Travel Guide: Key West

travel guide to key west wearing Lily Pulitzer

Do you know what is better than going to weddings? Its destinations weddings, especially to places such as Key Largo. One of Sam's good friends was recently married in Key Largo, so Sam and I headed down a few days early to spend some time in Key West. It was my first time visiting, and I absolutely LOVED it. I completely understand why it was such a raved about destination. What's better than nice weather, crystal clear water and a laid back culture? It truly felt like we were on vacation.

How to get to Key West:

Plane: The absolute easiest way to get to Key West is to fly down. Key West has a small airport on the southeastern side which is easily accessible to the rest of the island.

Drive: A more scenic option is to drive down to Key West from Miami airport. The drive takes around 3 hours 20 minutes and can fluctuate depending on traffic. Make sure your accommodations have parking on site since parking is limited. Luckily, Key West is walkable, for the most part restaurants, historical locations, or even events are generally located relatively close together. To put it in perspective, Key West is around two miles long and four miles wide. Note most parking garages are expensive. We opted to grab an Uber, so we did not need our rental vehicle during our time on the island or need to worry about parking around the city. An alternative way to get around the island is to rent a scooter, bike, or golf cart.

Ferry: There is a ferry from Fort Myers and Marco Island to Key West. The journey is between 3.5 and hours depending on weather. Pets are allowed on the ferry for an additional fee.

Things to Do:

Ernest Hemingway’s House: The house was home to Ernest Hemingway, the famous American writer known for "The Old Man and the Sea", "A Farewell to Arms", and countless other literature pieces. Guest are able to tour independently or take a guided tour. Guided tours usually run every 30 to 40 minutes and is included in ticket price. We took the guided tour and learned so many fascinating facts about Hemingway's life. One of the more interesting facts was that he was given a white, six toe cat by a ship captain. This cat's numerous descendants live on the property today. The cats are in the care of the groundskeeper.

rnest Hemingway’s House: The house was home to Ernest Hemingway, the famous American writer known for "The Old Man and the Sea", "A Farewell to Arms", and countless other literature pieces. Guest are able to tour independently or take a guided tour.
 One of the more interesting facts during Ernest Hemingway's home tour was that he was given a white, six toe cat by a ship captain. This cat's numerous descendants live on the property today. The cats are in the care of the groundskeeper.

Harry S. Truman Little White House: The Harry S. Truman Little White House name originated from President Truman's frequent visits. Truman spent 11 working vacations during his presidency and five additional visits after his presidency at this home. The house also has a historical significants from hurricane research, being the home to Thomas Edison while inventing weapons for war efforts, and the Key West Accord was created in the house. You can buy tickets online and get a discounted price. 

Harry S. Truman Little White House:  The Harry S. Truman Little White House name originated from President Truman's frequent visits this house including spending 11 working vacations during his presidency and five additional times after his presidency. The house also has a historical significants from hurricane research, being the home to Thomas Edison while inventing weapons for war efforts, and the Key West Accord was created in the house.

Southernmost Point: In Key West, you are able to visit the southernmost point in the continental United States. It is marked by a famous concrete landmark that can found at the intersection of Whitehead Street and South Street.

Southernmost Point: In Key West, you are able to visit the southernmost point in the continental United States. It is marked by a famous concrete landmark that can found at the intersection of Whitehead Street and South Street.

Duval Street: In the heart of downtown Duval Street is a collection of bars, restaurants, and shops. I could spend days on Duval Street finding the perfect souvenir, spot to dine, and entertainment. 

Duval street in Key West, FL. sloppy joe's bar

Key West Lighthouse: The lighthouse opened in 1848. Tourist are able to climb the 88 steps to the top. This lighthouse has the best sweeping views of Key West. 

Key West Lighthouse:  The lighthouse opened in 1848. Tourist are able to climb the 88 steps to the top in order to see the best views of Key West.
Key West Lighthouse:  The lighthouse opened in 1848. Tourist are able to climb the 88 steps to the top in order to see the best views of Key West.

Dry Tortoguas National Park: The national part was a bucket list item for me when visiting Key West. It is a truly unique national park that can only be visited by sea plane or boat because it is located 70 miles off the coast of Key West, so be prepared to spend a full day at the park. Tours can be booked in advance. The park is the home of Fort Jefferson and the tours will teach you about the incredible history of the fort during the Civil War. Snorkeling gear is provided free of charge, which allows guests to snorkel around the fort's moat and relax on the beach. 

Dry Tortoguas National Park: The national part was a bucket list item for me when visiting Key West. It is a truly unique national park that can only be visited by sea plane or boat because it is located 70 miles off the coast of Key West

Robbie’s: Robbie’s is located in Islamorada located on the keys. If driving this is the perfect place to stop and grab a bite more on that below. However, Robbie’s is known for feeding the tarpons. You can pay a small fee to get a bucket of chum to feed these fish. There was a whole school of tarpon during our time and roughly seemed about 100 of them. However, you hold the fish above the water and the fish will start circling and finally strike capturing the bait. I was absolutely to scared to get close. Sam loved every second. Peep the picture below with the tarpon. 

Robbie’s: Robbie’s is located in Islamorada located on the keys. If driving this is the perfect place to stop and grab a bite more on that below. However, Robbie’s is known for feeding the tarpons. You can pay a small fee to get a bucket of chum to feed these fish. There was a whole school of tarpon during our time and roughly seemed about 100 of them.

Seasonal Events:

Race World Offshore: This annual event brings the world’s top offshore boat racers to Key West. It consists of three days of racing but seven days of events. For our trip to the Keys, we accidentally visited during this event. We were able to watch the boat races at Fort Zachary. We paid a small fee to enter the fort, but the races was close to shore and easily viewable. There were so many different events to attend. We also got to visit the boat racing parade which is held on Duval Street. The boats are parked on Duval and every is able to view the boats and meet the race team including the drivers. Other events including a boat parade on the water, concerts, and an award ceremony.

Fantasy Fest: This festival is a ten day festival held every October. It is an all out costume party in true Key West style: parties, costumed marches, street fairs, elegant balls, and the Fantasy Fest Parade. This festival is an adult only festival.

New Year’s Eve in Key West: On Duval Street, head over to Sloppy Joe’s where thousands gather to see a man-made conch shell lowered from the roof when the clock strikes midnight. Another option is head over to the Historic Seaport and see a pirate lowered from the mast of the ship at midnight with cannons firing and music playing.

Race World Offshore: This annual event brings the world’s top offshore boat racers to Key West. It consists of three days of racing but seven days of events. For our trip to the Keys, we accidentally visited during this event. We were able to watch the boat races at Fort Zachary.
Race World Offshore 2021

Places to Grab a Drink:

Papa’s Pillar Ernest Hemingway Rum Distillery: “Developed in collaboration with Ernest "Papa" Hemingway's estate, Papa's Pilar Rum was crafted to celebrate the bold and complex nature of Hemingway – author, explorer, story-teller, conservationist, bon vivant and Key West local. Papa's Pilar Dark and Blonde expressions are born of hand-selected rums sourced from countries throughout the Caribbean for their age and distinct character.” During our visit, we signed up for the cocktail class and rum tour. I highly suggest this class, since you will personally make three cocktails where they will provide you with the recipes to take home, a discount off any rum bought, and a distillery tour. The mixologist made the class so interesting and fun (maybe the best Pina Colada I have made) mixed with the rich history of rum distilling and learning more about the famed Key West local, Ernest Hemingway, it could not be beat. 

Sloppy Joe’s: From being a speakeasy illegally run through the Prohibition Era to a well known bar in Key West. This bar is known for its history as well as it's liveliness with live music and dancing. Even Ernest Hemingway frequented this bar often. The bar also hosts the Ernest Hemingway Annual Papa Look Alike Contest, which occurs every July. You can even see the yearly winners pictures posted in the bar.

Margaritaville: In 1985, Jimmy Buffet opened up the original Margaritaville in Key West. Of course, a margarita is worth grabbing here. 

The Bull & Whistle Bar: This bar is for the more adventurous souls. The first floor is called The Bull. Local musicians perform nightly in the widely open room. The second floor is called The Whistle which sports pool tables, games, and a balcony. The third floor is called Garden of Eden. It is a rooftop bar where clothing is optional. Its really is a nude bar. Yes, people were fully nude. Yes, they respect privacy. Bouncers will ask you to put away your phone so no photos will be taken. No clothing lost here, but I loved the care free attitude. There is a dance floor in the middle with a DJ. After a certain time, a cover will be charged at the entrance of Garden of Eden.

First Flight Restaurant & Brewery: This building is the original location of Pan American World Airways and the location where they sold their very first flight tickets. Pan Am was the largest international flight carrier from 1927 to 1991. This place is truly unique with it also holding the title for the southernmost brewery in the USA. You can grab a seat outdoors for an intimate garden canopy diner. I highly recommend visiting during happy hour from 4 to 6 p.m. daily: 3.50 pints and $5 select cocktails. Sam was impressed with the beers and loved Havana Red, a rich amber ale.

Hank’s Hair of the Dog Saloon: No matter what time of day there always seems to be live music. Average bar drinks but tons of drink specials. 

Where to Dine:

Kermit’s Key Lime Pie: You cannot visit Key West without tasting the famous key lime pie. This place has been around more than 25 years. Try the key lime pie by the slice or get it on a stick dipped in Beligian chocolate.

Garbo’s Grill: Featured on Diners, Drive-Ins, and Dives by Guy Fieri. Operating out of a food truck this place is not to be missed. Known for their burgers and tacos. The Korean BBQ tacos are some of the most unique and savory twist for tacos I have ever tried.

The Seaside Cafe: Located on the grounds of the southernmost house. Known for classic mojitos, wood fire pizza, and lobster. This cafe has incredible sprawling views of the ocean. As you sit outside right on the deck. Highly recommend, going in the morning the honey butter lobster was absolutely incredible. However, very sweet so if your more of a savory person maybe split the biscuit and grab another dish. Also, well crafted cocktails the mojito was perfect.

Robbie’s: Not exactly in Key West but you will have to pass through Islamorada en route to Key West if driving. A very large menu that will please the whole family. Quality locally caught seafood. Also a great place to grab a drink. Average drinks but the trailer trash bloody mary is loaded and worth mentioning. Also if taking a charter out of the dock this restaurant will cook and prepare your catch.

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