A romantic trip to Key West offers the potential to make connections and memories you'll carry with you for life with warm weather, picturesque beaches, and stunning sunsets. This island at the southernmost tip of Florida offers a vibrant nightlife scene, fantastic restaurants, and a wide range of activities from quiet moments alone to exciting adventures all in one place.

Key West is a paradise for couples whether you're cruising the beach on rental bicycles, shopping shady side streets full of boutiques, or taking a sunset cruise. Check out some of the best things to do for couples on a romantic trip to Key West, and make the most of your journey to this tropical paradise.

  • 1

    Key West sunset cruise

    Watch the brilliant colors over the water

    Key West sunset cruise
    • Couples
    • Nightlife
    • Photo

    A Key West sunset cruise lets you experience the famously brilliant sunsets of this region in a uniquely romantic way. You'll get out on a yacht or catamaran with craft cocktails, champagne, wine, and light eats to kick back and let all of your cares melt away in the company of the person you'd rather be with than anyone else in the world. Snuggle up and watch the brilliant pink, orange, yellow, and red colors of the sun as it sinks below the horizon, casting its hues across the rippling waters.

    Any number of tour groups offer sunset cruises off the island's western shores. Just choose your favorite, book a cruise, and get out on the water.

  • 2

    Sunset Key

    Get an 80-minute massage followed by dinner

    Sunset Key
    • Couples
    • Food
    • Luxury

    Sunset Key resort is only 7 minutes from Key West by boat and offers a full island paradise with spa treatments and beachside pampering to unwind with true romance. Sunset Key is 27 acres of resort and spa where you'll enjoy a massage delivered by certified therapists for 80 minutes. Afterward, you can put on a soft, plush robe and head to a covered table where your personal waiter will serve up tropical dinner and champagne. It's all part of the spa's Sunset Romance Package.

    This is a way to add a touch of unique romance to your trip unlike anywhere else. Best of all, you don't even have to be a guest of the resort to take advantage.

    Location: Sunset Key, Florida 33040, USA

    Map
  • 3

    Mallory Square

    Catch circus performers and a nightly party

    Mallory Square
    • Couples
    • Luxury
    • Nightlife
    • Photo

    Mallory Square in Old Town is famous for its sunset celebrations, where circus-style entertainment goes on into the evening with games, food, and activities you won't soon forget. For a vibrant party atmosphere underneath the world-famous Key West sunset, a visit to Mallory Square is a must. If you want a more upscale experience, you can take a cruise just offshore with beer, cocktails, wine, and hors d'oeuvres.

    However you choose to enjoy the celebrations at Mallory Square, it's not only an adventure for couples, but also a great opportunity for social media photo ops. Get a front-row seat to the party and add a touch of romance on top.

    Location: 400 Wall St, Naval Air Station Key West, FL 33040, USA

    Open: Daily from 6.30 am to 11 pm

    Phone: +1 305-809-3700

    Map
  • 4

    Old Town

    Visit the historical quarter of Key West

    Old Town
    • Couples
    • Nightlife
    • Photo
    • Unusual

    Old Town is the downtown historic district with a vast array of experiences from quirky photo ops to quaint shops, fine dining, and breathtaking scenic beaches. Here you can ride a train to learn about the island's history, visit historic buildings, catch harbor views from a towering lighthouse, relax on the beach, catch a sunset party with acrobats, musicians, and magicians, visit a tiki bar, or take a ghost tour to learn some haunted history.

    Old Town is the heart and soul of local nightlife, so it's the place to come if you're looking to do some bar hopping. From refined beach cruises to fun train rides or intimate moments along the sand and surf, Old Town has it all.

    Map
  • 5

    Dry Tortugas National Park

    Take a day trip to historic islands offshore

    Dry Tortugas National Park
    • Couples
    • History
    • Photo

    Dry Tortugas National Park is 70 miles from Key West, accessible by seaplane and offering stunning views from 7 islands straddling 3 bodies of water in an island paradise. Here you can experience the Gulf of Mexico, the Caribbean Sea, and the Atlantic Ocean all in one place. You can take a tour of the ruins of Fort Jefferson or go snorkeling among colorful local sea life. You'll also catch staggering bird's-eye photographs of the islands from above as you fly over.

    If you prefer, you can take a ferry ride, which offers meals and a snorkeling and historic tour as part of the package. While here, you can pretend you're a castaway in paradise.

    Location: Florida, USA

    Phone: +1 305-242-7700

    Map
  • 6

    Key West Lighthouse

    Take a walk back in time

    Key West Lighthouse
    • Couples
    • History
    • Photo

    The Key West Lighthouse is a historic lighthouse and museum downtown with a restored keeper's quarters and offering astonishing views of the surrounding land and sea for miles. This can be a fantastic place to capture a selfie of your time together or share a kiss as the ocean and mainland roll away to the horizon before you. You can also explore the museum that offers tons of photos, artifacts, documents, and ephemera from the days when this beacon stopped ships from crashing into the reefs around the island.

    When you step into the keeper's quarters, you'll see how the people who maintained the lighthouse lived. It's like walking directly back in time.

    Location: 938 Whitehead St, Key West, FL 33040, USA

    Open: Daily from 10 am to 5 pm

    Phone: +1 305-294-0012

    Map
  • 7

    The Ernest Hemingway Home

    Visit the 19th century in this historic home

    The Ernest Hemingway Home
    • Couples
    • History
    • Photo

    The Ernest Hemingway Home offers a scenic walk down a historic street lined with palm trees and a view into the colorful past of the island. Here you'll see wooden cottages and gingerbread-style mansions dating to the 19th century as well as the home of the famed writer. The house is a museum of the life of the writer and is still furnished and decorated with period accuracy, which makes it feel like you've stepped back into a more romantic time where you can forget about the cares of the modern world.

    Best of all, the home is just an 8-minute drive west from downtown. It's ideal for a quick visit before heading to an evening party.

    Location: 907 Whitehead St, Key West, FL 33040, USA

    Open: Daily from 9 am to 5 pm

    Phone: +1 305-294-1136

    Map
  • 8

    Duval Street

    Take a bike ride along the famed shopping district

    Duval Street
    • Adventure
    • Couples
    • History
    • Shoppers

    Duval Street is Key West's premier shopping district and is dotted with world-famous attractions, cafés, and a historic movie theater. Among the more famous locations on Duval Street is Mallory Square, which is known for its sunset parties featuring circus-style performers, magicians, and live music. During the day, the square offers many independent shops and boutiques to find the perfect souvenir to commemorate your trip.

    A popular way to see Duval Street is by bicycle, and many rental places dot the street. It's just a 10-minute drive west of the center of downtown, making for an easy jaunt to spend the day shopping, dining, and visiting historic sites.

    Location: Key West, FL 33040, USA

    Map

    photo by qwesy qwesy (CC BY 3.0) modified

  • 9

    The Southernmost Point

    Snap a selfie just 90 miles from Cuba

    The Southernmost Point
    • Budget
    • Couples
    • History
    • Photo

    The Southernmost Point Buoy is a concrete buoy that's painted in red, white, blue, yellow, and orange and marks the southernmost point in the continental U.S. It makes for a great photo for your Instagram feed and is just a few steps from other prominent locations in town, including Old Town and the Key West Lighthouse.

    If you're looking to commemorate your trip, this is a great point to visit and share a kiss and a selfie. You can tell your friends that you've been just 90 miles north of Cuba from this point in Key West.

    Location: Whitehead St &, South St, Key West, FL 33040, USA

    Open: 24/7

    Phone: +1 305-809-3700

    Map