Ahhhh Key West, my second home. My family owns a week at Coconut Beach Resort there so I go every year. I have been a total of 7 times. Since the island is 1 mile wide you can assume I know my way around the island like the back of my hand. I fly out of Boston and currently there are no direct flights so I typically stop over in Tampa, Orlando, Fort Myers or Fort Lauderdale and get on a little hopper plane to make my way to the island. Just an FYI I have wicked bad flight anxiety and I survive if you get nervous about smaller planes. The airport in Key West is really tiny so not a ton of bigger planes fly in. Once you get there you can take a quick Uber to where you are staying. Also, if you want to try an alternate route I recommend flying into Fort Lauderdale renting a car and making the beautiful drive down the keys and 7 mile bridge.
Mallory Square at Sunset - I do this every single year and it never gets old. Key West celebrates the sunrise and sunset EVERY DAY, amazing right...my kinda place. I recommend getting to Mallory Square about an hour prior to the actual sunset. You will get to watch street performers and you HAVE to get the fresh made guacamole at the little stand that is there, it's too die for. Then prepare to watch an absolutely gorgeous sunset as long as weather permits, you may be able to see some massive cruise ships as well.
Mile 0 Sign - The very end of US1, gotta snap a picture here!
Southernmost Point Buoy - I would say this is probably the most photographed staple in Key West, if you are visiting you will have to take a picture with the big buoy.
Butterfly Museum - Talk a walk through to see hundreds of butterflies and colorful birds (including my favorite..flamingos).
Ghosts and Gravestone's Tour - My spooky self loves stuff like this so naturally this is one of my favorite things I have to share. I got to see Robert the Doll which is an infamous doll that so many horror flicks have been based off.
Aqua Drag Show - You best believe I go see my queens every year. I have been to many drag shows and nothing tops this one. In particular my favorite queen of all Faith Michaels. Make sure you go on the website and book a reservation in advance and you can check out the schedule of performers that way you don't miss out on seeing Faith. Be sure to bring cash to tip your gals!
Blue Heaven - If you are in Key West this is the most popular brunch spot that you can't miss. It's outdoor seating so make sure to dress accordingly based on the weather. I recommend getting there when they open so you don't have to wait in a line. Great Bloody Mary's and Mimosas. I get the Rooster special but their most popular item on the menu is the Key Lime Lobster Eggs Benedict.
The Raw Machine - If you didn't already know (which I'm sure you did) I am a vintage camper fanatic. The elite of the elitist is the Airstream, something I can only dream of someday owning. When I walked by this Food Truck style Airstream I stopped dead in my tracks. I had to get something from it. It has some wonderful healthy options, I got a acai bowl, if I'm being honest with you it wasn't anything special but the smoothie was great, super fresh and delish. I recommend going to check it out, it's really cool and you can grab a nice fresh smoothie while you are there.
Casa Marina - I like to go here when I get off the plane, you can take in the gorgeous views of the blue water, palm trees and island vibes. My favorite thing they have is their Key Lime Coladas...omg I want one right now. I usually get some chips and guacamole to snack on as well.
Margaritaville - Always have to visit Jimmy Buffett's stomping grounds. This past year I missed a surprise performance by him by literally 12 hours, I cried. Seeing him do a surprise show here is GOALS, why did I have to leave that morning. Maybe one year I'll get lucky enough, until then I'll keep on enjoying the snacks, drinks and live music.
El Siboney - Great Cuban food can be found here but I come for the sangria, it's my fave sangria of all time. I order a pitcher to go and drink it out by the pool at our resort.
Salute on the Beach - The name says it all, literally on the beach. What's better than amazing food on the beach? Not much if you ask me. The Fettucine Alfredo, house-made pasta with cream, italian cheese, peas & prosciutto is my personal favorite, YUM. My mom's favorite is the Sautéed Yellowtail Snapper with lemon cream sauce and spinach, I've tried a few bites of this myself and it is quite delish if you like seafood. Oh by the way, BEST KEY LIME PIE EVER, do not skip desert here even if you eat every single bite of your meal.
Better Than Sex - Make sure to make reservations beforehand, this place is very small and intimate and is very popular. If you have a reservation you won't have to worry. They serve wine and desert. I order a bottle of wine to enjoy and if you don't finish it you can take it to go. Love the Pinot Noir with the chocolate rimmed glass...WOW. I have also tried a bunch of different deserts and they all have been great, last time I was there I had a cheesecake and it was to die for.
Fat Tuesday's - Every night of going out on the town should start here. Or maybe just for a mid-day pick me up. I have brought every single one of my friends here and this always ends up being one of their favorite places. They have a straight up line up of smoothie style drinks in machines ready to go. You can get one flavor or mix some together, always be sure to add the extra floater of booze!
Rick's - I love this place because it has a huge outdoor deck area to hang at, they also have an awesome dance floor. Sometimes they have beer pong table going which is a bunch of fun as well.
Sloppy Joe's - Ahhhh the place where you go to close down the town and dance your heart away. I seriously cut up a rug here after a fun night of bar hopping to close out the night. Another one of my friends favorites when I bring them here. SO FUN, love you Sloppy Joe's.
The Garden of Eden - I debated on including this but how could I not..YOU'RE IN KEY WEST PEOPLE. Key West is one of the most accepting, laid back places I have ever been. I LOVE it. So this bar is on the roof of a three story building and clothing is ...optional. You can go up to the roof and observe without participating, it's usually a quick in and out but the reactions of taking people is priceless.
Mr Z's - Late night pizZA, this place is my JAM. I will shamelessly admit I went here 3 times on my last trip for late night pizza. It's seriously such good pizza and even better after a few drinks before you lay your head down to sleep. I found this place thanks to a Key West local. Oh my god I miss it.
Happy Hour the best hour:
Tiki House - Honestly there are so many amazing happy hours in Key West if I listed them all I would be here for days but this is a favorite of mine that I always like to hit. Buy One Get One Zombie drinks. The way they present their drinks is awesome, a little bit of fire, 151, cinnamon and bam it sparks, how cool. They have some other awesome drinks on their specials as well.
Parasailing - I did this most recently and it was so cool, a little scary but it was so worth it. I went through Sunset Watersports and they did a great job, I was lucky enough to be the only group out there so we go to soak up every minute of it like it was private excursion. We bought the photo package and it was worth it for some photos I'll have forever.
Sailing - I actually won this excursion one year. It was a sail on the Danger Charter and a kayaking tour. I really liked it, it was super windy so it was cold riding back after swimming but it was a really cool experience since I had never been sailing before.
Beaches and Pools:
If beaches are your top priority Key West may not be for you. It is not known for it's white sandy beaches...because they aren't your typical white sandy beach. Expect rocks and coral and crushed shells... at times seaweed. I'm fortunate where I stay because we have our own private beach but if you are looking for a public beach I suggest either Higgs Beach or Smathers Beach.
If you are looking to have a good time and swim in a pool I recommend spending a day at Dante's Pool and Bar. Weekends are the busiest, they have a DJ and everything. If you are looking for it to be a bit less crowded I suggest going during the week, they have really good Bloody Mary's by the way!