22 Romantic Things to Do in Key West for Couples

You can fly, drive, or take a ferry to Key West.

By Air:
Key West International Airport (EYW) is small but well connected. Major airlines like Delta, American, United, and JetBlue all offer direct flights from Miami, Fort Lauderdale, Tampa, Orlando, and several East Coast cities. The airport is just a few minutes from Old Town, so you can get to your hotel quickly after you land.

By Car:
Driving from Miami to Key West is one of the most scenic road trips in the United States. The 165-mile Overseas Highway (U.S. 1) connects the islands with 42 bridges, including the famous Seven Mile Bridge. The drive takes about 3.5 to 4 hours, but plan extra time for photos and short stops along the way.

PRO TIP: The stretch from Key Largo to Key West is the most beautiful part of the route. You’ll cross clear turquoise water, small islands, and endless ocean views. Well worth taking it slow and enjoying the drive.

By Ferry:
Another good option is the Key West Express, which runs daily between Fort Myers Beach and Key West (and seasonally from Marco Island). The trip takes about 3.5 hours each way, and the boat has indoor and outdoor seating, snacks, and drinks onboard.

Key West is small, only about four miles long and two miles wide, so getting around is easy.

Walking and Biking:
If you’re staying in Old Town, you can walk or bike to almost everything. Biking is the best way to explore, and there are plenty of rental shops. Many hotels offer complimentary bikes for guests.

Trolley and Conch Train:
The Hop-On Hop-Off Trolley and Conch Train Tour are fun and practical ways to see the main attractions, including Mallory Square, the Hemingway House, and the Southernmost Point.

PRO TIP: If you drove from Miami or anywhere else, park your car once you arrive in Key West and leave it parked until you head back. You won’t need it while exploring the island, and you’ll save on parking fees and stress.

Choosing the right hotel makes a big difference in Key West. Most couples prefer to stay in Old Town, where you can walk or bike everywhere. All the places below are our top choices, and always have high ratings for comfort, service, and location.

The Capitana Key West – A modern waterfront resort with a relaxed, boutique feel. It has a pool, small private beach, and a hot tub—plus free parking, which is rare in Key West. Rooms are spacious, and many have balconies with ocean views.

H2O Suites – Adults Only – This luxury, adults-only hotel is perfect for a quiet getaway. It offers all-suite rooms, and some come with private plunge pools. There’s also a rooftop pool and bar. Excellent service and spotless rooms make it one of the most romantic options in town.

The Reach Key West, Curio Collection by Hilton – An upscale resort with its own private beach, oceanfront pool, and on-site dining. Rooms are stylish, and the property feels private while still being close to the main attractions.

Eden House – A great mid-range choice with a friendly, tropical vibe. It has lush gardens, a pool, and hammocks for relaxing. Many rooms have porches or balconies.

Casa Marina Key West, Curio Collection by Hilton – A Key West classic. It offers a long stretch of private beach, two oceanfront pools, and a spa with couples’ treatments. The rooms are large and comfortable, and the sunsets here are beautiful.

PRO TIP: Book early—especially for winter and spring. Prices rise fast, and smaller boutique hotels often sell out months in advance.

Key West is warm year-round, but the best time to visit depends on what you’re looking for.

December through April is peak season. The weather is perfect—sunny, breezy, and around 75–80°F (24–27°C)—but hotels are expensive and crowds are larger. Book early if you plan to visit during these months.

May and October are great shoulder-season months with fewer crowds and lower prices. You’ll still get plenty of sunshine, and the water is warm for swimming and snorkeling.

June through September is hot and humid, with temperatures often in the upper 80s to 90s°F (31–33°C) and daily afternoon showers. It’s also hurricane season, so check forecasts before you go.

To help you plan your trip, here’s a map of all 22 romantic things to do in Key West for couples. Use it to group activities near each other and make the most of your time on the island.

PRO TIP: Click on the map below to open it in Google Maps and save it to your phone for easy access while exploring.

A fun and easy way to see the island together. The Conch Train Tour loops through Old Town, passing highlights like Mallory Square, the Hemingway House, and the Southernmost Point. You can hop on and off at different stops to explore at your own pace.

Time needed: About 1.5 hours for the full loop.
Cost: Around $45 per adult.

PRO TIP: If it’s your first visit, start here—it’s the quickest way to get your bearings.

You can’t visit Key West without snapping a photo at the Southernmost Point Buoy, the famous red, yellow, and black marker that sits just 90 miles from Cuba. It’s one of the island’s most recognizable landmarks and a fun stop for couples.

Time needed: 10–15 minutes.
Cost: Free.

PRO TIP: Go early in the morning for shorter lines. By mid-morning, it gets crowded. Bring a coffee from Cuban Coffee Queen and make it a quick photo stop before breakfast.

Every evening, locals and visitors gather at Mallory Square to watch the sun drop into the Gulf of Mexico. Street performers, musicians, and food stalls make it a fun, one-of-a-kind experience. It’s easily one of the most romantic and free things to do in Key West for couples.

Time needed: About 1–2 hours before sunset.
Cost: Free.

PRO TIP: Arrive 45 minutes before sunset to grab a good spot along the seawall. Afterward, walk over to the Historic Seaport for dinner or drinks.

The Ernest Hemingway Home and Museum is one of Key West’s most popular attractions. It’s where the author lived and wrote for nearly a decade, and you can tour his house, gardens, and studio. The six-toed cats that roam the property are descendants of Hemingway’s pets and have become part of the island’s charm.

Time needed: About 1 hour.
Cost: $19 per adult

PRO TIP: If you’re a fan of Hemingway, you can also book a guided walking and food tour, The Hemingway Experience in Key West. It includes stops at his favorite bars and hangouts, plus lunch, drinks, and an entrance ticket to the museum. It’s a fun way to see Key West beyond the museum walls.

The Mile Marker 0 sign marks the end of U.S. Highway 1, which runs all the way from Maine to Key West. It’s a quick but iconic stop for couples who have made the drive down the Florida Keys. The sign sits at the corner of Whitehead and Fleming Streets, just a short walk from the Hemingway House.

Time needed: 10 minutes.
Cost: Free

The Key West Butterfly and Nature Conservatory is a peaceful, glass-enclosed habitat filled with hundreds of butterflies, tropical plants, and a few friendly birds. It’s quiet, air-conditioned, and a great break from the heat. It is perfect for couples who want something relaxing and easy to enjoy together.

Time needed: 30–45 minutes.
Cost: $15.50 per adult.

PRO TIP: Butterflies are most active in the morning, so plan an early visit for the best experience.

The Key West Lighthouse is one of the best viewpoints on the island. You’ll climb 88 steps to the top, where you get panoramic views of Old Town, the water, and the surrounding islands. Afterward, walk through the small Keeper’s Museum to learn how lighthouse families lived and worked here.

Time needed: 45 minutes.
Cost: Around $17 per adult.

Duval Street is the heart of Key West’s nightlife, lined with bars, restaurants, live music, and people out enjoying the evening. It’s fun to walk it together, stop for a drink, listen to a band, or grab a slice of Key lime pie. Even if nightlife isn’t your thing, a stroll here gives you a feel for the island’s energy.

Time needed: 1–2 hours.
Cost: Free to explore; drinks vary.

PRO TIP: Start at the northern end near the Historic Seaport and walk south. Popular stops include Sloppy Joe’s, The Rum Bar, and The Smallest Bar in Key West. If you want something easy without planning, you can book a Key West Pub Crawl —a fun way to try a few bars and meet other travelers.

The Key West Shipwreck Museum tells the story of the island’s old wrecking industry, when ships routinely hit the reefs and locals made a living salvaging cargo. Inside, you’ll see artifacts recovered from shipwrecks and learn how the “wreckers” worked. You can also climb the museum’s lookout tower for great views of Key West.

Time needed: About 1 hour.
Cost: Around $19 per adult.

The Key West First Legal Rum Distillery is a fun stop for couples who enjoy learning how things are made. You’ll see the distilling process up close, hear a quick history of rum in Key West, and sample a few of their best flavors. Tours are short and low-key, so it’s easy to fit into your day.

Time needed: 20–30 minutes for the free tour.
Cost: Free guided tour; tastings included.

PRO TIP: Their Mojito-Making Class is worth it if you want something memorable to do together. It’s hands-on, includes tastings.

The Harry S. Truman Little White House was President Truman’s winter retreat, and it’s been preserved exactly as it was when he stayed here. A guided tour takes you through the rooms where he worked, relaxed, and hosted important guests. It’s a good choice if you enjoy history or want a break from the heat.

Time needed: About 1 hour.
Cost: Around $24 per adult.

PRO TIP: Guided tours often sell out during busy months. You can reserve tickets here, which lets you pick a time that fits your schedule.

The Mel Fisher Maritime Museum showcases treasures recovered from shipwrecks in the waters around Key West, including gold, silver, jewelry, and artifacts from the famous Nuestra Señora de Atocha. Exhibits explain how the ship sank, how the treasure was found, and the work involved in underwater archaeology. It’s one of the best museums on the island if you enjoy history.

Time needed: 1–1.5 hours.
Cost: Around $17.50 per adult.

PRO TIP: Start with the 1622 Fleet Exhibit. It’s the highlight and explains the story behind the Atocha treasure.

The Key West Historic Seaport is a great place for a slower, quieter walk along the water. You’ll find boats coming and going, small shops, restaurants, and plenty of places to sit and enjoy the view. It’s especially nice in the late afternoon when the boardwalk starts to cool down.

Time needed: 1–2 hours.
Cost: Free.

PRO TIP: If you want to learn more about the area and sample local food, you can book a Key West Seaport Food Walking Tour. It includes tastings like fish tacos, Key West pink shrimp, and key lime pie.

Key West has several beaches, each with a different vibe. Here are two of the best options for couples:

Smathers Beach
The longest beach in Key West, with soft sand, clear water, and plenty of room to spread out. It’s great for swimming, sunbathing, and renting kayaks or jet skis.
Cost: Free.

Fort Zachary Taylor Beach
It’s my favorite with clear water, good snorkeling, and a natural shoreline made of crushed coral. It feels calmer and more secluded than other beaches.
Cost: Small state park entry fee.

PRO TIP: Bring water shoes—the coral can be sharp. Stay for sunset if you can; it’s one of the best spots on the island.

A sunset sail is one of the most romantic things you can do in Key West. You’ll cruise along the water as the sky turns orange and pink, with music playing and the island in the background. Many sails include drinks and light snacks, and the atmosphere is relaxed and fun.

Time needed: 2 hours.
Cost: Varies by boat and package.

PRO TIP: The Key West Sunset Sail with Full Bar, Live Music & Hors d’oeuvres is one of the most popular options. You will watch the sun set and the moon rise off the coast of Key West on this relaxing sunset cruise aboard a 70-foot catamaran. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer, and soft drinks are included.

A day trip to Dry Tortugas National Park is one of the best things you can do from Key West. The park sits 70 miles offshore and is home to Fort Jefferson, clear water, and some of the best snorkeling in Florida. Getting there takes time, but the experience is worth it.

Option 1: By Ferry

The Yankee Freedom III ferry takes about 2.5 hours each way. The trip includes breakfast, lunch, snorkeling gear, and a guided tour of Fort Jefferson.
Time needed: Full day.
Cost: Around $190 per person.

Option 2: By Seaplane

The seaplane is the fastest way to reach the islands—about 40 minutes each way—and the aerial views are incredible. You can choose a half-day or full-day trip.
Cost: Around $350 for a half day and $700 for a full day.

Parasailing is a fun way to see Key West from above. You’ll take off gently from the back of the boat and float over the water with wide views of the island, the beaches, and the boats below. It’s calm, not scary, and a great shared experience for couples.

Fury Water Adventures offers reliable parasailing trips with tandem flights for two.

Time needed: About 1 hour total.
Cost: Varies by company.

A mangrove kayak tour is a peaceful way to see a different side of Key West. You’ll paddle through calm, shallow water and narrow mangrove tunnels while learning about the local ecosystem. The tours are relaxed, beginner-friendly, and a nice break from the busy parts of the island.

Lazy Dog Adventures runs the most popular tours, and the guides are excellent at spotting wildlife. You can book the Mangrove Kayak Eco Tour.

Time needed: About 2 hours.
Cost: Starts around $70 per person.

Santiago’s Bodega is one of the best places in Key West for a cozy dinner for two. The menu is full of shareable tapas, everything from grilled octopus to short ribs to their popular pear and avocado salad. The atmosphere is warm and inviting, making it a great choice for date night.

Time needed: About 1–1.5 hours.
Cost: Moderate; dishes are small-plate style.

PRO TIP: Reservations are recommended, especially for dinner. Try the beef tenderloin, meatballs, or Brussels sprouts—those are always favorites.

Blue Heaven is a Key West classic and a great spot for a relaxed breakfast or brunch. The outdoor seating, live music (on select days), and laid-back atmosphere make it a fun place to start the day. The portions are generous, and the menu has plenty of favorites. Their Lobster Benedict, pancakes, and breakfast sandwich are always good picks. Arrive early on weekends; lines can get long.

Time needed: About 1 hour.
Cost: Moderate.

Latitudes on Sunset Key is one of the most romantic places to eat in Key West. The restaurant is on a small private island just a short boat ride from the harbor, and the setting is beautiful—especially at sunset. The food is excellent, the service is top-notch, and the atmosphere feels special without being formal.

Time needed: 2–3 hours, including the boat ride.
Cost: Higher-end.

PRO TIP: Reservations book up fast, especially for sunset. If dinner is full, try for breakfast or lunch; you’ll still get the view. And if cobia is on the menu, it’s worth ordering. Save room for their Key lime pie or warm beignets.

Cuban Coffee Queen is my favorite and one of the best places to grab coffee in Key West. The drinks are strong, smooth, and consistently good, and the food options, like Cuban sandwiches and breakfast burritos, are great if you want something quick before exploring the island.

Time needed: 10–20 minutes.
Cost: Affordable.

PRO TIP: Visit the original Waterfront location on Margaret Street. It’s the most charming one and is close to the Historic Seaport, making it an easy first stop of the day.