Key West

Key West is one of our favorite quick get-aways. Though we have brought our kids before (10 & 11 at the time), it is really built as an adult playground. In this post we will describe Key West with just the adults. We took a trip to Key West with our high school friends, Anne and Mark and what a time we had!

Key West is the Southern-most tip of the continental United States. It is actually closer to Cuba (90 miles) than it is to Miami (130 miles). The island is 4.2 square miles located as the last key of the chain of islands, the Florida Keys. Each of the keys has its own charm, most known for fishing, water sports and on some you can even swim with the dolphins and rays. Today, you can fly directly to Key West (at least from Boston), so no need for the long drive through the keys unless there is a destination you choose to visit along the way.

About 26,000 people call Key West home, but this census fluctuates greatly with the season. The people of Key West are a perfect combination of flamboyant, honky-tonk and laid back. Many spend winter here and then go to summer elsewhere, opening up more housing for tourists etc… The high season runs January to April and culminates with a Conch Republic https://conchrepublic.com/ festival in late April that includes “the longest parade” and a naval parade. Key West has dubbed itself the Conch Republic back in 1982 to playfully show their independence of the U.S.

Weather

The weather is typically always tropical, 70’s – 90’s. It can be rainy in August-September, and Fall is hurricane season, so think about this when you book. I would say the best time to visit is January – May. The hotter it is, the less you feel like walking around Duval St. We went in February and it was hot – mid to upper 90’s.

Why go to Key West?

Because it’s fun and there is a perpetual party. From the moment you land in Key West, you know you are in a place like no other. There is a reason Jimmy Buffet loved this place and has a Margaritaville Resort and a Margaritaville restaurant at different locations here. Because time is irrelevant in Key West, many of the clocks have the hands laying at the bottom of the glass.

Duval St. is the headquarters of this fun and Sloppy Joe’s is the leader of the pack. The bars and restaurants on Duval St. are mostly all open air. The live music and laughter spill out onto the sidewalks and coax you to join in on the revelry.

Every night there is a festive, artsy “Sunset Celebration” held at Mallory Square. Street performers, food vendors, artists and a variety of Key West’s honky-tonk characters gather at the square around 2-hours before sunset as literal boat-loads of tourists come to celebrate. This was the highlight of my kids trip to Key West, enjoying this every night. They were pulled into a couple of the performances and these memories have lasted a life time.

Ocean Activities

Believe it or not, the beaches are not the biggest attraction in Key West. The beaches around the island are a bit rocky, not sandy and pristine. The best sandy beaches are near the Southernmost Point. If laying on a beach enjoying the sand and waves is your thing, then make sure to fully research the hotel or home you select to rent to ensure you are not disappointed with the beach near it. When you do go into the water, the locals tell you to do the “stingray shuffle” which means rather than picking up your feet to walk, you shuffle into the sand to avoid stepping on a stingray.

There are other ways to enjoy the ocean while in Key West as it boasts America’s only coral reef (ranked #3 in the world behind Australia and Belize). Excursions such as snorkeling, scuba diving, sailing, power boating and fishing are abundant. When we went years ago when our own kids were young, we did a snorkeling trip. The rest of the family had fun and said the fish on the reef were beautiful. I am not comfortable with anything in the water that requires me to take my glasses off, as I am unable to function without my glasses, and I cannot wear contact lenses. So, looking into vast water where I can only see shadowy fish figures in the distance between me and my family sent me back to the boat. However, don’t let my fears ruin a good thing for you. Everyone I have spoken to who has snorkeled here has loved it.

During this adult trip we pre-booked a scuba diving excursion for the guys with South Point Divers. Jim is an experienced diver, but he joined Mark in taking the instructional course in the morning prior to the dive in a local pool. The men met nice a young man from Norway who was diving alone and invited him along with us to lunch after the lesson and prior to the afternoon dive. Jim advised both men to eat lightly before diving, but apparently neither are good listeners, so you know there is a good story to go along with this!

On the boat, Jim jumped into the water for their second dive, but before Mark jumped in, he suddenly felt ill. Mark began to upchuck and ran for the side of the boat. Unfortunately for Mark, he forgot that he had flippers on and went flying, throwing up as he went. Luckily, he managed to clear side of the boat with his chum, so the captain didn’t get too upset with him. Seeing this, their Norwegian friend lost his lunch as well. Jim said this was one of the funniest things he had ever seen. They did manage to continue with their dive though and enjoyed the rest of their experience. Remember if you want to dive when on vacation to plan around your flights as you are not supposed to dive the day before flying.

We also pre-booked a schooner sunset sail with Danger Charters which was fantastic. There were about 20-30 people. The crew was fun and spent time to chat as they passed plenty of wine, beer and simple hors d’oeuvres. It was a fun, relaxing experience with a beautiful, though partly cloudy sunset. I recommend this excursion or any sunset sail and look forward to doing it again on our next visit.

Adult Walking Fun in Old Town Key West

Once on Duval St., just walk around from establishment to establishment – store, restaurant, bar etc… and take in the sights. There is no shortage of people watching in Key West. Roaming roosters join you as you move from place to place. There is plenty to keep you busy on Duval St. but be sure to wander along the waterfront and down Front St. for the full Key West experience. You can even find cigar shops where Cuban immigrants roll the cigars right in front of you.

On the corner of Fleming St. and Whitehead St., a block in back of Jimmy Buffet’s Margaritaville Restaurant is mile marker 0 where U.S. Route 1 begins (ends in Maine on the Canadian border 2390 miles away). For those of us who have ever sat in traffic on Route 1 in Saugus, MA, this is a photo-op you have to take advantage of.

If you walk to the end of Front St. you will arrive at the Truman Annex which got its name when Harry S. Truman had his “little white house” here. This area was originally Naval housing during the Spanish-American War and Fort Zachary Taylor still stands. There is also a soft sand beach and picnic area. This is a gated community of Key West homes and a great place to rent, which is what I will do for our next trip. It is proximal to both Duval St. and Southernmost Point.

You can also reach the Southernmost Point Café by walking 25 minutes from one end of Duval St. to the other (or you can uber). Southernmost Point Café is at the end of Duval St. and sits directly on a sandy beach with a little pier. A short walk down one block from the café is the iconic landmark, the Southernmost Point Buoy, the closest most of us will ever get to Cuba.

At the Key West Museum of Art and History at the Custom House there are fun outdoor sculptures that we stumbled upon one night after dinner, and we had a bit of fun with them. I’ve heard that they change the sculptures out quite often so you may never see the same ones on the next trip.

Key West’s Notorious Drinking Establishments

We started our vacation the night we arrived with a stop at Willie T’s for some dinner and “rum runners” the official drink of Key West. This is a fun place with signed dollar bills tacked all over the walls. We may have left one too.

Over the next days we would just wander around wherever our feet took us, but a must visit (several times) is Sloppy Joe’s for some live music, sing-alongs and adult libations. Anne and I entertained ourselves here while the boys were diving. Ernest Hemingway was a fixture at Sloppy Joe’s when he moved from Cuba to Key West, which was owned by a good friend of his. Many of his personal possessions can still be found in the saloon.

It’s never a trip to Key West without a visit to Hog’s Breath Saloon. This pub has rustic inside/outside seating with live entertainment. It is a quintessential Key West establishment. I often see people wearing Hog’s Breath t-shirts in my daily life, at the grocery store etc…

Jimmy Buffet’s Margaritaville is a fixture on Duval St. You can hear live entertainment and eat a cheeseburger in paradise! We have been here before and had fun but did not get there for this trip.

These popular spots are usually packed with tourists from the many cruise ships that arrive daily, so plan your time accordingly. The first tenders begin arriving on a staggered schedule around 10am and head back between 6pm and 8pm. Both Sloppy Joe’s and Hog’s Breath have live web cams so make sure to let your friends know when you’re visiting so they can keep tabs on your fun.

Food

Conch fritters and key lime pie are synonymous with Key West. Food in Key West was delicious, for example delicious clams with chorizo in garlic butter and conch fritter.

El Meson de Pepe – Delicious authentic Cuban cuisine in a family run restaurant with live music and great mojitos. This restaurant has indoor and outdoor seating right in Mallory Square. This was a highlight of our dining experience in Key West.

Conch Republic Seafood Restaurant – We had a great fried seafood lunch on the outside patio with great views of the marina and was also great for people watching. This is where the guys made poor choices prior to diving which had nothing to do with the quality of the food.

Southernmost Beach Café – The café is covered open air seating right on the beach. We had a very nice lunch and cocktails here while watching the turquoise ocean and sunbathers. This is one of those sandy beaches so we took our sandals off and dipped our toes in the water here. There is also a small pier to walk out and catch the breeze for a bit.

Kermit’s Key Lime Shop – Jim is known as the pie guy. He makes pies for friends for various occasions and key lime is one of our favorites. Every key lime store in Key West will tell you their key lime pie is the best, but we know that Kermit’s is the clear winner with just the right amount of tartness versus sweetness. Kermit even stands outside the store to pull customers in and was willing to take a photo with Jim.

Banana Café – This eclectic French bistro near the Southernmost Point Café is open 7 days a week for breakfast, lunch and dinner. We had breakfast which was delicious. There is indoor and outdoor seating on both floors. It was worth a stop on our southern walking tour.

Accommodations

We stayed at 24 North Hotel which was a very nice hotel with spacious rooms, decent food and bar and a great pool. It was a 15 minute drive from Duval St. near Sloppy Joe’s. There is a hotel shuttle bus that had a pickup every 30 minutes so there was no need to rent a car. The hotel is not situated near any sandy beaches so if that is you must have you are better off finding a hotel or a rental on the south side of the island.

On our next trip to Key West we plan on renting a house in the Truman Annex section. There are any number of rental agencies that handle rentals in the annex, and I’m sure some will be on VRBO as well.