No matter how many tips you read or how much planning you do, there is no way Key West will end up being a cheap vacation.
Hotels there are pricey; budget restaurants are hard to find.
But the reason Key West commands those prices is that it is a special one-of-kind city with layers of history going back hundreds of years, well-preserved architectural gems, a funky street life and more places to go and things to do than you’ll ever get to in a single visit.
Happily, it is possible to make Key West more affordable. The key strategies are:
• Go during the off-season, roughly June to November (September and November are the cheapest of all).
• Shop around for accommodations and consider compromising on amenities or location.
• Seek out affordable, casual restaurants.
• Take advantage of the many free and inexpensive things to do in Key West.
WHERE TO STAY
Even in the summer off-season, your first search for basic Key West motels will come up with rooms starting at $130 a night. I’ve tried several strategies to beat that price — some successful; some not.
What didn’t work: I used “name your own price” on Priceline twice in Key West. Both times I ended up in the eastern part of Key West, three miles from Old Town. There are eight or 10 hotels clustered on Roosevelt Boulevard at the entrance to the island. They share a shuttle service into Old Town, which helps with parking.
The problem here is that the location isn’t ideal and the price included unexpected add-on fees — a $10 “resort” fee at the run-down Lexington and a $19.81 parking fee at the very nice $140-a-night Marriott Key West Beachside Hotel.
I had better luck finding accommodations where I compromised on amenities. One of the great charms of Key West is the historic bed and breakfasts in Old Town. Many go for $200 to $300 a night. But there a few quality places where several bedrooms share a common bathroom, and the savings are great.
We stayed at the Key West Bed and Breakfast, 415 William St. (305-296-7274, www.keywestbandb.com), a turn-of-the-century house decorated with original art, vibrant color and serving a spectacular breakfast of fresh fruit and homemade blueberry coffee cake. Our second-story room was one of four sharing two bathrooms, which were kept impeccably clean. Off-season, these rooms go for $79 to $99. (We loved Mo’s room for $99.) Rooms with private bathrooms rent for $115 to $155 off-season — still a very good deal for Key West.
Similar rates are available at the Angelina Guest House, 302 Angela St. (305-294-4480, www.angelinaguesthouse.com), another old house full of character. Here, rooms with shared bath are $84 off-season with other rooms running $104 to $144. Another comparable option is the Curry House, 806 Fleming St., 305-294-6777, www.curryhousekeywest.com (not to be confused with the more expensive Curry Mansion). Shared-bath rooms are $99 and other rooms are $165 in the off-season.
You might also try the Blue Parrot Inn, 916 Elizabeth St. (305-296-0033, www.blueparrotinn.com). Its smallest rooms are tiny with double beds but start at $90 per person off-season and include private bathrooms.
The other alternative for a reasonably priced room is to stay in the Upper or Middle Keys and come to Key West for a day trip.
One favorite place nearby is Parmer’s Resort, 565 Little Torch Key. (305-872-2157, http://parmersresort.com). It’s 27 miles or 40 minutes outside Key West. During low season (September through mid-December), rooms start at $99. This is a 1950s-vintage Keys-style waterfront resort with pool, views and breakfast included.
Two other nearby choices: Sugarloaf Lodge (17001 Overseas Hwy., 305-745-3211, www.sugarloaflodge.net/Home.html) is 17 miles from Key West and offers waterfront rooms off-season starting at $120. Efficiencies at the Big Pine Key Fishing Lodge, 33000 Overseas Hwy. on Big Pine Key (305-872-2351), start at $109.
You can find summer rates lower in the motels of Marathon. These are an hour from Key West, but it’s a beautiful drive over the Seven Mile Bridge. We’ve stayed in some ordinary mom-and-pop motels in Marathon for $90 to $100 — the Blackfin Resort and Marina, 4650 Overseas Hwy., and the Kingsail, 7050 Overseas Hwy. These are not memorable; rather, they are just places to sleep while you fill your days with activities.
REASONABLY PRICED EATS
Key West is foodie heaven, with prices to match. Finding good buys in restaurants will take some planning: You may not stumble across these places when you get hungry unless you keep a map handy.
My best dining tip: Head to the historic Key West Seaport at happy hour. The boardwalk along the harbor is one of the best free activities in Key West. Folks are feeding tarpon from the docks, fishing charters are displaying their catches and all the colorful yachts and historic ships are on display, with flags snapping.
Many harbor restaurants have happy hours, but I can especially recommend Alonzo’s Oyster Bar, 700 Front St. All drinks and an extensive selection of appetizers are half-price from 5 to 6:30 p.m. and it’s easy to make a meal of it. We shared Alonzo’s sampler: four conch fritters, four Buffalo shrimp, four fish fingers and a pile of onion rings. That would be $17.30, but happy hour prices made it $8.65. We added two delicious sides of Granny Apple Cole Slaw (normally $2.10; now $1.05) and a beer and a glass of wine, and two dined for $22 including tax and tip. We sat outside overlooking the harbor in a setting that didn’t compromise on atmosphere.
Two other budget spots are nearby. Both are funky Key West and are legendary:
You can get reasonably priced diner fare at Harpoon Harry’s (832 Caroline St.; $9 to $11 for sandwiches; very popular for breakfast, which is served all day).
Right on Duval Street is a small treasure : the Conch Shack, (118 Duval St., 305-295-2494), a restaurant no more than 10 feet wide that accepts only cash and serves up fresh, reasonably priced fare. Three conch fritters are $4.50; a hamburger is $5. Seating is on stools at a counter.
You will find good options away from the main drag too. If you like wraps, sandwiches and salads, Lobo’s Mixed Grill, 5 Key Lime Square, is a good choice. A few steps off Duval in a tropical courtyard, Lobo’s is a friendly counter-service restaurant with dozens of menu items from $8 to $11.25.
As I asked Key West residents for suggestions for affordable dining, at least three people recommended the classic Cuban restaurant , El Siboney, 900 Catherine St. This is a traditional restaurant with table service and bargain prices — $10.75 for three different preparations of pork, $13.95 for grilled mahi or grouper, topping out at $19.95 for paella. It was all good and service was efficient.
It’s easy to be entertained by Key West: On your first visit, you might spend all day just wandering historic Old Town and joining the nightly street carnival at Mallory Square sunsets.
Here are several other free or cheap alternatives:
Bonnie Gross writes about her Florida travels for FloridaRambler.com