Romantic Weekend Adventure in Key West

Samantha Weck
Samantha Weck

Key West is at the southernmost tip of Florida. Here you can find amazing wildlife, beautiful views, and unlimited possibilities. You can drive, fly, or even sail to Key West. Key West has its own international airport which can be convenient for those who love to fly. You can’t go wrong with this destination as there is a little something for everyone. Especially, if you’re looking for the perfect place to have a romantic vacation with your partner.

When to Visit

Winter is Key West’s high season. This is due to lower temperatures and people wanting to escape the snow. You can visit, however, expect higher prices. The best time to visit is between the months of March and May. Temperatures haven’t risen too high yet, but most of the crowds have dispersed. Prices start to drop around this time as well. Summer and Fall experience high temperatures as well as hurricane season. Hurricane season is from June to November so if you wish to visit during these months, be sure to keep an eye on the weather forecasts and get travel insurance. No matter what though, there are things to do year-round at this destination.

Where to Stay

Despite being a small area, there are many accommodations to choose from. You can Airbnb it and stay in a vacation rental, or stay in a hotel. Both have large ranges depending on the amenities you are looking for. If you’re looking to have everything in one place, resorts are the way to go. Most of them have spas and restaurants on-site. One resort I recommend is Casa Marina Key West. They are a Waldorf Astoria resort. They have a restaurant and bar on-site. There is also a spa facility available so you and your partner can enjoy a relaxing weekend.

The Beach

There are multiple beaches throughout Key West though I would love to highlight two beaches. The first beach is Higgs Beach. There is a boardwalk there that is fun to walk on. It also hosts the only shore-accessible underwater marine park. Another beach is Fort Zachary Historic State Park. Not only is there a beach, but also nature trails and a restaurant on-site if you don’t want to wander far. My personal choice is Higgs Beach because I absolutely love animals and always found it romantic to go to an aquarium or zoo with my partner. It’s a fun date where we could be casual. There’s also a boardwalk if you want to take a break from the sand but still want to be near the water.

Things To Do

There are so many activities that you can do with your partner. The number one must do that I recommend is the Mallory Square Sunset event. On evenings with good weather, a variety of performers come out to Mallory Square to create a street festival. The sunset with all its pink and orange hues is perfect for a photo op or just to enjoy while listening to some fun music.

If you’re looking for a low cost way to explore the island, why not rent a bike? You can explore the area freely while feeling the ocean breeze as you ride around. Not into exercise? Not a problem. There are many sightseeing tours available walking tours, on and off trolley tours, kayaking and sailing tours. The possibilities are endless. Into spookiness? There are ghost tours available. Cuddling with your partner while listening to scary stories is a fun time. There are a variety of tours to meet your romantic and/or adventure needs.

Are museums or nature preserves an interest you and your partner share? A fun date idea would be to visit some of the historic homes in the area. You can tour Ernest Hemmingway’s former residence. The residence is open daily and they provide twenty to thirty-minute guided tours. You can walk in, but they do recommend reservations for the guided tour due to popularity. There are also beautiful gardens on-site that you can enjoy. Another residence to visit is the Audubon House Gallery. They feature a unique collection of Audubon art that’s also available for sale. Even if you’re not interested in art, they have tropical gardens on the property that is definitely worth a visit. One final place I recommend is the Key West Butterfly & Nature Conservatory. I absolutely love butterflies. They are so pretty and I love learning about the different species of butterflies. They offer special twilight toward if you’re looking for a more romantic setting and they can hold a private commitment ceremony if you’re looking to make this romantic vacation into something even more special.

The final activity I recommend is treating yourself and your partner to a spa day. Most resorts will have a spa on-site, but there are a variety of spa businesses throughout the area that offer a variety of services such as massages, facials, body wraps and more. Imagine getting spa services then heading back to your room and enjoying room service, some champagne and intimate alone time with your partner.

The Food

You will not starve when visiting Key West. There are many restaurants in the area that are within walking distance of your accommodations or the beach. Most restaurants will have seafood options, but if you’re not the biggest seafood fan like myself, they have other options available for you to enjoy.

For breakfast, I recommend are Banana Café and Two Friends Patio Restaurant. Banana Café has traditional American breakfast as well as sweet and savory crepe options available if you’re looking for something different. Two Friends Patio Restaurant has a smaller breakfast menu, but not any less good. They have mouthwatering omelette options and sweet pancakes. They also have key lime french toast which sounds absolutely amazing. That’s my next stop when I go to Key West. For lunch, I recommend Santiago’s Bodega and Seaside Cafe at the Mansion. Santiago’s Bodega is near Fort Zachary Taylor Historic State Park and Ernest Hemmingway’s Home and Museum that I mentioned earlier. They are the absolute perfect place if you love tapas dishes. They have a variety of cold and hot tapas for you and your partner to enjoy. They also do brunch on the weekends. Seaside Cafe at the Mansion has wood-fired sandwiches and artisanal pizzas which are the perfect light lunches during an active day. They also have frozen cocktails to help cool you down. For dinner, I recommend Southernmost Beach Cafe and El Meson de Pepe. Southernmost Beach Cafe is a blend of Caribbean and Asian-fusion cuisine. They have a fresh off the hook section on their menu for those who love fresh seafood, but also beef and veggie options as well. The restaurant has a fun atmosphere that makes you feel like you’re taken care of. El Meson de Pepe offers traditional Cuban dishes and is close to Mallory Square. You can have dinner there and then enjoy the sunset celebrations afterwards. They also have a patio bar if you want to sit outside.


Key West has so many options that you can customize the trip how you want to. Tripvector is very helpful with creating an interactive schedule that you can see. You can also wing it if you’re not the biggest planner. I am guilty of just making a list of activities, ranking them, then just seeing how my days go. Enjoy your time in Key West. You will not be disappointed.

Due to current circumstances with the pandemic, it is highly recommended to speak with the facilities you wish to visit to ask about their operating hours and covid-19 policies so that you may be able to make the most out of your trip.

Samantha Weck
Samantha Weck