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  • Writer's pictureLeah Lair Conner

Key West Vacation Review

Day 1 – We arrived in Key West at around 4:15 and made it to our cottage in time to see the first of many BEAUTIFUL sunsets. We stayed in the Sea Breeze Cottage, located in the Truman Annex area, and it was perfect for our family of six. I booked our house through, and everything went seamlessly. I recommend our exact property with no hesitation, but I REALLY recommend staying in the Truman Annex – lots of house and condo choices, and just a wonderful, easy location.

For dinner, we started off going to a place HIGHLY recommended by several folks, – Blue Heaven. It’s ranked (tripadvisor) #24 of 357 restaurants, and it’s probably most widely known for its key lime pie with a mile-high meringue and breakfast/brunch. Going there for dinner on a busy night might not have been the best idea. I actually stayed home and the family brought me take-out – I had a bad fall as soon as we got into our house. My husband and the kids only had to wait about 30 minutes or so for a table – I recommend making reservations for everywhere you want to go and everything you want to do, especially if you’re there during a particularly busy time (the week we were there, we were told, is typically the busiest of the whole year). Anyway – Blue Heaven. It was probably just an off night, but the family had a waiter that acted like their table was a waste of his time – and the food was particularly unstellar. In fact, the burger they brought home for me (I figured for take-out, something quick and simple like a burger would be just fine!) was still red and cold except for the searing on the outside. And it had been ordered medium. As I said, hopefully just bad timing, but it was off-putting enough that we didn’t want to waste time with a second chance.

Day 2 – We were planning, because of our excellent location, to not rent a car or anything and just walk or uber to the places we wanted to go. Because I was now going to be on crutches for the trip, that option was off the table. So – we rented a six-person golf cart! We used Key West Pirate Rentals ( and could not have been happier! Their staff was amazing, their vehicles were perfect and relatively new, and they also rented bikes, which the kids LOVED getting and riding around the island a couple of the days we were there. We definitely recommend getting a cart or scooters or bikes (or some combination thereof) as opposed to a car.

We went to Smokin’ Tuna Saloon - - to meet some friends that were coming in from West Palm Beach to spend a couple of days with us, at their recommendation, and it was FABULOUS! It’s tripadvisor ranked #67 of 357 restaurants, but it is the ONLY place we actually went to TWICE! The atmosphere was just perfect with mostly outdoor/uncovered seating, and they had a great stage with live music every day. It’s one of the venues that hosts the annual Mile 0 Music Festival ( every year, and we fell in love with it! The food was delicious and the staff were like family. We got to listen to a couple of musicians while we were there, and we recommend seeing them, too – Scott Kirby and Nick Brownell. We missed the opportunity to see Caffeine Carl, but several friends recommended seeing him there – we’ll just have to go back!

From there we headed back to have an evening/night in at the house, just visiting with our friends and having drinks on the patio.

Day 3 – On one of their bike rides, the kids had noticed a restaurant called Rams Head Southernmost – – and they wanted to go check it out. After a morning trip to the urgent car for a walking boot for me (and some staples in my scalp), we met our friends there for lunch, and AGAIN, we LOVED it! The atmosphere was like sitting outside in an open-air market. There were Key West chickens, including a few baby chicks, just running around the patio! Our staff was wonderful, and I had one of my favorite meals of the whole trip – stuffed avocadoes. It was difficult to pick just one thing, as their menu had tons of interesting choices. Their staff and drinks were also noteworthy, and their tripadvisor rating is #81 of 357.

After saying goodbye to our friends, we headed down to Duval Street to just bump around and see what we wanted next. Tod and I spent some time at Captain Tony’s having a couple of drinks and more, wonderful live music. Captain Tony’s is known for hosting Ernest Hemingway and Jimmy Buffet – but there’s a LOT more history there, too. Check out the Facebook page – or just do some searching. It’s a great place to go lose a couple of hours and enjoy music and ghost vibes. The kids just ran around Duval and did some shopping for a bit. Captain Tony’s is ranked #16 of 63 on tripadvisor for “nightlife” in Key West.

For dinner, we wanted pizza at home, so we picked up some INCREDIBLE pies at Clemente’s Wood Fired Pizza Trolley. I cannot even describe how good this pizza was! And tripadvisor agrees, ranking it #1 of 27 Italian restaurants on the island (and #3, overall). for some more info, but just do yourself a favor – if you like pizza at all, make this one of your meals!

While we were waiting on our pizza to be ready, Tod and a couple of the kids went into Fausto’s Food Palace, directly across the street from Clemente’s. We wanted to prepare at least one dinner as a family, and this was definitely the right place to get the goods! It’s the oldest running business in Key West, and perfect for food selections that are not just the ordinary stuff. Tripadvisor ranked #1 specialty food market on the island.

Day 4 – time for the beach! I think lots of people think “beach” when they think Key West, but it’s not actually known for its beaches and frankly, they’re not the best. If you’re looking for long, lazy days on the sand, this might not be your trip! They DO have some good beach options for day trips, though, and we LOVED ours. We went to Fort Zachary Taylor Historic State Park, where there’s manicured beach areas, fun walking/hiking trails, a café with pretty good beach food, picnic areas, and of course – the historic fort that available to tour at your leisure. It was a great day of relaxing!

For the evening, I had booked this night as “date night” for Tod and me. I booked the Southernmost Sunset Sail with full bar, hors d’oeuvres, and live music for us with http://www.keywestsebago – Sebago Watersports - and we loved it! Met some folks to visit with while catamaran cruising for about two hours and watching ANOTHER beautiful, unbeatable sunset.

After sunset, we made our way to Hot Tin Roof for dinner, and it definitely did not disappoint. We went on the recommendation of some friends of ours, AND because I have a huge connection to Tennessee Williams’ play, “Cat on a Hot Tin Roof.” for more info and booking a reservation. Again, I can’t stress the importance of making reservations just about anywhere! The restaurant and bar are on the waterfront (bonus!). We highly recommend the lobster mac-and-cheese, but there was not one part of our meal we didn’t thoroughly enjoy – including key lime pie and crème brulee for dessert! Restaurant ranked #87 by tripadvisor, but recognized as a top 10 restaurant in Key West by Travel & Leisure.

Day 5 – out exploring again! We decided to just drive around and look for a place to have lunch. It took some time (parking wasn’t the easiest/best for someone on crutches!), but we settled on El Meson de Pepe’s in Mallory Square for authentic Cuban food. The place, itself, was so gorgeous and interesting, inside, and it’s clear that it’s a family-run operation. Our service, drinks, and food were ALL excellent. Tod recommends the Cayo Hueso Cuban Mix (their version of a traditional Cuban sandwich), and I loved the Pepe’s Cuban Nachos – unlike any nachos you’ve ever had before, I promise. http://www.elmesondepepe for more, and it’s ranked #14 of 37 Caribbean restaurants on the island; #103, overall.

After a BIG meal and some adventuring around town, we found ourselves back at Smokin’ Tuna for drinks and appetizers and more live music. We met one of the owners and the organizer for Mile 0 Fest – had a great time chatting restaurants and music festivals all afternoon!

This was our night to eat dinner at home – orecchiette pasta and Fausto’s marina, ground beef added, and delicious bread from Fausto’s, as well. It was a great, low-key way to spend an evening in the middle of our week.

Day 6 – This was our BIG ADVENTURE DAY! I booked us a private charter boat through Lazy Dog Adventures, We all gave this day a full, five-star rating, all the way around! #8 of 313 Boat Tours & Water Sports in Key West, with LOTS of excursion options for a group of any size.

Since it was a little bit of a longer drive (15 minutes) to get to Lazy Dog, we decided we’d go early and have lunch at the restaurant next door, and that was a great decision. We all loved Hurricane Hole – the location right on the water, the service, the drinks, the delicious food – all of it – and we got to watch tarpons, jellyfish, and pelicans doing their things in the harbor while we dined. and ranked #42 on tripadvisor – it’s 100% worth driving out of the main area, especially if you’ve got a trip planned with Lazy Dog.

When you have a family of six, it’s actually more economical to book a private charter than pay price-by-head on a public excursion, but regardless – the private charter was awesome. Our captain (Lindsey – ask for her if you decide to do this – she was amazing!) took us out to the Mud Keys to just anchor the boat on a sandbar and let us flop ourselves into the shallow ocean water and relax. We also had kayaks (part of the package) to use to explore through the mangroves and other smaller keys of the area. Snacks and water were provided, but we also took on some of our own and alcoholic beverages. It was just about a perfect afternoon of water, sun, and fun – and heading out to the sandbars, regardless of how you get there or with whom you book, is the way to experience the “beach” in Key West.

Day 7 – feeding chickens, getting tattoos, more shopping, and more delicious food & drinks! We had a little group of chickens that came to our front porch each morning, and we all had fun feeding them breadcrumbs and making new animal friends. If you want to know what’s up with chickens and Key West, visit this site – - their history is super interesting/fascinating. And the hens and roosters are just gorgeous!

We started with lunch at Willie T’s – – another staple of Key West with lots of history and legend, and ranked #88, overall, by tripadvisor for restaurants on the island. The food was really good, as were the drinks, and they had live music going for us, too!

The kids wanted to rent bikes again, and our oldest daughter and I wanted to get tattoos, since it was our last full day and we wouldn’t be in the sun and/or water much. We chose Paradise Tattoo, mainly because it was very conveniently located on Duval Street. – tripadvisor apparently doesn’t rank tattoo shops, but we were thoroughly happy with our experience at Paradise. The staff was great, and the place was cleaner than most hospitals.

For the rest of the afternoon, it was time to barhop for Tod and me, while the kids adventured on their bikes. We started with drinks and live music at The Bull & Whistle Bar. The bar was fun, right on Duval with wide open, huge windows. - #23 of 63 in Key West for Nightlife (tripadvisor). We listened to Uncle Bob play there, for a while, and he was very entertaining and worth catching live during your stay. He has a Facebook page if you’re interested in learning more. We also spent some time at Mangoe’s – – for drinks and more live music. Mangoe’s is ranked #102 by tripadvisor, overall. Cujo & Rogue were playing, and we enjoyed them immensely – check out their Facebook page, and go see them, if you can!

For our last dinner at Key West, we went to the restaurant where our kids went on our date night for their “sibling meal” – New York Pasta Garden – Tripadvisor ranked #4 of 27 Italian restaurants, and #30, overall. This place was a real gem of a find! The atmosphere, food, and drinks were all perfect, and their waitstaff is just amazing. Most of them have been with the restaurant, like family, for over 20 years!

Day 7 – our last day on the island. After packing up and moving out of our little cottage home, we went to SALUTE’! on the beach for lunch. It felt like we were literally dining (great dining, at that!) ON the beach. Everything here was also just about perfect, and since it’s a sister restaurant of Blue Heaven, we DID get to enjoy the famous key lime pie! Tripadvisor ranked #79 of 357 restaurants.

Side note – while we were enjoying the beautiful patio and dining of SALUTE’! and passing a little time before needing to be at the airport, the kids decided to go adventure a little. The open-air artisan market that’s usually nearby was closed due to covid, but they found great little parks to explore – Clarence S. Higgs Memorial Park and the Indigenous Park. There was an African burial ground, a butterfly garden, walking trails with sculptures and memorials – just fun stuff to explore. I couldn’t find web info for the parks, really, but if you visit SALUTE’!, plan in some time to walk around and explore a little!

In closing, all six family members would 100% recommend Key West for a vacation, and we need another whole week, at least, because of things we missed out on – namely a dining experience at Latitudes, visiting The Ernest Hemingway Home & Museum, visiting The Dry Tortugas, having dessert at Better Than Sex, and beach dining at Louie’s Backyard These places are ALWAYS busy, so they require some good prior planning and reservations.

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