The Conch Republic

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People usually find it really strange that I’ve been visiting Key West since I was 12 years old. The drag bars, fantasy fest, and the general wild and free nature of keys locals isn’t exactly the type of environment you’d want your child in right?! Well I actually went down to Key West every summer for an extremely NERDY reason! I’d attend science summer camp focused on ocean conservancy, scuba diving, and marine mammal research. Key West is actually an amazing ecological epicenter of the south. And believe it or not, there is more to do in Key West than drink at a bar all day long! However, that’s a lot of fun too. Jordan and I decided to Honeymoon in the Keys. I’ll be honest, the 10 days seem like one big blur, so instead of boring you with our day to day itinerary, I’ll highlight my favorite restaurants, bars, shopping, beaches and where to stay and what to do.

10 Days in the Keys

Jordan and I decided to fly into Miami, rent a convertible and drive 3 hours down US 1 to Key West. If you’ve never been to the Miami area, or drove across a bridge longer than 7 miles, I’d highly suggest you do the same! It’s a blast, you really get a feel for how laid back the keys are, and because BTW there are more keys (islands) besides the largest, most concentrated, Key West. Some of the best scuba diving is actually found throughout the northern keys, and there’s hidden gems all throughout the archipelago. The drive is worth it. Endless ocean views, stopping for oysters, freshly caught fish or your first piece of Key Lime Pie will make the 3 hours fly by.

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Where to Stay

We stayed at the Cypress House for many reasons. Its located in the Old Town district, which is jam packed with historical houses and buildings. Also, the location of the Cypress House is off of the main street, Duval, a very walkable distance of one block. Its also located a block away from my favorite area of Key West, the Marina. The Cypress House also has a beautiful pool, free daily happy hour and breakfast and super friendly staff! Of course, there are tons of other similar b&b’s. I would recommend The Blue Heron, it has the same vibes, but a little farther off near Eaton street. And of course if your looking for a mainstream modern hotel, the Hyatt in the Harbor is beautiful!

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Where to Eat (If you don’t like seafood, you do now!)

Alonzzo’s Oyster Bar

This is my all time favorite restaurant in the Keys. The oysters are literally to die for. They also have THE BEST Key Lime Pie martini! And, their happy hour is pretty a good deal too. Half off appetizers and drinks from 4-6 daily. Alonzzo’s is located right in the marina just steps away from the water. Dine outside while you gaze out at the beautiful yachts, sail boats, and crowds walking by while listening to old timey 20’s and 30’s music tunes. Our favorite menu item is the Combo baked oyster app, bbq crispy shrimp and of course, the key lime pie martini. Ugh what I’d do for that meal right now.

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The Conch Republic

This restaurant is great for your standard, always yum, always good priced dinner. They have a ton of options, and I’ve never eaten a single thing here that I didn’t like. I’ve been coming to the Conch Republic since I was 12, and its always been delicious and hasn’t changed a bit. I always get lobster bisque, sword fish, and Key Lime Pie. It’s also in the marina, so great views. Their massive saltwater aquariums are also really fun to watch while you sit at the bar or eat your meal. All of the seafood is fresh caught daily and their boat is docked right out front!

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The Little Pearl

This is one of the hottest “up-and-coming” restaurants in Key West right now. It’s located way off the beaten path, in a less desired part of Key West. A true hidden gem. The Little Pearl is a reservation only, fusion food, foodie heaven (wine bar too). Its small, quaint, trendy decor, and a menu filled with options that you’ve never heard of before. I had the summer tomato ginger gazpacho, fresh swordfish with baby broccoli and fingerling potatoes finished off with a strange but amazing teriyaki concoction and for desert, a poached pear. Be sure to ask your waiter about the bullet holes in the window. The Little Pearl is small, it gets loud, but its superb fine dining with a trendy twist.

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The Blue Heaven

Tell anyone you’re going to Key West and they’ll tell you to eat here. A Key West classic, thanks to Kenny Chesney. He ate here once I guess but I’ve been going since before I knew that! The Blue Heaven is the quirkiest, coolest indoor/outdoor restaurant located in Little Cuba. Eat breakfast in the courtyard packed with random thrift store finds, chickens and cats running across your feet all while you watch live music. You have to have the lobster Benedict and their simple but delicious bloody mary.

A&B Lobster House

This was my first time eating at A&B, although its been open for as long as I’ve been coming to the Keys. It’s expensive. Like, really expensive. So if you’re going to eat here, you might as well go all out with a signature cocktail, lobster bisque, and the surf and turf. The ambiance of the restaurant is romantic. Its located directly above Alonzzo’s (mentioned above) so you’re still in the marina, but you get a birds eye view of it all. Jordan and I pretended that the massive white yacht in front of us was ours throughout our entire dinner LOL. #dreamon

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Angelina’s

This is the place to go if you’re drunk and you want pizza. Located right on Duval and underneath the popular “Rick’s” bar. Watch out for Brazilian swingers on the prey.

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Le Creperie

Located right across from the Blue Heaven, it has some very tough competition but truly holds its own. They have amazing crepes, fresh juices, smoothies and all things vegan for anyone that wants a healthy, but gourmet breakfast. After you eat here, walk across the street and snap a photo with one of the many awesome street murals.

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Where to Drink

Louie’s Back Yard

Have a drink and enjoy the endless emerald green/blue for as far as your eyes can see. Watch the pelicans dive for dinner before you grab the freshest catch yourself. Located right next to dog beach, it truly is one of the best views in Key West. The bar is built on a patio that seems as if you’re floating on the water.

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Flying Monkeys

The original slush bar (don’t be fooled by the other copy cats). Ask for the grain train, and grab a seat at the sidewalk bar to people watch as you try not to get brain freeze. If you’re hungry, try the wings.

Sloppy Joes & Hog’s Breath Saloon

I love these places. I don’t know why. They’re both very typical Key West, you’ll find a plethora of people, music and cold drinks.

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World’s Tiniest Bar

The owner built a bar in the middle of an ally. You can fit 3 people wall to wall, shoulder to shoulder. But you always have the best conversation and meet people from all walks of life. We met a really cool Canadian couple here that we ended up going out with 2 more times!

The Bull

Very similar to Sloppy Joes, except if you keep going up the stairs, clothing is optional. The 2nd floor however, is the perfect place to sit on the balcony and people watch while you have a cuban cigar if thats your thing.

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Irish Kevin’s

The entertainment and decor make this place. Its a blast, depending on who the live musician is! In our opinion, Monday’s musician was the best, he was so funny but also talented with the didgeridoo!?! Random.

Where to Shop

Bessame Mucho

After you eat at Blue Heaven, stop here, its just a block away. This store is probably one of the most beautiful boutiques I have ever stepped foot in. You can find everything from home decor, kitchen utensils, clothing, jewelry and body goods here. Its a mix of moroccan and french, the perfect eclectic mix. I didn’t even buy anything this time around because I was so overwhelmed, I wanted EVERYTHING.

Divers Direct

If you’re a scuba diver, or if you like to snorkel, stop here. They have a massive selection of gear, but I always find the best swimming suits and beach clothes here! Its at the very end of Duval, right before the marina.

Shell World

Okay - this sounds super corny and is probably horrible to support this type of business, but I always stop at Shell World on my way out of the keys. Its pretty cool (or really sad if your on the environmentalist side of seashells). You can pick up all kinds of cool souvenirs here, not just shells. They have gorgeous home decor thats coastal inspired of course. This time, I brought home a huge nautilus shell. I have no idea if these are harvested sustainably, but I’m going to guess that almost none of the shells actually come from the keys area. Nautilus live in the pacific, duh.

Duval ST Gallerys

So obviously I always stop in almost every gallery on Duval. There are tons! My favorite this year was Anna Sweet. She’s also a resin artist but also does underwater boudoir photography. I bought 2 pieces of art this visit to the Keys, a painting of a golden retriever that looks IDENTICAL to Yogi. I also bought a small sculpture of a distressed copper mermaid mounted on a piece of old lumber salvaged from a shipwreck. Key West quirky, and if you love art, you’ll have no trouble finding something to bring home.

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What to Do

Helicopter tour - We chose to do this our first morning in Key West. It was AMAZING! We chose the eco tour and spotted several sharks, pods of dolphins and sting rays in the waters below. It was so cool to see the keys from that perspective, and the feeling of being in a helicopter was so cool. They have other tours available, even one that goes over all the bridges in the keys!

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Mallory Square Sunset - Head to Mallory Square to catch the sunset and watch street performers. There is always a huge crowd of people so to get the best seat for sunset views, head over early.

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Sunset Sail - Walk to the Harbor and pick any boat. I suggest choosing a traditional pirate sailboat, as these feel the most authentic! Enjoy champagne at sea while you watch the most amazing sunset of your life.

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Ghost Tour - I’ve never personally done one of these, but my family has! Key West has such a rich history that dates back to the early days and you will hear some pretty creepy stories!

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Scuba Dive - The reefs aren’t that great in the lower keys anymore, at least not the reefs that commercial dive shops will take you. Unless you know a local, head to the upper keys for better scuba diving. My absolute favorite reef in the entire world (and I’ve dove in a lot of places!) is Looe Key off of Big Pine Key. There are also tons of shipwrecks you can do near Key Largo.

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Kayak - Another reason to head to the upper keys for a day, kayak through the mangroves to see manatees, juvenile fish, birds, and iguana.

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Charter a Boat - Charter a boat to go deep sea fishing OR jet skiing, parasailing, sand bar picnic, snorkeling, etc.. You can book private charters or go with the rest of the public group. This is a great way to get out on the water as they aren’t very many beaches with these types of activities readily available.

Beach Day - Our favorite beach in Key West is Fort Zachary Taylor state park. It’s clean, has great views, and has a family friendly crowd. There are signs that say no drinking, but you’ll notice that literally everyone on the beach is drinking. Bring a coozie to conceal your drink and don’t litter. Another beautiful beach to visit is Bahia Honda State Park farther north. You can actually snorkel right off of this beach to the sea grass beds and find baby squid, octopus, and conch.

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Visit the Butterfly Sanctuary - This is a great activity for a rainy day or looking for something quiet and relaxing to do. Spend time in the gorgeous dome atrium amongst plant life, bird species, flamingos, and BUTTERFLIES!

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Enjoy Key Lime Pie in the Harbor - Try Kermits chocolate covered Key Lime pie on a stick. It is TO DIE FOR.

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Lena Perkins Photography - Have a photoshoot done! Lena does 1 hr sessions and she is so talented. You’ll have a blast and photos to cherish forever! I’m so glad we did it, I love looking at our photos and remembering how much fun our honeymoon was!

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Of course, if you have any questions, feel free to contact me! I can surely help you out, I’m practically a Key’s pro. :)

*All photos shot with iPhone X

*Couples photography done by Lena Perkins.

Jessica Pence