The Ultimate Key West Guide for Couples

Whether you’re looking for exciting activities like party boat fishing charters, exploring the local food scene, or soaking up the sun on a private beach at the Pier House, Key West has something for every couple. From stunning sunsets at rooftop bars to indulging in chocolate-covered key lime pie on a stick, you'll find endless options to create unforgettable memories. This guide is packed with tips, recommendations, and must-do activities to help you plan the perfect Key West getaway.

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Flying in

Fortunately, we were able to fly directly to Key West, but usually travelers will fly to Miami, enjoy a night or two in the city and then make a mini road trip to Key West. If that’s something you’re planning to do, be sure to check out my Road Trip Essentials blog or, even better, my 7 Road Trip Safety Tips That Could Save Your Life blog to help you prepare for the journey.

**Bonus Tip**

You can easily book both your car rental and flight through Expedia, and while you're at it, be sure to sign up for their OneKey Rewards program. You’ll enjoy discounts, exclusive deals, and earn points right off the bat. It's too great of an offer not to share, especially if you're planning to book your flight, stay, and car rental all through Expedia!

View this Interactive Map that you can save and take with you!

Best Time of Year to Go

There’s really no bad time to visit Key West, though it's best to avoid hurricane season, which typically runs from June to Octoberish. While the risk of storms can disrupt your plans, the upside is fewer crowds during the FALL months if you can plan around that time. However, keep in mind that the later summer months tend to be hot and humid. We visited in April, and it was the perfect time—temperatures were in the low 80s, the weather was ideal for boating, fishing, and diving, with the added bonus of fewer crowds.

Where To Stay

We stayed at The Opal Key Resort for our trip, although we had initially hoped to book at The Pier House Unfortunately, there were no available rooms for our dates, but we were fortunate enough to gain access to their private beach for one day. It was an incredible experience, complete with a floating dock, delicious drinks, and a friendly bartending staff who made sure we had a exceptional experience. We’ll definitely book The Pier House on our next visit to Key West. That said, our stay at The Opal Key Resort was unforgettable. We enjoyed watching the sunset from the Rooftop Bar every evening, which offered stunning views. I believe the rooftop is exclusive to hotel guests, so it was a real treat to have nightly front-row seats to the breathtaking Key West sunsets and by the way, the food was top-notch.

Exclusive Rooftop Bar Sunset and food at The Opal

My barracuda I caught fishing on the flats with Feeling Fishy Boat Charters. Chris was such a great guide!

Usually I’m a Vrbo girl but look how prettyyy! The Pier House exudes a perfect blend of style and luxury offering some serious travel aesthetic vibes. I can’t wait to book this place for our next Key West trip.

Private Vrbo Home Rentals

While I typically prefer staying in private home rentals when I travel, Key West is one of the few exceptions. I love the added amenities that hotels offer, such as the private beach at The Pier House and the exclusive rooftop bar at The Opal Key Resort. That said, there are some incredible Vrbo properties on the island that are definitely worth considering with exceptional guest reviews. Plus, renting a Vrbo with another couple or two can help save money while still offering the luxury of private rooms. Some of these properties even have their own private pools, so you can enjoy your vacation experience without having to share it with a crowded public pool and their shenanigans. I have added a few exceptional Vrbos below that are worth considering. Click on the links below for more info and booking information. Vrbo's are listed in order they appear on the slide show.

1. Southernmost Belle

2. Casa Victoria Old Town

3. Chick-a-pea Cottage

4. Darling Duval

5. Lost Shaker of Salt

Mile 0 marker that can be found on the interactive map!

Where to Eat & Drink

Blue Heaven is a must for breakfast or brunch with its laid back ambiance, history, and unforgettable food, it is a go-to spot in Key West. The Eggs Benedict was phenomenal with the lobster benedict being the restaurant favorite but the real showstopper goes to their fluffy Key Lime Pie. I’ve heard great things about their banana nut bread as well but for sure do not miss out on a slice of key lime heaven if you stop by. Ernest Hemmingway is said to have frequented this spot.

Hanks Hair of the Dog Saloon was one of our favorite spots that we stopped at multiple times during our trip to enjoy some cold beer, a good happy hour, live bands, and a great food truck called Garbo’s. This place was always poppin when we stopped by and they had some really cute shirts to pick from, which is saying a lot from me because I’m really picky about apparel. Bonus: Dogs are welcome 😊

Fine Dining

If you are looking for a romantic fine dining experience with an unforgettable Ferry ride to the restaurant, Latitudes is the place to go. Be sure to book well in advance though, I suggest even before your trip because this place is always fully booked.

The service was exceptional—friendly, attentive, and genuinely welcoming. Each dish was expertly prepared and beautifully presented, showcasing the restaurant’s commitment to high-quality, delicious food. Dining on Sunset Key was truly special, and the ferry ride added a unique touch to the entire experience.

The White Tarpon Bar & Restaurant

I had the best Key Lime Martini with a graham cracker crust rim here! It is located right off the marina and is where we stopped right after our fishing boat charter. They have a great happy hour from 3-5:30 daily with half off domestic beer, well drinks & house wines with some $7 dollar bites as well.

From juicy burgers & cold beer to live music to stylish apparel at Garbos food truck, Hank's was one of our favorite hangout spots during our stay!

Kermit’s Key Lime Pie Shop: It is absolutely worth grabbing a bicycle rental and going for a ride down to Kermit’s Key Lime Pie Shop for a chocolate covered key lime pie on a stick and while you’re at it, take a bike ride down to the Southernmost Point of the Continental USA. You can’t get anymore southern than this. Here’s a photo of my hubby snapping a quick pic of me riding my bike rental by the monument since we don’t like waiting in line for pictures lol.

Things To Do

Southernmost Point of the Continental USA

This is definitely a great spot to snap a photo and take in the stunning coastal views! Just be prepared to wait in line for a picture, as it's a popular spot. As I mentioned earlier, we biked over to this area and stopped by Louie’s Backyard to meet up with some friends afterward. The restaurant served fresh seafood and offered beautiful views of the coast, right off the dock.

Fishing Boat Charters

During our time in Key West, we went on two fishing boat charters, and let me tell you, the options are endless—Party Boat Fishing Charters, Flat Fishing, Catamarans to the reef, and deep sea fishing, just to name a few. Our first adventure was on a Party Boat Fishing Charter, where we caught a few fish, but the real excitement happened when one guy was reeling in his catch and, out of nowhere, had his fish attacked and eaten by a barracuda! It was absolutely wild to watch!

We were really hoping to book a deep sea fishing charter to try our luck at catching dorado, tarpon, marlin, or other billfish, but unfortunately, the weather didn’t cooperate. We’ll just have to save that adventure for next time.

Instead, we booked a charter to the flats with Feelin Fishy Charters, where we had an absolute blast catching barracudas—one of which became lunch for a lemon shark! The shark bit our barracuda in half just as we were about to pull it onto the boat. (Ah, the circle of life…) This fishing experience was definitely the highlight of our trip. I only wish we had more time to spend out on the water, but I'm sure we'll get an opportunity in the future. Oh yeah, I caught the lemon shark biting our barracuda in half on video!

The Southernmost Point that can also be found on the interactive map

Lemon shark bites our cuda in half fishing on the flats with Feeling Fishy Charters. **Video is graphic**

Feed The Tarpons

I want to go back and do this so bad! It was honestly something that we just didn’t get around to and I regret not doing. I hear reeling a tarpon in is one of the most challenging and rewarding fights of a fisherman’s life but can you imagine how cool it would be to have one snatch a fish right out of your bare hands? Maybe I’m crazy, but it would be an epic photo to snap!

Duval Street

This street was Live at night! Irish Kevin’s was the place to be, where they cranked up the volume on songs like Sweet Caroline and Come on Eileen, to the max because everyone in the bar was singing along. The vibe was contagious and exciting every night, and the people were so friendly, which oddly, kind of gave off a community feel to it. We ended up going there almost every night we were in Key West—it quickly became our favorite bar.

Oh, and if you're into quirky spots, check out The Smallest Bar in the U.S., also located on Duval Street. It’s a fun little stop! If hopping around bars is your thing, don’t miss pub crawl called The Duval Crawl—it’s the perfect way to hit up some of the most iconic bars in the area!

Us at the Smallest Bar on Duval Street

Conclusion

From stunning sunsets and wild boat charters to delicious meals and lively bars, there's no shortage of things to do. Whether you're spending your day at a private beach, enjoying a fine dining experience on Sunset Key, or exploring the nightlife on Duval Street, or Tarpon Feeding with your bare hands, Key West has no shortage of activities to pick from. We made unforgettable memories during our time here leaving us itching to go back and make more! Check out my 5 Best Resorts in Key West for a more in depth look at the best resorts on the island! Thank you for coming to my coffee talk.

Cheers 🥂✨

&

God Bless

-Alinea