Long Weekend in Key West {What to Do}

Key West is such a fun little city to explore. Most of the major attractions are close together, so it makes for a perfect weekend getaway. Though the area is very touristy, Key West still maintains some of its historic charm.

Instagrammable Spots

US1 Mile Marker 0

At the corner of Fleming and Whitehead Street is the much sought after Mile Marker 0 sign.

Southernmost Point of the Continental US

Another popular spot is the Southernmost Point Buoy. Don’t be deterred by the long wait. It’s actually very thrilling to be able to say you’ve been to the southernmost point of the Continental US, and a picture proves it. Ha!

While there, take a few extra minutes to read the placards about the history of the island. It was in this spot that where the island’s Afro-Bahamian fishermen docked and sold their catch, and where they enjoyed the waterfront before the beaches were desegregated in 1969. Albert Kee – Key West’s unofficial greeter and African-American minister – is memorialized next to the buoy.

Fun Fact: Key West is closer to Cuba than it is to Miami!

Anywhere there is a rooster!

Must Visit

Key West Lighthouse

The Key West Lighthouse was built in 1847 after the US Navy established a base on the island in 1823. Its purpose was to guide military and commercial vessels navigating the shallow, reef-laden waters. It was decommissioned in 1969 as technological advancements made a lighthouse keeper redundant. Tours are available of the lighthouse and Keeper’s Quarters.

Hemingway House

A guided tour is included with the price of admission. Our guide Pauline from Poland expertly took us through each room, and the rich history of the house and Ernest Hemingway himself. 90% of the furniture in the home is original. Visitors are strictly forbidden from touching anything, but this rule does not extend to the cats. 🙂

The Hemingways had a polydactyl cat named Snow White. Today, there are 60 direct descendants remaining. The cats have always been named after famous people in Hemingway’s day. Polydactyl cats are very territorial, and tend to stay in the same spot day after day. So the guides know each one by name, based on their location.

Behind the house is Hemingway’s Studio. It remains exactly as it was when he left it. Though short, his time in this home was very productive. It is believed he wrote 70% of his work here.

If you visit, make sure to look for Hemingway’s last cent near the pool. The story goes that his second wife Pauline Pfieffer had the pool installed while Hemingway was away working on wife number 3. When he returned, utterly surprised by the $20,000 cost in 1938, he gave her all the money he had left in his wallet. “Pauline, you’ve spent all but my last penny, so you might as well have that!” Pauline then had the penny cemented in the flagstone patio.

Duval Street

When I think of Duval Street, I think of Bourbon Street in New Orleans, and Broadway in Nashville. Imagine a street lined with bars and restaurants, live music, art galleries, and colorful characters. Could there BE a more perfect spot for people watching?! The atmosphere is electric and the crowd never seems to die down.

We had lunch here one day (more on that later), visited an art gallery, drove through the area multiple times, and even biked up and down Duval Street, but the only picture I have is this one.

Womp, womp! I’ll do better next time.

Key West Cemetery

It is definitely worth visiting the Key West Cemetery and reading the more creative headstones.

Sunset Cruise

We tossed around the idea of a snorkel cruise or sunset cruise, and ultimately decided on the latter. The cruise was approximately two hours and included hors d’oeuvres and adult beverages. Service as impeccable. Once the sun set, the sail was lowered and everyone gathered on deck for pictures. A few weeks ago, the DH and I watched the sun set from the top of the Space Needle on the west coast, and here we were watching it set on the southernmost point of the Continental US. It was magical and not something we’ll soon forget.

If you’re in Key West and want a similar experience, here is my referral link: Land’s End Sunset Sail

Smather’s Beach

Thanks to the Florida Reef, the Florida Keys are an excellent destination for snorkeling, diving, and sport fishing. But its beaches are nothing like the Emerald Cost. They are made up of mostly ground coral, so pack your water shoes! And few resorts have a true beach. One of the popular public beaches to visit is Smather’s Beach.

Smather’s Beach

Parrot Key Hotel & Villas offers a complimentary shuttle service to Smather’s Beach. When you show your room card, you receive a complimentary umbrellas and chairs.

Fort Zachary Taylor

Fort Zachary Taylor houses the largest cache of Civil War armament in the world, and the park is the southernmost state park in the continental United States. In my opinion I preferred the Zachary Taylor State Beach to Smather’s Beach. The water was clearer, nearby trees provide shade, there are picnic tables, grills, and a short walking distance away is a splash pad for littles. It’s more conducive to spending the day. To me, Smather’s Beach was an excursion for a couple of hours.

Zachary Taylor State Beach

Getting Around


Key West Marina

The best way to get around is by bicycle. We rented bicycles at our resort one day and rode all around the island. It was easy to navigate the streets and we did not have to worry about parking. This made stopping for photos and tours super easy. The only downside was the 90+ degree temps. It felt like no matter how much water we drank, we never cooled down. Next time we do this – regardless of destination – we’re going to invest in cooling towels.

Car/Golf Cart

We drove into Downtown Key West on our two travel days for convenience. Parking is available, but fairly expensive.

Conch Train

The Conch Train is a Key West Staple. It is a guided trolley tour of the islands that’s withstood the test of time. And super cute too!

Conch Train

Parrot Key Hotel & Villas offers a complimentary shuttle service to downtown Key West.

What did we miss?

There was one activity briefly considered, and that was a visit to the Dry Tortugas National Park. It is a national park in the Gulf of Mexico, famed for Fort Jefferson, snorkeling, and beaches. It is a full day excursion, and one we decided to wait and do with the kids so they can get their National Park Passports stamped.

All the deets on where to eat still to come!

Long Weekend in Key West {Where to Stay} / Long Weekend in Key West {What to Do} / Long Weekend in Key West {Where to Eat}

As a full-service travel agent, I would love to be of assistance to you. I am passionate about what I do and pour that energy into crafting perfectly planned itineraries for you. Email ebony@familytraveladventuresllc.com to learn more.

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