Trip to Key West

Question

We are planning a trip in December and we are flying into Fort Myers and stay a couple days and then drive down to Key West with a stop in Marathon for the night. Looking for suggestions on a hotel in Marathon for one night and best places to eat also best area to stay in while in Key West and top hotels or Airbnb and must see's/do's.

Answer

Your December trip from Fort Myers to Key West via Marathon sounds wonderful — it’s a classic Florida Keys drive with plenty of scenic views and things to see along the way. Here’s a detailed guide for your stops, accommodations, dining, and must-see attractions.

Marathon – One Night Stop

Marathon is a great halfway point and has several well-reviewed hotels for an overnight stay. Since it’s just one night, you’ll want something comfortable, possibly with a pool, and close to dining options.

Tranquility Bay Beachfront Hotel & Resort: Upscale beachfront resort with spacious rooms, pools, and direct access to the sand. Perfect for a relaxing overnight stay.
Hawks Cay Resort: Slightly more resort-style with marina views, pools, and on-site dining. Offers both hotel rooms and villa-style accommodations.
Courtyard by Marriott Marathon Florida Keys: Reliable, comfortable, centrally located in Marathon with easy access to restaurants and convenience for a short stopover.

Dining in Marathon

Keys Fisheries: Famous for fresh seafood and casual outdoor dining, known for lobster Reuben sandwiches.
Island Fish Company: Great for sunset dining with seafood and Key lime specialties.
Castaway Waterfront Restaurant: Offers casual to upscale options with waterfront views and a relaxed atmosphere.

Key West – Best Area to Stay

For a December trip, staying centrally is ideal so you can walk to attractions, dining, and nightlife without relying heavily on transport. Popular areas include:

Old Town / Duval Street Area: Heart of Key West, walkable to shops, restaurants, bars, and attractions. Ideal for first-time visitors.
Near Mallory Square / Historic Seaport: Perfect for sunset viewing and proximity to historic Key West landmarks.
South of Truman Annex / Simonton Street: Quieter neighborhood with charming inns and easy access to beaches and restaurants.

Key West – Top Hotels & Airbnb Options

Ocean Key Resort & Spa: Luxury resort on the waterfront near Mallory Square, with spa, pool, and upscale dining.
Kimpton Lighthouse Hotel: Boutique hotel with rooftop bar and pool, close to Duval Street.
Santa Maria Suites: Offers spacious suites with kitchenettes, ideal for longer stays or group accommodations.
Airbnb: Options in Old Town, Truman Annex, or Bahama Village neighborhoods offer private homes, cottages, or condos with great access to key attractions.

Key West – Must See / Do

Sunset Celebration at Mallory Square.
Visit Ernest Hemingway Home and Museum.
Walk Duval Street for shopping, galleries, and restaurants.
Southernmost Point Buoy for a classic photo.
Fort Zachary Taylor Historic State Park for beach and snorkeling.
Optional boat tour: Key West sunset sail or snorkeling trip to nearby reefs.
Try local cuisine: Key lime pie, fresh seafood, and conch fritters.

Tips:

December is high season — book hotels and tours early.
Traffic can be heavy on US 1 approaching Key West, so allow extra time.
Consider splitting activities between walking in Old Town and driving to outlying spots like Fort Zachary Taylor or beaches.

With this plan, your overnight in Marathon breaks up the drive nicely, and staying in Old Town Key West keeps everything accessible for a chill, memorable Florida Keys experience.