8.10.2021

My 30th Birthday Trip to Key West!

Priya the Blog My 30th Birthday Trip to Key West!
Carina's contribution to the weekend: bucket hats that we all decorated with puff paint! Art created this one that says "Tropical Priyadise" come ON <3
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Christine MADE these koozies, the total hit of the weekend. I carry one in my purse today.
Priya the Blog My 30th Birthday Trip to Key West!
Galina was the activities and decor chair! She provided me with theme-y accessories to wear each night.
Priya the Blog My 30th Birthday Trip to Key West!When I was in middle school, I read a book that took place in the Florida Keys - and since that time, I've been dreaming of visiting the Keys! Turning 30 and celebrating a milestone birthday seemed like the perfect time to do it. Since living in Tennessee, I've traveled all over Florida (I've kinda made it a mission to just keep exploring a new place every time I go...) but the Keys were a new experience entirely. Galina, Carina, Carina's fiancé Michael, my best friend Christine, and of course Art made me feel SO loved and celebrated. It was probably the most special birthday I've ever had!

I love to put together "mini guides" for travel; both as a way to keep track of what we did, and as a reference in case you're planning or dreaming of a trip to the Keys. Planning travel can be overwhelming! I always start by asking for recommendations from people I trust to make things a little easier. Not sure if you trust me, but here you go!   

Priya the Blog My 30th Birthday Trip to Key West!
Hemingway House

Where We Stayed

  • Cardozo Hotel | The Art Deco Historic District in South Beach has back to back hotel options along Ocean Drive - right in the middle of it ALL, so perfect if you have a quick stay in Miami. I think we booked this on HotelTonight or something similar, not fancy but totally decent and included amenities (bikes, beach towels, etc.) We also had the best croquettes of our entire trip at the Call Me Cuban restaurant on property.
  • Tropical Inn | Key West seems to have plentiful B&B options just like this, in the style of old houses that have been turned into Inns (maybe?) This one was charming and had a leafy back garden with a pool. They were also very hospitable!
  • Hemingway's View House | It was a little tricky to find a house for 7 in Key West, but this worked out perfectly! It was spacious, clean, cool (AC units in each room) and though the location was super convenient (right off Duval St.) it was far enough away from party central that we didn't have any noise issues late at night.

Priya the Blog My 30th Birthday Trip to Key West!
Dinner at Little Pearl, our first night in Key West

Where We Ate

  • Como Como | One night in Miami - where to eat?! We selected this place on the spot (thanks, Eater!) and it did not disappoint. Still thinking about my esquites (roasted corn that tasted like mac & cheese) and the fried hamachi that we made into little tacos! The bartender also called me grandma, so I'll never forget this place. 
  • Little Pearl | If you're wondering if Key West is a destination for foodies - yes! This was my "fancy birthday dinner" for our first night in Key West. Art & I experienced a seafood-forward tasting menu that was super creative, and the place was very intimate. 
  • Hog's Breath Saloon | Surprisingly good bar food! Still thinking about this ceviche. This was also "the cool place" to have a t-shirt from when Art was in middle school, lol. 
  • 5 Brothers | I didn't actually go here, but did enjoy a breakfast sandwich and later a Cuban on the beach from here. This place is a gem! 
  • Southernmost Point Cafe | Feels just slightly nicer than your average Florida beach shack restaurant, but I will say, our entrees were really good. 
  • Blackfin Bistro | This was a last minute walk-in for dinner on our second night in Key West, and may have unanimously been the best meal of the trip! I had the best shrimp cocktail of my life (one of my favorite foods, btw), Art still dreams about his Yellowfin Tuna. Oh, and the staff was a hoot!

Priya the Blog My 30th Birthday Trip to Key West!
Mojitos (when in Rome!) at Call Me Cuban in Miami

Where We Drank

I mean, everywhere, really. But here's a few highlights.

  • Green Parrot | I remember this being my favorite bar for no specific reason. But maybe it’s just when the night hit the sweet spot. This was a recommendation from a server though, so that’s a good sign. 
  • Fat Tuesday | This feels like a Key West staple, right on Duval St. The music was really fun AND be sure to pick up a souvenir cup (full of the tropical drink of your choice, on tap) that makes an excellent reusable cup for your trip!
  • Garden of Eden | This is absolutely a Key West institution, and I don’t want to ruin the surprise, but I’ll just say - super tame late on a Saturday night. Don’t be scared!
  • Sloppy Joe's | Classic Key West bar with live music and loads of drink/food options.
  • Seaside Cafe at the Mansion | We would have gone here two nights in a row, as it is the perfect spot to kick off the night with a chill, seated frozen drink. Carina loved this Pina Colada!

Priya the Blog My 30th Birthday Trip to Key West!

What We Did 

Beach day at Bahia Honda | Key West is not a beachy place, it’s really geared towards boating/fishing. Our time all together was relatively short and our group wasn’t super into fishing, but I did want to find a chill daytime activity for Saturday that took advantage of where we were. So, after doing a little research, the beaches at Bahia Honda were unanimously rated the most beautiful in the Keys. We had a lovely day! The park is about 1.5 hours from Key West, and plan accordingly, they do cut-off at capacity. I think we sailed in around 11:30am as maybe the last car allowed in!

Priya the Blog My 30th Birthday Trip to Key West!
Art, Bourbon hunting on Islamorada!

Driving from Miami --> Key West


This was one thing I was most excited for on our trip! Key West does have its' own (small & fairly expensive) airport, but if you have the time and interest in adding Miami on to your trip, you can make the ~ 3.5 hour drive. This is the kind of gorgeously scenic, adventure-at-every-turn road trip that you could easily spread across a week. I'd love to do it again one day when we have more than one day to do it! But here are a few points of interest we found along the way.
 
  • Little Havana/Versailles Bakery | We had to stop in the Little Havana area on our way out of Miami! There are so many Cuban bakery options, and we picked Cafe Versailles at random for Cuban coffees, croquettes, and pastries and wow, now I’m hungry!
  • Postcard Inn | Super cute area to spend an afternoon, I wish we had more time! I spent the rest of the weekend trying to find a Key Lime Colada like I had here. Lots of comfy options for lounging and taking in the harbor views.
  • Beaches! | I did some research to find the “best beaches in the Keys” for our Saturday activity, and naturally wanted to stop and swim at each of them during our drive. Canon Beach was definitely a state park vibe with a buoyed off swimming area (I know they do rent snorkeling equipment and do excursions if you’re into that.) Anne’s Beach was described as a “natural” beach, and though it did have a lot of natural life, I had a very relaxing float in the shallow water. Sombrero Beach is totally part of a city park. Not a bad place to spend the day, but pretty crowded.
  • Chef Rolf's Tuna's | This was a recommendation from our server in Miami and the Grouper Reuben really hit the spot for a picnic lunch on Anne’s Beach! They also served us beers 2 go!
  • Baby's Coffee | Just outside of Key West. Excellent coffee shop and roastery that serves all kinds of food, and has a small grocery store perfect for prepping for a boat day. Key Lime Pie on a stick!
Priya the Blog My 30th Birthday Trip to Key West!
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