Is Key West Worth Visiting in 2023?
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As a Key West local since 1985, I know this town like the back of my hand. Family, friends (and their friends) always call me to find out where to go, what to do, where to stay when planning a trip to the Conch Republic.
So let me give you my insider’s view to your question:
Is Key West Worth Visiting?
Hell yeah! Key West is definitely worth visiting.
So you’re wondering why visit Key West? What makes this island city so special? It’s really in a class all its own. Measuring just 4 X 2 miles, this small chunk of land has so much fun, culture and natural beauty packed into it, you’ll be wondering why you didn’t visit sooner.
While Key West is known as a party town (and it is!), there’s much more to do here beyond a rum and coke. Of course, you will want to check off the tourist bucket list and take your photo at the Southernmost Point and visit the Ernest Hemingway house.
But there’s other good reasons to visit Key West and it’s what I suggest, especially for first-time visitors, to really get the flavor of the place.
10 Best Things To Do in Key West
1. Watch Sunset From the Right Place
Most people will be jammed onto festive Mallory Square with the nightly street performers, and local craft and food booths. You should definitely do this one evening when visiting Key West.
But to get a more laid-back sunset experience, with a bar, a seat, and live music, head over to The Galleon, a time-share property providing a great view as the sun dips into the ocean.
Depending on the time of year you’re visiting Key West, the exact location of sunset will shift. So ask some locals or at your hotel where the best viewing spot will be.
2. Explore the Architecture
As much fun as Duval St is, please venture off this main drag. While the water and the beach are wonderful, the historic homes tucked throughout Old Town should not be missed.
They are reminiscent of New Orleans, New England, and the Bahamas because early sailors and shipbuilders traversed through all these areas.
3. Go To Happy Hour
You can save some coin by turning happy hour into a light dinner. Many restaurants and bars have great happy hour deals including small bites; Alonzo’s and Southernmost Beach Bar Cafe are reliable choices.
Get a free weekly newspaper, on just about every street corner, for a current listing of happy hours and musical entertainment.
4. Learn Key West History
The Customs House, a large red brick building in the heart of Old Town, is a must-do, especially if you are a history buff. You will not believe how many times Key West has reinvented itself.
The musuem, a beautifully restored building itself, has rotating exhibits downstairs with permanent exhibits upstairs chronicling Key West history. From rum smugglers to shipwreckers to spongers and cigar makers, it’s a very colorful past.
5. Kayak or SUP the Mangroves
In addition to a snorkel trip on the reef, kayaking the mangroves is another way to enjoy that turquoise blue water. If you prefer a more serene, quiet water experience, this may be right up your alley.
Key West Mangrove Kayak Eco Tour has been rated 5/5 over 1000 times. Let the numbers speak for themselves! If you’re looking for a trusted company to take you out on the waters, this is a great place to start.
6. Go Gallery Hopping
Key West is known for its writers and artists and there is no shortage of artwork in this town. In addition to the commercial galleries located throughout Old Town, check out The Studios of Key West with its rotating exhibits and rooftop view. The bookstore next to it is also top-notch.
If you’re visiting during winter months, gallery show openings happen just about any night of the week. Meet the artist, have a glass of wine, and window shop. Even if you’re not buying, it’s lots of fun.
7. Picnic at Fort Zachary Taylor
This state park located smack downtown has lots of shade trees, a fort to explore, picnic tables/grills for a very full day of enjoyment. Water shoes of some type are a good idea; it’s pretty rocky getting in and out of the water. It’s also a great spot to watch sunset. The admission fee includes exploring through the fort and beach access.
8. Dance, Dance, Dance
Live music abounds and none of it with a cover charge. And most of it can be heard right from the sidewalk.
The Green Parrot Bar brings in some of the best bands. Even if you’re not a night owl, they have a 5:30 pm soundcheck set you can catch before dinner.
9. Play at a Sandbar
Several outfitters offer trips to nearby sandbars and Boca Grande, a deserted island. There is nothing more fun than being in the middle of the ocean and the water is only ankle deep.
10. Attend a Live Performance
Multiple theatre houses, an outdoor amphitheater, and several clubs with quality drag shows means the talent in this town is busting at the seams. Plus, you can enjoy live music at just about every bar in town without a cover charge.
How Many Days Is Enough in Key West?
It depends.
If you’re flying right into Key West vs making the drive down from the mainland, then you can do the town justice with 4 nights/5 days. Any less than that just won’t give you enough time to check out all the wonderful dining options and daytime activities.
If you’ve flown into Miami and you’re driving down, then do it leisurely and enjoy the 135 miles with water surrounding you on all sides. In this scenario, plan on at least 6 nights/7 days.
Where to Stay in Key West
Is it worth staying in Old Town with higher lodging rates or should you stay on the outskirts and save money on a hotel?
This, too, depends on what kind of traveler you are. Old Town is walkable or a bike ride to everything you’ll want to do. For this convenience and ambiance, you will pay more at adorable guest houses, Air B&Bs, and hotels perched on the water.
For a larger hotel with a sunset view, a great on-site restaurant, and a hopping outdoor cocktail scene, check out The Ocean Key House.
If you’re after an upscale boutique hotel, then The Marquesa is divine, as is their restaurant.
If you’re venturing further out (and by this I mean 1-2 miles away), then you will need some kind of transportation (more on this in the next section). Many of the hotels provide shuttle service to Old Town so that’s always an option.
Most of these are chain hotels located along the boulevard where you’ll also find supermarkets, Home Depot, and the routine stores found in every town.
The Capitana is fairly new and has more “charm” than most others in this area. Though it doesn’t have a beach, it fronts the water with lounge chairs situated under lots of shade trees.
The Perry Hotel, on Stock Island another 5-10 minutes further away, is a self-contained resort with a marina, restaurants, and 2 pools with outside bars. So if you want to be away from the mayhem of downtown but still be on the water, this might suit you.
✅ Top Oceanfront Resort: The Ocean Key Resort & Spa
✅ Top Mid-Range Hotel: The Capitana
✅ Top Resort (Outside Downtown): The Perry Hotel
How To Get Around in Key West
Honestly, a rental car is not necessary and parking is a hassle. That said, depending on where you are staying…on the outskirts in New Town or in Old Town..will determine what kind of transportation you’ll want.
Renting a scooter is a lot of fun if you use some common sense. I’ve seen way too many drunk people crash and burn, so consider it defensive driving.
Golf carts have become increasingly popular which is ideal if there are 2 or more of you traveling together.
In my opinion, a bicycle is the way to go. It’s inexpensive, quick, and easy.
It also affords you a slower pace to explore the cemetery, those little lanes in Old Town, to meander along Smather’s Beach. The hotels on the outskirt are within biking distance, but it will definitely take a little more time and effort to get to and fro.
If you’re doing late-night partying, there’s always the option of getting an Uber back to the hotel and retrieving your locked bike the next day…wherever it may be. So, yes, Uber or a taxi is definitely another readily available option.
When’s the Best Time of Year to Visit Key West
Of course, escaping to Key West in the middle of winter is the dream choice. It really is the only place in the continental US where you can pretty much be guaranteed great weather in the winter.
Granted, a cold front can move in for a few days which basically means wearing pants, not shorts. Back in the day, it wouldn’t be unusual to see locals riding their bikes bundled up in bathrobes to keep warm.
I’m not going to lie: summer is hot and humid. So it just depends on your tolerance for heat and humidity. The good news is that the ocean temp hovers between 80F-85F so you can splash around in this all day long. This can be one of the best times to visit Key West.
The seas are flat so it’s great weather for fishing, kayaking and stand-up paddle boarding. And the town is just less crowded which just makes for an overall great experience. Lodging rates will be lower compared to the high winter season too.
The fall and spring are glorious too and, compared to when I first moved to town in ’85, there is hardly any real downtime. Of course, there’s hurricane season starting in June, and ending early November but if we worried about every possibility, we’d never leave our house, right?
If you are going in the fall, make it September. That’s when lots of restaurants still have amazing discounted deals as it, historically, was always the slowest month of the year. It’s nice to know some things never change.
Over time, Key West has added lots of festivals and events to the roster. Check out The Florida Keys tourism website for a calendar of all the planned events. From a wine festival to a Nashville songwriters’ music fest, there’s plenty going on year-round these days.
So….
Is Key West Worth Visiting?
I think you get the picture. It can be a serene day on the water or an all-out dance party; it can be a high-end dining experience or a flip-flop meal at a food truck. It’s quirky, brash, and definitely not vanilla pudding boring.
If you’ve got an open mind and a hankering to get away, pack your bathing suit and get down there. It’s definitely worth the visit.
WANT SOME HELP PLANNING YOUR NEXT TRIP?
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Talk soon, Donna