Key West sunset from Mallory Square

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Ultimate Guide To A Low Key Visit To Key West

I have been to Key West more times than I can count. I went in my younger days because it was an excellent place for a fun day and an even more fun night. Then I took a 15-year hiatus from visiting. In 2015, I married my partner of 22 years, and we decided to go to Key West for a quick honeymoon. Key West was the first real trip we took together in 1994, so we thought it would be poetic. But we had changed a lot in the 15 years we had been away. And so had Key West. Yes, it is still a party town, but it is also a place you can visit after you no longer want to party until dawn. We had to find new things to do and experience a new Key West vacation. So here is my Guide To A Low-Key Visit To Key West.

Key West At-A-Glance

  • You don’t need, and more accurately, you don’t want a car.
  • Rent a bike for your entire stay; it makes getting around easy and fun.
  • Avoid the big chain hotels; the real Key West is found in the smaller inns and guest cottages.
  • This is not the place if you are looking for wide, long white-sand beaches.
  • Things you don’t want to miss include a sunset at Mallory Square, a day trip to Dry Tortugas National Park, a bike ride around the island, a sunset cruise, or a snorkel adventure.
  • The best food on the island is lunch or dinner at Garbo’s Grill.
Why Key West

You may ask why vacation in Key West. The answer for me is simple: it’s EASY. It’s easy to get to, and flights from the eastern United States are plentiful. Once you land, you don’t need a car. Time moves slower here. It’s like visiting a more exotic destination, not just South Florida. Think a Caribbean island you could drive to!

Getting Around

Flying is the best way to go. You can drive to Key West, but it is a long drive from South Florida. It takes about 4 hours to go 160 miles. If you have traffic, it can take a lot longer. But for those who love a road trip, it’s a once-in-a-lifetime experience; the overseas highway is beautiful. Driving gives you an opportunity to check out some other sights through out the keys, including Key Largo, Big Pine Key, and the beautiful Bahia Honda State Park. EYW (the Key West International Airport) has a whopping 6 gates; by gates, I mean doors. You walk to and from your plane on the tarmac, which is fantastic when you arrive mid-winter from the cold and snowy north.

Once on the ground, I suggest you skip the rental car. It’s more of a hassle to find parking than it is worth. Parking lots a far and few in between, and costly, plus on-street parking is hard to come by. Also, the town of Key West is compact and easy to walk or bike. Leave the terminal and find a taxi or Uber. No matter where you stay in Key West, getting there won’t take more than 10 minutes.

The lay of the land entails knowing a few streets. Duval is the main road, and the tourist drag, bars, restaurants, and shopping are all focused around Duval. It runs the length of the historic district along with Whitehead and Simonton St., your primary focus, with Mallory Square on one end and the Southernmost Point on the other.

When to go

A visit to Key West is good any time of the year. But summer is brutal; the humidity is very high, and so are the bugs. It is also hurricane season, so your travel plans can be impacted by a storm. Winter is the high season from January until May, and October can be very appealing (this is Fantasy Fest, so it’s like a combo of Halloween and Mardis Gras). Prices are highest in the winter and cheapest in the summer. The crowds in January-February are more laid back. March sees more spring break visitors, thus a little rowdier. Summer seems to bring a few more families and party groups. But overall, the best time to visit is February-April. 

Where to Stay

The charm of Key West is the architecture. The historic bungalows and old conch-style homes are what make it unique. Therefore, avoiding large chain hotels is how to get the real Key West experience. My top picks include The Marquesa Hotel, one block off Duval but a world away. On the National Register of Historic Places, the vibe is old Key West. Rooms are housed in old-style cottages surrounding the pool areas. It is the perfect place to stay, but it can be rather expensive. Another low-key option is the Kimpton Winslow’s Bungalows, a series of cottages giving you that Old Key West feel.

Another favorite option is Alexander’s Guest House. An LGBTQ guesthouse that is gay-owned and operated. In the ’80s and ’90s, Key West had almost as many gay accommodations as it did mainstream. Today, there are far fewer “gay guesthouses.” Alexander’s is a welcoming and charming place. 

Low-Key Key West Things To Do

Yes, there is lots of partying and drinking to be found, but we are looking for the Low-Key Key West, so here are a few ideas of the best things to do:


Bike the Island. With so much charming architecture on every street, a bike ride lets you take it all in. Almost every hotel or guesthouse can arrange bikes for the day or your entire stay. It’s the easiest way to get around the island and enjoy the sights.


A day at the beach. Key West is not known for its beaches, and the reason is they could be better. Smather’s Beach is along the airport section of the island and is where you will find soft, sandy beaches. You will also find a lot of seaweed and sometimes red tide. If you want a day at the beach, visit Fort Zachary Taylor State Park. They have a lovely beach where you can rent chairs and an umbrella. It’s peaceful, and the water is generally calm. You will also see large cruise ships coming and going just offshore. Fort Zachary Taylor is also a good place for a bike ride or walk, and you can explore the pre-Civil War fortress.


If you haven’t had enough forts, I recommend you check out Dry Tortugas National Park. (If you hold an America the Beautiful pass, show it at check-in for the ferry or seaplane, and the park entrance fee will deducted or not charged.) It’s a day trip from Key West by ferry (longer but cheaper) or seaplane. Here, you can explore Fort Jefferson, one of the nation’s largest 19th-century forts, and snorkel or dive the coral reefs that are a massive part of this park. Only 1% of the park is dry land; the rest is underwater. This is one of the best places to see marine life in the Florida Keys. This trip will take an entire day, and come prepared for the sun; shade is hard to come by here.

Check out the Key West Cemetery. It is a quirky tropical island version of much larger cemeteries in Paris (Père Lachaise) and New Orleans. It’s both creepy and fascinating. Every time I visit, I have to search the cemetery for the headstone of B. P. Roberts and his famous epitaph that says, “I Told You I Was Sick.” It’s worth a stroll or bike ride around (which is a great way to get around the entire island).


A trip to Key West is never complete without a visit to the nightly Sunset Celebration at Mallory Square. Although this has changed over the years, it’s more commercial now. It is still the perfect ending to a day in Key West. It is like a nightly arts festival with street performers (some have been there since my first visit in 1994), food, drinks, and arts and crafts. Culminating with a fantastic sunset and a cheering crowd. Fort Zachary Taylor Park is also a great place to watch the sunset in a more subdued environment.

Some of the other must-dos on a first trip are to visit the Southernmost Point in the continental United States. Technically, Hawaii is home to the southernmost point in the US, but don’t quibble over details. It’s a good photo opportunity (go early or be prepared to stand in line to take that photo). Travel a little further along Whitehead Street to the corner with Fleming Street and find the “0 Mile Marker” sign, another photo op. Take a cruise, either a sunset party cruise or a daytime snorkeling cruise, which gives you a new perspective on the island. See a drag show on Duval, or at least have your picture taken with one of the drag performers. Visit the Hemingway House, the Ernest Hemingway home is where lived and created several famous works, while in Key West. And walk Duval Street and stop in some famous bars, Sloppy Joe’s, Hog’s Breathe, 801 Bourbon Bar (home of the famous drag shows), Jimmy Buffet’s Original Margaritaville, and/or The Smallest Bar (which is really small).

Key West Sunset with a sail boat on the water.
Where to Dine

Key West has a lot of great dining options. All it takes to find good food is to wander off Duval Street. Most of the places on Duval are more touristy and have lower quality (although there are exceptions). One of my favorite breakfast places is La Grignote, a French bakery, and cafe that is actually on Duval. The pastries are wonderful, along with the Eggs Benedict and French toast. Other breakfast choices include Blue Heaven, a don’t-miss just for the atmosphere, and the Lobster Benedict. And an NYC transplant, Sarabeth, which has the most heavenly lemon ricotta pancakes.

Some great dinner options include Off the Hook Grill Key West. Serving great seafood but is also known for a strange Key West menu item, the Gobbler (which is thanksgiving dinner). The Flaming Buoy Filet Co. is a great intimate option just off Duval. You will find friendly and attentive service here.

And you must try Key Lime pie. Try Key Lime Pie Bakery, Pepe’s Cafe, Kermit’s, or Key West Key Lime Pie Co. But one thing to know is that key lime pie should be yellow, not green. So if it’s bright green, give it a pass; it’s not authentic key lime pie.

But hands down, where I want to eat every day is Garbo’s Grill. It’s a food trailer tucked behind Hank’s Bar on Caroline Street. All seating is outdoors. I love the Korean BBQ here and the fish tacos. I try to make it at home (I have nearly perfected it), and it is always my first and last stop in Key West. Check out my Korean BBQ Taco Recipe here.

Drinks With A View

I love a drink with a view, and here are some places to get that in Key West. Sunset Pier is good for a cold beer or a frozen cocktail (you must have at least one during a Keys vacation) and a snack. Another excellent location for a drink during sunset is Bistro 245, the upstairs bar. It’s open seating, and you can grab a front-row stool and watch the sunset with a cocktail.

Key West can be as wild and wonderful as you like, or you can go low-key and relax by the pool, have a cocktail, enjoy some live music, and watch the sunset. No matter what your vacation style is, escaping to this tropical getaway is an easy and wonderful choice.

Below are links and resources to help you plan The perfect trip

Travel Resources

  • HOTELS and are great resources for accommodations around the world. Book almost any hotel directly from these links.
    The best places to book tours and activities are Viator or Get Your Guide . From great food tours to guided hiking adventures to local walking tours, you will find great experiences to add to your travels here.
    EatWith is a great resource for authentic culinary experiences with passionate locals worldwide. Connecting travelers with hosts in over 130 countries, providing unique, intimate, and immersive experiences in private homes and exclusive venues.
    Trainline is Europe’s leading train and coach app. They work with over 210 rail and coach companies to help their customers travel to thousands of destinations across 45 countries. 

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