Your Guide to a Romantic Island Getaway | Things to Do in Key West for Couples

Looking for fun things to do in Key West for couples? You’re in the right place! My partner and I went on a tropical getaway to Key West and had the most incredible time, discovering so many awesome adventures along the way. Now, it’s your turn!

Whether you want romance and relaxation or some tropical fun in the sun, we’ve got just the adult Key West activities for you from day to night. We’re talkin’ adrenaline pumping watersports and outdoor excursions, historical and artistic sites, yummy foodie finds, lively nightlife, group couple activities and ways to turn up the romance on your trip. I even mention clothing optional activities for my nudist friends. This is an adult vacation after all. No kids allowed. This is your guide to a romantic island getaway. Read on! 

In this blog, I share…

• Things to Do in Key West for Couples
• Outdoor Adventure
• Museums and Galleries
• Romantic Key West Activities
• Naked and Unafraid: Activities for Nudists in Key West
• Explore Nightlife in Key West
• Where to Grab a Drink in Key West
• Where to Eat in Key West
• Where to Get Key Lime Pie
• Where to Stay, Hotels in Key West

Plan a Fun Trip to Key West

For only being 4.20 sq miles, there are a lot of Key West activities to explore! From Caribbean style bars, oceanfront restaurants and live entertainment to watersport adventures, quirky boutique shops and beautiful sights, the “Conch Republic” has it all.

Home to the famous and the infamous alike, Key West has had an incredible cast of characters that has shaped it into the destination that it is today. 

As the Southernmost Point of the United States and the last island in the chain that makes up the Florida Keys, Key West ends at Mile Marker 0 where your adventure begins.

Things to Do in Key West for Couples

Whether you want to be outdoors soaking up the sun or stay cool inside, there are so many fun Key West activities that I couldn’t possibly list them all here! I’ll do my best to list the ones I think you’ll enjoy.

Key West by Day

Outdoor Adventure

• Jet Skiing

I’ve been jet skiing more times and places than I can count. But, this Key West jet skiing tour was my favorite! It’s one of the best things to do in Key West for couples since you can ride with each other.

The adrenaline junkie that I am, I took the throttle while my brave partner sat behind me. Since he refused to hold on to me and opted for my life jacket’s straps instead, I was never really sure if he had fallen off and kept turning my head around while navigating the route so the waves didn’t flip us over. The ride was nothing short of exhilarating!

Later, we reached a more calming point where we hopped off our jet skis and did some swimming.

It sounds silly but somehow, it felt like we were on a mission to escape the big waves coming after us, which brought us closer together.

Book your tour here.

• Snorkeling

This was a great tour. You start off taking a boat ride out to an area with plentiful marine coral reefs. The trick is to not swim fast but rather, lie on the surface of the ocean and let the marine life come to you. You can also do a snorkel with dolphins or, with breakfast and mimosas. Now, that’s my kind of morning. 😉

• Beachside Parasailing

There are few experiences where you get to feel like a bird. Parasailing is one of them. It felt incredible to fly through the wind as our legs dangled high above the water! Every now and then, the boat driver would slow down to let us dunk into the water which was awesome. This experience is not for those scared of heights!  

Book your adventure here.

Would you and your S.O. rather be on the water than in the water? Don’t worry!  There are plenty of other things to do in Key West for couples.

• Dolphin Sunset Sail

This sailboat takes you around the beautiful Florida Keys as you watch dolphins and enjoy wine & tapas pairings. I also mention more fun boat trips later in this blog. Read on!

• Oceanside Bike Ride

It’s so fun to grab a beach cruiser and ride along the water or through Old Town Key West. Many hotels even offer free bike rentals. If yours doesn’t, there are plenty of rental places all around town. You can also rent a surrey bike.

• Explore Key West’s historic Old Town

During the day, explore Key West’s historic Old Town, where you’ll find Mallory Square.

Do some shopping and pick up a souvenir, catch a Conch Tour Train, or visit Key West’s Aquarium or Shipwreck Museum, or admire the Key West tree lined streets and beach cottages while strolling hand in hand with your honey, as long as you don’t mind the occasional rooster clucking passed you on the sidewalk.

• Explore Duval St.

This 8 block stretch which runs from the Gulf of Mexico to the Atlantic Ocean, is undoubtedly Key West’s most popular (and busiest) street.

On Duval, you’ll find everything from shops, tour companies and art galleries to key lime pie bakeries, Jimmy Buffet-esque restaurants (even Margaritaville) and tropical themed biker bars. Do the “Duval Crawl” and go bar hopping up and down the block.

• Hit the Beach

While locals and frequent visitors like myself typically don’t go to Key West for the beach, (that’s what you do in other Florida keys) if you do want to have a beach day in Key West, there are some great spots.

Fort Zachary Taylor Historic State Park and Beach (a.k.a. “Fort Zach”) has the perfect waterfront set up for a day of picnicking or having a BBQ (grills available). You can also take a stroll, dip in the water or ride your bike. It’s very spread out so there is no problem avoiding crowds.

If you’re looking for a less crowded, more laid-back beach vibe, Higgs Beach is for you. It’s much smaller than the other beaches like Smathers.

However, if you do want a lively beach atmosphere, you’ll love Smathers Beach. Not only does its clear blue water and white sand make it a beautiful beach, it also has modern conveniences like restrooms, picnic tables, showers, food vendors and sundries as well as equipment rental for fun activities like parasailing, kayaking and more!

• Southernmost Point of the US 

This concrete buoy marks, as the name implies, the southernmost point of the contiguous United States (lower 48). Don’t forget to snap a pic in front of Mile Marker “0” sign as well where you’re just 90 miles from Cuba, closer than Miami.

Pro Tip:

Crowds are abundant at sunset. There is also limited street parking. To avoid wait times and get a clear shot without people, early morning hours and midweek are best, but don’t worry if you can’t. People are generally very courteous and politely wait in line while others are taking photos. Be kind and do the same. 

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Museums and Galleries

There is so much history and art to explore in Key West!

• The Hemingway Home & Museum

Not to be outdone as one of America’s foremost wordsmiths, Ernest Hemingway, a Key West local, enjoyed his fun in the sun which is evident by the location of his stunning home.

The Hemingway House is for anyone interested in history, literature, architecture, art or just a fan of the author himself. It’s open to visitors, except maybe me…

It’s possible I’m blacklisted and will never be invited back after dipping my toes in Hemingway’s swimming pool (couldn’t help myself).

The Tour

My partner and I enjoyed wandering off on our own more than the tour itself which was a bit crowded and shorter than expected.

Must See

Get a peek into his private study where he wrote some of his most classic novels and get a look at the coin he threw into the then wet pavement during an argument with one of his wives. If you’re a cat lover, you’ll adore the “cat garden” on the property which is home to 60 polydactyl (six-toed) cats.

Book a tour

But, Hemingway’s home isn’t the only famous house in Key West…

• Truman’s Little White House

For history and architectural buffs, this is definitely a stop for you. 

Built in 1890, the house served as naval quarters for officers until it became a sanctuary and working White House for several presidents in office when they needed a reprieve like President Harry S. Truman who frequented the Little White House from 1946-52. One thing is for sure, the Little White House is surely the most laid-back place for all its epic history.

The Tour

We got a combo package. The tour itself is pretty short and sweet. We walked around the house and watched a short movie on Harry S. Truman before relaxing on the benches outside to admire the charm of Key West and take in the warm air and sunshine.  

Take a look around the house as well as the grounds. There’s so much to see. The tour is a nice way to get out of the humidity for the afternoon.

Book your tour here.

FUN FACT

Key West Roosters & Chickens

The most photographed residents in Key West are these beautiful, plumed birds who are descendants from Cuba/Florida’s cockfighting days (thankfully outlawed). You’ll see these guys roaming around throughout the town. Take heed though, even the new generation hasn’t forgotten their fighting instincts. They are all fiercely protective of their space. So don’t get too close.

• Key West Museum of Art and History

Here, you can explore Florida Key’s culture through the museum’s vast collection of art pieces and historical artifacts. The museum’s exhibits are continuously updated.

After touring all that the inside has to offer, walk outside in the back and see the many life sized, painted sculptures they have including Key West’s own Hemingway. They’re fun for photo opps. 😉

• Wyland Gallery

If you only stop at one art gallery on your Key West trip, make it this one. I’ve been a fan of world-renowned marine life artist Robert Wyland (or, “Wyland” as he’s better known), ever since my mom introduced me to him. His large scale paintings are absolutely beautiful, from his Whaling Walls series across the country to his life-like sculptures. A big bonus to visiting his gallery is…you never know if the artist himself will be in the gallery. What a treat. He truly is one of the greatest artists of our time. You may have even seen his larger than life murals of under the sea life gracing the side of buildings.

If you or your honey have a favorite sea creature, a cute way to commemorate your time in Key West would be to create your own custom keychains then you’ll always remember your trip together. You can even make the keychain of the two of you, you just upload the image.

Romantic Key West Activities

A lot of places in Key West are laid back, casual and dare I say divey, which can leave the romantic type of couple wondering where they can share a more elegant, special experience. Luckily, there are many romantic activities in Key West.

• Couples Massage

Get ready to unwind with a beachside massage at day spa, Spa al Maré. Relax while listening to the waves crash and feeling the calming breeze on your skin.

If you and your partner want to feel especially pampered, book a package with Key West’s only full-service spa, The Spa at Pier House, where you’ll be pampered from head to toe.

And if you like your spa treatment to linger long after the massage is over, you’re sure to be impressed with the elegant tropical atmosphere that Spa Terre has created. They also offer amenities like whirlpool tubs and a pool bar.

• Personalized Beach Picnic

Now you can enjoy your very own picture worthy beach picnic set up for you and your loved one by Picnic Lane or Key West Picnics. You can even request a theme or special occasion.

If the culinary experience has your heart more than the cutesy decor, try…

• Elegant Beach Dinner

Four Marlins Restaurant offers an incredible “Tide to Table” dining experience right on the sand. Call 305-293-6250 to make a reservation.

After dinner, take a short stroll out to the gazebo and sneak a kiss at sunset.

• Romantic Boat Experience

Being surrounded by strangers on a boat while listening to someone over a microphone has the tendency to kill romance. For a more intimate time, charter a private boat instead.

Private Luxury Boat

This luxury boat offers full day and 1/2 day charters for up to 6 people, taking you wherever you wish to go in the lower Florida keys. Based on your answers to their questionnaire, they will even create a personalized experience for you.

Private Tiki Boat Sunset Cruise

For a less expensive, more laid-back option, try a private tiki boat which holds up to 6 people.

If you’d rather have the food, alcoholic beverages and live music already there for you, try…

Dolphin Snorkel & Sunset Dinner

Get ready for a full day of fun with this cruise adventure! In the morning, head out on a 3-hour dolphin snorkel adventure with a break in between to relax and get dolled up at your hotel before returning back on the boat in the evening for a lovely sunset dinner and drinks (open bar) with live music.

• Proposal Package

Hey, it’s your tropical getaway, if you love birds want to get hitched, who am I to stop you? 😉 For the especially romantic who want memories to last a lifetime together, this proposal package includes everything you need to set the scene and pop the question including transportation from hotel, dinner, decor and more. All they’ll have to do is say, “I Do”.. (crossing fingers)

• Engrave Jewelry

What better way to commemorate your romantic trip together than by getting something engraved? Emeralds International has a selection of Key West-esque pieces to choose from and even offers engraving.

• Sexy Skinny Dip

We all want the kind of steamy romance we read about in novels, maybe minus the cops getting called. Get a private pool in your hotel suite and go to town!

Adult only hotel H2O offers Deluxe King Suites and Superior King Suites with your own private pool, patio & bench swing.

Want more room to spread out? Opt for a private pool by renting a beach cottage instead. Marriott Bonvoy members will earn rewards toward their stay.

You might also like…

Miami to Key West Drive: What to Do in the Upper to Middle Florida Keys

Getting My Scuba Certification in Florida: It Starts with the Right Dive Shop

Naked and Unafraid: Activities for Nudists in Key West

And for those with the “anything goes” attitude for whom romance does not ooze from every pore… I’ve got some Key West activities that add a little extra excitement. These clothing-optional facilities and excursions offer you the chance to be free and uninhibited.

Luckily, Key West is open minded. Try La Te Da, a hotel, restaurant and bar or Garden of Eden (I share more about later in this blog).

• Clothing Optional Boat charters

Many offer nude sunset and cocktail cruises as well as nude watersports like snorkeling and swimming with dolphins.

Cruise Bare

If you’re a naturalist thrill seeker wanting to enjoy sailing on a cruise, this is for you.

First time? Nervous, novice nudists (say that 3x fast), Read this.

Dream Catcher Charters

Grab a cocktail and snack and get ready to relax! This tour company offers 4, 6 & 8 hour custom boat charters for groups of up to 6 people to do whatever you desire – snorkeling, swimming, fishing, you name it. They provide the equipment, all you need to do is bare your body and soul. For best rates, text: 1-305-304-0497

Clothing Optional Charters

If dolphins, snorkeling and sunsets sound like your cup of tea, this charter is right up your alley! Since they only book private charters, you must have your own group assembled. If you’re hoping to be put with other nudists, they recommend connecting with nudist organizations on social media for friends to book this charter with.

For more info, call 305-800-NUDE, yes that’s really their number.😉

Of course, you’re under no obligation to strip down on these excursions. Not to mention, you can do the same activities that don’t have nudity.

Key West by Night

Explore Nightlife

When the sun goes down, Key West comes alive in a whole different way.

• Key West Sunset Celebration at Mallory Square Dock

After a day of fun, head to Mallory Square Dock for Key West’s nightly sunset celebration, which starts 2 hours before the sun goes down. You’ll get to take in the beautiful waterfront views while enjoying street performers, arts and crafts and food vendors.

Grab a drink and take a stroll around with your partner. You can also check out Sunset Pier nearby, which is an eclectic and colorful tiki themed bar over a long deck with seafood, frozen cocktails and live music.

• See a show

Key West Theater is a great venue to see a show. The building was originally built in 1848 as a church and has since been converted to a fully functioning entertainment venue offering a large variety of shows and performances.

My partner and I always make it a tradition to see as many comedy shows in different cities as possible. We really enjoyed the line up here. 

• Do the “Duval Crawl”

If Duval Street is known for anything, it’s for making drinking a sport. Hey, it ain’t the “Duval Crawl” for nothin. 😉

But Duval isn’t the only street known for its bar scene…

Where to Grab a Drink in Key West

• Sloppy Joes

Made famous by Hemingway who was a frequent customer, Sloppy Joes is a great place to grab a cocktail.

• Captain Tony’s Saloon

As the original home of Sloppy Joe’s from 1922-1937, it has a reputation for being a divey spot with loads of character. The bar is named after Captain Tony who was mayor of Key West for a bit. Hemingway used to come here to drink while he wrote.

Listen to live music, have a drink and gaze up at the ceiling which has dollar bills and bras hanging from it. Before you leave, don’t forget to try your luck at tossing a coin into the mouth of a big fish above the bar’s entrance. 😉

• The Bull & Whistle Bar

One of the last standing open-air bars in Key West, The Bull and Whistle Bar is a local a treasure. Hemingway, Fidel Castro and Tennessee Williams were among its famous guests. The bar has 3 levels.

1st: “The Bull (live music, lively)

2nd: “The Whistle” (more low key, games, pool table, balcony)

3rd: “Garden of Eden”

Walk upstairs and you’ll find clothing optional bar, “Garden of Eden” which has lounge chairs and umbrellas for sun bathers as well as nightly music with a DJ. Some said removing clothes removed their inhibitions. However, there’s no pressure to remove clothes. There’s also body painting for anyone interested. No cell phones or cameras allowed.  

Now it’s time for something to eat!

Where to Eat in Key West

In typical Keys fashion, these restaurants’ atmospheres are very laid back and chill. Below, I’ve listed my favorite spots for food and entertainment. 😊

• Margaritaville

Key West is home to Jimmy Buffet, the genius who built his empire writing beach hits like “Margaritaville” and “It’s 5’oclock somewhere” while also enticing us with our bellies and vacation mindsets.

Key West is the original Margaritaville which, if you’ve never been, screams tropical beach getaway with boats you can dine in, a plate of sky high nachos, live music and a ceiling design of a world map to make you feel like a world traveler who’s just discovered paradise. For those not a fan of seafood, there are plenty of other tasty options.

You can also stay at his Margaritaville Beach House hotel.

Happy Hour is at the bar from Monday – Friday from 5 – 7 PM.

• Bahama Village Market

Just a few blocks from the Ernest Hemingway Home & Museum, we stumbled upon Bahama Village Market, a fun outdoor space with live music, sky deck, Rams Head Southernmost restaurant with a bloody mary bar and tropical plants all around.

My favorites:

• Tuna tartare
• Chicken wings
• Watermelon & feta salad
• Milkshake with pineapple, rum, coconut and vanilla ice cream

• Alonzo’s Oyster Bar

For lunch, we grabbed a table outside with views of the water. It wasn’t long before we noticed a crowd surrounding the dock. Running to get a better look, we saw Florida’s famous big Tarpon splashing out of the water. We also saw sharks. It was an awesome sight to see!   

What to order:

They primarily serve seafood and are known for their oyster dishes. The keys were experiencing red algae, so I opted for the mahi mahi, snapper and crab and avocado salad instead, which was our favorite.

• Pincher’s Crab Shack

For a no fuss seafood restaurant with relaxed vacation vibes, try Pinchers on Duval Street. I recommend sitting on the balcony for a view.

What to order:

Anything, literally. You can’t go wrong with their crab, which is what they’re best known for. Crab connoisseurs will appreciate all the different variations on the menu like Old Bay seasoned blue crab clusters, soft shell crab, crab cakes, crab & cheese dip, Alaskan snow crab, king crab, you name it!

• Amigo’s Tortilla Bar

I ended up eating at this Mexican joint a couple times. Get a seat at the front of the restaurant to people watch.

How about some dessert?

Where to Get Key Lime Pie

You can’t leave Key West without hav­­ing a slice of key lime pie that made the city famous around the world!

• Key Lime Pie Bakery

This delicious Key West gem from 1856 is the self-proclaimed birthplace of key lime pie, which is delicious. If you like coconut, you’ll also love their coconut cream pie!

• Key Lime Pie Company

After watching an episode of CNBC’s The Profit, with Marcus Lemonis, a business wizard who I adore, I had to stop in to see how he saved this once struggling business. The pies were very good. You can even watch them being made.

• Kermit’s Key West Key Lime Shoppe

Try key lime pie with a twist. This bakery serves up delicious frozen, chocolate dipped slices on a stick and was voted top 10 desserts in America by Food Network and rightfully so, they’re addictive. You can even have it delivered to your home!

Where to Stay in Key West

Now that you know what things to do for couples in Key West, let’s dive into where to stay. These are my favorites…

• Amsterdam’s Curry Mansion Inn | Old Town, Key West

Built in 1869, this adorable B&B was originally owned by William Curry, who is said to be the first self-made millionaire in Florida. Many people stayed here including Ernest Hemingway himself. (I know, if only you had a nickel for every time we mentioned his name)

The current owner, Patsy is very friendly and made the stay a romantic experience for my partner and I, even giving us room #207 which had a very romantic feel to it, even the part of the B&B it was in , secluded with a balcony and hallway full of vintage finds and interesting memorabilia. We also had access to 360 degree rooftop views of Key West access via the stairs next to our room. Absolutely explore the hotel, there’s so much to see.

In the morning, before setting out for adventure in the city, we enjoyed complimentary breakfast poolside. You can even order an omelet made to order. In the evening, we relaxed at the B&B’s cocktail hour where we listened to live music.

For some private relaxation, take a dip in the hot tub. We also enjoyed some private time on our room’s balcony on the rooftop terrace, while puffing some cigars we got earlier on Duval St… That is, until a street fight broke out across the street and the cops were called then, we got the heck out of there.

This was a very romantic stay. I can’t recommend this place enough for the history, architecture and charm.

Location

This B&B is conveniently located a few blocks from the waterfront. Most of the activities I’ve mentioned in this guide like Mallory Square and Duval St. are also close.

Book Amsterdam’s Curry Mansion Inn

• Double Tree Hilton, Grand Key Resort | New Town, Key West

If you want an environment that’s authentic to the Florida Keys, be among the iguanas at Double Tree Hilton, Grand Key Resort where you can sip on refreshing drinks poolside with iguanas all around. Just don’t be surprised if you take a swim and come back to them throwing a party in your cabana and stealing your drink (true story).

We loved having lunch in our cabanas. We also got drinks from the pool bar.

Included in stay: free shuttle, downtown and Key West International Airport (5 min away); access to Sunset Watersport Beach Club; parking; 2 bottles of water daily.

Location:

Located in New Town Key West on the opposite end of the island than the previous hotel mentioned. This is the hotel for you if you want to be close to the airport and Smathers Beach which the hotel’s shuttle will take you to both.

Book Double Tree Hilton

That’s a Wrap!

Thank you for reading my guide for things to do in Key West for couples! I hope you got some ideas for your trip. If it was helpful, please share it with your friends!

Have you ever been to Key West? What was your favorite thing? If you’ve never been, would you take a trip? Leave me a comment below!

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Fact Check:

At Real Girl Review, we value truth and always strive for accuracy. Posts are updated regularly. If you read something that still doesn’t sound right, contact me at gv@realgirlreview.com. I will investigate the facts and make changes as I deem necessary.