Unlocking the Keys: Your Quick and Dirty Guide to Key West
The Florida Keys are one of the most overlooked vacation destinations in the US. A tropical oasis with idyllic crystal clear waters, year-round warm temperatures, great beaches, a nightlife that gives New Orleans a run for its money, and a “Keep the Keys Weird” vibe that is reminiscent of a geriatric Austin (it’s not that old – but you’ve definitely got a wide range) - all stretched along one highway for about 100 miles, making the Florida Keys a convenient getaway for anyone in the states.
Now let me be perfectly clear, when I say the Keys, I mean Key West. There are of course many other islands but if you’ve got a long weekend of 3-4 days, I’m not going to sit here and bullshit you – head to the farthest Key for a perfect combination of a good time, great food, beautiful beaches, warm weather, relaxing strolls, bike-riding, great jogging, and, believe it or not, a little culture.
where to stay in Key West
Best camp site
Adjacent to Key West is quaint Cow Key, home to Boyd’s Campground. Just a 20 minute Uber ride from famed Duval Street, Boyd’s Campground offers several waterfront campsites for RVs and tent campers. It’s a well-run property and I highly recommend for anyone.
Amenities
Heated pool
Private hot showers
Pool table
Laundry room
Boat launch
Game room
Hotel tips…
Hotels are not cheap in the Keys. If you’re looking to kick your feet up and relax at a resort here then be prepared to spend $300/night to $700/night. Since we’ve never stayed in a hotel in the Keys we figured we would send you to this list from TripSavvy - The 9 Best Key West Hotels of 2020.
Find the AirBnB that’s right for you…
I’m a firm believer that a Key West AirBnB is the way to go. In fact, Key West is rapidly becoming exclusively an AirBnB town. Every block we turned down has renovations happening. The house flippers and HGTV wannabes have definitely discovered Key West.
There are countless multi-bedroom properties for $100-$200 per night that don beautiful beach house designs and all come with small pools to cool off from the hot tropical sun.
Take a look at some sample properties we found for ~$100, ~$150, and ~$200
Dog-friendly condo with private deck and shared swimming pool
~$120/night (plus fees)
Enchanting Seaside Cottage
~$170/night (plus fees)
Perfect Harmony @Casa East
~$200/night (plus fees)
Best Key West Beach…
Without a doubt head for Fort Zachery Taylor State Park. This park is a 15-20 minute walk from Duval and features an excellent beach, historic Fort Zachery Taylor, and a small restaurant to grab burgers and other snacks/drinks. There is ton of seating and shade all throughout the park area. It’s not very large and can get crowded in the summer but overall it’s one of the best way to spend a relaxing day in Key West.
what to bring besides the obvious…
aquasocks – the beach does have a decent amount of coral and shells on it so walking along the water can be tough
hammock – there are some great trees to set up a hammock and relax
picnic food – there are picnic tables all along the water for a scenic meal
There is no alcohol allowed in the park, however, you can purchase alcohol from Cayo Hueso Cafe, which is located right on the beach surrounded by picnic tables and shady trees.
fees
$6.50/vehicle
$2.50/person (walking or bike entry)
where to eat in Key West
Best Key West Breakfast
Cuban Coffee Queen - this “food truck” style morning coffeeshop/breakfast sandwich location is the BOMB.com. Seriously, wake up early and head over to try some fantastic coffee, refreshing smoothies, and some of the tastiest breakfast sandwiches I’ve ever had anywhere, not just Key West.
I had the Sunrise Special (Half Key Wester Sandwich + 12 oz Cuban coffee) for only $6.50 and a Hang-Over Helper Smoothie for $8.50. The half sandwich alone was more than enough for me and the smoothie gave me some much needed refreshment.
Best Key West Brunch
Blue Heaven but call ahead to make reservations. This isn’t the only blog telling you to go there and for good reason. It’s on many lists for being the top brunch spot in Key West. We were able to walk in because we arrived mid-day in the middle of the week. I went with the Yellow Submarine - snapper fillet on a baguette.
Best Key West Dinner
Half Shell Raw Bar has some quintessential southern beach town low-country seafood baskets. We got ours with stone crab legs, oysters, and conch soup.
Late Night Munchies
Angelina’s Pizzeria has us covered for some quality late night pizza right in the heart of Duval Street. Seating is located in a small alleyway with public restroom available.
Quick Stop On the Way to Key West
Stop at Robbie’s to feed the massive tarpon as well as the obnoxious pelicans. Holy smokes! Let me tell you what, I’m pretty sure tarpon and pelicans are those most aggressive land and sea creatures alive.
What we did in Key West
Duval and Whitehead Streets run parallel to one another and are the spots to go in KW.
Art Galleries: This one won’t be for everyone but there are a shocking amount of GOOD art galleries along Duval Street. Walk in and browse the unique styles, paintings, drawings, and sculptures. Key West has a very unique art community, grab a beer and walk in and out to explore this fun sub-culture.
Embrace Conch Republic Life: Key Westerners know how to relax, drink and they know how to have a good time.
Dante’s Pool Bar: if you’re in town on a Sunday, check out Dante’s and bring your bathing suit. This waterside pool bar gets wild as the bachelorette and bachelor parties take over. Come to have fun or to people watch. Either way it’s worth spending some time.
See: Beaches: Re: Zachery Taylor State Park
Pro-Tip: Spend a day at the Dry Tortugas National Park (BOOK IN ADVANCE!)
I have been dying to go to the Dry Tortugas National Park for so long but all my trips to Key West have been either spontaneous or for an occasion like a bachelor party where it’s hard to break away from the structure of the plans. In addition to that, most tour groups are booked a few months in advance so it’s going to be nearly impossible to walk up and find space (as I discovered on our most recent trip where the boat captain almost laughed me off the dock for asking if they had space for the day).
The Dry Tortugas are about 2-3 hours by boat from Key West (about 70 miles) and are known for Fort Jefferson, which is a massive unfinished fort that takes up the majority of Garden Key. The Dry Tortugas National Park is also known for incredible diving and snorkeling with several wrecks and reefs to explore. They are only accessible by boat or seaplane so plan accordingly.
Photo courtesy of goodfreephotos.com
Photo opps
Hemingway House - home to famed writer and adventurer Ernest Hemingway. The house is kept up by his descendants and it’s current residents are about 50-60 polydactyl (six-toed) cats. Bring cash for the entrance fee as they do not accept cards.
Southernmost Point of the Continental US – it’s a short walk. Take the damn photo. It’s for the ‘gram.
Advice from a local
We reached out to the wonderful Meredith Reiber, former Conch Republic resident, and her father, current native of the island, to get their advice on where to go if you’re visiting Key West this summer.
Food
Breakfast
La Creperie – Breakfast hot spot
Glazed Donuts – Need I say more?
Southernmost Beach Resort – Beachfront breakfast and lunch
Lunch
Amigos Tortilla Bar – If you’re looking for great lunch right along Duval
BOs Fish Wagon – Cash only seafood lunch spot
The Boat House – Happy hour lunch spot
Happy Hour
Louie’s Backyard – Great sunset happy hour $$$
Schooner Wharf – great hole-in-the-wall sport. Come as you are and meet some locals
Dinner
Santiagos Bodega – “Favorite restaurant EVER!!”
La Trattoria – Authentic Italian $$$ but worth it
Desert
Better Than Sex – “Great desert restaurant”
After Hours
Sloppy Joe’s – A tourist spot that you won’t be ashamed to show your face in. Live music and Ernest Hemingways favorite bar
The Conch Republic – Great live music and food
Smokin’ Tuna – Great music and vibes
Something for Everyone
Mallory Square – stop by for a sunset and see various street performers
Butterfly Museum – If you need something to keep the kids distracted
Truman House
Hemingway House
Conch Train Tour
Break a Sweat
Lazy Dog Paddling – Work off that Duval Street hangover with some paddle yoga, paddle boarding, kayaking, and eco tours of the Keys
Yoga
Advice from a few better blogs than ours
Wanderlustyle – How to spend 3 days in Key West
Dear Wanderer – Weekending in Key West
Jess Ann Kirby – Key West Travel Diary: Where to Eat, Stay, Go
Travel? Yes, Please – 3 Days in Key West Itinerary
A short list of shit to do at the “other” Keys
Islamorada is known for having some of the best fishing in the world so rent a boat and get out on the water
Key Largo, the northernmost Key, is known for being a nice weekend getaway for south Floridians but its main attraction is the John Pennekamp Coral Reef State Park. The park is 70 nautical miles and features the only living coral reef in the continental US.
Marathon has the famed 7 Mile Bridge, which you’ll be driving on as you make your way to Key West. Marathon is known for being a bit more family-friendly and has theaters, museums, and miscellaneous festivals hosted on the island.
Big Pine Key is known for having well-preserved natural beauty. Break out the yoga pants and throw on some hiking shoes to explore many nature trails and explore other outdoor activities like kayaking and exploring the Blue Hole.