Now that we've owned Bougainvillea Villa for 3 whole entire years (!), we've really started to feel like we're learning our way around and we feel a little more like a local and less like a tourist every time we stay. We make it a rule to try at least one new restaurant every visit-which really isn't that hard. We like to ask around-that's the best way to find out the inside scoop (see the blog on Fantasy Fest for a prime example). Here are a few things we've learned over the past three years:
First: read the local paper as often as you can! The Shell station at the entrance to our neighborhood sells it from a box and I try to walk the dog up there every day-exercise and information! The paper usually has a Dining Out page and, particularly during the off-season, many restaurants have some great specials. We would never have thought to try the restaurant at The Pier House hotel, but they had a 3 course dinner special for $20 and it was delicious! They've cut it back to just a 2 course special we've noticed. Also check out the inside of the front page. It's very entertaining! There's a column that prints phone messages to the paper ON ANY TOPIC! This is just a great way to get a feel for what it's like to actually live in Key West. Occasionally, whoever writes the weather forecast is in humorous mood and the forecast can actually make me laugh out loud. There's the section on "Today in Key's History" which always contains the diary entry of a resident from the late 1800's. I can't remember his name but his diary entries contain lots of detail. Finally, at the bottom of the page, the paper lists the cruise ships that are in port and the time of their arrival or departure. We have never really been impacted by the cruise ship crowds but it would be good to know that your waterfront view from the Margaritaville resort restaurant is going to be blocked because there are 3 ships in port that day.
Some Happy Hour tips we've learned: The Tavern N' Town at the Marriott Beachside is where the locals go for happy hour. The place is packed! Happy Hour is from 5-7 and they offer 2 for 1 drinks and small plates at the bar. We are fortunate to have an outstanding real estate agent, who stuck with us for years before we actually took the leap and bought our house. She has subsequently become a good friend and I love to go to Tavern N' Town with her! She always knows a number of people there; wish I could remember everyone she's introduced me to. Go early or you won't get a seat. It's all inside and it's quite dark in there and if you're a little cold-natured (like I am) you'll want to take a sweater as they keep the AC set pretty low. It's hard to imagine going somewhere inside when it's so nice outside but the drink prices are hard to beat and your chances of striking up a conversation with a local with some inside information to share is pretty high. Our other favorite Happy Hour place is the Hurricane Hole, which is on the left just before you cross the Cow Key Channel bridge into town. In fact, the Hurricane Hole is just our happy place, period. It's the first place we go when we get in to town. They have the BEST painkillers on the island. No happy hour pricing on them but always worth full price. Their happy hour is from 4:30-7:00 and includes half price wine, beer and well drinks as well as special pricing on appetizers. If you're headed for downtown, it's hard to beat the Half-Shell happy hour for food and drink specials (again, wine, beer and well-drinks). We love to get a seat on the water but it can get hot in the sun in those spots in the summer. If you order a pitcher of beer it comes with a gallon size zip-lock bag of ice in it to keep it cold. If "umbrella drinks" are what you want, you can't beat Dante's. An amazing rum-filled fruity drink is $3.75 Monday-Thursday from 4-8. Plus, if you order a drink or food, you can swim in their pool. This is especially helpful if you've decided to ride a bike downtown!
We've found Patriot's Country in Key West too. Island Dogs bar and grill on Front Street is it if you're a Pats fan. If there's a Patriot's game on I'd say 98% of the patrons are Pats fans or else they just stumbled in by accident. Go a couple of hours before the game starts if you can or you'll have a hard time getting a place by a TV. You can sit out on the sidewalk and still hear what's going on if you don't have to watch every minute.
We have a boat so we haven't gone on any of the tour boats. If you bring a boat there are some great snorkeling spots that are easy to reach-in particular one out off Fort Zachary by the tower. The tour boats go there so the best time to go is in between their tours (between 11-1). If you want to go snorkeling just ask us how to get to the good spots by boat; my husband knows the way! We do highly recommend the sea plane trip to the Dry Tortugas. The service was great, you can take your own small cooler and snorkel gear or get some from the company and the views from the air are spectacular. There is no AC on the planes though so be prepared to be a little warm until take-off. It was amazing to me to land and then take off from the water.
One final piece of insider information: Michael's Restaurant has an amazing fondue! You just won't find it on the menu unless you sit at the bar! By all means go one night and have an outstanding dinner but be sure to make a return trip, grab some seats at the bar and ask for the fondue menu. If you like fondue, this is the best I've ever had.