Romantic Things to Do in Key West for Couples on Vacation

Looking to turn up your vacation romance by researching Key West attractions for couples? Smart! Whether you’re planning a honeymoon (or an intimate wedding!), anniversary trip, or spontaneous escape with your favorite person, Key West offers the perfect mix of tropical beauty, laid-back luxury, and unforgettable experiences. From a sunset sail and oceanfront dinners to secret gardens and hands-on adventures, our island paradise is made for connection. To help you plan the perfect retreat for two, we’ve curated 11 unique things to do in Key West for couples – organized by Eat, Drink, Play, and Stay. 

Eat: Romantic Dining Experiences in Key West

Food is one of the most romantic ways to connect while traveling, and in Key West, couples are spoiled for choice. Here, food and romance go hand in hand, whether you’re dining barefoot on the beach or sharing a fine meal under the stars.

1. Latitudes on Sunset Key

Dine on a private island with candlelit tables right on the sand and breathtaking views of the Gulf. Accessible only by a short ferry ride, Latitudes offers refined cuisine and impeccable service in one of the most romantic settings in the Keys. Sunset reservations book quickly – plan ahead. Bonus: The Spa at Sunset Key Cottages welcomes appointments from non-guests of the hotel. 

Website | Phone
Ferry departs from 245 Front Street, Key West, FL 33040

2. Hot Tin Roof

This oceanfront restaurant at Ocean Key Resort serves Caribbean-meets-Southern fare in an elegant, open-air setting. Watch the boats drift by as you share tapas and sip craft cocktails. It’s an ideal dinner spot after a day of exploring Old Town. Bonus: Ocean Key Resort features an on-site spa that is open to both hotel guests and non-guests by appointment.

Website | Phone
0 Duval Street, Key West, FL 33040

3. Picnic at Fort Zachary Taylor Beach

Skip the reservations and pack a picnic for two. With shaded picnic tables, gentle surf, and unbeatable sunset views, this beach offers a relaxed, scenic spot to share a meal and toast the moment. Great for couples who prefer barefoot romance and quiet beauty. Note, park entrance fees apply. Bonus: Explore the Fort, kick back with beach rentals, and enjoy frozen treats and ice-cold drinks at the on-site café.

Website | Café Phone
601 Howard England Way, Key West, FL 33040

Drink: Raise a Glass Together

Whether you’re sipping your way through a wine flight or shaking your own signature cocktail, Key West has a way of making every sip as vibrant as our sunsets. Check out these perfect Key West date night spots!

4. The Roost

This intimate wine and cocktail bar just off Duval Street offers a cozy, speakeasy-style escape from the crowds. Choose from curated wines or creative cocktails and enjoy them in a refined but relaxed atmosphere. A perfect way to start or end a romantic evening.

Website | Phone
508 Fleming Street, Key West, Florida 33040

5. Papa’s Pilar Rum Distillery

Named after Hemingway’s beloved boat, this working distillery offers tours, tastings, cocktail-making classes, and more. Learn the story behind the rum, mix up your own creation, and sip together in a setting full of character and charm. Voted #1 Best Craft Distillery Tour by USA Today 10Best!

Website | Phone
201 Simonton Street, Key West, FL 33040

Play: Make Memories Together

Adventure, nature, and discovery – there’s no shortage of shared experiences that will leave couples smiling and swooning throughout your time in Key West. Whether you’re sailing at sunset or wandering through a butterfly garden, these activities are pure magic.

6. Sunset Sail with Danger Charters

Few experiences compare to sailing into the sunset with a glass of wine in hand. Our Wind & Wine Sunset Sail combines sweet sea breeze, fine wines and gourmet appetizers, and of course, an unforgettable view – all aboard one of our classic schooners. A sunset sail is an absolute must experience during your romantic Key West getaway. We can’t wait to welcome you aboard! 

Website | Phone
Tours depart from the Danger Chandlery Store and The Perry Hotel & Marina

7. West Martello Tower & Garden Club

Tucked away on Higgs Beach, this historic Civil War fort has been transformed into a lush tropical garden filled with orchids, palms, and history. It’s quiet, romantic, and completely free – an ideal place for morning coffee or a slow afternoon stroll.

Website | Phone
1100 Atlantic Boulevard, Key West, FL 33040

8. Key West Butterfly & Nature Conservatory

Step inside a glass-enclosed sanctuary brimming with butterflies, flamingos, and exotic plants. The temperature-controlled space feels like a dream, making it a peaceful, visually stunning spot for couples to relax and connect.

Website | Phone
1316 Duval Street, Key West, Florida 33040

9. Dry Tortugas by Seaplane

Board a seaplane for a short but scenic flight to Dry Tortugas National Park – a remote island chain featuring white-sand beaches, clear water, and the historic Fort Jefferson. It’s an adventurous, all-day escape that feels like your own private world.

Website | Phone
3471 South Roosevelt Boulevard, Key West, FL 33040

Stay: Escape to Somewhere Special

When the day winds down, Key West’s romantic boutique inns offer the perfect hideaway. From lush courtyards and quiet elegance, these stays are destinations in themselves, each with its personality and perks.

10. Stay at Simonton Court Historic Inn

A tranquil, adults-only escape tucked into the heart of Old Town, Simonton Court is made up of beautifully restored Victorian homes wrapped around tropical courtyards and serene swimming pools. The grounds feel like a secret garden, and the charming architecture gives every stay a sense of timeless romance. Close to Duval Street, but far enough to enjoy the quiet.

Website | Phone
320 Simonton Street, Key West, FL 33040

11. Stay at The Perry Hotel & Marina

An award-winning property that’s often ranked among the most romantic hotels in Key West, The Perry Hotel & Marina offers a stylish waterfront escape on tranquil Stock Island. This boutique resort combines modern design with coastal charm, featuring oversized balconies, marina-view rooms, and a relaxed, upscale vibe. Couples can enjoy craft cocktails by the pool, dine at on-site restaurants, or walk directly to the marina for a Danger Charters sunset sail! It’s the perfect blend of luxury, privacy, and adventure.

Website | Phone
7001 Shrimp Road, Key West, FL 33040

Now that you’re equipped with what to do in Key West for couples, all that’s left to decide is what you’ll do first! We sail 364 days of the year – book your tour for the day that suits you best, and we’ll take care of the rest. Fair winds and following seas!