Florida Keys Valentine’s Day Getaway: Best Date Night Dinners & Romantic Day time Dates

Florida Keys Valentine’s Day Getaway: Best Date Night Dinners & Romantic Day time Dates 

A Florida Keys Valentine’s Day getaway delivers something few destinations can: oceanfront dining, island privacy, and unforgettable experiences — all in one seamless trip. February brings ideal temperatures, calm seas, and peak-season ambiance, making Valentine’s Day one of the most romantic and highly searched times to visit the Keys.

This guide is structured exactly how couples plan their trips:
First — where to book the perfect Valentine’s dinner.
Then — the most romantic date ideas and experiences.

Best Valentine’s Day Date Night Dinner Spots in the Florida Keys

1. Snook’s Bayside – Key Largo

A Florida Keys classic, Snook’s offers bayside sunset dining, fresh seafood, and relaxed island ambiance. It’s one of the most scenic waterfront restaurants in the Upper Keys, perfect for couples who want romance without formality.

The Vibe: Sunset views, outdoor tables, tropical cocktails, and relaxed sophistication.

2. Old Tavernier – Tavernier

A long-time local favorite offering Italian-American cuisine, seafood, and intimate indoor dining. Old Tavernier provides a cozy, romantic environment ideal for couples who value food quality and atmosphere.

The Vibe: Quiet, warm ambiance with elevated comfort dining.

3. Pierre’s – Islamorada

Set beneath palm trees at Morada Bay, Pierre’s is widely regarded as one of the most romantic restaurants in the Florida Keys. Candlelit tables, ocean breezes, and French-Caribbean cuisine create a signature Valentine’s experience.

The Vibe: Iconic setting, refined cuisine, and one of the best sunset views in the Keys.

4. Kaiyo Grill & Sushi – Islamorada

An upscale sushi and seafood destination blending Japanese technique with Keys flavor. Kaiyo offers a modern, intimate dining atmosphere — ideal for couples who prefer sushi and creative cocktails over traditional steakhouse fare.

The Vibe: Elevated sushi, stylish setting, and a lively but intimate vibe.

5. Nikai Sushi – Cheeca Lodge & Spa, Islamorada

Located oceanfront at Cheeca Lodge, Nikai Sushi offers refined Japanese cuisine in a luxury resort atmosphere. Dining here pairs sushi craftsmanship with tropical resort ambiance.

The Vibe: Sushi lovers + ocean views + luxury setting = perfect Valentine’s formula.

Marathon & Middle Keys Valentine’s Dinner Picks

6. Florida Keys Steak & Lobster House – Marathon

A Middle Keys favorite for surf-and-turf dining. Known for generous portions, high-quality steaks, and fresh lobster, this is a celebratory Valentine’s dinner spot.

The Vibe: Classic steakhouse experience with Florida Keys flair.

7. Rhum House – Grassy Key

A stylish, chef-driven restaurant offering creative dishes and craft cocktails. Rhum House feels intimate, trendy, and sophisticated — perfect for couples wanting something unique.

The Vibe: Elevated menu, modern ambiance, and excellent cocktail program.

Key West & Luxury Island Valentine’s Dinner Destinations

8. Latitudes – Latitudes

Located on private Sunset Key, Latitudes is accessed by ferry and consistently ranked among the most romantic restaurants in Florida. Oceanfront tables, candlelight, and sunset views create a flawless Valentine’s experience.

The Vibe: Private island arrival + sunset dining + luxury service.

9. Little Palm Island – Little Palm Island Resort & Spa

Accessible only by boat or seaplane, Little Palm Island offers the ultimate private island dining experience. This is one of the most exclusive Valentine’s dinners in the Florida Keys.

The Vibe: Total seclusion, barefoot luxury, and unforgettable ambiance.

10. A&B Lobster House – A&B Lobster House

A historic fine-dining steak and seafood restaurant overlooking the Key West harbor. A&B offers refined service, premium cuts, and a classic romantic dining atmosphere.

The Vibe: Old-world charm, waterfront views, and upscale cuisine.

Romantic Valentine’s Day Date Ideas in the Florida Keys

Private Sunset Cruise or Sail

One of the most searched Florida Keys Valentine’s Day activities, private sunset sails offer champagne, calm waters, and uninterrupted sunset views.

Private Sandbar Picnic

Charter a boat to a secluded sandbar for champagne, catered charcuterie boards, and barefoot island time. Zero crowds, full flexibility, and pure Keys romance.

Couples Snorkeling or Reef Excursion

February delivers some of the clearest water of the year, perfect for reef exploration and half-day ocean adventures.

Seaplane or Scenic Flight

Soaring above turquoise waters delivers one of the most unforgettable Valentine’s experiences in the Keys. You can take a Seaplane to the dry Tortugas or do a helicopter tour of the Florida Keys. Experience the calm islands and 50 shades of turquoise waters!

Couples massage and Spa Day at your Resort

Many hotels here offer 5 star relaxation and various spa treatment packages that suit every couple and make for the perfectly calming and romantic day!

Why Valentine’s Day Trips Often Lead to Florida Keys Home Purchases

Valentine’s weekend consistently attracts second-home buyers and lifestyle investors. Many couples first experience the Keys during February and return later to explore ownership.

Common motivations include:

• Winter escape lifestyle from low northern temperatures and snow storms
• Waterfront living appeal along with the most beautiful 70 degree weather and turquoise water
• Strong vacation rental demand
• Long-term appreciation
• Strong listing activity, giving buyers a wealth of property choices and homes to view and select from

A Florida Keys Valentine’s Day getaway is best built around one unforgettable dinner and one memorable experience. Whether it’s dining barefoot on a private island, cruising at sunset, or sharing sushi oceanside, the Keys deliver romance that feels authentic, effortless, and unforgettable. February is peak season — availability favors early planning.