I’m welcoming my tanned, slightly sunburnt self back to the cold and rainy weather of Indiana.
This past week, for the first time in 11 years, my whole family- mom, dad, brother, & myself, went on a vacation.
I am patting myself on the back for suggesting this shindig. My brother is in the middle of a move to Tennessee and I just graduated college, so I thought this would be a great time for a nice getaway before we are all heading home to our separate states.
We ate, drank, and adventured around Key West for 7 days and I want to share my picks of things to do around the island!
Eat & Drink
Blue Heaven: Outside, large patio and bar. Live band with more of a local vibe. Amazing food and cozy bar area inside as well. My dad claims this place had the best Key Lime pie the whole trip!
A & B Lobster House: Top 5 nicest restaurants in Key West. Over look the water while eating dinner and finish the night in the Cigar Bar.
Half Shell Raw Bar at the Marina: Key Was is a huge tourist trap so it was a bit difficult to find those local spots. This one definitely gave us more of a local feel & we loved it.
B.O.’s Fish Wagon: Also more of a local feel, awesome decor and even better food. Get the fish tacos!!
Blacken Bistro: Super small intimate place, would be ideal for a date night. WARNING: no hard liquor, only beer & wine.
Bagatelle: Hit for happy hour, great drinks & apps.
DJ’s Clam Shack: Didn’t eat anything here due to food allergies, but it’s been on Diners, Drive-Ins, and Dives. Family that did eat here said the clams and lobster rolls were great!
Amigos Tortilla Bar: Day of the Dead decor with everything from guac, carnitas, tacos, and the best margaritas- gotta stay hydrated, yanno?!
Pescado Food Truck: You can’t miss this bright yellow truck located in the parking lot of a Chevron Gas Station on White Street serving up incredible food with even better owners! If you go, get the conch salad!
Date & Thyme Organic Cafe & Grocery: If you know me, you know I had to find the organic cafe in town! This one is serving up yummy smoothies, coffee, & juices. A lot of breakfast and lunch options as well as organic staples you would find in a grocery store.
Cuban Coffee Queen: WARNING- you will get addicted to Cuban Coffee so drink with caution. If you will be in Key West for a while, get the local stamp card to get your 7th cuban coffee free!
El Meson de Pepe: Authentic Cuban food, great atmosphere and it’s right on the side of Mallory Square. 5 of us shared different things on the menu. Tamales, Cuban sandwiches, and a sampler of their best selling dishes. Everything was ridiculously yummy. If you are a coffee addict like me, get the Cuban Coffee. Huge jolt of energy and even better flavor- I’m telling you guys I’m addicted to this stuff.
Latitudes: Wish we would have made it here. Take a ferry to this restaurant on a private residential island across from Key West. I highly recommend going here, but make sure you make a reservation at least a week in advance.
Captain Tony’s Saloon: This is the first bar Ernest Hemingway owned before moving down the street to Sloppy Joe’s (see bellow). More of a “college” bar if you ask me but to each their own.
Sloppy Joe’s Bar: The bar Hemingway moved to after Captain Tony’s Saloon’s rent was raised. Huge restaurant & bar. 4 separate bars in the whole place, live band, cool atmosphere. Walk in grab a drink and continue walking down Duval St. or stay a while and listen to the live music.
Hog’s Breath Saloon Pub: World-famous Bar in Key West. Cool vibe definitely check it out!
Things to do & see
Duval Street: Walk down it, pop into all the bars, clothing stores, art galleries, & restaurants. I would call this the Bourbon Street of Key West.
Hemingway’s House and Museum: Hemingway lived in Key West from 1931-1939, he wrote some of his best books in this house and it is a huge part of the town history. As I mentioned earlier, he owned two of the bars on Duval St, Captain Tony’s & Sloppy Joe’s..
Take a guided tour or self guided tour through the grounds and transport yourself back to the 30s. At the time Hemingway was living in Key West he owned a six-toed cat.. Today there are over 50 cats that live on the grounds with half of them being six-toed cats. Yes, you read that correctly, SIX TOES. I am the biggest cat person ever so you already know I was swooning over these unique & friendly felines.
Mallory Square Sunset Celebration: A nightly sunset celebration held in the heart of downtown. Watch street performers, listen to local musicians, and taste local food from street vendors all while getting the best views of the sunset.
Mel Fischers Maritime Heritage Museum: Browse the extensive collection of artifacts from17th century shipwrecks like the Atocha and Santa Margarita at the museum, dedicated to the man who spent 16 years looking for these treasures.
Truman’s Little White House: The 33rd President of the United States Winter White House. Step back in time and take a stroll through the house where so many have been.
Visit Mile Marker 0 on 501 Whitehead Street and the Southern most point at the corner of Whitehead Street & South Street
Rent a golf cart/ bike/ scooter for the day!
Fort Jefferson and The Dry Tortugas: Visit the largest masonry structure in America. Located 70 miles west of Key West. Venture out to the island by seaplane or catamaran ferry (can I suggest the seaplane. The seas were very rough the day we went and I could have gone without the seasickness.) Choose to take a tour of the historic fort, snorkel in the coral reefs around the grounds, walk around the moat. If you are lucky enough you will get a glimpse of one of the only salt water crocodiles in Florida, & if you are brave enough you can even camp on the island for a few days.
If you are planning a trip to Key West this is the #1 thing I would put on your todo list. Amazing views of the ocean, beautiful turquoise waters, and lots of history. Definitely check it out!!
Visit one of the marina’s in Key West and talk to the captains of each boat to book a trip, stop by a Fury Kiosk, or book online through Fury here.
– Charter a boat
– Jet Ski
– Deep Sea Fishing
– Sunset Cruise
Where to Stay
We rented a condo in the Truman Annex right next to Truman’s Little White House. If you are going on a family vacation and plan on staying for a week or more I would definitely recommend trying to stay in the Annex. It’s a gated community with amazing views of the ocean and walking distance from Duval Street, Mallory Square, and almost every other attraction around town.
Weather Station Inn: An old weather station turned Bed and Breakfast hints the name, right? This 8 bedroom Bed and Breakfast is also located inside the Truman Annex which offers a great location and the intimacy of a B&B.
The Westin Key West Resort & Marina: This hotel is in the same area as the Truman Annex and the Weather Station Inn, so The Westin is in a fantastic location and walking distance from so many things around town!
My family and I had such a great time and I hope we don’t wait 11 more years for our next family vacay! I hope this helps you if you ever plan on visiting Key West!
I’m curious, have you ever been to Key West? If so, what are some of your favorite things to do/see on the island & what could you go without doing?!
Can’t wait to start adding more travel posts to le blog for you guys–
Talk soon babes!