Cruising Old Town Key West by bicycle is one of the best ways to get around. You'll see more of the island's character with a leisurely pedal down shady lanes lined with white picket fences. Get up close and personal with the Conch-style architecture--pastel wood buildings with gingerbread trim, louvered shutters, tin roofs and wrap-around porches. As an added bonus, you don't have to worry about parking, but be sure to lock up your bike. Eaton Bikes carries mountain bikes, road bikes, beach cruisers, tricycles and more. Rentals include free bike delivery and pick up anywhere in Key West. Watch out for the free-roaming chickens!
Recommended for Romantic Things to Do because: Take a leisurely bike ride down narrow shady lanes lined with historic architecture.
Claudia's expert tip: If it's been a while since you've ridden a bike, give it a test-drive before you hit the streets.
Take a magical nighttime paddleboarding trip from Ibis Bay Beach Resort where the boards light up the waters below. After dark, you can glide through the shallow waters of the bay with waterproof LED light bars illuminating the sea creatures beneath your board. In depths of only three-feet, normal boats can't access these pristine areas teeming with wildlife. As you ply the placid waters, you can imagine that you are the only two people alive in this peaceful universe. You'll discover lobsters, crabs, turtles, rays and many species of local fish without even getting wet. The relaxing activity is perfect for an evening attraction away from the bars.
Recommended for Romantic Things to Do because: Take a magical nighttime paddleboarding trip where the boards light up the waters below.
Claudia's expert tip: Keep an eye out for the myriad of fish and other sea life you'll spot along the way.
Take a seaplane 70 miles from Key West to the Dry Tortugas where it's easy to pretend you're castaways in paradise. These seven islands straddle the Gulf of Mexico, Caribbean Sea, and the Atlantic Ocean. The shallow waters surrounding the islands are perfect for snorkeling amid the ruins of Fort Jefferson. Tour the fort to learn about its construction and Civil War prisoners like Samuel Mudd--the doctor who assisted John Wilkes Booth after his injury. These remote islands are only accessible by seaplane of the ferry. A half-day trip by plane runs $329 per adult but offers a stunning bird's eye view. The Yankee Freedom II is the only ferry to the park, starting from $175, which covers entrance, meals, snorkeling and the tour of Fort Jefferson. Visit the Dry Tortugas Park website for rules, regulations, and what to bring.
Recommended for Romantic Things to Do because: Take a seaplane to the Dry Tortugas where it's easy to pretend you're castaways in paradise.
Claudia's expert tip: Book the afternoon trip on the seaplane, and you'll be treated to a spectacular Key West sunset.
Grab a kiss at the top of Key West's iconic lighthouse. Built in 1847, it was originally powered by 15 oil lamps that helped guide sailors to the island. Although it no longer serves as a functioning lighthouse, visitors can climb the 88 winding steps to the top for 360-degree views of the city and the ocean. Admission includes entrance to the museum (the former keeper's quarters), where audio and visual recordings are available as well as glass display cases of the previous owner's possessions. Photographs and quotes from lighthouse keepers and their families show that the now obsolete way of life will never be forgotten. Note that it closes at 4:30 p.m., so don't try to wait for the sunset. While many lighthouses in the U.S. are not open to the public, Key West's tower invites visitors to explore and learn about the past.
Recommended for Romantic Things to Do because: Grab a kiss at the top of this 1847 lighthouse as you enjoy 360-degree views of the island.
Claudia's expert tip: Prepare for a workout; you'll have to climb 88 winding stairs.
Enjoy a picnic for two on this well-maintained, sandy beach with chairs, umbrellas and water sports equipment for rent. Completed in 1866, the fort played important roles in the Civil War and Spanish-American War. On the third weekend of each month, see the fort come alive as local re-enactors engage the public in historic demonstrations. This 54-acre state park is also home to several nature trails, a stunning coral reef for snorkelers, picnic tables and a beachfront café. Fishing is permitted in certain areas. The three-story fort once held the largest collection of Civil War cannons in the U.S. (many of which are still there). Admission to the park is $2.50 when walking or biking.
Recommended for Romantic Things to Do because: Enjoy a picnic for two on this sandy beach in the shadow of a three-story brick Civil War Fort.
Claudia's expert tip: On the third weekend of each month, see the fort come alive as local re-enactors engage the public in historic demonstrations.
Escape into these enchanting gardens filled with soothing music, birds, turtles, fountains and over 80 species of butterflies. The entrance to the conservatory offers a wealth of interesting information about the life cycle and behavior of these stunning insects. Take a breather on a butterfly-shaped bench and try to get a close-up photo of a camera-shy Blue Morpho. You'll wind up staying longer than planned. Cocoons are on display in the glass-enclosed pupae room toward the rear and are clearly labeled with the species name. At any time, 1200 to 2,000 butterflies reside in the conservatory, and if one chooses to land on you, it's a sign of good luck. Don't miss the two pink flamingos named Rhett and Scarlett hanging out in the Koi pond.
Recommended for Romantic Things to Do because: These enchanting gardens are filled with hundreds of butterflies, birds and babbling brooks.
Claudia's expert tip: Keep your camera ready. When a butterfly lands on you, you'll want to capture the moment. It's a sign of good luck.
Find a cozy nook, perfect for cuddling, at this classy wine bar. The Little Room Jazz Club & Wine Bar is a refreshing change from the Duval Street Troprock scene. Settle in early to get a great seat for the show and to save some bucks with their happy hour. From 5pm-8pm daily, enjoy two-for-one food and drink specials. Discover a new favorite glass of wine from the extensive listing, as you listen to live jazz, blues and even Cuban-fusion bands. If you're feeling peckish, they have light snacks like rosemary and sea salt kettle chips, as well as meat and cheese plates. Specialty cocktails include Hemingway's "Death by Champagne," which mixes absinthe bitters, lemon and Lillet Blanc with champagne and the Cuban Fig Roast that combines burnt sugar syrup, Cuban coffee, cream sherry, cardamaro, mission fig bitters and a bucci ice cube. The furnishings have an elegant, polished look, and both indoor and outdoor seating is available.
Recommended for Romantic Things to Do because: Cuddle in a cozy nook at this classy club with a glass of wine and swanky live music.
Claudia's expert tip: Don't miss their happy hour daily from 5pm-8pm for two-for-one specials.
The journey from bustling Key West to Sunset Key only takes seven minutes, but the boat ride to this 27-acre island paradise will transport you a million miles away. Their couples' Sunset Romance Package is the epitome of indulgence. Lovebirds can unwind in their private thatched-covered cabana beachside while two therapists work their worries away during eighty-minute massages. The sounds of the water lapping the shore and the cool breezes caressing the skin calm the senses. Afterward, you'll don a fluffy blue robe and walk just a few steps to a linen-covered table. Your personal waiter will serve up champagne and tropical delights from their Latitudes Restaurant.
Recommended for Romantic Things to Do because: Couples can escape to the spa on this private island in under ten minutes for a romantic evening like no other.
Claudia's expert tip: You don't have to be a guest of Sunset Key to enjoy the spa.
Key West is famous for its circus-style sunset celebration on Mallory Square. For a more upscale (and less crowded) experience, hop on Danger Charters Wind and Wine Sunset Sail, where you'll have a peaceful front row seat to the sun's departure, replete with world-class wines. Each cruise is limited to a maximum of 25 people, which creates an intimate cocktail party vibe. Eight different fine wines, a selection of cheese, fresh fruits, beer, and hors d'oeuvres are served aboard the Danger Prize, a 65-foot schooner. A mellow mix of reggae, Jimmy Buffet, Salsa and Bossa nova music plays over the speakers in rhythm with the wind rippling the canvas sails. As the sun slips below the horizon, keep an eye out for the Keys' mystical green flash.
Recommended for Romantic Things to Do because: Skip the crowds on Mallory Square for a peaceful sunset sail and wine tasting.
Claudia's expert tip: Ask someone to take your photo as the sun goes down. Add in a kiss for the best romantic souvenir.
The name says it all. This intimate after-dinner cafe is guaranteed to set the mood for the rest of your evening. Indulge in sinful concoctions like Tongue Bath Truffle and Between My Red Velvet Sheets Cheesecake. Pair with their Choco-Cab--cabernet served in a chocolate-rimmed wine glass. It's so tasty you'll be licking the rim. The Kiss me Carolyn is a dessert in itself with Ayala champagne in a caramel-dipped wine glass dusted with bruleed raw sugar. Dark lighting is offset by menus that light up and flashlights on the table. It's no surprise that they've been voted the top decadent dessert spot in the United States.
Recommended for Romantic Things to Do because: Indulge in decadent desserts with scandalous names like Tongue Bath Truffle from this over-the-top dessert cafe.
Claudia's expert tip: Reservations are a must for coveted seats in this intimately-lit restaurant.