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Key West Highlights & Best Stops Along the Drive

...and we're back! Please excuse my extended absence over the last few months as I took a much needed break to recharge my blogging batteries. The end of 2019 crept up so quickly, I barely had time to process time with a busy new project at work, long weekdays and fleeting weekends. Last year was filled with highs and lows, but some of the greatest highlights included new travel adventures, spending time with friends and family, and moving into a new fancy, apartment in downtown Manhattan. Now that 2020 has approached us, it's time to set big goals for the decade and embark on new adventures. I think the 20s' are going to be the most pivotal and transformative years in my life, hopefully with big milestones I hope to hit personally and in my career. No pressure!

My first trip of 2020 was a low-key long weekend down in Miami and Key West as an early birthday celebration. I've spent a lot of time in Florida for leisure in work over the years, and nothing beats Florida's sunshine and warmth during the frigid winter months in NYC. I'd never been to Key West before, so I was very excited for the beautiful drive down from Miami and for all the yummy seafood and key lime pie along the way. Keep reading for all of my recommendations for stops and snacks along the way to Key West and my top picks for activities and food in the 786.

Best Stops Along the Drive to Key West...

The drive along the Florida Keys down to Key West from Miami takes about three and a half hours. Along the way to the southernmost populated Key, there are many activities and restaurants to stop to grab a delicious bite before heading back on the road.

The Fish House (Key Largo)

The promise of fresh seafood for lunch in Key Largo was all it took to get me out of bed bright and early in the morning. The Fish House is a hot spot we heard about from our friend who stopped by after hearing about the restaurant in Diners, Drive-ins and Drives. Apparently he had the "best seafood in his entire life" here. So you know we had to check it out to verify the claims ourselves. We chowed down on lobster bisque and stuffed mushrooms, followed by the main attraction - a yellowtail snapper prepared Matecumbe style. The house specialty is topped with fresh tomatoes, shallots, basil, capers, olive oil and lemon juice, then baked to flaky perfection. Fish House has a large seafood menu with great prices, fast service, and a bikini-bottom atmosphere. Make sure to check it out!

Robbie's of Islamorada

If you only have time for one stop on your way down to Key West, make it Robbie's. Located within the village of Islamorada, which spans 5 different keys (Tea Table Key, Lower Matecumbe Key, Upper Matecumbe Key, Windley Key and Plantation Key), Robbie's has been a beloved institution for the last two decades. It's home to the famous tarpon feeding, where you pay $2.50 for admission and $4.00 for a small bucket of fish to hand-feed hungry tarpon on the dock out back. To be completely honest, I had no idea what a tarpon was before sticking my fish out. So trust me when I say I'm glad I didn't fall into the water and get eaten by the 5 foot fish when it came out to devour lunch. Between the hungry pelicans eyeing my bucket of fish and the half dozen massive tarpons leaping out to eat, the entire situation was very overwhelming but also so much fun! This is a great activity for all ages, but if you're not into feeding the fish with ore fish or getting attacked by pelican, sit back and watch the show while you grab a drink at the outdoor bar or sit down for some fresh seafood.

At Robbie's you can also do some light souvenir shopping at the open-air market, rent kayaks and boats, and sign up for jet skiing adventures and eco-tours. It's seriously a one-stop shop for absolutely everything under the sun. I only wish we had more time to spend here!

Blond Giraffe Key Lime Pie Factory

I will be the first to admit that when it comes to desserts, I never liked key lime pie in any capacity. That is, of course, until I went to Key West...I made it a priority to eat as much key lime pie as I could to make up for all the years I avoided it. Blonde Giraffe Key Lime Pie Factory is located between Key Largo and Plantation Key, and this cute (and very green) local shop is key lime HEAVEN. Blonde Giraffe store sells over 170 items, everything from cookies and candies to fresh pies and frozen, dipped slices. Grab a slice to go for the car ride or head out back to the cute patio to enjoy.

John Pennekamp Coral Reef State Park (Key Largo)

Key Largo is well-known for its incredible diving and snorkeling, so head to John Pennykamp State Park on your way to and from Key West for some fun water adventures. From snorkeling and scuba diving to glass boat bottom boat tours and kayaking/paddling boarding, you can pretty much do everything here! Check out their website for information on how to book specific tours, hours of operations, and admission fees. We only made an hour stop at the park to do a short hike prior to lunch, but I would definitely head back in the warmer months and spend a half or full day exploring. The park has so much to offer and their tours look like a fun way to explore the keys.

Mrs. Mac's Kitchen (Key Largo)

This local favorite is a must-visit in Key Largo. Mrs. Mac's serves up an extensive breakfast, lunch and dinner menu in a cozy, eclectic space decorated with license plates from all over the country. Don't miss their conch chowder, crispy coconut shrimp and their fresh catch of the day. We went with the blackened mahi mahi, which filled us up for the ride back to Miami. Portions are as generous as they are delicious!


Southernmost Beach Resort

I spent a considerable amount of time researching the best places to stay in Key West and ended up choosing the Southernmost Beach Resort due to its incredible location right in the heart of downtown. This charming resort is only 1 block away from the famous Southernmost point and located at the end of bustling Duval Street, making it extremely convenient to get to attractions, bars and restaurants without acar. The rooms are pretty standard and comfortable, but the amenities, private resort dock and central location make this resort a true gem. Don't be alarmed if the roosters wake you up in the mornin!


- Book in advance for the best deals because prices can get hefty during peakmonths and weekends.

- Parking available on site for a $25 daily fee

- Bike rentals available for a small fee

- You will be charged a daily resort fee, so take advantage of the amenities and enjoy the resort

Duval Street

A trip to Key West must include a stroll down the famous Duval Street. This 1.25 mile stretch runs north and south from the Gulf of Mexico to the Atlantic Ocean. Lined with dozens of restaurants, bars, souvenir shops, there's plenty to do and keep the entire family entertained. Visit the aquarium, stroll through the many art exhibits, take a trolley ride or just people watch! Duval street is busy round the clock, but the lively nightlife makes Key West as fun as it is. We kept returning to Sloppy Joe's but I recommend bar hopping to really get to know Duval Street inside and out (The Rum Bar, Garden of Eden, Rick's Bar, Willie T's...the list goes on and on).

Southernmost Point

The Southernmost point in the continental United States is marked by an anchored concrete buoy at the corner of South Street and Whitehead Street in Key West. It was established as a tourist attraction in 1983, and crowds have swarmed here for decades to visit and photograph one of Key West's most popular attractions. Before the buoy was anchored, there was only a concrete sign to mark the landmark. Throughout the years, the structure has been through quite a few design iterations with different words and symbols added before it finally reached its current painted state. The buoy stands 12 ft tall and 7 ft wide.

I recommend visiting early in the morning if you want to take photos of or with the buoy. The queue can actually get quite long during the day as tours stop by and it gets expectedly busier. The Southernmost Point, as the sign says, is Home of the Sunset, so do't miss the cotton candy skies on a clear, sunny day!

Fort Zachary Taylor Historic State Park

Fort Taylor is a must-visit in Key West with a rich, historic background and equally impressive natural backdrop for bird watching and swimming. It predates the Civil War and is a National Historic Monument housing the largest cache of Civil War armament in the world. If you're interested in learning about the fort's historical significance, tour guides and information panels describe the role the fort played in the Civil and Spanish-American War.

Even if you're not a history buff, Fort Taylor is also a wonderful place to soak in the sun at one of Key West's most beloved beaches - the Fort Zachary Taylor State Park. It's the perfect place for the entire family to enjoying a lunch picnic, snorkeling , swimming, snorkeling and fishing. The park is located on the southern edge of Key West, just a few minutes drive from downtown. Fun fact = It is also the southernmost state park in the continental United States!

Lazy Dog Kayaking

One of the most exciting parts about visiting Key West are all of the opportunities for water adventures! Located just 15 minutes away from downtown Key West in Stock Island, Lazy Dog Adventures if your one-stop shop for equipment rentals (paddleboat/kayak) and boat excursions and tours. We chose to rent a double kayak, self-guided tour, which gave us 4 hours to explore the local waters and historic salt ponds. Luckily for us, there weren't many people out on the water the day we went, so our ride was extremely peaceful and romantic. Rental prices and tour options are extremely affordable at Lazy Dog, and offer many day-of options which I found were hard to come by at Key West establishments. One experience I found that I would have wanted to try was a kayaking tour in a clear kayak with Clearly Unique Charters.


DJ's Clam Shack

DJ’s clam shack is a Duval Street staple serving up some of key west’s freshest seafood. From their overstuffed, 1-pound lobster rolls and fried clams to their crunchy,fried conch fritters and calamari, get your seafood fill at this no-frills hot spot. Previously featured in Diners Drive-ins and Dives.

Thirsty Mermaid

If you're looking for a delicious, locally sourced seafood spot in Key West, look no further than the Thirsy Mermaid. They do an amazing happy hour everyday from 4-6 and have a large raw bar selection with East and West coast oysters. I was absolutely obsessed with my seared diver scallops, but our chowder and yellowfin tuna carpaccio didn't disappoint either.

Better than Sex

This romantic dessert restaurant is perfect for date night or for a bachelorette party! It was a fun experiencing choosing from the extensive iPad menu, and I thoroughly enjoyed the clever and sexy dessert names and descriptions. Better Than Sex offers everything from alcoholic dessert beverages to decadent cakes and pies. I enjoyed the unique experience and would recommend to check it out to satisfy your sweet tooth after (or before) dinner.

Southernmost Beach Cafe

Located just steps away from the famous Southernmost Point of the Continental US, Southernmost Beach Cafe is a casual beach-side restaurant serving breakfast, lunch, and dinner. Don't miss the delicious frozen drinks and their incredible coconut shrimp with pineapple dipping sauce. What a great find right next to our hotel and directly on the beach!

Key Lime Pie Company

The Key Lime Pie Company on the northern end of Duval and Green Street has hands-down the best key lime pie I've ever had. Their pies are freshly made with a base of condensed milk, making it creamy, smooth and dense like a rich cheesecake. They also offer gluten-free, extra tart and chocolate-dipped slices. It was so good we came twice in 12 hours!

Best of luck planning your next trip to Key West and hope you are able to check out some of my top recommendations. Enjoy that key lime pie ;) !

#KeyWest #Travel #UnitedStates #Florida

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