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50 Romantic Things to Do in Key West for Couples

by Roslie
Key West Florida Grass path to Smathers Beach

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Key West, Florida, is the perfect place for a romantic getaway. Couples can easily find quiet and romantic date ideas such as private sunset sails or decadent desserts in a speakeasy-style restaurant. And, for the adventurous couples out there, finding adrenaline-filled activities for two is easy! Ideas include jet-skiing, parasailing, and more.

If you’re the laid-back type who enjoys tours, history, and culture, you don’t have to look far. Key West is full of vibrant history and culture, and there’s an activity for every personality style! Tour themes include maritime history, literary history, paranormal happenings, and more.

We’ve compiled a list of 50 things to do in Key West for couples, from romantic date ideas, adventurous ideas and casual, laid-back experiences. Whether you want an upscale experience or a romantic vacation that encapsulates the iconic Key West vibe, you’ll find it all on this list.


Please keep in mind these details are subject to change. Due to COVID-19, social distancing and face coverings may be required. Be sure to check local health officials’ safety regulations and each establishment’s website for updated information before making final plans.

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Romantic Sunset Cruises in Key West

Is there anything more romantic than a tropical sunset? Yes, there is — a tropical sunset experienced aboard a boat. Take your love on a romantic sunset cruise with any of these Key West tours.

Sail Boat on water in Key West, Florida

1. Sunset Tiki Boat Tour

A sunset tiki boat tour is a great way to spend a romantic evening 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 views of Key West that you won’t get on land.

2. Sunset Sail on Schooner America

Take a sunset sail on the beautiful 105-foot-long schooner, America 2.0. A sunset cruise on this beautiful ship is the perfect romantic date idea that includes food, drinks, and great views.

3. Sunset Party Cruise by Catamaran

Is a party date more your vibe? Check out the sunset party cruise on a spacious catamaran! Includes live music, appetizers, drinks, and views.

Key West Day Trip Ideas

If you’re looking for a great way to spend a day from Key West, check out these day trip ideas!

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. You’ll see sharks feeding right off the edge of the boat! Cold drinks, snacks, and sunglasses included.

Romantic Things to Do in Key West for Couples

If you’re looking for romantic things to do in Key West, this list has plenty of ideas. From iconic Key West mainstays to off-the-beaten-path ideas, check these out!

6. Duval Street

Duval Street Key West Florida

Stroll the main drag of downtown Key West: Duval Street. This street is one of the most popular destinations with restaurants, shops, world-famous pubs, and more! A stroll down Duval Street is a must for a date in Key West.

7. Mallory Square Sunset Celebrations

Mallory Square holds nightly sunset celebrations and hosts visitors worldwide. The festivities begin two hours before sundown and features magicians, jugglers, clowns, psychics, musicians, and more.

Oh, and it’s a great place to catch a sunset with that special someone!

8. Old Town Literary Walking Tour

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. The Key West Seaport makes a perfect location for date night in Key West!

10. Southernmost Point Buoy

Key West Florida Southernmost Point Buoy

You can’t go to Key West without stopping at the Southernmost Point in the Continental US. Be sure to snag a picture with your sweetie to commemorate!

11. Mile Marker Zero

Mile Marker Zero is a famous photo spot that marks the beginning (or end) of the 2,369-mile-long US 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. Get a feel for Caribbean heritage with a variety of restaurants, bars, and 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 located 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

Did you know you can walk from one large body of water to the other in Key West? Duval Street is 1.2 miles long and will take you from the Atlantic to the Gulf, and we think that’s a pretty unique thing to do!

Key West Date Ideas: Key West Tours

A tour is a great way to get to know Key West intimately, and these tours are great 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 a 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!

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.

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 your someone special. This 90-minute tour takes you past notable places in Key West and includes legendary local stories, too.

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 grants admission to the Sails to Rails museum.

19. Key West Food Tasting and Cultural Walking Tour

If you and your significant other are foodies, you’ll love the Southernmost Food and Cultural Walking Tour. 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

No romantic trip to Key West would be complete without stopping at some (or all) of these iconic locations.

20. Key West Lighthouse and Keepers Quarters

Key West Lighthouse - Florida

Are museums your thing? Check out the Key West Lighthouse and Keepers Quarters Museum. 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 cats!

If you love distilleries (or rum), check out the Key West First Legal Rum Distillery free tour! This is a great place to kick off your Key West date with a complimentary rum sample.

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 garden and forest 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

At the Key West Butterfly and nature conservancy, you can walk among hundreds of living butterflies and colorful birds in a veritable tropical paradise.

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, Gulf of Mexico, or both. You might also 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 is a leisurely 3-hour bicycle tour 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. You can even sip on margaritas on the afternoon tour!

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 different tropical reef locations. This trip is three hours long, and if you choose the combo trip, you’ll enjoy a 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! You’ll take a dolphin-watching tour 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

Take to the skies and see the Keys from above with this Key West parasailing tour. This tour is one hour long. You’ll be lifted high above the emerald, green waters of Key West and ride through the sky with your sweetheart.

Where to Eat on Date Night in Key West

Visitors on the island can enjoy some of the best restaurants in Florida at some of the most beautiful and romantic locations. If you’re looking for a romantic Key West restaurant, here are some top choices.

33. El Mason de Pepe

Enjoy authentic Cuban food in Mallory Square at El Meson de Pepe. This staple in the Key West restaurant scene has been serving up authentic Cuban food and drinks for more than 30 years!

34. Better Than Sex Dessert Restaurant

Better Than Sex is a dessert restaurant that serves incredible desserts in a speakeasy-like atmosphere. This restaurant is located steps away from Old Town Key West and is the perfect place for a romantic date night dessert.

35. Latitude’s Restaurant

Latitude’s Restaurant is a perfect place for a romantic seafood dinner in Key West. If you want delicious, upscale oceanfront dining, this is the place for you.

Best Places for a Romantic Night Out in Key West

Many bars line the streets of Key West, but some are better for a romantic night out than others. They’re all unique in their own way. Whether you are looking for a speakeasy or want to experience Key West nightlife like a local, check out these places!

36. The Rum Bar at Speakeasy Inn

The Rum Bar is located in the lobby of the Speakeasy Inn, the former home of Key West – Cuban rum-runner, Raul Vasquez. The vibe in the rum bar is laid back — you’ll experience good music and plenty of conversation. Try one of their 350+ rums from all around the world!

37. Rick’s Key West

Rick's Key West Florida Bar

Rick’s entertainment complex is one of Key West’s most popular nightlife areas. Comprised of eight bars, there’s something here for every personality type. Enjoy karaoke, live music, dancing, and much more.

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 St, the Green Parrot is the perfect place to go if you want to experience a Key West locals’ watering hole.

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!

39. Smathers Beach

Key West Florida Grass path to Smathers Beach

Smathers Beach is Key West’s largest beach; this beach stretches for almost two miles. The sand at Smathers beach is brought in from the Bahamas because tropical storms always wash the sand away. This beach is the perfect spot for a romantic picnic.

40. Fort Zachary Taylor State Park and Beach

Fort Zachary Taylor State Park is so much more than just a beach. But if you’re looking for a beach, it’s great for that too! Explore a civil war fort or just spend the day relaxing at the beach.

41. Higgs Beach

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

42. Simonton Street Beach

Simonton Street Beach is located at the end of Simonton Street on the Gulf side of the island. This is a small beach near downtown where you can swim or sit and relax while planning your next activity.

Best Places for Key Lime Pie in Key West

Unless you’re allergic or really don’t like Key Lime Pie, you can’t visit Key West without stopping at one (or all) of these places. These Key Lime Pie shops make a great stop on your date in Key West!

Key lime pie on white plate

43. 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!

44. 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!

45. Key Lime Pie Bakery

The Key Lime Pie Bakery has Key Lime Pie, 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.

46. Key West Pride Parade

Key West is an LGBTQ+-friendly town and the Key West Pride Parade is the perfect Key West Festival for LGBTQ+ couples and allies! Key West Pride takes place in June each year.

47. Key West Food and Wine Festival

The Key West Food and Wine Festival is the perfect festival for foodies. This festival takes place at the end of January, where you can taste the best food, wine, beer, and more.

48. 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.

49. 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.

50. New Year’s Eve in Key West

There’s no festival more exciting than New Year’s Eve in Key West. Key West’s New Year’s Eve celebration is even covered live on CNN. Experience the biggest party of the year!

You can choose to see 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.

Recap

Key West is the perfect place for a romantic getaway. Planning your trip and activities in advance will ensure that you have the experience of a lifetime!

Key West Florida Sunset Pier

Impress your significant other with a full itinerary, but don’t forget to schedule some downtime to relax on the beach!

With delicious restaurant options ranging from casual to fine-dining and activities ranging from quiet and romantic to adrenaline-filled adventure, there’s something for every personality in Key West, Florida.

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