Last updated on April 6th, 2021
Beautiful Key West / Photo Courtesy of Key West Tourism
by Carolyn Ray, Publisher, JourneyWoman
Need a winter getaway? Look no further than Key West!
If you need a winter escape, look no further than Key West, Florida. Although I grew up in Florida, I never made it to Key West until a few years ago and now I can’t stop returning. The warm breezes, stunning sunsets and laid-back lifestyle re-energized my love for the Sunshine State. Now it has become an annual destination, where I can relax, get grounded, and spend my days doing just about anything. Even though you’re in the U.S., it really feels like you’re in the Caribbean, with brightly coloured houses, a quirky vibe and no shortage of things to do. Or not – it’s your choice.
Key West is the most southernmost city in the contiguous U.S., 90 miles from Cuba. It’s about a 3.5-hour drive from Miami across the Seven-Mile Bridge, and it’s worth doing the drive at least once. Flights are also available from major airports in the US, and there are major cruise ships that dock every week (see the schedule here).
Key West is only five square miles, but I’ve never been bored! You can walk or bike from one side of the island to the other in minutes, and there is no shortage of unique experiences.
My three must-do activities
There are three must-dos when you are in Key West. You absolutely must:
1. Ride a bike or walk: Whether you drive or fly to Key West, you simply don’t need a car. A taxi from the airport to the Old Town costs about $9. Rent a bike from one of the many bike rental shops for about $12-15 a day and feel the wind in your hair!
2. Enjoy the water: I’m always surprised how many people visit Key West but don’t go to the beach or out on a boat. There are tiki boats, sail boats, and cruise ships! Not to mention Fort Taylor Beach, in my opinion, the best beach in the Keys.
3. Stay in locally-owned guest houses for a unique experience: Not only is the cost more reasonable, but you’ll also enjoy a much more authentic experience staying at a guest house.
Fort Taylor Beach / Photo Credit: Carolyn Ray
Where to Stay
There are almost 500 hotels and guesthouses in Key West. Try to stay at a locally owned guest house, and book directly to get the best prices and service. Keep an eye out for ‘resort fees’, which are generally only applied by the larger resorts, but it’s worth checking before you book. I prefer the west side of the island and is close to Duval Street, but not on it. For longer stays, Truman Annex is a good choice.
- Simonton Court: First, the entrance: you walk through a palm tree oasis into a heavily-treed private area of little cottages and four swimming pools. It’s so quaint. Try to stay in a cottage if you can and enjoy one of the four swimming pools outside your door. Mine had an outdoor seating area that I loved. 320 Simonton Street www.simontoncourt.com
- Avalon Bed and Breakfast: At the quiet end of Duval Street, this is my go-to place. It’s reasonably priced and the rooms are a good size. Try the top floor King Room, which has its own private balcony where you can people-watch. Bike rental is across the street. 1317 Duval Street, www.avalonbnb.com
- Southernmost Guest House: Facing the ocean, you can see the sunrise and the tourists flocking to the Southernmost Point. Built in 1984, this Victorian house has lovely gardens, a pool and large rooms with a balcony that wraps around the house. Very reasonably priced. 1327 Duval Street southernmostpoint.com
- Lighthouse Court Hotel: Location, location! Directly across from Hemingway House, this quaint hotel has a nice swimming pool and breakfast is included. 902 Whitehead Street lighthouse-court-hotel-key-west.hotel-ds.com/en/
Tip: Avoid places on Eaton, Duval and Truman Streets, which can be noisy due to car traffic unless you have a room at the very back.
Where to Eat
My favourite lunch at la te da in Key West / Photo Credit: Carolyn Ray
Key West has over 200 restaurants, and the food is fantastic. Here are a few of my favourites that have a special ambiance. They’re the ones I return to each time. (Note: Places marked with an asterisk (*) have great margaritas – Journeywoman tasted and approved!)
- Santiago’s Bodega: More than just delicious tapas, wonderful sangria! What more could you want! 207 Petronia Street santiagosbodega.com
- Blue Heaven: Probably the most authentic restaurant in Key West. Live music, delicious food and great service in a historic place that used to be a bordello! Have the special and don’t forget the Key Lime Pie! 729 Thomas Street, blueheavenkw.com
- Bagatelle: Ask to sit on the second floor so you can watch the street below and hear the music from Hog’s Breath Saloon. (I really enjoy their fried artichokes). 115 Duval bagatellekw.com
- La te da*: A hotel, restaurant and cabaret – I go just for the crab meat, avocado and shrimp salad. Oh, and a margarita. 1125 Duval Street lateda.com
- Coffee Plantation: Off the beaten track on Eaton Street, it’s an oasis, with quirky furniture and welcoming staff. And you can buy real estate while you’re there. 713 Caroline Street www.coffeeplantationrealtycafe.com
- Southernmost Beach Café: If not just for the view of the ocean, sitting on the beach. The margaritas are pretty good too. 1319 Duval Street www.southernmostbeachresort.com/dine/southernmost-beach-cafe
Where to Listen to Live Music
Schooner’s Warf for the vibe & No Name Pub for the pizza/ Photo credit: Carolyn Ray
As you walk along Duval Street, each block has its own vibe. There are many bars with live music. These are some of my favourites.
- El Meson de Pepe*: This Cuban bar is the perfect place for sunset at Mallory Square. You can enjoy the sights and sip on a margarita at the same time! 410 Wall Street www.elmesondepepe.com
- Green Parrot*: Always welcoming, always has great live brands. I like the back bar so I can enjoy the view of the whole place. 601 Whitehead Street www.greenparrot.com
- Sloppy Joe’s: You just can’t miss coming here. Period. Best place in town for rock and roll, with a female lead. Plus you see all the Hemingway memorabilia. 201 Duval Street sloppyjoes.com
- Schooner Wharf Bar*: Located at the marina, this is an all-around great place. The sticker-covered bar, the service, the live music and the food. At the foot of William Street www.schoonerwharf.com
- No Name Pub: A local favourite on Big Pine Key about halfway to Miami. See if you can find the “Journeywoman was Here” dollar bill on the wall! nonamepub.com
On the Water
On the Water with Danger Charters / Photo Credit: Carolyn Ray
If you don’t get in or on the water, you’re missing an amazing view of Key West. There are several sunset cruise operators, so try different ones! Remember if you do different tours, such as the snorkeling trips, with the same operator to ask for a discount.
- Danger Charters: I’ve been on the Wine and Sunset Cruise three times and never regretted it, although I did lose my hat on the last trip! Ask for the all-women crew! www.dangercharters.com
- Schooner Appledore: A little more casual than Danger, still a fun cruise, and the captain let me pilot the boat. appledore2.com
- Dry Tortugas/Fort Jefferson: A full-day trip to Fort Jefferson, 70 miles west of Key West, that leaves from the marina. The colour of the ocean is worth the time and distance. That said, eat a light breakfast and try to pick a less windy day. And then just drink in the turquoise waters and white sand beach. www.drytortugas.com
- Fort Taylor Beach: No visit to Key West is complete without a visit to Fort Jackson. There’s a café which serves decent food. Go to the far right hand side of the beach which is less rocky. Ride a bike and pay $2.50 per person for the day, which includes Fort Taylor. Bring your goggles if you want to exercise. You can also BBQ, picnic and get married there! www.fortzacharytaylor.com/beach.html
Standing in front of Hemingway House / Photo Credit: Carolyn Ray
- Hemingway House: Tours run every few minutes. You’ll be regaled by the tour guides about Ernest, but just remember, it was Pauline’s money that bought the house, the car, and everything else! www.hemingwayhome.com
- Key West Butterfly and Nature Conservatory: Worth it just to see the Scarlett and Rhett, the resident flamingoes, who ‘flamingle’ at sunset. Open daily, about $12 with passes available 1316 Duval www.keywestbutterfly.com
- The Turtle Hospital: Don’t miss it. There are 90-minute tours several times a day, starting at 9 am. 2396 Overseas Highway. Register in advance online here: www.turtlehospital.org
- Key West Museum of Art and History at the Custom House: Several interesting exhibits including the history of Key West, the construction of the Flager Railroad, the USS Maine, Hemingway, Fantasy Fest and Tennessee Williams. www.kwahs.org/museums/custom-house/visit. Tickets are $5 (Key West Arts and Historical Society)
Scarlett and Rhett, resident flamingos at the Key West Butterfly Conservatory / Photo Credit: Carolyn Ray
Key Weird Museum poster / Photo Credit: Carolyn Ray
- Harry Truman White House: It’s almost like stepping back into the 1950s. Not much has changed, an interesting tour on a rainy day. Open 9-4 pm with lower rates online. www.trumanlittlewhitehouse.com
- Southernmost Point Buoy: The closest you can get to Cuba. Always crowded. Go as early as you can (like sunset) to avoid the lineups. www.cityofkeywest-fl.gov/egov/apps/locations/facilities.egov?view=detail&id=79
- US 1 (US Highway 1) officially begins in Key West and runs 545 miles *877 km) into Georgia. Take a photo next to the sign near the Monroe County Courthouse at the intersection of Fleming and Whitehead (Walking distance from Hemingway House and the Green Parrot).
The Southernmost Point Buoy / Photo Credit: Carolyn Ray
US1 Sign / Photo Credit: Carolyn Ray
- Key West Literary Tour: There’s more to Key West than Hemingway; in fact, it’s home to 7 Pulitzer Prize winners. Take a 90-minute walking tour with the Key West Literary Seminar, which recently purchased the home of Pulitzer Prize-winning writer Elizabeth Bishop. Bishop lived here for 10 years, writing her first poetry collection North & South: A Cold Spring.
Read about Carolyn’s Literary Tour here
There are many cute (and not to cute) places to shop, although many of them cater to the cruise ships, which arrive almost daily. Here are a few alternatives:
- Judy Blume’s Books & Books @ The Studios of Key West, 533 Eaton Street, Open Daily, booksandbookskw.com
- Shadow and Fish: My go-to place for super cute bags, swimwear, and dresses, 1024 Duval Street with a sister location across the street if you need other sizes.
- Ron Jon Surf Shop: A surfer’s mecca with t-shirts, tropical wear, more oriented to men but still some cute things for women. Before you go, see if your hotel has discount coupons. 503 Front Street. www.ronjonsurfshop.com/location/detail.aspx?LocationId=12
- Fausto’s Food Place: Grocery store established in 1926, making the oldest running business in Key West. Along with the wine, beer comes friendly people and paper bags (not plastic!) www.faustos.com
Please note: Journeywoman did not receive any incentives or commission from any of the places listed here. The Florida Keys and Key West provided a list of tourist attractions, three of which I toured with a media pass. More to do on their website at www.fla-keys.com.
Things I still want to do
Tour Amsterdam’s Curry Mansion: Built in 1869 by one of the wealthiest men in Key West, 511 Caroline Street currymansion.com
Key West Food Tours www.keywestfoodtours.com
Honest Eco, all battery-powered water tours honesteco.org
Stay at the Moorings Village in Islamorada, where the Netflix series Bloodline was filmed. themooringsvillage.com