped for a spicy watermelon margarita at Sunset Pier then moved on to Mallory Square to take some touristy photos. The sun was now out so we made our way back to the inn via the Truman Annex and admired the gorgeous homes. Beautiful, quiet area. I would definitely stay here if we opted for a home rental vs. an inn.

We threw on our suits, grabbed some beach towels and were contemplating if we should walk over to Higgs Beach before or after lunch. My feet hurt so we decided to do lunch first on Duval and then see where the day took us. We chose Caroline’s which was a great choice...fun, bustling place in the heart of KW with really good food. Unfortunately there was also major road construction going on right in front. I had the shrimp BLT and Mark had a bacon & fried chicken salad. That was an awesome salad with some of the best fried chicken I have ever tasted. Then since it was too late for the beach, we hung out on the comfy chairs in front of the Speakeasy, had some Painkiller cocktails (these rivaled the originals from the Soggy Dollar Bar in the BVIs), and watched the passers by.

We opted to do another happy hour crawl this evening and eat along the way. This was quite against our nature too. But we had big, proper breakfasts and lunches each day and it was so much fun last night. This would be my last Duval trek on foot as we planned to pick up bikes first thing the next morning. First stop was Turtle Kraals...I really wanted to see the turtle races! But first we had some drinks and tasty skillet nachos. Loved the signature Tipsy Turtle cocktail. I had forgotten that this place has a rooftop bar so was bummed that we had spent our time there downstairs and indoors. The races were fun but my turtle didn’t win. We walked along the docks to catch the last bit of pink in the sky then headed over to a bar we saw last night that looked cool. The Island Dog. But on our way, we happened upon the Legal Rum Distillery where it appeared a tasting was going on. We got a little tour and Mark paid $10 for a shot glass and a sample of 4 rums. The $65 bottle was incredible. Then we had a drink outside at Island Dog’s and decided to end the night at The Rum Bar. This is quite a happening little spot we had just below us, but never was it very loud at bedtime. After the fine rum sample, Mark was hooked. He decided to get a glass of a good sipping rum which he very much enjoyed. I had some prosecco and we chatted with the great bartender, Mindy. She makes a mean Hurricane as well. We also met some new friends from Sweden and had a wonderful time talking to them. Last stop of the night was the classy LaTeDa a few doors down. By the end of the night, my feet were swollen, blistered sausages; but I was happy.

Key West is a magical hangover-free zone it seems. Not once did I wake up feeling any kind of ill, which kind of amazed me. In addition to the rooster wake-up call, we were also treated to the sounds of street cleaning machines and garbage trucks most mornings. And I mean 5:30 AM early. No matter, I wanted to see the sunrise anyway. I walked down to the pier at the end of Duval and 5 minutes before sunrise, a low cloud deck enveloped the island and that was that. Thankfully it burned off by 8:30 and at 9 am we walked the block to Tropical rentals and picked up two bikes for the remainder of our stay. It was a gorgeous day and we flew down Whitehead in search of the beach at Ft. Zachary Taylor. This was so much better than walking! Why did we not rent them sooner?? We admired more homes on the way, paid our nominal entrance fee into the park and cruised to the shoreline. Thank goodness we had bikes, that would have been a long and un-fun walk. We had the beach almost to ourselves for a while. It is a pretty beach, flanked with Casuarina Pines and palms, though much of it is coral pieces and shells. But we did find a nice sandy area. We basked in the warm sun all morning then decided to pedal over to Garbo’s Grill for lunch. I had been looking forward to this meal most I think since it is the #1 rated restaurant in KW. It is actually a food truck set in a pleasant palm tree lined yard, next to another small restaurant. I got the Mahi tacos and Mark got the Mahi burrito. They were fabulous. Huge filets of fish seasoned to perfection, grilled perfectly and set atop a bed of shredded cabbage, mangoes, fresh jalapenos, cilantro and drizzled with their homemade Caribbean sauce. Then we rode back to Ft. Zach for a little more beach time.

After we showered, we decided to relax a bit outside at the Rum Bar. We met a fun couple from Texas who were big Caribbean travelers as well so we spent some time talking to them and then biked down to Sunset pier to finally watch this famed evening attraction. While this is a primo spot for viewing the sunset, it was the most overrated place we went. It was packed and hard to get a seat, much less a good view, and the singer was way too loud; and not really my cup of tea. And the bartenders weren’t that nice. But it was a good sunset. Next we headed over to Smokin’ Tuna Saloon, one of only two places that we visited twice, aside from the Rum Bar. We went there on recommendations from friends to try the tuna dip and listen to Scott Kirby play. That tuna dip is delicious and so addicting. Rum punch was good too. We figured a proper dinner was in order this night so we went to Blue Heaven. Love the atmosphere at this place. Cool, funky, tropical outdoor garden setting under the palms. Mark had the signature citrus beurre blanc yellowtail snapper which was melt in your mouth amazing. I had the jerk chicken which was outstanding as well. Then we rode home and decided to check out Grand Vin wine bar next door to the Speakeasy. I was disappointed to learn that Lush wine bar is no longer across the street from the Speakeasy. We got a glass of wine, planted our behinds on one of the high hand-painted benches out front and commenced with our new sport of people watching. We talked with a group of people from Arkansas for a long while then figured it was a good time to take photos at the Southernmost Point Buoy. Finally we called it a night.

Wednesday dawned dreary, and this time it didn’t burn off. It was chilly (relatively speaking) and dismal all day. So much for the useless weather forecast of sunny skies. Our plan was to ride over to Stock Island, check out Higgs and Smathers on the way, have lunch at Hogfish Grill then spend the afternoon at the beach. Since it wasn’t a beach day, we opted to just ride to the island for lunch. It was already a long ride but since we took the scenic route, it was even longer. On a nice clear day it would have been much more enjoyable, but it was foggy, misty and windy. We did ride to end of White Street pier and stopped at a fort taken over by the KW Garden Club along the way. Tropical gardens and a huge Banyan tree with a walkway cut through it. Love Banyan trees. We finally made it to Hogfish. Restaurant is off the beaten path at the shrimp docks and set in a big Tiki hut. Very cool. Owner is from Maryland too. Mark tried the signature hogfish sandwich smothered in mushrooms and swiss cheese. Delish. And so were the fries. I had the seafood ceviche with calamari, scallops, shrimp and hogfish. Also very good. Then we turned around and rode back. We stopped at the North end of Smathers just to have a look. I was very pleasantly surprised. Pretty white sand beach lined with towering Royal Palm trees. And calm, clear shallow water. Several people on TripAdvisor had steered me away from this beach so I am glad I checked it out. I would avoid the more touristy area where they sell concessions and rent watercraft, but the section where we were was lovely, and I will definitely return. It may be manmade, but it’s a very nice beach. We did lay our towels out and just relaxed for a little bit and Mark took a quick power nap.

This evening I attempted to ride my bike in a maxi skirt because I sure as heck wasn’t going to walk. We decided to hit Santiago’s Bodega for a glass of wine and maybe some tapas. It’s a very nice restaurant but a bit dark and not really what we were looking for this evening. But I did happen to see how the bartender made their sparkling sangria so definitely going to try it at home. After a glass of wine, we went back to Kelly’s because I had to have another key lime margarita before we left. Actually I had two. And they were pretty strong. Also tried their smoked fish dip which was good but not as good as Smokin’ Tuna’s. We sat at the rail overlooking Caroline street and chatted with some nice folks from St. Louis. Then back onto the bikes to make our way to Conch Republic Seafood Company. I impressed myself with my ability to ride without catching my skirt in the chain or getting hit while navigating the busy downtown area at night, while inebriated.

Conch Republic has a great atmosphere for a large bustling bar. It was still happy hour which meant bogo drinks. I got a wine and then a token for another which had to be used before 7 pm. I didn’t need the first glass, much less the second. Mark ordered a Miller Light which only entitled him to another ML or comparable then he saw they had Virgin islands Mango Ale (one of his favorites) on the menu. So he got one and a token for another. Good lord we were in trouble. Super fun bartender too. Here we made friends with a mother and daughter from NJ. We thought it was a good idea to eat again so we had the cracked conch. Excellent. But we were still craving that tuna dip so we maneuvered our drunk selves back to Smokin’ Tuna for more of that dip. That stuff is like crack. I sensibly decided to cut myself off but Mark had another beer...or three. I have no idea. After all that we hit the store to pick up some Smokin’ Tuna gear. And the last stop was Blue Heaven so I could get a shirt. I very much related to that chicken on a bike, which is their logo. Then somehow we made it home without getting lost or killed.

Thankfully and miraculously I woke up with not a bit of a hangover or even a headache, because I was determined to see the sunrise. We pedaled over to White Street pier which affords the best vantage point. Then we enjoyed looking at the homes along White & South Streets as we rode back. Last stop was to take the obligatory (daylight) picture in front of the Southernmost buoy. We showered, finished packing, took the bikes back, had one final breakfast, one last stroll down Duval, then back to reality.

Key West is a great city with something for everyone. And I love that it is such a dog friendly town. I had lunch next to two huge Great Danes, watched the sunrise with a 180 lb. Newfoundland, sipped a glass of wine with a Chihuahua on the seat next to me and enjoyed watching a guy and his dog (who looked very much like one of mine) across the street every morning as they took off for the beach. Add to that all of the cats and roosters, and I was in heaven. A few places we rode by that looked nice to stay were Pineapple Cottage, Tropical Inn and Mermaid & Alligator (the latter two I had also considered for this trip).

While we generally prefer quieter locales and rarely go out at night, it was great to be able to walk and bike everywhere, and it was liberating not to be tied down by a strict itinerary of my own creation. But while we did pack in a lot, there were many things we did not get to do this trip which is one reason that a return trip, sooner rather than later, is a must. Next time I will do as many of the following as possible: Go on a sunset cruise, take a seaplane to the Dry Tortugas, have dinner at Latitudes on Sunset Island and visit a number of other bar/restaurants (including Paseo, Pepe’s & Flaming Buoy), spend a day at Smathers, go to a drag show, do some deep sea fishing, try the lobster benedict for breakfast at Blue Heaven, and last but not least…eat a slice of key lime pie. Cannot believe I did not have one!! I realized it when it was too late. Again, I blame the cocktails. One day I would also like to visit during the House & Garden tours (which we missed by a day this trip) and/or the Food & Wine Festival. Thanks to everyone for the suggestions of things to see, do, eat and drink, including Vicki H whose recommendations are always spot on.

Attached is a link to my Facebook photo album instead of the usual Shutterfly since it’s easier to include captions. Enjoy!

https://www.facebook.com/media/set/?...1&l=8c5f06bf27

taconictraveler

Fun report and very good pics. Glad we're going to FL in ten days or the photos would have made me cry!!

Ackislander

Great report on a great town, though you have so much energy I have to take a nap!

You are not too hard on the eyes, either? No offense!

Kristen1206

Thank you! I wish I still had it to look forward to! And no time to nap during precious vacation hours

tch912

Kristen, I am from Maryland also and Key West is on my short list. I usually go to the Caribbean also. I loved your trip report. To write a report like yours I would be walking around with a note pad . The pictures were awesome. The picture with the sign pointing to Greenbelt was hilarious because I go through Greenbelt daily on my way to work. I never wear flip flops when walking . My friends laugh at me because I am always the one with tennis shoes and footies. My feet may be hot but never hurt and as soon as I get to a destination I take them off to cool off and when I start walking again I put them back on. Thanks for the report, I enjoyed it.

Kristen1206

Thanks tch! After day 2 I had to make a couple of notes on my phone to make sure I didn't forget anything At Turtle Kraals there is also one of those directional signs pointing to Rehoboth Beach but my pic came out blurry so I didn't post. Where are you in MD? I live in Centreville on the shore (just past the outlets) and work in Crofton. I did 4 full days in Disney a few years ago in my flip flops but that was in September so my feet were flip flop broken in. Thankfully I had brought some other shoes to wear. And I knew better than to bring any wedged heels!

tch912

Kristen I walk to Fort Meade High School track on the army base and I am around the corner from Anne Mills mall. Even at Disney World I had my comfortable tennis shoes. I usually buy the light weight cross trainers.

sharona

Thanks for the TR Kristen! I always love reading your reports and all the details. And thanks for the heads up on the Caribbean board. We haven't been to Key West yet but it's definitely on the list. Too many places, too little time.

flpab

Love your report. KW is like our second home so was nice to get a positive report. Rehoboth, grew up there. Alonzo's is our happy hour place and next door the boathouse has great happy hours. Your pictures were so nice. I have laser lights on my KW bike. I bought some new lights for my wheels also. Will be there in two weeks and we take ours with us. Only way to get around for sure. I am trying that tuna dip.

Kristen1206

Thanks! We saw lots of lit up and decked out bikes. Good idea to bring stuff down to bedazzle them with . Enjoy your trip! I can't wait to go back.

Inakauaidavidababy

What a fun read! Thank you for sharing your wonderful adventures.

Debbielynn

Lovely pictures!

Kristen1206

Thank you!

ishkribbl

Kristen- looks like y'all had a great time! Thanks for the fun report and I am bookmarking it all- have not been to the keys in probably 30 years (OMG- getting so old!) but keep planning to do it again some day.

Kristen1206

Ish...it was never somewhere I was in a huge hurry to run back to, but we had the best time and I am already planning a return trip. Nice to do a remote trip and then a more lively trip and so on. Lots more to see and do than I remember and it's such a cute town. I could live there! Not sure if you have ever done Atlantis, but that was a one and done visit for us. KW is a different class of busy, in a good way.

Bostonblondie226

As a fellow writer of lengthy trip reports, I wanted to say that I really enjoyed yours. Your story about the art gallery was hilarious! In the words of Jimmy Buffett, after this latest Boston snowstorm, "I want to go where it's warm", so I'm looking at a quick jaunt to Key West. I'm thinking of spending 4-5 days -- do you think there's enough to do in Key West or should I split time with Miami? What did you think of Hemingway's house?

Thanks again for a fun read!

NeoPatrick

What a wonderful report. How fun.

One comment, not meant to be offensive. I was once told that Key West has more alcoholics per capita than any other city in the US. It's easy to see how that's possible, isn't it? Drinks just go down so easy there!

To, Bostonblondie226, in my opinion there are two Key Wests. One is a place to go for some fun and high energy for a day or two. The other Key West is a place to go when you can relax, completely veg out, and just feel the atmosphere. If you are interested in the latter, you definitely need at least 5 days!

Kristen1206

Bostonblondie...We were there 4 nights and I wished it was longer. We initially were only going to go for 3 nights. So glad we went with 4. Next time I will do 5+. We spent one full day on the beach, and you can easily spend a good part of a day, biking around and seeing the sights. To take in everything on Duval, 1/2 - 1 full day. Then if you want to do a boat trip or any tours, that takes another day. We did not go into Hemingway's house, just looked from the outside. And of course there is much to see on the other keys if you want to rent a car. Personally, I would spend my time in Key West vs Miami.

Kristen1206

NepPatrick...I can totally see how that would be true. Don't get me wrong, I do enjoy a glass or two of wine at home, but something about KW just makes you want to imbibe! There are fun bars everywhere you turn. Plus they ask if you want it "to go." And since everything is walking distance, why not!

flpab

Bostonblondie, just got back from four nights, that is what we usually do but have done seven and never run out of things to do. We have our bikes but Eatons will rent you some. Just take a few clip on and off lights if you are out at night. I have a blinder light with a usb port. I have to say it was good this trip except for two Key West taxis that almost ran over me. One actually waved she was sorry. You do have to be very careful. I love getting around on my bike and my butt hurt this trip so pedaled a lot. We loved Banana Café on Duval. Hemingway's house, the Truman White house are good to see.