Perfect 5 Day Itinerary
Our annual family trip (2018) was a success. We usually try to go somewhere new each year, but some places are too good to pass up. Especially Key West when there are endless things to do, so we decided to return here. This trip had some big shoes to fill, but I would do both itineraries all over again.
We flew into Fort Lauderdale thanks to Spirit and their super cheap direct flights from Myrtle Beach. After picking up our rental car, the road trip officially began. Honestly, I highly recommend driving through the Keys. The views are amazing, and it’s all part of the fun making stops along the way. It’s a drive you don’t want to miss.
Our first stop this trip was at Robbie’s Marina. This place is well known and a little touristy, but it’s a must-see. You can’t miss it! It’s located on the right off the main road at mile marker 77.5. The food, drinks, and views were just what we needed to begin our vacation. You must feed the tarpons before leaving. It’s a few bucks for a bucket of fish and worth every penny.
The Gates Hotel Key West
Our next stop consisted of checking into our charming hotel. The Gates Hotel in Key West welcomed us with rum punch and live music by the pool while we waited to check in. The rooms here are beachy chic and very on trend. Their pool is a standard pool with nothing to write home about, but the pool bar and the food truck make this place unique. I’m still thinking about those fish tacos.
The hotel is located right when you make it into Key West which means it is a little far from all the action. However, they provide a shuttle that runs every half hour to Duval Street. We found this helpful and not a hassle at all. This hotel was a great budget-friendly option for staying in Key West.
Our first stop in Key West was Wine-O Lounge at the La Concha Hotel for a much-needed wine tasting. This place is a hidden gem. It’s very trendy and a lot different from other spots in Key West. They also have a fantastic cheese plate to enjoy with the tasting. If you have time, try to check out the hotel’s rooftop.
The first night we made dinner reservations at Mangoe’s. I’m still dreaming about the lobster sushi roll — one of the best rolls I’ve ever had. We ended our night at a place we stumbled upon called Cowboy Billy’s: A honky tonk with a riding bull and nonstop country music. First night=success!
Day 2 consisted of our favorite activity. We charted a private boat to take us fishing and to sandbars for the day. Our charter began at 9 am, so we quickly grabbed Starbucks at the hotel before rushing to the marina. We booked with Fun In The Sun Charters our first trip to Key West a few years ago and had a blast, so we knew we wanted to book again. This company is very personable with incredible rates.
The first activity of the day included fishing. Each of us was able to catch a few yellow snappers that we would later eat for lunch. After we caught lunch, we boated through the mangroves to a secluded sandbar. We were able to see a stingray, tons of fish and even caught a nurse shark. Before the sharks lured in, we enjoyed swimming in the crystal clear water. At the end of the tour, our guide fileted our fish for the marina to cook for us. To me, this is what I call life — a day on the water catching your lunch. Ugh, I already want to go back.
Our next stop included dinner on Duval Street. Bagatelle is a historic home turned restaurant on Duval Street. We had a fantastic time eating lobster mac and cheese on the upstairs wrap around porch overlooking the hustle and bustle down below. This restaurant is rated one of the best in Key West for obvious reasons. It’s ambiance and detail to food are incredible.
We spent the rest of the evening strolling along Duval Street stopping in from place to place. We always have a great time at Kevin’s Irish Pub, and I even made a little cameo at The Smallest Bar in the United States.
Day 3 started with breakfast at Sarabeth’s. This restaurant came highly recommended. We sat outside on the patio which had plenty of fans to keep us cool. My dad is a pancake fanatic and is very peculiar. His favorite pancakes include my mom’s (of course) and McDonald’s (smh). To my surprise he gave Sarabeth’s pancakes an 8/10, so it’s definitiely worth a visit.
After a fun-filled two days, we decided to add in some relaxation by the hotel pool. We enjoyed fish tacos from the hotel’s food truck, The Blind Pig and soaking in the pool on a very humid August Day. Unfortunately, the live music was setting up when we had to leave for our next planned activity.
Key West is known for their Sunsets, and they even have nightly celebrations at Mallory Square dedicated to their sunsets. Another way to enjoy them is by boat. Our first family trip to Key West we had a blast on a Catamaran with Fury Adventures, but this time we decided to something a littel different.
We booked the Wine & Sunset Sail with Danger Charters. The Sunset Sail began with champagne followed by three different white wines and three different red wines. The company did a great job of explaining the wines and also paired each with hor d’oeuvres complete with chocolate covered strawberries at the end. If you are not much of a wine drinker, they also provide craft beers and sparkling water. We had a great time chatting with the crew and other guests which included a group from South Carolina.
After the Wine & Sail, we were pretty hungry, so we walked over to the restaurant First Flight to have another meal of lobster. I guess you all are sensing a theme at this point, and to our defense, this trip was during lobster week in Key West, so it was only natural to take advantage of the fresh catches. This restaurant has been on my bucket list for a while due to its unique history.
The First Flight Island restaurant is the former building of the Pan Am Airways Key West Headquarters. The first international airline ticket in the US was sold right here. The first actual flight in 1928 was from Key West to Havana, Cuba with seven passengers on board. We learned all of this history right in the restaurant. It’s an excellent restaurant full of American history, fun ambiance, and delicious food.
We decided to spend the rest of the weekend hanging out in Miami. Before beginning the beautiful road trip on the way back, we stopped at Matt’s Stock Island Restaurant. It’s the first island on the way out of Key West. This restaurant has a modern rustic feel with delicious food.
After 3.5 hours in the car, we checked into The Confidante Hotel. I’ve wanted to stay here every since discovering the Instagram-worthy hotel. The colors and decor are straight out of the fifties. I highly recommend this place.
That night we headed out to Wynwood for dinner at the Prohibition. We’ve been here before and wanted my parents to enjoy the great food and atmosphere. This restaurant has a speakeasy vibe that delivers food family style. After dinner, we had dessert at Beaker & Gray. I would go back to Miami just to have the mini cookie dough doughnuts with mini vanilla milkshakes. OMG, so amazing.
The last day of our adventure was spent poolside at The Confidante Hotel relaxing with margaritas and jalapeno popsciles. We flew out this afternoon, but still wanted to enjoy some time in the sun before heading back to reality. Key West continues to be one of our favorite destinations, and it’s right here in our own backyard. If you have any other suggestions or recommendations for Key West or Miami, leave them in the comments down below.
Key West Must-Haves