Traveling to Key West? These Tips Will Save You Big on Your Trip

People watch the sunset in The Florida Keys.
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Spending a few days in Key West can be the perfect antidote for life’s little stresses; here’s how to live the life of a “Conch” for a few days without having to cope with a big credit card bill when you get back to the real world.

Stay Smart to Save on Lodging

Old Town Key West has a collection of lovely but often pricy bed-and-breakfasts and small inns.

If your budget calls for bunking-up rather than a romantic getaway, consider staying at the NYAH resort. Here, the rooms can be converted from double occupancy to accommodating a half-dozen guests — without costing more.

And at NYAH, you’ll still get the pleasure of staying in a classic Key West courtyard-style hotel with multiple swimming pools and a buffet breakfast included.

If you’re feeling romantic and adventurous, stay via Airbnb on a boat or houseboat — doing so is actually a local tradition among Key West’s year-round residents. There are several marinas on Key West and Stock Island with floating accommodations for rent, both docked and moored.

Collect and Use the Free Drink Coupons

Two cups of beer are left in the sand at a beach.
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Key West is the kind of town where your bar tab can easily exceed your expenses for food and entertainment, but you can keep costs under control by collecting and using the ubiquitous 2-for-1 drink coupons that bars and restaurants around town offer.

Coupons can be found in display racks in hotels or other tourist information locations, or you can ask the concierge or front-desk staff at your hotel for them.

My wife and I saved at least $50 on our recent Key West trip by using drink coupons — that was especially sweet because the coupons aren’t just offered by hole-in-the-wall bars. We scored coupons for some of the best and most popular watering holes in town, like Irish Kevin’s, Conch Republic Seafood, and the Island Dogs Bar. These places are all located right in the middle of the Old Town action. Each offers live music, so you’ll have some entertainment to go with your half-priced cocktails.

Pro tip: Drink coupons typically apply to domestic drafts or well drinks, but if you want to drink something a little fancier, most bars will simply discount your BOGO drink the cost of a well drink.

Enjoy the Best Free Show in Key West, Every Night

People crowd around an entertainer to watch him perform at Mallory Square in Key West, Florida.
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What’s the No. 1 attraction in Key West? It’s not a bar, and it’s not a museum — it’s the nightly sunset celebration in Mallory Square.

Every evening, thousands of visitors line the edge of the square to watch the sun settle under the horizon, flanked by countless boats of every shape and size taking sunset sails.

But unlike going for a sail, seeing the sunset from the shore costs you nothing, and there’s plenty to amuse you while you wait for the ball to drop. Enjoy street performers, food vendors and, of course, some of the most amazing people-watching anywhere.

Pro tip: If you want to sit rather than stand to watch the sunset, head upstairs to the Sunset Deck at the Margaritaville Resort and Marina. There, you won’t have to peer over the heads of strangers to get an unimpeded view of nature’s best light show — and you can toast the day’s end with a scratch-made margarita, tiki drinks or a mojito.

Leave Your Car at Home

People walk around Mallory Square in Key West, Florida.

Driving the Overseas Highway to Key West is a fun adventure that everyone should do at least once. But once you get into town there’s really no need to drive anywhere. If you fly into Key West International Airport, you’ll need a cab or Uber to get to your hotel, but after that you really can rely on any of three options to get around: your feet, a bike or public transportation.

At just a few square miles in size, Old Town Key West is eminently safe and walkable at almost any time of day. You can easily make your way up Duval Street and between Mallory Square and the marina.

The beaches and some attractions, such as the Hemingway House and the Key West Lighthouse Museum, are better reached by bike than on foot. Fortunately many resorts offer guests free use of bikes during their stay, and there are plenty of bike-rental shops, too. Typical cruiser bike rentals can be had for $10 to $15 per day.

On a bike, you can get almost anywhere in Key West — old town and new — or beyond. In fact, when we recently stayed at The Perry Hotel on neighboring Stock Island, it was a fun and breezy ride (mostly on marked bike paths) from our resort, over a couple of bridges, through new town and into Old Town — under a half-hour each way.

Pro Tip: The new Duval Loop buses, which went into service in 2017, make 16 stops all around downtown Key West and the city’s historic seaport. The free bus service from Car Free Key West operates from 6 a.m. to midnight and runs all the way to the Southernmost Point marker and South Beach.

Maximize Your Entertainment Dollar on Land and Sea

Money hidden in the sand on a beach in St. Petersburg, Florida.
Carmen Mandato/ The Penny Hoarder

For $49, The Key West Attractions Vacation Pass from the Key West Attractions Association is a good deal if you’re planning to take a sail excursion, ride a trolley,  take a Conch Train tour, visit a museum or the aquarium, or, well, drink.

The pass gives you two-for-one deals on excursions tickets and drinks, as well as discounts on activities and attractions that will make up the upfront cost in no time.

Pro Tip: Thinking of doing a snorkel trip, renting jet skis or going parasailing? Do all three for one price with Fury Water Adventures’ Ultimate Adventure outing. At $125 for adults and $90 for kids, it’s cheaper than paying for all these activities separately, and the six-hour catamaran cruise includes playtime on a floating inflatable water park in the middle of the Key West Bight, plus two meals and drinks.

Free rides, free fun, and two-for-one drinks and cruises — those are the “keys” to a budget-friendly trip to Key West!

Bob Curley is a travel writer specializing in New England, the Caribbean and beach destinations around the world. He writes for AFAR, Coastal Living,, Wedding Style, Business Travel and many other publications.