Love, Laughter, and Laid-back Vibes: A Couple’s Guide to Key West Fun

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Jake Cain is an entrepreneur and writer from Cincinnati, Ohio. He spends his free time driving around the country in his late 90’s conversion van, affectionately known as the “Monster Van” with his wife and 3 boys.

We recently had the chance to get away as a couple in Key West, and we soon learned that this laid-back paradise is the perfect spot for a fun and relaxing couples trip. 

From resorts to boat rides and even a little shopping, here are our top must-do items for couples vacationing in Key West. 

Spend a Day at The Marker Key West Harbor Resort

The Marker Key West
Image Credit: The Marker Key West.

Enjoying a day pass to The Marker Key West Harbor Resort was truly a VIP luxury experience, and it came without the price tag of an overnight resort stay. The resort’s reasonably-priced day pass got us access to three saltwater pools, walled off from the busy surrounding seaport by the rooms of the resort. When we weren’t lounging by the pool in our private cabana, we used the resort as a home base to explore Key West’s Historic Seaport. It was a perfect blend of sightseeing and relaxation. 

Explore With a Private Boat Tour

Key West Boat Tour
Image Credit: Jake Cain.

We thought we’d seen all of Key West’s hidden gems, but our private boat rental through GetMyBoat proved us wrong. We swam through mangrove tunnels, relaxed on secluded sandbars, and even got a glimpse of the unique world of houseboats, all while enjoying the laid-back charm of our guide. If you’re not exactly “boat people” but want an unforgettable aquatic adventure, renting a boat with a captain is undoubtedly the way to go in Key West – an experience that turned out to be the highlight of our trip!

Stop by the Original Margaritaville Store

ukulele on beach

If you find yourself in Key West, you have to swing by the OG Margaritaville store on Duval Street – it’s like stepping into Jimmy Buffett’s personal stash of island vibes. That makes perfect sense, too, considering Key West is widely believed to be the inspiration for Buffet’s “tropical rock” vibe. This shop has everything Margaritaville, from cool threads to margarita gear. If you’re up for the full-on Parrothead experience, extend the chill vibes to your accommodations and check out the Margaritaville Key West Resort. 

Enjoy a Brew at the Waterfront Brewery

Image Credit: Deposit Photos.

For a laid-back spot to soak in the Key West vibes, you have to hit up the Waterfront Brewery. It was our first stop before hitting the Marker for our resort day, and it was the perfect start to a relaxing day. Tucked away in the historic seaport, it’s got this cool, easygoing atmosphere – perfect for kicking back with your significant other. This brewery serves up beers brewed on-site and has a robust menu. Grab a craft brew, enjoy the waterfront view, and let the good times roll! 

Soak up the Vibes at Mallory Square

Mallory Square Key West
Image Credit: Deposit Photos.

When you’re in Key West, you can’t miss the iconic Mallory Square. It’s the heart of the party, especially when the sun starts its daily descent. Head there for the famous sunset celebration – street performers, live music, and just an all-around good time. The vibe is so lively, and you’ll catch that perfect Key West sunset that everyone talks about.

Sip Your Way Through a Craft Cocktail Tour

Mocktail Cocktail
Image Credit: Depositphotos.

Embark on a Key West Craft Cocktail Crawl for a taste of the island’s hidden gems. Join a local guide on a journey through five unique spots, each with its own story – from a historic mansion to a converted hospital-turned-boutique hotel. During the crawl, you’ll get to try out delicious craft cocktails and a few gourmet bites, all while soaking in the city’s history and culture. 

Take a Snorkeling Trip

Photo Credit: Deposit Photos.

Take a dip into the clear waters with a laid-back snorkeling sesh – you’ll find a bunch of companies doing these cool trips, and many of them include kayaking and sailing, too. Cruise around with friendly crews, check out the colorful fish, and get up close to the coral reefs. Whether you’re a pro or just testing the waters, these snorkeling excursions are the real deal.

Get Spooky With a Ghost Tour

ghost town
Image Credit: Nathan Wright on Unsplash.

The chill, vibrant side of Key West? That’s easy to find. But this town has a spooky side, too. If you like the adrenaline burst of a good scare, try out one of Key West’s ghost tours. Walking and trolley tours will take you through the most haunted spots in town, dishing out an equal serving of history and fright. 

Take a Stroll on Duval Street

duval street key west
Image Credit: Deposit Photos.

It’s not a trip to Key West without hitting up Duval Street – it’s like the heartbeat of the island’s vibe. This iconic strip is lined with quirky shops, cool bars, and live music joints. It’s a chill spot for a casual wander, and if you’re up for it, dive into the vibrant nightlife scene. Duval Street has that perfect mix of laid-back charm and lively energy, making it a must-see for soaking in the Key West spirit.

Enjoy the Key West Butterfly and Nature Conservatory

Image Credit: Deposit Photos.

Couples looking for a sweet spot to just be together in Key West should definitely swing by the Butterfly and Nature Conservatory. Picture this: a tropical haven with butterflies fluttering around. It’s a relaxed vibe, perfect for a leisurely stroll hand in hand. Trust me, it’s a magical escape and a fantastic way to enjoy each other’s company in Key West.

One Night in Key West’s Margaritaville: Why We’re Already Planning a Return!

margaritaville beach house
Image Credit: Margaritaville Beach House.

We’re not strangers to wasting away in Margaritaville, but we recently visited the Key West location for the first time. From the relaxing vibes to the perfect location, one night wasn’t enough. Check out why we’re already making plans for a return trip here: 

One Night in Key West’s Margaritaville: Why We’re Already Planning a Return!

Beer Paradise Found: My Journey to Oktoberfest in Margaritaville

margaritaville oktoberfest
Image Credit: Margaritaville Island Resort Riviera Maya

No, we weren’t sipping on tequila and lime, but it was still an unforgettable experience! We had the chance to see just how great island vibes and Oktoberfest can be together- come check out the beer paradise! 

Beer Paradise Found: My Journey to Oktoberfest in Margaritaville

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