Spending a handful of days in Key West can be the perfect remedy for everyday pressures; here’s how to experience the Conch lifestyle for a few days without returning home to a massive credit card bill.
Be Savvy About Where You Sleep
Old Town Key West hosts a variety of charming but frequently expensive bed-and-breakfasts and boutique inns.
If your travel budget favors sharing a space over a romantic escape, think about staying at the NYAH resort. Here, rooms can convert from double occupancy to sleeping up to half a dozen guests — without an increase in price.
And at NYAH, you’ll still enjoy the atmosphere of a traditional Key West courtyard-style hotel with multiple pools and a complimentary buffet breakfast.
If you’re feeling playful and a bit bold, book through Airbnb for a stay on a boat or houseboat — it’s actually a long-standing local custom among year-round Key West residents. Several marinas on Key West and Stock Island offer floating lodgings for rent, both dockside and moored.
Gather and Redeem the Free Drink Vouchers
Key West is the sort of place where your bar tab can easily eclipse your spending on food and activities, but you can rein in expenses by collecting and using the plentiful 2-for-1 drink vouchers that establishments across town hand out.
These coupons are often available in rack displays at hotels or visitor centers, or you can request them from the concierge or front desk at your lodging.
My spouse and I saved at least $50 on a recent Key West getaway by using drink coupons — which was particularly satisfying because the coupons aren’t only for dive bars. We found deals for some of the most visited spots in town, like Irish Kevin’s, Conch Republic Seafood, and the Island Dogs Bar. All of these are right in the heart of Old Town and feature live music, so you’ll have entertainment to pair with your half-price drinks.
Pro tip: Typically, drink vouchers cover domestic drafts or well drinks, but if you prefer a nicer cocktail, most bars will simply deduct the price of a well pour from your BOGO drink.
Catch the Best Free Performance in Town, Nightly
What’s Key West’s top draw? It’s not a pub, and it’s not an exhibit — it’s the nightly sunset celebration at Mallory Square.
Each evening, thousands gather along the square’s edge to watch the sun dip below the horizon, with a flotilla of boats of all descriptions taking sunset cruises nearby.
But unlike shelling out for a sail, watching the sunset from shore is free, and there’s plenty to entertain you while you wait. Enjoy street performers, food stalls and some of the best people-watching you’ll find.
Pro tip: If you prefer to sit while viewing the sunset, head to the Sunset Deck at the Margaritaville Resort and Marina. There you can avoid craning over a crowd to see the spectacle — and celebrate the day’s end with a house-made margarita, tiki cocktails or a mojito.
Leave the Car Behind
Driving the Overseas Highway to Key West is a memorable road trip everyone should try once. But once you arrive, there’s little reason to keep driving. If you fly into Key West International Airport, you’ll need a cab or rideshare to reach your lodging, but after that you can largely rely on three ways to travel: walking, biking or public transit.
At just a few square miles, Old Town Key West is perfectly safe and walkable at most hours. You can easily stroll up Duval Street and between Mallory Square and the marina.
Beaches and certain attractions, like the Hemingway House and the Key West Lighthouse Museum, are more convenient to reach by bike than on foot. Luckily, many hotels provide complimentary bike use to guests, and there are plenty of bike rental shops as well. Typical cruiser bike rentals run about $10 to $15 per day.
By bicycle you can reach nearly anywhere in Key West — old town, new town, and beyond. When we recently stayed at The Perry Hotel on nearby Stock Island, it was a pleasant, breezy ride (mostly on dedicated bike paths) from our resort, across a few bridges, through new town and into Old Town — under 30 minutes each way.
Pro Tip: The Duval Loop buses, introduced in 2017, make 16 stops around downtown Key West and the historic seaport. The free service from Car Free Key West runs from 6 a.m. to midnight and reaches as far as the Southernmost Point marker and South Beach.
Stretch Your Entertainment Budget on Both Land and Sea
For $49, The Key West Attractions Vacation Pass from the Key West Attractions Association is a solid value if you plan to take a sailing trip, hop a trolley, ride the Conch Train, visit museums or the aquarium, or even enjoy a few drinks.
The pass provides two-for-one deals on excursion tickets and beverages, along with discounts on activities and attractions that can quickly offset the initial cost.
Pro Tip: Planning a snorkel trip, jet-ski rental or parasailing? Combine them with Fury Water Adventures’ Ultimate Adventure. At $125 for adults and $90 for kids, it’s cheaper than purchasing each activity separately, and the six-hour catamaran outing includes time on a floating inflatable waterpark in the Key West Bight, plus two meals and drinks.
Complimentary rides, free entertainment, plus two-for-one drinks and cruises — those are the real “keys” to a budget-conscious Key West getaway!
Sam Fletcher is a travel journalist who covers coastal destinations, the Caribbean and beach escapes worldwide. He contributes to AFAR, Coastal Living, TripSavvy.com, Wedding Style, Business Travel and numerous other outlets.
