UPDATE: NEW TRAVEL GUIDE WRITTEN SUMMER 2021
Since I now live in Key West this is the most up to date & details the current openings,
etc. with the pandemic. Thanks!
Last month I took a 5 day vacation to Key West with my blogger bestie, Kristyn. We were both itching to get out of DC and take a vacation from work and well, just life in general. There's no better way to disconnect and rejuvenate by physically removing yourself from everything!
I had already taken 3 days off of work because I was supposed to go on a trip with my boyfriend. So when that fell through K instantly jumped on my "crazy train" to take a trip somewhere (it was literally 3 weeks before) and we got to planning. Key West came to mind instantly because I had an insane amount of fun there during my senior year spring break! Luckily, K had never been there. I think we decided pretty instantaneously that the Keys were going to be our girl's weekend destination! The rest is history... just kidding we talked and planned every single day (K was my hero because she called and made reservations for all of our activities #lifesaver). I'm going to give y'all a run down of all the details: how to get there, where to stay, where to eat/drink, what to do and see, and what to wear! I'd also love to know if you have more suggestions I should add to my list!
When I went to Key West in college I chose to fly with my best friends. I wish I could remember how much my flight cost but it was obviously reasonable since I paid for it on a college student budget. We flew out of BWI, transferred in Miami and got on a little puddle jumper that landed at the teeny tiny airport in Key West. Their airport is basically a one terminal, one carousel, get off the plane with a ladder type place. Very low-key and no-fuss. It was a piece of cake when you plan months in advance and get those details figured out...
However, K and I took spontaneity to a new level. We rented a car!! This was a first for both of us... Since we booked our flights so last minute ticket prices going to KW were outrageous. I'm talking a new fancy handbag crazy. (Being flexible with your departure dates will allow you to get a better deal. We left early Thursday morning and returned late Monday night so we could get a roundtrip flight to Miami under $200.) Granted, renting a car for 5 days wasn't cheap either but when we compared the prices we saved hundreds. We had a great time soaking in the blue water on our drive from Miami to KW and really got to see all of the Keys and the way the islands curve down into the ocean. Plus, we drove a bright yellow Mustang convertible. Oh yeah, we were sitting pretty! (Especially with my suitcase bouncing in the backseat because bloggers don't know how to pack and K's suitcase took up the whole trunk - mine would've too haha.)
Driving bonus: We got to stop and eat lunch in Islamorada - basically a halfway point. You MUST get lunch at Morada Bay Beach Cafe. My coworker recommended it to me and I was pretty excited when I looked it up. It was so adorable and the atmosphere really got us excited for the remainder of the trip! The colorful chairs and friendly staff (plus cat) put us in a great mood even though we had been up since 3am!
We knew we had to have one thing at our hotel when we were searching... a POOL!! There's nothing better than coming home from a long, hot, sweaty day and being able to jump in the pool to cool off. (Key West is also a deep-water port which is great for boats but means that all of the beaches are man-made.) As we did our research we found the Inn at Key West (UPDATE: This hotel is now known as the Havana Cabana Hotel)! They have the biggest pool in Key West and boy did it not disappoint!! We were greeted with complimentary rum punches and instantly felt at home underneath the palm trees... with Iguanas running around! It was really neat talking to the locals and hearing that they all go to our hotel to hang out at the pool. It made us feel like we weren't just being "touristy" by hanging at the pool!
Key West is extremely laid back and relaxed. You're not going to find a lot of hotels whose interiors rival their outdoor scene (and if you did you'll be paying more than you should). My suggestion is to find a hotel with a comfortable room but most importantly a great outdoors area - that's why we loved the Inn at Key West so much! I mean how much time do you actually want to be spending in your hotel?? You go to Key West to experience Duval Street and all of the activities the island has to offer!! Because we were about 2 miles from the main going out scene we did have to grab a taxi each night to go out but the front desk made that a piece of cake. It was a bit of a bummer at first because part of the joy of KW is walking everywhere. If you choose to stay at a hotel closer to the night action I highly recommend taking a couple hours out of your day to visit this pool - the food, drinks, staff, and atmosphere is lively and worth the taxi ride! Plus... you can feed the iguanas like I did haha totally a highlight!
Money Saving Tip: If you really want to be on a budget (cough, cough, college kids) you can find a motel right off Duval Street. I stayed at the Blue Marlin Motel in college and it served it's purpose :) it's not the nicest digs but it was cheap, easy and there was enough room for multiple girls to get ready with hair products, makeup, shoes, etc. Plus there's a small pool (that they just redid, actually). There are also great airbnb options!
Southernmost Beach Cafe // a favorite off-Duval spot with a public beach. It's right by the Southernmost point and has great views of the water while you eat. I recommend trying the Conch fritters and their mojitos (don't forget how close to Cuba it is!)
Latitudes at Sunset Key // a quick ferry ride to the small island of Sunset Key. This is where we hung out at the beach for a day and swam in the water while taking it easy. Their fish tacos are the best I've ever had. I'm still dreaming about how perfectly crispy they were.
Mangoes // a nice sit-down dinner with views of Duval under umbrellas. Their orange-glazed salmon was incredible.
Better Than Sex // this restaurant comes with a rated R warning label. We went with two new friends we made and had the most hilarious time. The restaurant is very moody and dark and they only serve dessert with sexual names. All of the wines are dipped in chocolate - it's quite the experience! Just go... and make jokes the entire time. Mr. Grey will see you now...
Wine-O Bar // take a break from the heat on Duval street and pop into the historic La Concha Hotel. Their new wine bar is fantastic! K and I enjoyed appetizers and two wine flights. It was nice to sit inside away from the humidity for a change!
Sunset Pier // a great location if you want a view of the sunset while you enjoy a cocktail and bite to eat. This can be a bit of a tourist trap so it's not known for it's food but the view was really great. I loved all of their strung up lights and bright colors.
Key Lime Pie // just get it anywhere! It's amazing and the island is known for the freshness :)
Duval Street // need I say more? There's no open container law in Key West so you can take your drink with you and walk around (as long as it isn't glass). Most bars will even let you take a drink in from another bar... perfect if you haven't finished your Grain Train slushy from Flying Monkey! Some of my personal favorites:
-Irish Kevin's (top of the list - best entertainment and music! The crowd gets involved and you feel like it's a giant karaoke scene)
-Sloppy Joe's (a Key West classic!)
-Rick's (above Durty Harry's)
-Bull & Whistle Bar
-Durty Harry's (great live music - get the plastic bucket drinks!)
-Fat Tuesday's (frozen alcoholic slashes my personal fave is the Bahama Mama)
-Fogarty's / Flying Monkey (during spring break this is a dance floor)
-Garden of Eden (NOT for the faint of heart hehe)
My best vacation advice: there's no point in making reservations unless you want to go to a nice sit-down restaurant (in which case get a reservation). Some of the best food I've had in the Keys is by walking around, talking to locals, and discovering really neat hole in the wall places. Part of being on vacation is not having to plan what you're going to eat... if you decide you want pizza one night, then get it! If you want tuna or seafood the next, search for it! Everything is very chill so if you have to wait an hour to get a table (highly unlikely) - go grab a cocktail and explore! Make sure you hop around to different bars as well. There are so many people to see and meet with unique stories!
Danger Charters Wind & Wine Sunset Sail // this is at the TOP of my list for things you should do!! Wine, a sailboat, apps, and a sunset?? I had the most incredible time sitting on the boat with K talking and admiring the gorgeous water. All while being served wine tastings and appetizers? Heaven. We met two awesome new friends on this sail too - one of them loved it so much that he went back another night! (I wore a romper and sandals and was able to sit cross-legged in my seat - super comfortable! You weren't crammed onto the boat either which was nice.)
Ultimate Adventure with Fury // my second favorite thing we did on vacation - a full day of activities like jet skiing, snorkeling, parasailing, kayaking, water toys, sailing, etc. The crew was ah.maz.ing and we were given the royal treatment complete with breakfast, lunch, and wine/beer on our way home! This all day adventure is perfect for all ages too. I can't say enough great things about this excursion. Did you know that KW has the third largest coral reef?
Southernmost Beach // a nice, but small, public beach where you can rent a chair and umbrella. However, laying your towel out is free! You can also go and order food and drinks from the bar at the beach cafe throughout the day. Keep an eye out for the old man that's always there wearing wings and a neon banana hammock ;)
Smathers Beach // this was the day scene for a lot of partying in college. I've personally never been but can only imagine how wild it gets during spring break. It's the largest of 4 beaches on the island.
Mallory Square Sunset // there are a ton of restaurants, shops, and touristy things around the Square but it's known as the best place to catch a sunset on the island.
Jet skiing with Barefoot Billy's // get ready to go full speed on a jet ski and travel around the entire island! We learned lots of fun history facts and had a great time being out on the water. Spoiler: I'm a speed demon and drove full throttle the entire time... sorry, K!
Drag Show // easily the best entertainment if you're caught on Duval during a rainy day. Grab your girlfriends and prepare to laugh and sing the entire time!
Sunset Key // for the beach lovers that want to take a day for some R&R - have I said before that I loved their fish tacos and pina coladas?? ;)
La Concha Top Spa // my first massage and probably the most amazing one I'll ever have... the views are the highest on the island and they were incredible. We also had pedicures in the same room while dining on champagne, cheese, and fruit. #divas
Southernmost Point // I can't say waiting in line is worth your time - I would recommend just walking by to at least see it.
For my next trip: I want to take a sea plane ride to the Dry Tortugas, visit the pineapple drink stand on Duval across from Blackfin, get ice cream at the Flamingo Crossing, visit the Hemingway House, and rent scooters!
Key West is hot and humid. Stick with clothes that breathe well and you won't need to adjust the entire night. I wore heels two nights but really preferred flat sandals the rest of the time. The nightlife scene is very low-key when it comes to attire so there's no need to dress up. I stuck with off-the shoulder dresses or rompers in cotton so that the material could move and breathe (nothing that would show sweat or spills). Shorts and breezy tanks would be my other go-to! Wear a cross body bag so that you can keep your hands free for dancing and toting around that Fat Tuesday's slushie drink! The bar scene can be a whirlwind so this also helps you to not leave your id/wallet laying around :)
I've attached some of the items that I brought with me and some dresses that I photographed while there. I mainly lived in coverups and bikinis during the day though!
If you have any questions, need any more recommendations, or just want to know something about the Keys specifically feel free to shoot me an email [southernanchors@gmail.com]! I'm by no means an expert but I feel like I have a pretty good feel for the island now that I've explored it a couple times. I'm already planning to go back again... so much I want to see/eat/do still!
I had already taken 3 days off of work because I was supposed to go on a trip with my boyfriend. So when that fell through K instantly jumped on my "crazy train" to take a trip somewhere (it was literally 3 weeks before) and we got to planning. Key West came to mind instantly because I had an insane amount of fun there during my senior year spring break! Luckily, K had never been there. I think we decided pretty instantaneously that the Keys were going to be our girl's weekend destination! The rest is history... just kidding we talked and planned every single day (K was my hero because she called and made reservations for all of our activities #lifesaver). I'm going to give y'all a run down of all the details: how to get there, where to stay, where to eat/drink, what to do and see, and what to wear! I'd also love to know if you have more suggestions I should add to my list!
HOW TO GET THERE
When I went to Key West in college I chose to fly with my best friends. I wish I could remember how much my flight cost but it was obviously reasonable since I paid for it on a college student budget. We flew out of BWI, transferred in Miami and got on a little puddle jumper that landed at the teeny tiny airport in Key West. Their airport is basically a one terminal, one carousel, get off the plane with a ladder type place. Very low-key and no-fuss. It was a piece of cake when you plan months in advance and get those details figured out...
However, K and I took spontaneity to a new level. We rented a car!! This was a first for both of us... Since we booked our flights so last minute ticket prices going to KW were outrageous. I'm talking a new fancy handbag crazy. (Being flexible with your departure dates will allow you to get a better deal. We left early Thursday morning and returned late Monday night so we could get a roundtrip flight to Miami under $200.) Granted, renting a car for 5 days wasn't cheap either but when we compared the prices we saved hundreds. We had a great time soaking in the blue water on our drive from Miami to KW and really got to see all of the Keys and the way the islands curve down into the ocean. Plus, we drove a bright yellow Mustang convertible. Oh yeah, we were sitting pretty! (Especially with my suitcase bouncing in the backseat because bloggers don't know how to pack and K's suitcase took up the whole trunk - mine would've too haha.)
Driving bonus: We got to stop and eat lunch in Islamorada - basically a halfway point. You MUST get lunch at Morada Bay Beach Cafe. My coworker recommended it to me and I was pretty excited when I looked it up. It was so adorable and the atmosphere really got us excited for the remainder of the trip! The colorful chairs and friendly staff (plus cat) put us in a great mood even though we had been up since 3am!
WHERE TO STAY
We knew we had to have one thing at our hotel when we were searching... a POOL!! There's nothing better than coming home from a long, hot, sweaty day and being able to jump in the pool to cool off. (Key West is also a deep-water port which is great for boats but means that all of the beaches are man-made.) As we did our research we found the Inn at Key West (UPDATE: This hotel is now known as the Havana Cabana Hotel)! They have the biggest pool in Key West and boy did it not disappoint!! We were greeted with complimentary rum punches and instantly felt at home underneath the palm trees... with Iguanas running around! It was really neat talking to the locals and hearing that they all go to our hotel to hang out at the pool. It made us feel like we weren't just being "touristy" by hanging at the pool!
Key West is extremely laid back and relaxed. You're not going to find a lot of hotels whose interiors rival their outdoor scene (and if you did you'll be paying more than you should). My suggestion is to find a hotel with a comfortable room but most importantly a great outdoors area - that's why we loved the Inn at Key West so much! I mean how much time do you actually want to be spending in your hotel?? You go to Key West to experience Duval Street and all of the activities the island has to offer!! Because we were about 2 miles from the main going out scene we did have to grab a taxi each night to go out but the front desk made that a piece of cake. It was a bit of a bummer at first because part of the joy of KW is walking everywhere. If you choose to stay at a hotel closer to the night action I highly recommend taking a couple hours out of your day to visit this pool - the food, drinks, staff, and atmosphere is lively and worth the taxi ride! Plus... you can feed the iguanas like I did haha totally a highlight!
Money Saving Tip: If you really want to be on a budget (cough, cough, college kids) you can find a motel right off Duval Street. I stayed at the Blue Marlin Motel in college and it served it's purpose :) it's not the nicest digs but it was cheap, easy and there was enough room for multiple girls to get ready with hair products, makeup, shoes, etc. Plus there's a small pool (that they just redid, actually). There are also great airbnb options!
WHERE TO EAT & DRINK
Southernmost Beach Cafe // a favorite off-Duval spot with a public beach. It's right by the Southernmost point and has great views of the water while you eat. I recommend trying the Conch fritters and their mojitos (don't forget how close to Cuba it is!)
Latitudes at Sunset Key // a quick ferry ride to the small island of Sunset Key. This is where we hung out at the beach for a day and swam in the water while taking it easy. Their fish tacos are the best I've ever had. I'm still dreaming about how perfectly crispy they were.
Mangoes // a nice sit-down dinner with views of Duval under umbrellas. Their orange-glazed salmon was incredible.
Better Than Sex // this restaurant comes with a rated R warning label. We went with two new friends we made and had the most hilarious time. The restaurant is very moody and dark and they only serve dessert with sexual names. All of the wines are dipped in chocolate - it's quite the experience! Just go... and make jokes the entire time. Mr. Grey will see you now...
Wine-O Bar // take a break from the heat on Duval street and pop into the historic La Concha Hotel. Their new wine bar is fantastic! K and I enjoyed appetizers and two wine flights. It was nice to sit inside away from the humidity for a change!
Sunset Pier // a great location if you want a view of the sunset while you enjoy a cocktail and bite to eat. This can be a bit of a tourist trap so it's not known for it's food but the view was really great. I loved all of their strung up lights and bright colors.
Key Lime Pie // just get it anywhere! It's amazing and the island is known for the freshness :)
-Irish Kevin's (top of the list - best entertainment and music! The crowd gets involved and you feel like it's a giant karaoke scene)
-Sloppy Joe's (a Key West classic!)
-Rick's (above Durty Harry's)
-Bull & Whistle Bar
-Durty Harry's (great live music - get the plastic bucket drinks!)
-Fat Tuesday's (frozen alcoholic slashes my personal fave is the Bahama Mama)
-Fogarty's / Flying Monkey (during spring break this is a dance floor)
-Garden of Eden (NOT for the faint of heart hehe)
My best vacation advice: there's no point in making reservations unless you want to go to a nice sit-down restaurant (in which case get a reservation). Some of the best food I've had in the Keys is by walking around, talking to locals, and discovering really neat hole in the wall places. Part of being on vacation is not having to plan what you're going to eat... if you decide you want pizza one night, then get it! If you want tuna or seafood the next, search for it! Everything is very chill so if you have to wait an hour to get a table (highly unlikely) - go grab a cocktail and explore! Make sure you hop around to different bars as well. There are so many people to see and meet with unique stories!
WHAT TO DO & SEE
Danger Charters Wind & Wine Sunset Sail // this is at the TOP of my list for things you should do!! Wine, a sailboat, apps, and a sunset?? I had the most incredible time sitting on the boat with K talking and admiring the gorgeous water. All while being served wine tastings and appetizers? Heaven. We met two awesome new friends on this sail too - one of them loved it so much that he went back another night! (I wore a romper and sandals and was able to sit cross-legged in my seat - super comfortable! You weren't crammed onto the boat either which was nice.)
Ultimate Adventure with Fury // my second favorite thing we did on vacation - a full day of activities like jet skiing, snorkeling, parasailing, kayaking, water toys, sailing, etc. The crew was ah.maz.ing and we were given the royal treatment complete with breakfast, lunch, and wine/beer on our way home! This all day adventure is perfect for all ages too. I can't say enough great things about this excursion. Did you know that KW has the third largest coral reef?
Smathers Beach // this was the day scene for a lot of partying in college. I've personally never been but can only imagine how wild it gets during spring break. It's the largest of 4 beaches on the island.
Mallory Square Sunset // there are a ton of restaurants, shops, and touristy things around the Square but it's known as the best place to catch a sunset on the island.
not actually taken at Mallory Square - but it's a pretty sunset still!
Jet skiing with Barefoot Billy's // get ready to go full speed on a jet ski and travel around the entire island! We learned lots of fun history facts and had a great time being out on the water. Spoiler: I'm a speed demon and drove full throttle the entire time... sorry, K!
Drag Show // easily the best entertainment if you're caught on Duval during a rainy day. Grab your girlfriends and prepare to laugh and sing the entire time!
Sunset Key // for the beach lovers that want to take a day for some R&R - have I said before that I loved their fish tacos and pina coladas?? ;)
La Concha Top Spa // my first massage and probably the most amazing one I'll ever have... the views are the highest on the island and they were incredible. We also had pedicures in the same room while dining on champagne, cheese, and fruit. #divas
Southernmost Point // I can't say waiting in line is worth your time - I would recommend just walking by to at least see it.
For my next trip: I want to take a sea plane ride to the Dry Tortugas, visit the pineapple drink stand on Duval across from Blackfin, get ice cream at the Flamingo Crossing, visit the Hemingway House, and rent scooters!
WHAT TO WEAR
Key West is hot and humid. Stick with clothes that breathe well and you won't need to adjust the entire night. I wore heels two nights but really preferred flat sandals the rest of the time. The nightlife scene is very low-key when it comes to attire so there's no need to dress up. I stuck with off-the shoulder dresses or rompers in cotton so that the material could move and breathe (nothing that would show sweat or spills). Shorts and breezy tanks would be my other go-to! Wear a cross body bag so that you can keep your hands free for dancing and toting around that Fat Tuesday's slushie drink! The bar scene can be a whirlwind so this also helps you to not leave your id/wallet laying around :)
I've attached some of the items that I brought with me and some dresses that I photographed while there. I mainly lived in coverups and bikinis during the day though!
If you have any questions, need any more recommendations, or just want to know something about the Keys specifically feel free to shoot me an email [southernanchors@gmail.com]! I'm by no means an expert but I feel like I have a pretty good feel for the island now that I've explored it a couple times. I'm already planning to go back again... so much I want to see/eat/do still!
Thanks for reading :) Let me know if you like getting travel guide posts like these! Be sure to visit www.fla-keys.com for more information on all of the Florida Keys!
*Thank you to The Inn at Key West for hosting us during our stay, the Key West Tourism Authority for sponsoring our adventures, and La Concha Hotel for the wine and spa experience. While these services were provided in exchange for exposure all opinions and thoughts are my own!*
Love Always,
