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Discover 50+ Romantic Things to Do in Key West for Couples

by Roslie L.
Published: Updated:
Florida Keys Beach

Are you in the mood for a whirlwind escape where you can bask in the sun and swim through turquoise seas? For the ultimate romantic getaway, look to South Florida. There is an endless array of romantic things to do in Key West for couples looking for fun in the sun.

Treat yourself to private sunset sails, decadent desserts, and speakeasy-style restaurants. Indulge your adventurous side with jet-skiing, parasailing, and kayak tours. Soak in the rich literary and maritime history as you listen to tales of local myths and legends. It’s all here at your fingertips.

Let’s count down the top 50 things to do in Key West for couples to inspire your dream trip. From five-star spots that’ll make you feel like royalty to chill escapes that’ll make you forget about the world, there is no end to the incredible things to do in the Florida Keys.

Here is your ultimate list of unique things to do in Key West for couples ready to fall in love all over again.

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Romantic Places to Stay in Key West

If you’re looking for romantic places to stay in Key West, you’ll find plenty of choices. Here are a few of our top picks for an unforgettable vacation in the Florida Keys.

Romantic Sunset Cruises in Key West

Is there anything more romantic than a tropical sunset? Indeed, there is! Experiencing that breathtaking view from the deck of a ship sailing off into the sunset takes the experience to a whole new level. Look to these romantic cruises when it comes to the best place to watch the sunset in Key West.

Sail Boat on water in Key West, Florida

1. Sunset Tiki Boat Tour

A sunset tiki boat tour is perfect for a romantic night out in Key West. This small cruise is a great date idea if you want to escape the crowded tourist areas, see a beautiful sunset, and experience the best views in Key West.

2. Sunset Sail on Schooner America

Another place to get one of the best views in Key West is on a sunset sail on the gorgeous 105-foot-long schooner, America 2.0. A sunset cruise on this beautiful ship is an unforgettable experience. As a perk, they offer hors d’oeuvres and complimentary drinks (which makes it one of the most romantic places for drinks in Key West).

3. Sunset Party Cruise by Catamaran

Is a party date more your vibe? Opt for a sunset party cruise on a spacious catamaran with live music, appetizers, drinks, and, of course, those magical views.

Key West Day Trip Ideas

While visiting the Florida Keys, you’ll want to plan for at least one day trip to experience the beauty of the local flora and fauna. Here are a few Key West day trips that we adore.

4. Dry Tortugas National Park Day Trip

Dry Tortugas National Park is beautiful and remote, and what better way to get there than on a catamaran cruise? This Dry Tortugas National Park day trip is a great way to spend a romantic day with your main squeeze.

5. Shark and Wildlife Viewing Adventure

Get up close and personal with your boo and marine wildlife on this catamaran tour, where you can witness sharks feeding right off the edge of the boat. This tour includes cold drinks, snacks, and even sunglasses.

Romantic Things to Do in Key West for Couples

When it comes to romantic things to do in Key West, from iconic Key West mainstays to off-the-beaten-path ideas, here are a few of the hotspots and hidden gems you can’t miss during your epic Florida Keys vacation.

6. Duval Street

Duval Street Key West Florida

For nightlife in Key West, there is no place like Duval Street. This iconic street has some of the best restaurants in Key West, world-famous bars, trendy cafes, shopping, and anything else you might be after. The street is just over a mile long, so you can easily see it all from start to finish.

Plan a daytime trip down Duval Street to experience historical sites, shop for souvenirs, and cool down with ice cream. At night, Duval Street is filled with all the best Key West adults-only activities like cabaret shows, pub crawls, LGBTQ+ hotspots, and more.

Planning Tip: There is a free Key West hop-on, hop-off bus that operates on the Duval loop and takes you through the best places in the town. Grab a map to save for easy travel across town.

7. Mallory Square Sunset Celebrations

The nightly sunset celebrations at Mallory Square bring in travelers from around the globe. The party starts two hours before sundown and features magicians, jugglers, clowns, psychics, musicians, and more. It’s easily one of the most fun things to do in Key West and something you’ve got to experience at least once.

8. Old Town Literary Walking Tour

If you’re looking for unique things to do in Key West, explore the historical tours to uncover some of the one-of-a-kind things that make this place so unique.

The Key West Literary Seminar holds a Literary Walking tour every Friday and Sunday. For 90 minutes, you’ll stroll through downtown and learn stories of writers who have called Key West home.

9. Historic Key West Seaport

The Key West Historic Seaport is a twenty-acre facility full of world-class dining, shopping, live music, museums, and more. This is a one-stop destination when planning where to go for a date night in Key West.

10. Southernmost Point Buoy

Key West Florida Southernmost Point Buoy

One of the top unique things to do in Key West that you can’t do anywhere else, stopping at the Southernmost Point in the Continental U.S., is an essential visit. Be sure to snag a picture with your sweetie to commemorate!

11. Mile Marker Zero

Another local landmark (and one of the unmissable things to do in Key West for free), Mile Marker Zero is a famous photo spot that marks the beginning of the 2,369-mile-long U.S. 1 highway. Head to the corner of Fleming and Whitehead Street to snag a picture of this iconic spot.

12. Bahama Village

Bahama Village is a 12-block area in Key West where the first Bahamian settlers arrived in the 19th century. You can get a feel for the rich Caribbean heritage that has left a deep mark on the region at the many Caribbean restaurants, island bars, and handicraft shops in Bahama Village.

13. Waterfront Playhouse

Catch a show with your person at the Key West Waterfront Playhouse in the heart of Mallory Square. The Playhouse is right next to the sunset celebration and “when the sun sets, the curtain rises at the Waterfront Playhouse.”

14. Walk from the Atlantic Ocean to the Gulf of Mexico

One of our favorites of the many unique things to do in Key West is to take an epic adventure over the seas by walking from the Atlantic Ocean to the Gulf of Mexico. By trekking the 1.2-mile-long Duval Street, you’ve traveled from the Atlantic to the Gulf, and that is certainly something to brag about!

Key West Date Ideas: Key West Tours

A tour is an ideal way to better appreciate Key West and its fascinating history and culture. These tours are our prime picks for a romantic day with your significant other.

15. Key West Mangrove Kayak Eco Tour

Couple Kayaking in the Florida Keys

The Mangrove Kayak Eco tour is an unforgettable and unique thing to do for couples in Key West. You’ll paddle a kayak through mangrove creeks and get an up-close and personal look at the distinct coastal environment. This tour is even dog-friendly, so bring your furry friend.

16. Key West Ghosts and Gravestones Tour

If you and your boo (pun intended!) are looking for a fright, check out a Key West ghost tour! Learn about Key West’s supernatural history with the Ghosts and Gravestones tour, one of our Top Ten Key West Ghost Tours. Yes, this place is so spooky that you can go on nearly a dozen terrifying tours.

On this one-hour tour, pass some of the most haunted places on the island, with stops including the Shipwreck Treasures Museum.

17. The Key West Conch Train

The Key West Conch Train tour is a fun and cute way to experience Key West with someone special. This 90-minute tour takes you past notable places in Key West and includes legendary local stories, too, so you can learn as you go.

18. Key West Old Town Trolley Tour

If exploring Key West attractions at your leisure is more your style, try the Key West Trolley Hop-on, Hop-Off Tour. This tour also gives you admission to the Sails to Rails Museum, so it’s a practical money-saving pick.

19. Key West Food Tasting and Cultural Walking Tour

Key West has a rich culture and history that is well worth exploring. To get an insider’s look into the local food scene and history, check out the Southernmost Food and Cultural Walking Tour. It’s a great opportunity to learn about the Cuban and Caribbean influences on Key West food and culture—tastings included!

Iconic Places to See for Couples on Your Florida Keys Road Trip

A romantic trip to Key West would only be complete with stopping at some (or all) of these iconic locations.

20. Key West Lighthouse and Keepers Quarters

Key West Lighthouse - Florida

If museums are your thing, be sure to check out the Key West Lighthouse and Keepers Quarters Museum. And, for one of the best views in Key West, walk up the 88 steps to the top of the lighthouse for a panoramic view.

21. Hemingway Home and Museum

The Hemingway Home Museum is undoubtedly one of the most iconic places in Key West. See where the author lived and wrote and say hello to the resident polydactyl (six-toed) cats!

If you love distilleries (or rum), check out the Key West First Legal Rum Distillery free tour! It’s a bucket list experience for rum lovers (and one of the best things to do in Key West for free).

23. Key West Tropical Forest and Botanical Garden

Stroll through the rare ecosystem at the Key West Tropical Forest and Botanical Garden on your romantic day in Key West. There are 15 acres of native gardens and forests full of native plants, birds, and butterflies.

24. Key West Shipwreck Treasure Museum

Key West Shipwreck Treasure Museum Tower

The Key West Shipwreck Museum will take you back in time as you explore the unique maritime history of Key West – including how it became the wealthiest city in the United States.

25. Audubon House and Tropical Gardens

Journey to the beautiful Audubon House and Tropical Gardens on your Key West date. This grand home reflects the elegance and lifestyle of a wealthy Key West family during the days of a burgeoning shipwrecking industry.

26. Key West Butterfly Conservancy

You can walk among hundreds of fluttering butterflies and colorful birds in a veritable tropical paradise at the Key West Butterfly and Nature Conservancy.

Adventurous Things to Do in Key West for Couples

Are you more of an adventurous couple? Plan an adventure date with one of these awesome and adventurous activities.

27. Jet Ski Tour of Key West

JetSkiing Miami Beach Florida

Adventurous couples will love jet-skiing through the Key West waters. You choose your tour through the Atlantic Ocean, the Gulf of Mexico, or both. This tour is a prime opportunity to see dolphins, stingrays, sea turtles, and manatees!

28. Guided Bicycle Tour of Old Key West

A guided bicycle tour of Old Town Key West is a fun and active way to explore and learn about this incredible island. This leisurely three-hour bicycle tour will take you through the major landmarks in Key West.

29. Snorkeling Adventure

On this three-hour snorkeling adventure, you and your date will enjoy a sail on a state-of-the-art catamaran and snorkel along North America’s only living coral reef. Once you’ve worked up a thirst, you can sip margaritas and take some of the best views in Key West.

30. Key West 2-Stop Reef Snorkeling Trip

On this double-dip snorkeling tour, you’ll head out on a high-speed catamaran and visit two tropical reef locations. This trip is three hours long, and if you choose the combo trip, you’ll enjoy a Key West sunset cruise after snorkeling, complete with complimentary champagne.

31. Key West Dolphin Watch and Snorkel Eco-Tour

Combine snorkeling with dolphin-watching on this tour! The Key West dolphin watching and snorkeling eco tour will bring you to see bottlenose dolphins and then cruise to the backcountry waters of the Florida Keys for some snorkeling and marine wildlife spotting.

32. Key West Parasailing Flights

For the best view of Key West, embark on the Key West parasailing adventure and soar high above the emerald-green waters with your sweetheart.

Where to Eat on Date Night in Key West

You can experience the best restaurants in the Florida Keys at the impressive foodie hotspots dotting the city. While there is great food around every corner, these romantic Key West restaurants stand out.

33. El Mason de Pepe

Enjoy authentic Cuban food in Mallory Square at El Meson de Pepe. A local fave, this place has been serving up authentic Cuban food and drinks for over 30 years. On top of having fabulous food, this is one of the best Key West romantic restaurants, thanks to the stunning sunset view and live music.

34. Better Than Sex Dessert Restaurant

Another one of our go-to romantic restaurants in Key West, Better Than Sex, is a dessert restaurant that serves incredible desserts in a speakeasy-like atmosphere. Just steps away from Old Town Key West, this is the perfect place for date night.

35. Latitude’s Restaurant

Latitude’s Restaurant is perfect for a romantic seafood dinner in Key West. When it comes to upscale oceanfront dining in the Florida Keys, this place is number one.

Best Places for a Romantic Night Out in Key West

Key West has a variety of bars, some ideal for a romantic evening while others are more suited for a lively night out. From intimate speakeasies to bustling dance spots, there is something for everyone. Here are the top nightlife destinations in Key West.

36. Rick’s Key West

Rick's Key West Florida Bar

Rick’s Entertainment Complex is one of the hubs of nightlife in Key West. With eight distinctive bars, there’s something here for every mood. Enjoy karaoke, live music, dancing, and much more.

37. The Rum Bar at Speakeasy Inn

The Rum Bar can be found in the lobby of the Speakeasy Inn, which used to be the home of Raul Vasquez, a famous Key West – Cuban rum runner. The atmosphere in the bar is very relaxed, where you can enjoy good music and lots of conversation. With over 350 rums from around the world, it’s easy to see why this is one of the must-visit nightlife spots in Key West.

38. Green Parrot

The Green Parrot Bar is a Key West icon with a casual atmosphere, live music, and great drinks. Located on the corner of Whitehead and Southard Streets, this popular Key West bar is the perfect place to go if you want to experience a local watering hole.

39. See a Drag Show

Key West is famous for its drag shows, and while it might not be the first thing that pops into your mind when you imagine a romantic night out, you’re sure to have a fun and memorable evening.

Hotspots like Aqua Bar and Nightclub have a drag show almost every weekend, while ​​801 Bourbon Bar has everything from drag shows to bingo to karaoke. La Te Da is a must-see for a cabaret with an impressive line of shows. Last but certainly not least, you can start your day off with a bang at the Sunday Drunken Drag Brunch at Mangoes.

Key West Beaches for a Romantic Picnic or Day at the Beach

A day at the beach is always an excellent idea for a romantic day together. Plan a cute beach picnic or choose a beach to sit together and watch the sunset. Not only will it be a highlight of your Florida Keys trip, but it’s also one of the best things to do in Key West for free.

40. Smathers Beach

Key West Florida Grass path to Smathers Beach

Stretching for almost two miles, Smathers Beach is the largest beach in Key West and one of the best beaches in the Florida Keys. This beautiful place is perfect for a romantic picnic or just a lazy afternoon under the sun.

41. Fort Zachary Taylor State Park and Beach

Fort Zachary Taylor State Park is so much more than just a beach. Explore a Civil War history, hike, fish, snorkel, dive, paddle, or just spend the day relaxing at the beach at southernmost state park in the continental United States.

42. Higgs Beach

Clarence S. Higgs Beach is located on the Atlantic Ocean near the Waldorf Astoria’s Casa Marina Resort. Easily one of the best views in Key West, this beach has over 16 acres of oceanfront vista with turquoise waters and plenty of things to explore, like restaurants and more.

43. Simonton Street Beach

Simonton Street Beach is situated on the Gulf side of the island, at the end of Simonton Street. This beach is a small oasis near downtown where you can swim, relax, or plan your next activity.

Best Places for Key Lime Pie in Key West

You can’t leave the Florida Keys without trying one (or all!) of the best key lime pies in Key West. It’s guaranteed to be one of the sweetest experiences on your trip and your favorite dates in Key West.

Key lime pie on white plate

44. Kermit’s Key Lime Shoppe

Kermit’s Key Lime Shoppe is an iconic stop for key lime pie and so much more. Stop here for sweets, souvenirs, and more!

45. Key West Key Lime Pie Co.

The Key West Key Lime Pie Co. has award-winning key lime pies and cute souvenirs. If you’re looking for a key lime pie-themed date idea, take a class at the key lime pie Co. and learn how to make their award-winning pie yourselves!

46. Key Lime Pie Bakery

The Key Lime Pie Bakery has some of the best key lime pie in the Florida Keys, along with cakes, saltwater taffy, tea, cookies, souvenirs, and so much more. Stop by this bakery for a unique Key West experience and pick up some souvenirs while you’re at it.

Key West Festival Date Ideas

Key West festivals are a tradition for locals and tourists alike. Here are some of the best festivals perfect for a romantic Key West getaway.

47. Key West Pride Parade

Key West is an LGBTQ+ travel hotspot, and the Key West Pride Parade at the Key West Festival is the place to be every summer. If you are in the Florida Keys in June, don’t miss it.

48. Key West Food and Wine Festival

The Key West Food and Wine Festival is the perfect festival for foodies. This annual January festival brings the world’s best food, wine, beer, and other culinary delights to the Florida Keys.

49. Key West Key Lime Festival

The Key West Key Lime festival is a quintessential Key West experience. This festival takes place in July, and if you love key lime pie, you don’t want to miss this.

50. Hemingway Days Festival

Literary lovers will love the Hemingway Days festival in mid-July in Key West. This festival commemorates the life of Ernest Hemingway, who left a powerful legacy in Key West. Even if you miss it, you’ve got to check out the pics from the Ernest Hemingway look-alike annual contest!

51. New Year’s Eve in Key West

There’s no festival more exciting than New Year’s Eve in Key West. It is such a big deal that Key West’s New Year’s Eve celebration is even covered live on CNN. Look no further for the best party in the Florida Keys of the year.

Choose between seeing a giant conch shell lowered at Sloppy Joe’s Bar, a pirate wench lowered from the mast of a schooner in the Historic Seaport, a key lime wedge lowered at Sunset Pier, or Sushi, a local drag queen lowered from a Duval Street balcony.

Travel to Key West FAQs

When you’re planning the perfect Key West vacation, there are a few things that you should know before you go. To help you get started, here are a few of the most common questions we get on Florida Keys travel.

Key West, Florida Souvenir Store

Is Key West good for a honeymoon?

With a perfect blend of romantic ambiance, beautiful beaches, and vibrant nightlife, planning a honeymoon in Key West is a fabulous idea. The Florida Keys’s all-inclusive honeymoon resorts bring in lovebirds from around the world, while the quaint historic inns are perfect for couples after a tropical charm. From watersports to sunset cruises, there is never a dull moment here.

Is Key West a good vacation for couples?

Absolutely. While much of Florida is popular with families traveling with kids, the Florida Keys is famous for its adults-only hotspots. Whether you want to explore the hopping Key West nightlife or unwind in an upscale lounge, there are endless things to do in Key West for couples looking for a romantic getaway.

Is Key West fun at night?

From bustling street performances to intimate jazz lounges, the iconic Duval Street comes alive at night. Start your evening with fresh seafood at a waterfront restaurant, then soak in the glow of the city lights and the sound of live music in the air as you bar hop around town.

Which part of the Florida Keys is best for honeymoons?

Honeymoons in Key West are popular thanks to the city’s romantic ambiance, historic charm, lively nightlife, and diverse range of things to do. With beautiful beaches, water sports, and unique attractions, it’s a well-rounded option that offers something for everyone.

Is Key West expensive?

While there are free things to do in Key West, it is a relatively pricey destination. The good news, however, is that you get what you pay for. The Florida Keys are famous for their upscale hotels, romantic experiences like private cruises, and bucket list experiences like diving the Gulf of Mexico. If you’re looking for an unforgettable escape, it’s well worth it. 

How many days do you need in Key West?

How long you need in Key West depends on your plans. You can see the best of the Florida Keys in a long weekend or have a laid-back experience of lounging on the beaches for a week or more.

Can you walk around Key West?

Key West is a very safe place to visit. Walking through busy parts of town during the day or night is fine. While the Florida Keys have low crime rates overall, it’s still wise to use good judgment when out and about in Key West, particularly after dark and around busy spots like Duval Street and Mallory Square.

What is the best street to walk on in Key West?

Duval Street is one of the best places to walk in Key West. Stroll up and down while you explore the best shopping, bars, and restaurants in Key West. Once you have seen the key landmarks, explore the cozy neighborhoods and side streets where Key West’s rich history and architecture shine.

Romantic Things to Do in Key West: Final Thoughts

Key West Florida Sunset Pier

When it comes to romantic things to do in Key West, you are spoiled for choice. With gorgeous beaches, world-class restaurants, and upscale hotels, it is the perfect place for a romantic getaway. From sailing to sampling Key Lime Pie, can easily impress your significant other with a full itinerary of fun things to do in the Florida Keys.

Looking for more adventure? Grab our guide to Exploring the Florida Keys: 101 Unique Things to Do in the Florida Keys.


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