Key West – it conjures up images of Ernest Hemingway, Jimmy Buffet, blue/green waters shimmering in the glow of spectacular sunsets, a slow, easy island lifestyle, sipping cocktails in the harbor and sauntering down Duval, each place as appetizing as the last!
I’ve always been curious about this place, as the southernmost point in the US and just 90 miles away from Cuba! Did my imagination match up to the real thing?
We got there by air, but once in town walked well over 120,000 steps! We discovered little gems every day because we travelled mainly on foot! Follow along with me as I share our experiences in the Conch Republic!
Day 1: March 29th- We got in a 11:30am and dropped our bags at Marrero’s Guest Mansion. Our room wasn’t ready so we began checking out the area. We stumbled onto this cute little restaurant called Frita’s Cuban Burgers.
We had the Frita Confundita burger and the Cubanito sandwich. The Confundita was especially delicious, a burger with shredded pork, Frita’s sauce, caribbean slaw and tiny crispy julienne potatoes. This family run spot was cozy, authentic, affordable and a great place to start our trip!
We headed back to Marrero’s and settled into our room. Every room there is unique and the design of the entire place was terrific-colorful and fun! In the lobby they offer free water, soda, coffee, tea anytime and then a 3:30pm happy hour with complimentary wine & beer – very nice!
On the recommendation of our host we headed to El Meson de PEPE restaurant, which is close to the popular sunset spot Mallory Square.
We sat outside and ordered the two combination platters to try out a variety of offerings. The food & Sangria were good but the chickens were everywhere. They are beautiful to look at and add to the flavor of Key West, but were under our feet while we were eating and one grabbed the cuban bread right out of my husband’s hand at dinner-the roosters clearly rule this place!
We visited the memorial sculpture garden next to the restaurant, with busts and plates honoring the contributions of people who made Key West what it is today. We headed to famous, Mallory Square to watch the sunset and it was a spectacle. Jugglers, musicians, acrobats, you name it, they were there, and so were the crowds. The performers were entertaining but it wasn’t the best spot to actually watch the sunset, as people were several deep at the water…maybe they can install bleachers?
Day 2: March 30th – We walked through Truman Annex, which is an area originally part of a naval station and now a development with high-end conch style vacation rentals, to Fort Zachary Taylor State Park. There we discovered a beautiful, shady park with a rocky but pristine beach. We headed to the civil war era fort there and jumped in on an ongoing free tour with a wonderfully knowledgable woman as our guide. This hour-long tour was definitely worth the time! We then walked along the water which was really rough due to high winds that they’d been having for a few days.
Exhausted from our long walk we came upon Blue Heaven Restaurant (which was on our list of spots to visit) and were more than happy to sit down and enjoy the Lobster “BLT” Benedict which was out of this world!
The key lime pie was also scrumptious, the thick layer of meringue just melted in your mouth! The place had a really good vibe about it and I’d say it deserves a spot on the Key West must visit list!
We walked by Green Parrot on our way back and stopped in, listening to Tony Baltimore & Wilde Awake for an hour or so – the place has a chill vibe, wasn’t seedy (like some of the bars are there) and the band was excellent!
We were tired out from all the walking and so headed back to our room early to relax on the balcony of our new room at Marrero’s (the same room wasn’t available all three nights).
While on the balcony, the Ghost Tour Trolley stopped in front of our place and although we couldn’t hear what the guide was saying, we realized that Marrero’s Guest Mansion was part of the tour and therefore…must be haunted!!! I did some research and discovered that Enriquetta Marrero and her children’s spirits are believed to be keeping watch on the mansion.
You would think our discovery that Marrero’s was haunted would have kept us up that night, but it wasn’t a ghost that did it. In my trip planning research, I hadn’t come across anything that mentioned a rooster issue in Key West!!! Hens and roosters are everywhere and they ROOST anytime from midnight-daybreak. Ours happened to roost in a tree right outside our room and kept us up all night! They are beautiful but we were ready to strangle this rooster-it crowed from 2am-7am every few minutes!
Day 3: 3/31-We managed to rally and headed out at 9:30am that morning with the goal of checking out the other beaches that Key West offers. We walked Duval all the way down to the Southernmost point. There was no doubt that we had arrived there 🙂
We walked along to Higgs Beach and just past that we discovered the Fort West Martello, a civil war fort at 1100 Atlantic Boulevard. This is now maintained by the Key West Garden Club and offered a beautiful collection of orchids, cactus and other flora and was a complete surprise to us, since it wasn’t on the street map that our B&B had given us.
We continued along the Atlantic Blvd. to the Key West Aids Memorial and African Cemetery at Higgs Beach ,where over 1,400 Africans were rescued from the slave trade in 1860.
The water was wild due to the wind and was crashing into the sea wall and over it, so in many spots, there was really little beach to be found!
We decided to continue to walk to El Sibboney for lunch (which was worth it) but we put in too many steps that day and needed to go back to our room for a long nap!
Day 4: April 1st – I was excited about a solo kayaking trip that morning and was all ready to go but they forgot to pick me up! Ok, everyone makes mistakes! They were sincerely apologetic, refunded 1/2 the price for the trip back to me and rescheduled me for the following day.
Since we were checking out of Marrero’s that day, we figured we’d do a load of laundry at the Hills Laundromat (I would suggest you find another laundromat if you plan to do your own). We then checked in to The Tropical Inn, located right on Duval street but with a beautiful tropical oasis behind the inn. We relaxed there and then headed to Sunset Pier for Pork Belly tacos and burger (both delicious). Several locals had told us this was the best place to watch the sunset without being in the throngs of people at Mallory Square and they were right!
Day 5: April 2nd – My rescheduled solo kayaking trip this morning took me through the mangroves. It was a bit of a workout, but so good to be on the water! Some in our group saw a manatee and nurse shark on the outing, but I have to admit I didn’t paddle towards them once alerted.
We walked out to beautiful Fort Zachary Taylor park for the afternoon. Water shoes would have made going for a swim a lot more comfortable, but we managed and the water was warm and clear! We rented lounge chairs for $12/per day which was great and they also had umbrellas available, but no towels. There was a concession stand that offered a variety of snacks, lunch items and beverages (alcoholic drinks as well).
Day 6: April 3 – We started our 40th wedding anniversary celebration by taking it easy, in preparation for the special evening we had planned. We did take the advice of our host at The Tropical Inn and walked around the corner to the Moon Dog Cafe for a small fig and gorgonzola pizza which was very good. We took an apricot custard pastry to go and it was amazing!!! Later, we walked down Truman and Simonton, past the Key West cemetery (reminiscent of the above-ground cemeteries in New Orleans). We stopped at DJ’s Clam Shack (which was featured on Guy Fieri’s Diners, Drive-Ins and Dives) where a super friendly man named John walked us through options and we decided to split a lobster roll to hold us over until dinner – it was awesome! We then relaxed at our Inn for a few hours.
Our special anniversary treat was a reservation at Latitudes. What a treat! We boarded the boat that would take us out to Sunset Key and rounded the island to see the tiki torches lining the restaurant’s shoreline. The boat ride was included with our dinner reservation and felt exclusive!
Latitudes is a beautiful experience for a special occasion and there were many birthday and anniversary celebrations that evening in addition to ours. We ordered the lobster bisque (very good) and wedge salad with gorgonzola, grapefruit segments, pistachio, bacon, date jeers vinaigrette (delicious) and then the snapper and grouper dishes. The snapper was really good, but the accompanying rice/sauce was a bit short on flavor. The grouper was complimented well by the fried potatoes, beans and slaw. The service was great, professional but not stuffy and Sunset Key and Key West were beautiful from the water at night, all lit up like jewels!
Day 7: April 4 – We arrived at our final hotel, Fairfield Marriott – relaxed by the pool, then headed to Martin’s for Happy Hour wine and Tapas on the recommendation of John at DJ’s Clam Shack. They offer 1/2 price tapas and drinks from 4pm-6pm daily. Grilled lamb chops, pork tenderloin, sea scallops florentine, baked brie with poached pear and fettuccine saffron alfredo. All delicious, with great service and a good deal!
Day 8: April 5 – Our final day started at the Key Butterfly & Nature Conservatory right at opening (9am) which was great because few people were there yet. Loved that you can wander through at your own pace because I love flamingos and spent a lot of time just watching them.
We relaxed by the pool through the hot part of the day, where the other common wildlife there (iguanas) at one point jumped in the pool, swam across and scrambled out the other side!!! A guest sitting next to me then confessed that while I was sunbathing on my stomach, in a world of my own this guy was underneath my chair. I thanked him for not waking me up to tell me that!
We took a final walk along the water and at Sunset Pier one more time and felt satisfied that we had seen quite a bit of what Key West has to offer.
Trip Wrap Up
Key West is a beautiful place to visit. Most nice accommodations in springtime are $400+/night and many of the restaurants are on a $$$$. On the other hand, a week in a condo in Sea Isle City, New Jersey costs roughly the same and Key West is worth it!
If you are on a modest budget, the only way to save is to do a shorter trip. We had locked in a week-long stay in order to take advantage of a low airfare before discovering that hotel rates were so high or would have done the same.
All in all, the Key West I had imagined was there! A cool, laid-back place, all about a good time!
Trips ups
Fairfield Inn Stay: The pool was nice and big and they do shuttle you to Old Town but the hotel needs a refresh! I always try to work a Marriott hotel into our trips to earn/use points. I think for this trip the Marriott Beachside might have been a better choice, albeit more $$$.
Not packing water shoes. Best beach and swim area is at Fort Zachary Taylor Historic park but it is hard on the feet.
Rooster Prep: They are beautiful, but loud! You may want to download a white noise app to use if you are staying at a local B&B.
Never finding the free Duval Loop bus – We had asked a few merchants about it and they weren’t even sure if, when or where it was running. We got our steps in but if you are doing a shorter stay it would be very helpful.
Best Moves
Marrero’s Guest Mansion stay: It may be haunted but it was a great stay! Fun design, large rooms, free continental breakfast, complimentary happy hour and free water, soda and coffee anytime. There were three women running the inn and they were all friendly and very helpful!
Restaurants: Blue Heaven-Great food and fun relaxed atmosphere. Martins Happy Hour 4pm-6pm everyday-delicious tapas. DJ’s Clam for lobster rolls. Frita’s for an authentic, cozy meal. Latitudes for a special occasion evening.
Sunsets: Mallory Square – visit one time to be entertained. Sunset Tiki Bar – it looks exclusive to guests but it is open to the public, located within the Galleon Resort. Sunset Pier – music, good food and great views! Fort Zachary Taylor Park – concessions close at 6pm but you can stay until the sun sets.
Talking to locals: We got a lot of help from locals and got a better feel for what its like to live there. The locals were friendly and inviting!
If we do this again…
We might decide to go in February, before spring break (although we didn’t run into a spring break problem on our dates). The town doesn’t offer many beaches so a pool becomes very important, because its hot! Find a place with a good size pool and relaxing scene to provide respite from the heat and crowds on Duval and Mallory Square.
Amytripsalot 
7 responses to “Exploring Key West”
Sounds like you stopped in all the right places. Great input on where to eat. All sounds great except for those pesky roosters!
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Thanks for reading! The roosters are fun and really beautiful, if the one hadn’t kept us up we would have loved them 🙂
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Locals say they don’t even hear them anymore!
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Looks like you had a fantastic trip and you both look very well-rested! The tropics will do that for you. Happy Anniversary!
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Thanks Neda, we had a really nice time!
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Enjoyed reading your travel blog!
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Totally enjoyed your thoughtful Key West insights. I went there 4 years ago and wish you had gone there 5 years ago, so I would have gone there well-informed!
Looking forward to reading about your Italy trip next…(I’m going next year, so thank you in advance!)
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