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Any trip to Key West should have some plans about how what you'll do, when you'll get there and how you'll arrive. Plans are a necessary evil. Wether you are flying direct or driving you should include consider visits along the way to experience some of Incredible fishing and pristine waters of the Florida Keys that abounds with a myriad of tropical fish. There are literally tens of thousands of square miles of water that is from 3in to 20ft deep surrounding the Florida Keys.
Then there's the sights and sounds of Key West, Duval St. The historic fort and old lighthouse as well as many other touristy places that are abundant in Key West. The vibe very much reminds me of New Orleans. A total party atmosphere everywhere.
If its your first visit, I would recommend at least five days. Otherwise three or four days is enough. Christmas is very nice there as well. Prices always seem high to me, but that might be just me.
Going down from Miami on US# 1 there are plenty of places for dining. In Islamorada, Morada Bay is a good place with an outdoor dining area in the sand just off the water. They also host events. Literally dozens of possibilities. It's all up to you.
Another stop could be Robbie's Marina where you can take a few moments to munch on some truly local fare at the Hungry Tarpon. Also there at Robbies for your pleasure are jet ski and sail boat rentals.
Probably the most amazing sight at Robbies are the tarpon. After you pay a small fee and get a bucket of bait you can hand feed the ginormous tarpon that hang out in the shade around the dock. They take on a mob like mentality and will chase a dead minnow like a pack of wild animals.
For the best experience ask a travel advisor for help or do your own research. The Florida Keys and Key West site is an excellent resource. A local paper, Keys News provides valuable up to date news about events and local happenings.
My first visit to Key West began with myself, my brother, Niles and his son Nick gathering in Fort Lauderdale. This was an auspicious occasion with Nick just graduating. We picked up our rental car at FLL and began our road trip down thru Homestead and then hopping the keys one at a time as far south as you can go. It's a solid 4hr drive with no stops. For those who want to get there quick there are flights direct into Key West (EYW).
Seriously though, the overseas highway is a great way to relax and unwind. An easy drive across miles and miles of blue water and bridges. Just watch the speed limits and your departure flights on the way out to be sure you have adequate time for driving back to civilization. From personal experience we have left early and taken another night in Fort Lauderdale so we didn't have to rush that return drive.
We have since returned to Key West a number of times and had lodgings at several different places. But our preferences are to be near sunset pier and old town. One of the nice things about staying near the old town area of Key West is that everything is within walking distance.
We drove from Miami a few times as well as flew into the tiny airport. As for lodging Courtneys Place is centrally located, has rooms, cabins and even a few houses complete with kitchens. Great concierge service as well. It is only a couple of blocks off Duval. Once we asked our hostess Nikki to find us a half a bushel of oysters while we were away jet skiing. Nikki was an excellent host and we found our oysters iced down just as we had requested. Later that evening we fired up the grill for several rounds of the succulent Drago Style Char Grilled Oysters. She was more than happy to oblige and was able to obtain some of Apalachicola's finest oysters.
Southern Most Beach Resort is another good choice for a few nights in a hotel. Great location at the end of Duval, very near the southernmost point of the continental US. They also have a private beach and cafe/bar right there on the beach. They have beachfront and interior rooms. There's also a French Pastry shop on Duval that's just a block or so. Unbelievable, delicious quiche but more about LaGrignote later.
Parrot Key is on the Western side but isn't the best of locations. It's priced reasonably and has decent rooms. It is surrounded by lush gardens and sandy areas for sunning or sitting in the shade but water access is limited to a pier. The pools in the interior areas of the hotel are nice and overall the facility is well kept.
Kimpton has a number of properties there. We stayed at Kimpton Winslows Bungalos and found it to have a good location and to be very well managed as well as being superbly landscaped. The rooms are small but very nicely appointed. Many have balconies or patios. The bar inside the hotel property was great as well as being adjacent to one of the pools. All the staff was helpful, friendly and knowledgeable.
All in all there are hundreds of places to find lodging. B&B's, rentals, hotels, motels and resorts as well.
Duval Street is the main thoroughfare in the middle of Key West old town. This is where a large number of restaurants, bars and other shops are located. All time favorites are Captain Tony's, Sloppy Joe's and Rick's which is a kind of and entertainment complex not all for children. Which by the way, I would not recommend taking children to the Duval St area.
One of the nice things about staying near the old town area of Key West is that everything is within walking distance. Restaurants, bars, shopping, literally anything and everything and sometimes nothing you would want.
Hemingways Home and Museum is open 9-5 if youre a fan. We have always wanted to go but for some reason we've never been. Just know admission is cash only. There's the home and museum along with plenty of cats.
Fort Zachary Taylor Historic State Park
This is a great place to spend the day. In fact its one of the public few beaches on Key West. Higgs Beach and the adjacent county beach are ok but in my opinion Fort Zachary has it all with shade and sun. Even a snack bar which is pretty good with drinks. The line gets really long at times but they do have a decent selection of snacks and drinks.
The fort is a good destination as well. Similar to other military sites it was originally constructed around the Civil war era then updated around WW2.
Fort Jefferson
There are many sights to see in the Florida Keys but for me personally, my favorite is Fort Jefferson in the Dry Tortugas National Park. The "dry" name might seem odd but it refers to the lack of fresh water. Plenty of salt water, but NO fresh water. It is a fabulous area about 70 miles west of Key West and can be reached by boat, ferry or plane. There are restrictions for private boats so be sure and check before making that trip. Our favorite is the Yankee Freedom Ferry that leaves daily. I recall it being a good two hour ride from departure. It has a bar (on return trip only) and souvenirs, maybe some snacks but no real food.
The waters are simply amazing as you pull up to the Fort. Even more amazing is how people survived here for nearly thirty years as the Fort was built. The Dry Tortugas are named so because there is NO fresh water. The five acre masonry brick fort is the largest in the Northern Hemisphere. Construction began in 1830 on the massive structure intended to protect the entrance to the Gulf of Mexico.
Fort Jefferson is simply fascinating from a historical perspective as well as an engineering point of view. Construction was halted due to the invention of "rifling" in cannons. Old cannon balls would bounce off the thick brick walls but not so much rifled artillery shells. At any rate it served a number of different purposes since its completion or should I say non-completion. I know for a fact there's great snorkeling and I believe camping as well. The camping though is subject to a myriad of regulations and requirements. See the site here. It's an all day experience. We were hungry, tired and sunburned when we returned. We had a great time!
During any day it's entirely possible to charter a flat fishing trip. Keep in mind the number of people and size of boat. Generally on flat fishing there may limited room for fishing. There are numerous captains for hire. Check with your travel advisor or hotel concierge.
We chartered a backwoods fishing trip with Almost There Charter Service. The water was calm, the weather was HOT, and needless to say the only thing flowing more than sunscreen was ice cold beer! The two highlights of the fishing trip were Nick landing a 6ft nurse shark in the rain and the incredible beauty of the flats. We took a dip in the azure waters and tasted, if only for a few brief moments the sweet saltiness of how the life might be in the Conch Republic. We only caught one fish that day so maybe the fishing was just bad that day.
For dinner, upon recommendation of my good friend (and Conch wannabe) Charlie Starr, we headed down to the harbor for dinner at A&B Lobster House. Its location overlooks hundreds of sailing vessels, charter boats and yachts providing a second story panoramic view right on the water. The drinks and entrees are great as well!
Another evening we stopped off for a nightcap at the Rum Barrell which has since closed. My brother made the choice of 23 year old rum accompanied by several rounds of billiards on the rooftop. We finished the evening with some late night sight seeing as well.
Durty Harrys (Ricks) is a huge place with something for most everyone. You can easily spend time and $ enjoying several drinks as well as admiring the natural beauty of the local and not so local scenery.
Tuesday was another hot day and being the only day we had no real plans we decided to rent jet skis. There was discussion of taking the jet skis somewhere and snorkeling. I went and spoke to our hostess Nikki and she recommended the Island Tour Charters out of Hurricane Hole Marina. An great concept where a guide leads a pack of wild and crazy touristas on jet skis all the way around Key West. The guide leads the way and stops frequently to check on everyone and give historical perspective as well as make humerous remarks. There's plenty of "play time" for gunning round on the skis and its well worth the $120 fare and lasts about 2 1/2 hours. Complimentary draft beer is served after the ride. The hot wings are optional.
Duval Street is the main thoroughfare in the middle of the old town. This is where a majority of restaurants, bars and other shops are located. All time favorites are Hogs Breath, Captain Tony's, Sloppy Joe's and Rick's which is a complex of entertainment, not all for children. Which, by the way, just me but I would not recommend taking children to the Duval St area.
Restaurants, bars, shopping, literally anything and everything and sometimes nothing you would want.
Hemingways Home and Museum is open 9-5 if youre a fan. We have always wanted to go but for some reason we've never been. Just know admission is cash only.
Nine One Five
One evening I recall was very entertaining starting out with a stroll down Duval St and a fabulous tapas dinner on the upstairs veranda at 9 one 5 Restaurant and Bar. We had tuna ceviche as well as a number of dishes it was all an artistic as well as a culinary delight. The whole fried snapper is fabulous. Recommend getting reservations and balcony seating.
Hogfish
We dined here several times. Always good. Its a little off the beaten path located in Safe Harbor up on Stock Island. It has a good view but the main attraction is the whole fried Hogfish. Crispy goodness and so delicious! Wide variety of other selections too, laid back atmosphere, on a harbor. They stay busy unless you're there off season or off time. I would call especially if its a weekend. One of our favorite places.
Martins
We had dinner here on our first night in town. We first sat at the bar and had a fabulous blue martini. The olives were hand stuffed with delicious soft blue cheese. They were also skating. We were quickly seated on the back patio which is lushly decorated with tropical greenery. For starters we had the scallops Florentine and the grilled lamb chops both were done well and tasty. For our entrée we shared the lamb osso bucco. This dish is plenty large for two people to share. The service was a little slow but the staff was knowledgeable and friendly. Recommend reservations.
La Grignote
We stopped in for breakfast and found the staff friendly and knowledgeable. The sundried tomato and garlic quiche was unbelievably rich and moist with a thin layer of goat cheese and big chunks of roasted garlic. The quiche loraine and other pastries are amazing as well. Ive only been to a couple of other "french" bakeries on the island and, well all I can say is don't miss out on this place. The fabulous quiche is literally over 2 in thick!
Louie's Backyard
Great location right on the water. I like going for lunch. We've been at least once and enjoyed the dining and surroundings as well as the water being right there. Definitely make reservations well in advance especially if you are going for a sunset here. Food is good and a bit pricey. The outside dining is the best. Drinks are good, staff is friendly and the Chefs are creative.
A&B Lobster House
Great service, good food and fantastic location. This place checks all the boxes. Recommend balcony seating at sunset. Make your reservations accordingly.
More than one morning of any trip must start with a breakfast at Blue Heaven. It is the place referred to in the Jimmy Buffett song bearing the same name. They have an incredibly eclectic menu and as everywhere else in Key West they begin serving anything you want for breakfast. I recommend the Mimosas and Lobster Benedict. Delicious!
Blue Heaven is also famous for having a bakery providing fresh baked breads, rolls and supporting the cuisine of the restaurant.
Wandering throughout the restaurant, you see the usual key west locals: cats, chickens, roosters as well as several baby chicks. There is also a gift shop with lots of nice t-shirts and trinkets. The outdoor shower was a favorite stating "Showers $1 - To watch $2".
They offer a brunch on Sundays but go early as it is very popular. Did I mention it is a must dining experience here in Key West?
Latitudes
This is our absolute favorite restaurant in Key West. Don't go here looking for budget dining. Do go here for the best atmosphere, service and food It's a magical place that you should spend with a loved one. Romantic absolutely beyond, way beyond. Make this a special occasion and don't miss this opportunity. Excellent 5 stars! Go just before sunset and plan on making your reservation years in advance, literally.
View from our table