Key West, Florida Travel Guide || Fall 2023

I’ve spent a lot of time in Florida this year and finally made my way down to Key West. The Florida Keys are a string of islands stretching 120 miles off the southern tip of Florida. These waters are between the Atlantic Ocean and the Gulf of Mexico making them one of the most sought-after destinations for fishing, boating, snorkeling, and scuba diving.

And while there are over 200 Keys, you probably know the area best from Key West. My dad spent extensive time here when he was in my twenties so this destination has been high on my bucket list for as long as I can remember. It turns out there’s no better spot for a weekend trip with your college friends. Even in September, their low season, the island was hopping with authentic cuisine, friendly locals, and a darn good time.

You’ll leave here hungover and sunkissed—the true recipe for a good time! Per usual I’m spilling all the details from my weekend trip complete with going-out recommendations, favorite restaurants, things to do, and more. Enjoy!

Transportation In The Keys

My only complaint about Key West is that getting here is a hop, skip, and jump. Many people from Florida choose to drive here as the 113-mile adventure takes you over dozens of bridges and the bluest water.

However, if you’re out of state, flying in is the easiest way to get there. However, because Key West is such a tiny island (just 4 miles big!) most commercial airplanes are too big to fly in here. Therefore, you have to get on a smaller prop plane for the final leg of your destination. Most of these smaller planes leave out of Miami, Fort Lauderdale, or Tampa so it’s a short-hour flight. And a gorgeous one at that!

We flew Silver Airlines in and out of the Key West International Airport (EYW). The planes are pink flamingos, too cute! You walk right onto these tiny planes and they have minimal space so you’ll want to pair down for this vacation. Because it’s a prop plane it rides super low so you have a stunning view of the water the entire flight.

This is the tiniest airport I’ve ever been to—literally took five minutes to get through security and the “gate” area is just one big room. You definitely won’t need to arrive more than an hour before your flight. It’s the Keys, everyone’s on island time (also known as nobody is in a rush!).

Where To Stay 

If you know me, you know I am a huge Marritott lover, so when I saw Key West had a beachside property, it was a no-brainer! As always with Marriott, this property had amazing service, the friendliest staff, and exceptional amenities. Whether you’re headed on a family vacation, a romantic getaway, or even a girl’s weekend, Marriott Beachside is the place to be!

Things I loved about this hotel

• Free Airport Shuttle— This hotel is just five minutes away from the airport. Call the hotel upon arrival and they’ll send over a shuttle to pick you up!
• Downtown Transportation— They also have a shuttle that runs downtown every hour from 8:00 a.m. to 11:00 p.m. No need to worry about Ubers, just hop in and you’ll be down and around the action in no time. They pick up a quarter after. We saved so much money this way and the drivers were happy to share all of their favorite spots and best recommendations. The best way to get around is if you don’t have a rental car as this property is on the opposite side of the island.
• On-Site Restaurant— I always love when a hotel has a restaurant on-site. Tavern N Town is a 5-star restaurant with a chic feel, perfect for celebrating any “special occasion”. They are also open for breakfast if you’re not wanting to go far.
• Free Water— My mom taught me at a young age that the best hotels offer free water bottles at the front desk. You can come down here and request one as often as you’d like, free of charge.
• Daily Housekeeping—I’ve never seen a cleaning crew work as hard as they did at Marriott Beachside. Our room was left spotless each night of our stay.

Here’s a look at the pool area which is tucked into the center of the rooms. They have tons of loungers, umbrellas, and a huge pool where we spent most of our time relaxing. There are changing rooms and restrooms here for your convenience. There is also a poolside bar and grill here called Chicken Walk where you can enjoy a yummy afternoon appetizer and fruity drink!

Despite the beaches in Key West being manmade, this Marriott has done an amazing job. They’ve imported tons of sand and have several palm trees and beach chairs overlooking the water. This is the perfect spot for some relaxation time.

There are two different docks along the beach/backside of this property where you can partake in jet ski tours, kayaking, paddle boarding, and more.

As for our room, we stayed in one of their 1 Bedroom Presidential SuiteS and it was huge. Here’s a look at the gorgeous bedroom. We had an amazing waterfront view and the coziest bed.

We were living like queens with this spacious room—we had a full kitchen (dishes, stove, refrigerator, and sink), dining room, and living room. There was also a washer and dryer in this unit. This is the perfect hotel to book if you’re planning an extended stay and/or traveling with kids as there’s plenty of room to spread out.

The bathroom was gigantic—with a large tub, double sinks which made getting ready a breeze, and a sectioned-off walk-in shower. There was also a half bathroom in the main living area.

Our room also had a large walk-out balcony with a stunning view of the beach.

A spiral staircase led us up to our private rooftop access (aka the perfect spot for a sunset glass of champagne).

We couldn’t have asked for a more comfortable three-night stay. I cannot say enough good things about this Marriott location and would definitely stay again. Ready to book a trip to Key West? Browse their different suites and current availability here.

Where To Eat

From what I’ve heard, Key West has some of the freshest seafood in Florida. We gathered tons of recommendations from locals and made our rounds to a few different spots. I so wish we had longer here as there were plenty of other restaurants we were dying to try—Half Shell Raw Bar, Big Cheezees, Chart Room, and Bagatelle just to name a few.

Tavern N Town 

Menu // Directions

Tavern N Town is the restaurant located within our hotel and was named the best overall restaurant in 2022. They are known for their buy one get one free happy hour special as well as their “free birthday entree”. We had to stop in and see what all the hype was about! Lauren and I shared their fresh catch of the day which was served with tomatoes, mushrooms, and lemon butter over linguini and it was phenomenal. Some of the freshest, most tender fish I’ve ever had. We also got the parmesan-crusted chicken which had a hint of lemon butter and basil. It was bursting with flavor. 10/10 on both!

I highly suggest finishing off your meal with a key lime bar. This is their spin on key lime pie and it was phenomenal with a tangy whip and a crunchy base. Wash it down with a key lime martini for good measure. It’s very moody here and the perfect spot for a “fancy” meal.

Two Friends Patio 

Menu // Directions

Every person who gave us Key West recommendations suggested Two Friends so it was a no-brainer. This adorable patio restaurant has live music all day which if you know me, is so my vibe. We came for breakfast and I got their scramble with peppers, onions, tomatoes, and cheddar cheese. it was served with breakfast potatoes and toast and was truly the hugest portion. The perfect place to fuel up to beat a hangover and kick start your day drinking, haha.

Kaya Island Eats 

Menu // Directions

This spot is so underrated, oh my gosh. We popped in for shrimp and fish tacos and they were some of the best I’ve ever had. The seafood was so fresh and the portions were huge. Each order comes with just two tacos but they are stuffed to the brim with pineapple slaw, cilantro aioli, and yummy lime crema. I wish we had room to try more things on the menu—everything sounded delicious. Fruity Island seafood dishes are my fav!

We did try their key lime pie and I hate to say it but I was not overly impressed with it here.

Cuban Coffee Queen

Menu // Directions

Sometimes the only way to beat a hangover is with a $12 smoothie packed full of fresh fruit and good ole antioxidants, lol. Cuban Coffee Queen is one of the only spots on the island that serves smoothies and despite being pricey, they are so good. They also have traditional Cuban breakfast sandwiches here if you want a to-go meal.

Best Bars 

People come to Key West to party. Duval Street is a mile-long strip that’s bar after bar after bar. Each spot has its own vibe with live music all day every day. And when I say all day every day, I mean people are up and starting their day drinking with a bloody marry at 9:00 am vibes. Key West has a huge retirement community so there are lots of older people, dads, and bachelorette parties.

The easiest way to describe Key West is the Nashville of Florida, lol. It’s an experience like no other. Get ready to bar hop, you certainly won’t be home before midnight haha.

Sloppy Joes 

Menu // Directions

My parents used to spend all day at Sloppy Joes when they vacationed in the keys so we had to check it out. They play live music all day every day and it’s a mix of oldies, Jimmy Buffett, and other island classics. I had my favorite drink of the trip here—they made a mean rum runner! Also a good spot to fuel up on some drunk food if you need a quesadilla or fries mid-bar hop.

Ricks 

Directions

Ricks is a must-hit bar that has several different levels. Up top there’s a huge dance floor and DJ for more of a “club” vibe. However, on the ground level, there’s karaoke every night. If you know me, you know I never say no to karaoke. We sang for hours with new friends and bachelorette parties. I had the most fun here!

Irish Kevins 

Menu // Directions

Irish Kevins is your typical Isirsh pub serving green jello shots with whipped cream and all the good vibes. There’s a mix of musicians playing here and it’s a good bar to stand around and meet people in while singing along.

Fat Tuesday

Menu // Directions

If you want a frozen daiquiri or pina colada this is the place to be. It’s one of the few spots that’s all young people. They’ve got TVs for more of a sports bar feel, darts, fuseball, and more. Loud, modern music bumping all night long.

Tiki House 

Menu // Directions

If you want a local spot, this is the place to be. It’s your typical vibe and was nearly empty every time we went in. I love this type of bar because it means you can request as many songs as you want, leaving you with your own private concert. Good vibes here!

Must Do Activities 

If you’re not eating, drinking, or lying in the sun, here are a few things to add to your itinerary!

Boat Day With Barefoot Billys 

You have to find a way to get on a boat during your stay in Key West. Whether you meet someone fun at the bar who invites you out for the day, do a charter, or book an excursion through a company like Barefoot Billys it’s a nonnegotiable. The water here is some of the bluest I’ve ever seen and Key West is home to the third largest barrier reef in the world.

We booked a day visit with Barefoot Billys and had an absolute blast. There were only 15 other people with us and we spent several hours cruising, stopping to see the dolphins. We then suited up and snorkled for an hour seeing the largest corals and prettiest fish. I’m so sad I didn’t have the GoPro with me. The footage would have been epic; it was an unreal experience.

They had snacks, water, and beers on board for us. Such a fun day and a great way to catch some rays if you’re a sun lover like me.

Sunset at Mallory Square 

At sunset, everyone on the island heads over to Mallory Square. This is a huge stretch along the water where people sit and watch the sun go down while listening to live music, watching street performers, and sipping on fruity cocktails. It’s a cool atmosphere and it feels less like a tourist attraction and more like a community event.

Walk Through The Historic Seaport Area

Over by Mallory Square is a whole historic area full of presidential homes that have been turned into Inns and Museums. There are all kinds of landmarks dating way back to the Christopher Columbus days. You can also learn a lot about Cuba over here, as Key West is less than 100 miles away from it!

There are a few outdoor pop-ups, ice cream shops, and clothing stores over this way as well. it’s really neat and most of the buildings are original to their time so it gives me a lot of Charleston vibes over here. A beautiful area you must see!

Explore The Marina 

There is another marina area with colorful houses, coffee shops, and Jimmy Buffett’s recording studio. We visited just a week after his death and the building was flooded with notes, flowers, cards, and mementos from locals and friends. It was really sweet to see. Supposedly this is where several stars have come to record their hits. There’s nothing to do here other than walk around but it’s a neat area to check out.

What To Wear

Not sure what to wear to Florida in the middle of fall? It’s no different than your typical warm weather vacation in the middle of June—you’ll be greeted by endless sunshine and eighty-degree temperatures. Also known as you will be sweating and need a swimsuit. I’m sharing all 10 outfits I wore throughout my stay and links to shop in my Fall in Florida Outfit Guide.

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If you couldn’t tell, Key West is less about laying out at the beach and more about being downtown making memories with your crew. I can’t think of a better place to have a college reunion/bachelorette party/special occasion celebration. My parents have been talking about coming down here next spring for their 25th Anniversary and I certainly hope we do!

Despite being such a small island, there are so many local businesses packed in. I could’ve spent weeks exploring all the nooks and crannies of the Keys. Guess that means I’ll be back soon. Until then…

Latest Post: 10 Outfits To Wear On Your Florida Vacation This Fall
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