Your Ultimate Travel Guide to Key West, Florida

First things first, like always this blog post has a companion video. Check it out before you dive in.

When you visit Key West, there are a few things you need to think about: (1) Where to Stay, (2) What to Do, and (3) Where to Eat. We have you covered on all accounts!

DuVall Street in Key West

WHERE TO STAY

We covered this topic in another blog post, so if you want to know more about our favorite B+B in Key West, check that post out.

To recap… the best place to stay in Key West is Amsterdam’s Curry Mansion Inn. The rooms are huge! The B+B itself is absolutely gorgeous. The innkeepers live on sight and make this place feel like a true home away from home.

When you stay at the Curry Mansion you’ll get a delicious breakfast, a two-hour open bar cocktail party each night, included parking, free WiFi, and access to laundry service.

The innkeepers, Phil and Nancy, live on site and have an incredible staff that can help you with anything. They’re around to give recommendations on restaurants, activities, and other things to enrich your Key West stay.

If you book a stay with the Curry Mansion, make sure you tell them we sent you!

WHAT TO DO

Okay, so there are a lot of things to do in Key West, but which things are worth the time and worth the money? We’re here to give you the nitty gritty on some of the most popular travel attractions:

(1) Ernest Hemingway House
(2) Conch Tourist Train
(3) Sightseeing Trolley
(4) Southernmost Point
(5) Aquarium
(6) Shipwreck Museum

Old Town Key West

The Ernest Hemingway House

Full disclosure… we came to the Hemingway House for one reason and one reason only: the cats.

Hemingway had quite the fondness for cats, especially the polydactyl variety, AKA cats with six toes. Since Jenni is a little bit cat obsessed, we knew we had to venture into the world of Hemingway to find these beauties. Was it worth it?

Yes. Yes it was.

However, if you want to get your full $15 worth, we suggest taking the included tour of the house. Your guide will walk you through the rooms and talk about Hemingway’s life, inspiration, and process. There’s also a gift shop where you can pick up his books or some cat merchandise.

Conch Tourist Train

The tourist train is definitely one of those fun touristy things to do. You get to see the main sights of Old Town Key West and get jarred around inside a tiny train.

Tickets are about $47 for one day of hop-on-hop-off capabilities. That’s a per-person price and the train only takes you through Old Town.

If you want to see the main sights like the Southernmost Point and Hemingway House, then this is a good option. It’s kind of a novel experience and not something you can enjoy everywhere.

However, with the steep ticket prices, we actually recommend the trolley over the tourist train. The next section will tell you why.

Conch Tourist Train

Sight Seeing Trolley

Much like the tourist train, the trolley is a hop-on-hop-off experience. However, not only does it take you through the popular sights in Old Town Key West, it also takes you into the newer part of the city. This is very convenient if you’re staying in a hotel or resort in New Town. You can pick the trolley up outside most of the major hotels on that side of town.

You see the same sights, but the ride is a little less bumpy.

The windows are also open (no panes) so you can get really great video and photos (the same as the tourist train).

Tickets run $42 for one day (per person).

Old Town Trolley Southern Most Stop

Southernmost Point

You can’t go to the southernmost city in the continental United States and NOT visit the Southernmost point. However, how you see it can make all the difference.

During daylight hours, the line is always long for people getting photo-ops. If you want a photo of you in front of the marker, you’ll have to wait it out. However, if you just want a shot of point itself, you can get a great one by riding the Conch Tourist Train.

That’s actually how we got our shot.

However you choose to photograph or film the Southernmost Point, you have to see it. Come on! It’s a hallmark of Key West.

Southernmost Point of the Continental United States

Aquarium

Entrance into the aquarium is $15. For that price you get to enjoy one touch-tank with some conchs and have the potential of witnessing a shark feeding. There’s also a tank with amputee turtles (which are very cute) and two walls of pet store style fish tanks.

If you like to visit every aquarium you come across on your travels, then go for it! Otherwise, I’d run down to your local pet store and check out the fish. It felt like the same thing.

However, there is a VERY LARGE SNAKE in a cage as you leave the aquarium. So that could be worth seeing if you’re into reptiles.

Shipwreck Museum

Just like the aquarium, entrance into the Shipwreck Museum is $15.

Key West became one of the nation’s richest cities because of shipwrecking. It was the industry in the Keys for years, and it’s how many of their millionaires were made.

The museum does a great job of teaching you the history behind the industry, what it meant to the Key West area, and more. You also get to see some cool shipwreck treasures.

This attraction is more unique than the aquarium, and you’ll only find one like it. We recommend the $15 entrance fee if you like museums and you want to learn more about what made Key West so wealthy back in the day.

WHERE TO EAT

There are several incredible dining options all over Key West, but we want to share our two favorites: Lagerhead’s Beach Bar and Caroline’s Café. Both of them are very different but DELICIOUS.

View from Lagerhead’s Beach Bar

Lagerhead’s Beach Bar

First of all, you can’t beat the view at Lagerhead’s. You’re eating right on the beach and we got the chance to see a stunning Key West sunset from their patio.

The food is fresh and delicious.

We started with the conch ceviché and we still think about it to this day. They serve it with several different kinds of crackers and HOLY MOLY, y’all! It’s to die for. Delicious. Unbelievable. You need to try it.

For our meals, Joanie B. got the fresh grouper tacos and Jenni had the Cuban sandwich. The tacos were a little bit spicy, absolutely fresh and delicious. Jenni is a bit of a Cuban aficionado and Lagerhead’s wasn’t number one on her ‘Best Cuban’s List’ but it was still delicious. The ratio of meat to other goodness was perfect. The bread just needed to be toastier for maximum deliciousness.

Lagerhead’s is a small, local beach bar with amazing people and yummy food.

Caroline’s Café

Caroline’s wasn’t on the original plan for Key West. However, after extending our stay in the city, Joanie B. had to look up some more places to eat and came across Caroline’s.

We ended up eating their for lunch and dinner on our last day in town.

It was so good!

The best conch fritters in town. Delicious food all around. And the service was unbelievable!

On the same property as Caroline’s you’ll find two lounges, Caroline’s Other Side and The Abbey. They’re both beautiful with a great atmosphere. This is all located in Dr. Joseph Porter’s home.

He was one of the doctor’s responsible for eradicating Yellow Fever in Key West back in the 1800s.

Conch Fritters at Caroline’s Café in Key West

THANK YOU!

Thank you to all of you reading this and to those that made this post (and Key West series) possible:

(1) The City of Key West
(2) Amsterdam’s Curry Mansion Inn
(3) Lagerhead’s Beach Bar
(4) Travelon Travel Bags

If you’d like to support this wild ride, become a Patron, we have some awesome reward tiers. Sometimes we even pick up little gifts for you along our travels.

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Ultimate Travel Guide to Key West