A romantic weekend in Key West
Enjoy two full days of sightseeing, snorkeling, and sweet moments in Key West, Florida.
Edited by Taylor Cahan | November 13, 2025
Key West is a place where romance feels effortless. Palm-lined beaches, pastel architecture, and golden-hour skies create a dreamy backdrop for couples looking for a quick weekend away. Wander Old Town Key West’s historic lanes, toast the sunset at Mallory Square, and dive into reef adventures just offshore. With so much packed into a compact island, a weekend here means you can savor iconic sights and intimate moments without rushing. Book a room at the landmark Casa Marina Key West, Curio Collection by Hilton, to enjoy the largest private beachfront in the area, an adults-only pool, and inviting amenities to help you make the most of your two full days in Key West.
Day 1
Morning
After checking in, begin your romantic getaway at the popular Ernest Hemingway Home & Museum. Arrive early — doors open at 9 am daily — to enjoy the lush gardens and meet the famous six-toed cats before crowds gather. Guided tours run every 15 minutes throughout the day, sharing stories of Hemingway’s life in Key West. Afterward, slip into a nearby café to grab a coffee and plan your next stop. Just a short walk away, you’ll find the Tennessee Williams Museum, the climbable Key West Lighthouse, and free flying butterflies and exotic birds at the Key West Butterfly & Nature Conservatory.
Afternoon
It’s 5 o’clock somewhere! Spend the afternoon alternating between the hotel’s private beach and two oceanfront pools. Sip tropical cocktails and sunbathe in a private cabana, enjoy shareable bites from Dorada, and launch jet skis, kayaks, and paddle boards right from the beach. If you’re looking for a quiet afternoon stroll, the hotel is also a short walk from Key West Gardens at Fort West Martello, a serene park nestled within historic stone arches and towers.
Evening
For the ultimate romantic experience, reserve Casa Marina’s “Toes in the Sand” private dinner on the beach. Or make your way to Mallory Square in Old Town Key West for the nightly Sunset Celebration with local food vendors, street performances, and stunning waterfront views. After, explore Duval Street’s pastel conch houses, photo-worthy corners, and sweet shops like Kermit’s and Mattheessen's to indulge in the island’s signature Key lime pie. End your evening at with drinks and live music at any of the vibrant bars in the area.
Day 2
Morning
Start your second day with breakfast from your guest room terrace. Then head out to a reef snorkeling excursion to Sand Key or the Western and Eastern Sambo Reefs. Sand Key sits near the iconic lighthouse and is known for gentle currents and colorful marine life, while the Sambo Reefs offer protected coral gardens and varied depths. Calm seas make for the best snorkeling, so check conditions and book with a reputable local operator. Bring reef-safe sunscreen, a rash guard, and a waterproof camera to capture the underwater scenery.
Afternoon
After your aquatic adventure, unwind by the pool or book a side-by-side couples massage at Spa al Maré across the street from the hotel. If you’re interested in more things to do in Key West, check out a dolphin watch tour or deep-sea fishing charter. When hunger strikes, enjoy a light lunch at a local spot — think fresh seafood, conch fritters, or Cuban sandwiches — or opt for Casa Marina’s unique “Cook Your Catch” experience where their chefs will prepare your fresh-caught fish during lunch or dinner service.
Until next time!
Key West is a place where romance lingers long after the sun sets. Whether you’re planning a honeymoon or a spontaneous weekend, every visit offers new memories to share. Until next time!
Disclaimer: We used AI assistance to generate this content. All information was reviewed by Hilton's team to ensure it meets our standards for accuracy and ethics, allowing us to better match your travel needs and connect you with the right stay.
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