WHEN IT COMES TO WALLET FRIENDLINESS, Key West doesn’t historically rank on the “affordable” end of the spectrum. Between all of the brand spanking new luxury hotels and our love for high-end craft cocktails and decadent meals, it can be all too easy to blow your vacation budget before your island getaway even gets off the ground. And sure, you can totally come to Key West and stay at a five-star resort for $500 a night but what’s the point in dishing out all that dough if the only thing you’ll be doing in your room is rinsing off your sandy, bronzed beach bod and sleeping the sleep of the blissfully inebriated?
Deal hunting may be time consuming, but if you do a little digging there are tons of budget-friendly options here — so don’t write off Key West as an unaffordable vacation destination just yet. And now that we’re deep into summer, thinner crowds mean some of the island’s best restaurants and bars are offering unbelievable price cuts on drinks and dishes so enticing you wouldn’t even mind paying full price.
Since we’re all pinching pennies during the leaner summer months, we’ve compiled a series of options for visitors looking to experience some of the best our island has to offer without breaking the bank. So step away from little Sally’s piggy bank, put the hammer down and read on for our recommendations on how to get the most out of your time here for as little green as possible.
Start your day off like a local with breakfast at Sandy’s Café (1026 White St.), a laundromat-slash-24/7 Cuban/ Mexican food stall. (We know that combo sounds weird, but trust us, it works.) Sandy’s is a great place to get your morning jolt of caffeine on the cheap: order one of its deliciously addictive bucchis — essentially a shot of espresso done the Cuban way, i.e., served piping hot and tooth-achingly sweet. Pair it with a toasty-warm pan Cubano slathered with cream cheese and guava spread, and maybe a ham croqueta with stuffed potatoes. The grand total? A whopping $4.16, before taxes.
Don’t worry about the sugar high from the caffeinated kick-in-the-butt — you’ll burn it off by renting a bike up the street at Island Bicycles (929 Truman Ave.), which lends out beach cruisers via a storefront Bob Marley would certainly have frequented if he were in need of wheels. Don your helmet (the helmet, locks and lights are included in the daily $12 rate) and continue southeast down White Street toward the ocean, where you’ll intersect with the Key West AIDS Memorial at the entrance to the Edward B. Knight Pier, a 1,000- foot cement walkway straight out into the ocean with spectacular views.
Enjoy the scene, chat up a local fisherman and then double back down the pier onto White Street and head left to reach West Martello Tower. This historic military fortress, built circa 1863, was declared a National Historic Site in the mid-1970s and is now run by the Key West Garden Club, which uses the picturesque grounds as its headquarters. It’s free to enter the lushly-landscaped space (though donations are encouraged), which boasts ample views of the Atlantic thanks to its position perched above Higgs Beach. Lose yourself in the ruins of the property, take a moment to savor the view in the gazebo perched atop its highest point and luxuriate in the (free) sea air.
Now that you’ve secured your mode of transportation and had your first taste of Key West’s historic architecture, explore the rest of the island’s best-kept properties by way of the Pelican Path, a free, self-guided tour of the 50 most historic buildings in Key West. The path is the brainchild of the Old Island Restoration Foundation, whose tireless efforts to preserve the architectural heritage of Key West have resulted in the protection of 188 buildings, ranging from tiny cigar maker’s cottages to spectacular gingerbread-laden Victorian mansions.
The Pelican Path map can be downloaded for free off the internet, or you can pick up a copy at the Key West Chamber of Commerce at 510 Greene St. Take your time biking lazily from spot to spot, but be sure to step inside the Oldest House & Garden Museum (322 Duval St.) when you get to it. Not only is it a mere $5 to enter, the property boasts a fabulously shady garden out back, perfect for resting your tired limbs after a few hours of sightseeing. And the property recently opened the Old Island General Store, which showcases unique gifts not found anywhere else in Key West. Admission to the store is free, but what you walk out with is up to you.
Once you’ve worked up an appetite for lunch, there are a few spots we wholeheartedly recommend. Head over to El Siboney (900 Catherine St.) for authentic Cuban food at unbeatable prices — $7.95 buys you the best Cuban Mix outside of Havana. Or swing by Sinz Burritos (500 Truman Ave. #1), where the hippest-looking staff south of Brooklyn will happily serve you an overstuffed burrito or a trio of droolworthy yet surprisingly healthful tacos for under $15.
If neither of those sound right, make your way to Kojin Noodle Bar (601 Duval St. #4), a blink-and-you’ll-miss-it locals favorite on Southard Street just off Duval Street, where a half portion (roughly the size of a large mixing bowl) of their buttery-soft beef tenderloin pho will set you back a measly $9. Vegetarians can sub in tofu, or go wild over the Miso Hot Pot, priced at a competitive $8.50.
Midday hunger satiated, grab your kids (or just your inner child) and head on over to the (free!) splash park at the newly unveiled Truman Waterfront Park (21 E. Quay Road). After you’ve soaked yourself to the bone, take a short ride up the road to Fort Zachary Taylor Historic State Park (601 Howard England Way); bonus points if you’re on a bicycle rented from any of the transportation outfits on the island — like Island Safari Rentals, Eaton Bikes, Island Bicycles or We Cycle — which cuts your entry fee down to $2.50.
The park is home to one massive, Civil War-era military fort, and to Key West’s most beautiful beach. There are plenty of shady picnic tables, walking trails and snorkel-friendly coral heads if you’ve remembered to bring your gear. If not, the Chickee Hut on site will rent you a mask & snorkel for $15 (the hut’s also an excellent place for a cheap snack, with pizzas, hot dogs and ice cream all priced under $6).
The park is open until sunset, but you’ll want to head back to town in time to take advantage of the many tempting happy hours happening island-wide. Of particular note is the Conch Republic Seafood Company’s (631 Greene St.) 2-for-1 beer, wine and premium well drinks offer, all served harbor-side with a fantastic view of Key West’s historic seaport from 4-7 p.m.
Or take advantage of the smaller summer crowds at the newly opened Onlywood Grill (725 Caroline St.), whose normally reasonable menu gets downright cheap thanks to their happy hour special. From 4-7 p.m. seven days a week, Onlywood Grill offers 50% off signature cocktails, well and call drinks, wines by the glass and beers. Combine that with an $8 mini pizza Margherita and a robust $7 order of meatballs and you can walk out with a full belly for under $25. P.S. We hear pizza pairs quite nicely with a crisp glass of rosé.
General Horseplay (423 Caroline St.), a relatively new locals’ favorite on Caroline Street half a block off Duval Street, offers Key West’s closest thing to a casino at their happy hour, where, from 3-6 p.m. from Monday through Friday, you can roll the dice to decide the price of your drink. Roll a one or two and pay just $1 or $2, while rolling a three gets you half off, and a four, five or six just encourages you to try again (such is the nature of gambling).
After a delicious drink or two (may the die-rolling odds be ever in your favor), you might need a nosh. We suggest ambling down to Santiago’s Bodega (207 Petronia St.), where you can score a handful of its delicious tapas for a mere $5 plus half-priced drinks from 3-6 p.m. At that price, might as well make that glass of sangria a whole pitcher — we won’t judge.
If you’re craving something a little more posh, head uptown. While its upscale dining room (with prices to match) makes it one of Key West’s most popular special occasion restaurants, if you can find a way to get seated by 6:30 p.m. at the normally pricey Tavern ‘n’ Town (3841 N. Roosevelt Blvd.), you’ll enjoy your fancy-pants meal for just $19.95 per entrée — so go ahead, order the steak. And you might as well pair it with a glass (or two) of Cabernet — drinks are 2-for-1 during happy hour.
Tucked away at the corner of Fleming Street and Grinnell Street, a tiny garden with fabulous food beckons: Azur (425 Grinnell St.), whose Mediterranean themed menu laden with fresh fish boasts a whopping 50% off all food through September if you dine between 5:30 and 7 p.m. Enjoy dining to the sound of a trickling waterfall as you order plate after plate of walnut-stuffed eggplant, branzino with rosemary, house-made gnocchi and the restaurant’s famed charred octopus with za’atar spice.
Assuming you ate early, there’s still time to make it over to the Sunset Celebration at Mallory Square (400 Wall St.), where street performers and colorful-sky-worshippers jostle for the best view of Key West’s most famous, free nightly show. It’s worth experiencing once, but if you’re sick of the crowds (or feeling bullied into tipping a lithe 25-year-old for his acrobatic skills) enjoy the same view with approximately 99% fewer people by watching from the Truman Waterfront. Just head straight through the Truman Annex toward the USCGC Ingham, one of only two preserved Treasury class U.S. Coast Guard Cutters, which now operates as a museum
(and which, incidentally, offers its own happy hour on Friday and Saturday evenings, where $10 buys you entrance to the ship and your first drink). Park your bike, grab a spot on the pier and settle in for a spectacular show, weather permitting.
If hurricane season has rained all over your evening sunset plans, fear not: in a world where a couple of movie tickets and a small popcorn can cost as much as a bottle of Veuve Clicquot, the independent, volunteer-run Tropic Cinema (416 Eaton St.) remains refreshingly affordable, with general admission tickets for adults priced at $12 ($10 for the matinee) and for kids at $8.75 ($7.25 for the matinee). Consistently rated as one of the best cinemas in Florida, the Tropic offers a mix of independent and major release flicks, plus a concession stand that will knock your socks off (though if you’re wearing socks in Key West, you should probably reexamine your lifestyle). Key lime pie, craft beer, popcorn topped with actual butter, brie and crackers, artisanal candies — heck, they’ll even sell you an entire bottle of wine and let you bring it into the theater with you. The screens may be smaller than your average megaplex, but that’s part of the charm.
Finally, if you’re wondering where you’re going to lay your head at the end of such an exhaustingly affordable day, you might want to take advantage of the Eden House’s ongoing special of Deluxe rooms for as low as $110 through Oct. 11. With a prime downtown location and tropical oasis-style amenities (think floating in a pool surrounded by palm trees, hammocks and waterfalls) you’ll sleep like a rock, dreaming about all the ways to spend the cash you saved — after all, what’s the fun in being frugal if you don’t get to sit back and enjoy it? ¦