Key West – What to Do & Where to Eat and Drink
For several years, we have been entertaining the idea of making Key West our retirement destination. I had never visited, but spent a lot of time in Gulf Shores, AL as a kid and had a strong feeling I would fall in love with Key West. Pat, my husband, has been there several times for business and he is a big fan.
While our son was traveling with his high school exchange program, we decided to take advantage of the opportunity for an adult only trip. We finally booked a trip to Key West so I could check it out for myself.
Why target Key West for retirement? We are looking for a laid back vibe (no shirt, no shoes….no problem!), a location with lots of water-focused activities (kayaking, boating, fishing, and snorkeling), great food, and fabulous music. After a wonderful week visiting Key West, it checked all our boxes and is definitely part of our retirement plan. Check out my Key West Retirement Dreaming Pinterest Board. A girl has to dream and plan.
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Traveling to Key West
Flying directly into Key West is convenient, but prices can be high and availability low. When Pat traveled to Key West for business, he flew directly into Key West. For our trip, we decided to take our time and drive the scenic route through the keys.
Flying into Miami offers competitive prices and availability. We took an early morning, direct flight out of Chicago. Upon arrival in the late morning, we made our way to the rental car center and hopped into a convertible. We decided to drive away from the airport before putting the top of the car down. Good thing! Not long after leaving the airport, we ran into a terrible thunderstorm with torrential rain.
We continued on our way and merged onto Highway 1. Just as we crossed the bridge over to the keys, the storm began to clear. We drove on to Key Largo and stopped for lunch at Mrs. Mac’s Kitchen. I enjoyed the famous Key Lime shake. We shared the fried okra and the blacked mahi mahi sandwich I ordered was delicious. Ohhhhh, we could already tell this was going to be a fabulous vacation.
The scenery along the drive was beautiful and got us really excited about the upcoming week. Including our stop for lunch at Mrs. Mac’s, the journey took approximately 4 hours. We travelled in June, Wednesday-Wednesday which helped us avoid weekend traffic.
Where to stay
I did quite a lot of research and read many reviews to select our accommodations. Normally, we book apartments or houses using VRBO. Key West rentals and hotels can be very expensive. We settled on The Duval House, which was lovely. A simple breakfast was available daily, the grounds were beautiful, it had a pool and it was centrally located in Old Town Key West right on Duval. We stayed in a small cottage at the back of the property, so no problems with noise. Parking was available for an extra charge. Overall, a great value.
What to do
There is something for everyone in Key West. We hit a few tourist attractions, but the highlights for us were water activities and live music. Unfortunately, we didn’t do any fishing on this trip. Something to look forward to for our next visit.
Walking around Key West
Key West is a wonderful town for wandering. So much to see and lots of interesting architecture, Something that can’t be missed is the sunset celebration every evening at Mallory Square. A different frame of mind – everyone stops what they are doing to watch the sunset. It’s a super social atmosphere and there is plenty of entertainment in addition to the color and beauty of the setting sun.
Other spots not to miss include Mile Marker 0 and Southernmost Point. It’s also interesting to walk through the cemetery, which is located in the center of Old Town. Free walking tour guides are available to help you explore the above ground vaults among chickens and iguanas. You can even find the grave of the real Sloppy Joe.
We also enjoyed a walk around the West Martello tower with the lookout and gardens. Just a short walk from the tower to the Edward B. Knight Pier. It was interesting to watch all of the people fishing from the pier. However, no one was catching anything during our visit.
Kayaking
Pat and I really enjoy kayaking and I make it a point to kayak during our vacations if possible. This trip was no exception. We rented kayaks at Hurricane Hole Restaurant, Bar & Marina. We purchased a map and went out without a guide. One of our favorite spots was the lagoon connected to the canal that runs along Riviera Drive in Key West. We saw horse shoe crab and also observed interesting jellyfish (Cassiopea) that were upside-down. They looked like beautiful flowers embedded in the seaweed. Glad nobody tipped their kayak. Yikes!
Sailing, Kayaking and Snorkeling
Sailing, kayaking and snorkeling were definitely on my bucket list for this trip. I discovered Danger Charters during on-line searches and had to book a trip based on the stellar reviews.
On this trip, you sail on a schooner through the waters of the Key West National Wildlife Refuges. We had a perfect day for sailing. The boat anchored and then we were able to kayak around the mangrove islands. Just as we were entering the water to begin snorkeling around the sponge gardens and coral patch reefs a terrible thunderstorm approached. We hoped to wait it out, but had to head back to shore missing out on our snorkeling adventure.
This excursion was definitely a highlight of the trip for me, even missing out on snorkeling. Unfortunately, we weren’t able to rebook since this was our last full day in Key West, but the charter company did refund a portion of our charter expense. This was generous and unexpected. We will definitely be back.
Here are some of my favorites picks for a day kayaking, snorkeling, sailing or even lounging at the pool.
Hemmingway House
There’s something intriguing about the great author Ernest Hemingway and stories of his great hunting and fishing adventures. This home is worth a visit and the docents do a wonderful job of moving large groups through the property and grounds, while providing great stories and information.
Audubon House Museum & Tropical Gardens
I was a bit surprised the house is in no way related to or affiliated with the National Audubon Society. However, if you love nature there is plenty to see and learn here. The Museum was established in 1960 by Key West native Colonel Mitchell Wolfson and his wife.
The home was originally built in the American Classic Revival architectural style of the mid 1800’s by Captain John Huling Geiger, Key West’s first harbor pilot. Captain Geiger raised a large family in the house and planted beautiful tropical vegetation. It was the beautiful plants which drew Audubon to the property during his visit in 1832. Audubon used cuttings from plants growing on the property in many of his art works, which you can view on your tour.
Shopping
We discovered Fausto’s Food Palace while wandering around town. When I saw it had been around since 1926, I knew it was special and had to check it out. I bough a few souvenirs including a Key Lime Margarita grilling sauce (check out my recipe below) and Chow Chow. I love chow chow on crisped bread or crackers spread with goat or cream cheese. Yum!
This marinade was delicious. I used it for our classic Shrimp from Hell recipe. Doesn’t get much easier than this.
Shrimp from Hell
- Clean and shell shrimp (about 24 large shrimp).
- Marinate shrimp. I allowed the shrimp to sit in the Key Lime Margarita grill sauce for 3-hours in the refrigerator. I also threw the extra sauce over a few scallops in a separate bowl.
- Place the shrimp on a slice of jalapeño pepper (you can substitute poblano peppers for less heat).
- Wrap shrimp and pepper with a slice of bacon and secure with a toothpick. I typically buy a pack of thick bacon that has about 16 slices, so I cut these long slices in half and use these to wrap the shrimp.
- Grill until the bacon is the desired level of crispiness, but don’t overcook the shrimp. Plan for about 20-30 minutes on a medium grill and flip half-way through. Put scallops on first, as they will take longer to cook.
- Enjoy with a cold cocktail!
Live music
The Green Parrot turned out to be one of our favorite spots. We were always able to find a seat, enjoy great music, and make new friends that we still stay in contact with. Such a laid back atmosphere. Everyone is having fun and friendly.
Sloppy Joe’s is iconic and no visit to Key West is complete with an afternoon or evening hanging out, having a few (or many 😉) drinks and enjoying live music and the ambience of Sloppy Joe’s.
More spots to grab a drink and enjoy live music
Other spots we enjoyed included Fogarty’s and Durty Harrys Bar. I love how the outdoors blends with the indoors at all of these Key West hangouts.
Irish Kevin’s Bar was a favorite of Pat’s. A little crude and part of the entertainment involved embarrassing people or goofy drinking games. Wasn’t really my thing, but very popular based on the crowds and we did have a fun time while we there.
Sunset Pier is a great place to stop for a drink. It gets extremely crowded so I recommend you camp out early for wonderful views and certainly great people watching.
Where to eat in Key West and Nearby
The food in the keys is fantastic, especially if you enjoy fresh seafood. Grouper was out of season during our visit, but we enjoyed plenty of oysters, shrimp, mahi mahi, and hog fish (delicate, white, moist meat). A common misconception is that all food in the south is fried. Not true. I ate plenty of healthy grilled seafood and vegetables.
Our favorite restaurants and bars
Thirsty Mermaid Happy Hour. This is a must do. I learned this tip from an on-line search. Great spot for a cold beer and delicious appetizers. We enjoyed steamed mussels and steamed clams
I also enjoyed Apalachicola oysters. These wild oysters are harvested from Apalachicola Bay in the Florida panhandle. Local oystermen shovel the bivalves off the bottom with long, rake-like tongs from small skiffs. Taste slightly salty and slightly sweet. No need for heavy cocktail sauce.
The Schooner Wharf Bar was a great spot for a sandwich and views of the boats docked in the marina. Lots of great options and little distinction between indoors and outdoors.
Bo’s Fish Wagon was a fantastic accidental discovery. This was one of the most casual places I have dined. This is definitely a ‘dive’ worth the experience. My grilled taco with guacamole and slaw and side of black beans was delicious.
Half Shell Raw Bar had a nice happy hour special on a dozen raw oysters. Along with a good salad, I called this dinner. Request a table along the dock so you watch the tarpin come up to the dock begging for food.
Late night spots for a quick bite after a few drinks and several sets of music include Pizza Joe’s and Jack Flats.
After kayaking, we had lunch on the dock at Hurricane Hole Restaurant, Bar & Marina. It offers a nice view of the marina, kayaks and standup paddle boards departing and returning and the tiki bar boats. I enjoyed a delicious shrimp wrap with fries and a cold beer. What a great meal after a great adventure.
At Geiger Key Marina we saw a group pull up in a boat to have their fish grilled for a nice meal with friends. The grill is open and near the dock seating so you can watch them grill the fish and enjoy the delicious smell of grilling food. Geiger Key is yet another spot with great live music.
Dante’s Key West Pool Bar & Restaurant is a spot we didn’t get to visit. This is on my itinerary for our next trip, especially if we fish. They offer ‘Hook & Cook’ and will prepare fish that you catch served along side dishes. The pool doesn’t look bad either 😉.
The trip back to Miami and on to Chicago
We headed back towards Miami after breakfast on Tuesday. Our arrangement was to spend our last night in Miami Beach before our Wednesday morning departure. On the way back, we grabbed lunch at Sparky’s Landing at Key Colony Beach behind the Holiday Inn. I ordered the tuna club, which I do recommend.
Return Trip
We spent last night in Miami Beach at the Casa Victoria Orchid. The hotel worked out well for us, but we did have to pay a resort fee and didn’t get to take advantage of the bikes or other amenities. It was in a great location and we could walk to the beach and stroll along Ocean Drive. Overall, it was nice and a great value for the area. I love the Art Deco architecture in Miami Beach.
Havana 1957 Cuban Cuisine – Dinner and a refreshing Mojito.
I can’t wait to get back to Key West. We would love to hear your travel tips and recommendation so we can book new adventures on our next trip.
Take care friends.
I can’t live without my summer dresses, flip flops and Teva sandals.