I remember the first time I went to Key West, back in 2001. I'd done NO research; I figured that I would drive onto the island and everything that I wanted to see and do would be right there...as soon as I passed the city limits sight...in a nice neat little package. Nope. In fact, if you don't know what to expect in Key West, you WILL miss something or you WILL NOT fully enjoy your time there.
Where to Stay
It dawned on me this morning, as we drove off the island, that if I didn't know WHERE to stay in Key West, then our trip would have been completely different, and possibly, quite a headache.
You see, Key West is like many tourist towns. The closer you are to the attraction, the more it will cost you...or does it? Not necessarily. As you arrive on the island, there are plenty of brand name, chain, and discount hotels. However, those hotels are a few miles away from Duval Street, Mallory Square, the attractions, and the nicer beaches. While in many destinations, this might not be a problem, but in Key West, parking is a premium and "free" parking doesn't really exist. Basically, you can save some money or have the comfort of your chain hotel brands, but you're going to have to drive down to Duval Street everyday and night, and spend sometimes $10 just to park on a muddy lot on some back street. OR, you can take your chances and park in a residential spot and either have your car towed or rack up a nice $35 parking ticket.
Another potential tourist problem is that most non-Florida visitors expect ALL of Florida to be a beach. Even in Key West, where you're surrounded by water, the island is not one big beach. In fact, some hotels that look to be directly on the water really aren't, and what looks like a "beach" isn't. Most "beaches" in Key West aren't what many people think of when they think "beach." Waves are minimal at best; grass & sea weed are common; water clarity isn't always great. Don't get me wrong...beautiful beaches in the Keys do exist. You just have to know where to go. Staying directly on the water with a beautiful beach comes with a nice price tag.
Tip:
I've been going to the keys for years, so here's my suggestion. Stay down town. Stay within walking (3-4 blocks) of Duval Street. There are plenty of small hotels, resorts, bed & breakfasts, and private homes for rent. No, they aren't part of some massive chain, but that's what makes them so fantastic. The quaint, Key West-style bed & breakfast can be more personal, more romantic, more fun than any Best Western, Holiday Inn, Marriot, Sheraton-style hotel. Likewise, by staying within walking distance, you can ride your bike, rent a scooter, catch the trolley, or even just walk to all the restaurants, attractions, the beach, and the marina. We suggest trying a few of the following...BedandBreakfast.com, AirBnB, VRBO.com, Homeaway.com. We normally stay at the Blue Parrot Inn, but this last trip was a condo rented through 1800Atlantic in their "Old Town Properties" section.
Where to Drink
It's not advertised, but Key West is a walk & drink town. Once you're on Duval Street, you'll notice everyone walking around with adult beverages, and you'll be sure to want to join them. However, plan on spending some money doing so. A single frozen beverage from Fat Tuesday's will set you back at least $7. Margaritas at Margaritaville can be over $15, depending on the size. I'm by no means saying don't drink. I'm saying be smart about it.Tips:
1) Stop at Publix, Winn Dixie, or any number of liquor stores on your way into town and buy your own. Pack a plastic cup, water bottle, or sleeve of Solo cups, make your own beverage, and walk around town with your own.
2) Years ago, Millie's was the only place doing it and everyone realized how smart it was. Now, several stores offer bottles & cans of beer and other adult beverages. Many of them will even give you plastic cups. Millie's, at the end of Duval Street, heading toward Mallory Square sells everything from beer and wine to frozen key lime pie on a stick. They won't open your beer for you, but they'll point you to the bottle opener attached to a wooden post at the door. A beer at Millie's will set you back $3-4.
Where to Eat
Restaurants in Key West are by no means hard to find. However, not all restaurants are created equal. I have a theory that if a restaurant has to have people stand out on the corner passing out coupons or hawking their "specials," then they need the business. In turn, if a restaurant parking lot is full or locals recommend it, then it usually is going to be great, and they don't need to pass out coupons and freebies.
Tips:
1) Half Shell Raw Bar: This one epitomizes the fresh & local-everyone eats there-it gets packed at peak hours-rule. This one is also nothing fancy. It's an unassuming wooden building at the marina; it's open air, with basic wooden tables & picnic benches. However, the food is top notch. During lobster season, you can get several lobster specialties. Jeremy always eats the Lobster PoBoy--lobster is flattened and deep fried before being loaded down with cheese and cole slaw on fresh bread. As for me, I've eaten everything from a steamed lobster dinner to lobster blt to fried oysters. You really can't go wrong here.
2) El Siboney: This is an accidental discovery, and honestly, I think the locals are trying to
keep it a secret. We found it while riding bikes one day, and noticed that at 9am, the smell of Cuban pork roasting was so thick, I stopped my bike in the middle of the road. We asked a lady at our bed & breakfast, and she quickly recommended it as a local favorite. El Siboney is located on Catherine Street, several blocks off of Truman (US 1), and will be the freshest Cuban food you will ever eat. Oh, and make sure you're hungry when you go, because a single plate of roast pork, black beans, rice, and bread will feed a small army. Again, it's nothing fancy, but it's worth the hunt.
3) Croissants de France: This is an easy find. It's on Duval Street, and you really can't get fresher pastries anywhere in Key West. Croissants filled with everything from chocolate and raspberry to ham & swiss or spinach & feta. Gigantic beignets are filled with Nutella or key lime. The pastries are made fresh daily, and later in the afternoon, they discount the daily baked goods by 50%. My suggestion is to have breakfast there at least once. Treat yourself to something decadent.
4) Glazed Donuts: This one is a bit harder to find, but definitely not hidden. Located on Eaton street, just a few hundred feet off of Duval, they make donuts with fresh, local, and seasonal ingredients. It's a simple concept done right. They make donuts; they make them huge; they make them right. It's a no-brainer. If you're willing to have fresh croissants one morning, then you have to indulge with fresh donuts one morning.
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