Ava McDonnell
If you’re looking to plan a Valentine’s escape without leaving the state, you’ve come to the right place. Florida has no shortage of destinations, but the best trips depend on what kind of experience you’re looking for. Whether that’s quiet and coastal, historic and charming, or vibrant and indulgent, the locations will deliver memorable experiences for couples celebrating this year.
Below are some of the most romantic areas in Florida to celebrate Valentine’s Day, complete with ideas on what to do and where to stay.
Key West
Key West is a small island with a distinct laid-back energy and a strong focus on the water. Its streets are narrow and walkable, lined with pastel-colored houses and small shops. Despite its size, it has a surprisingly active nightlife and plenty of dining options, giving couples the ability to balance relaxation with social and culinary experiences. The atmosphere is casual, slightly eclectic, and feels like a step away from the mainland.
Where to stay:
Romantic Activities:
- Sunset sail on a catamaran or private boat tour
- Couples snorkeling trip to the reefs
- Dinner at Latitudes or Louie’s Backyard for waterfront dining
- Strolling Duval Street while exploring local art galleries
- Visiting the Ernest Hemingway Home & Museum
St. Augustine
St. Augustine has a rich, lived-in feeling thanks to its centuries of history. Cobblestone streets, Spanish-era architecture, and narrow lanes create a sense of continuity, making it a good destination for couples who enjoy history and culture. The city is compact, so most sites, restaurants, and galleries are walkable, which makes it convenient to explore without relying on transportation. Evenings tend to be quiet outside the main historic district.
Where to Stay:
Activities:
- Evening horse-drawn carriage rides
- Haunted tour downtown
- Wine tasting at San Sebastian Winery
- Sunset along the St. Augustine Bayfront
- Visiting Castillo de San Marcos for a scenic and historic stroll
- Exploring Flagler College’s unique architecture
Naples
Naples is quiet and well-organized, with a strong focus on high-end shops, galleries, and beachfront resorts. Its streets are clean, easy to navigate, and less crowded than other Gulf Coast towns. The vibe is more reserved than Key West or Miami, catering to visitors who want predictable luxury, quiet beaches, and a slower pace.
Where to Stay:
Activities:
- Walking along Naples Pier at sunset
- Dolphin watching
- Couples spa treatments at The Ritz-Carlton Spa
- Beach picnic with takeout from a local restaurant
- Wine and dine along Fifth Avenue South
- Visit the Naples Botanical Garden
Amelia Island
Amelia Island is a barrier island with a strong focus on nature and history. Live oak-lined streets and marshes cover the landscape, and there’s a notable absence of high-rise hotels, giving it a low-key feel. The island’s energy is measured and calm, with a small-town coastal vibe. The beaches are wide and rarely crowded, making it good for couples who prefer a slower, outdoors-focused experience.
Where to Stay:
Activities:
- Horseback riding on the beach
- Kayaking through the island’s marshes
- Couples spa treatment with ocean views
- Sunset walks on Fernandina Beach
- Exploring Fort Clinch State Park
Miami Beach
Miami Beach feels more like a city than a small town, with high-rise hotels, busy streets, and a mix of international visitors. Its energy is constant, with dining, nightlife, and cultural activities happening late into the night. The beaches are wide but busy, and the overall atmosphere is glamorous and cosmopolitan. This destination works for couples who enjoy urban energy alongside beach access.
Where to Stay:
Activities:
- Rooftop cocktails with panoramic ocean views
- Private cabana or beach day at South Beach
- Dinner at Joe’s Stone Crab or the Faena Restaurant
- Sunset helicopter tour over Miami
- Exploring Art Deco Historic District by foot or bike
Anna Maria Island
Anna Maria Island is narrow and long, with small streets, local shops, and mostly low-rise development. Its energy is slow and casual, with a focus on beach life and local dining. Unlike more tourist-heavy areas, it maintains a community-oriented feel. This makes it appealing for couples who want to disconnect and enjoy simplicity without commercialized attractions.
Where to Stay:
Activities:
- Watching sunset from Coquina Beach or Bean Point
- Renting a tandem bike or golf cart to explore
- Private paddleboarding or kayaking in Gulf waters
- Dining at The Sandbar or Beach Bistro on the beach
- Explore the island’s local art galleries, farmers’ markets, and boutiques
Each destination has its own personality, whether you’re looking for nature, culture, or urban energy, and plenty of activities to make a Valentine’s getaway memorable. By choosing a location that matches your style you can create a weekend that feels personal, enjoyable, and distinctly Floridian.
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