Recommendations on places to stay and restaurants

Question

My sister and I are taking my 2 adult daughters to Key West for a 30th birthday celebration right after Christmas. Looking for recommendations for a nicer hotel, BNB or airbnb and restaurants. Thank you. We are only staying for 2 nights, driving from the gulf side of Florida. Any recommendations for our drive to Key West is appreciated too!!

Answer

Lovely plan — Key West is a joyful place for a milestone birthday: walkable Old Town, great restaurants, bars and sunset scenes, and plenty of boutique hotels and B&Bs that feel special. Because you’ll be there right after Christmas (a busy time), I’d recommend booking sooner rather than later for the best rooms and restaurants. Below I’ve split this into where to stay (nicer hotels / B&B / Airbnb-style ideas), restaurants for a celebratory night (and other meal ideas), a few drive-stop suggestions for a scenic Gulf-side → Key West route, and some practical tips for a short 2-night visit.

Where to stay — nicer hotels, B&Bs and boutique options

Marquesa Hotel (offers Café Marquesa on site) — Upscale boutique feel in Old Town; rooms are elegant and the on-site Café Marquesa is frequently cited as Key West’s top fine-dining option (perfect for a birthday dinner).
The Saint Hotel Key West, Autograph Collection — Adult-friendly boutique with stylish rooms and a rooftop bar vibe; great location near Old Town energy but a quieter, design-forward stay.
Historic Old Town Inns / Guesthouses — Key West has many converted historic homes (gardens, small pools, private porches) that feel intimate and celebratory — these are perfect for a girls’ weekend when you want charm and privacy. Search for Historic Inns in Old Town for a curated list.
Upscale resort option (if you want resort amenities) — If you prefer a marina/resort feel with spa or pool time, consider boutique resorts on the edge of Old Town or on nearby islands (book early — resort rooms fill fast after holidays).
Airbnb idea — A historic conch house or a renovated carriage house in Old Town gives a special, private-feel stay — check for properties with good reviews, proximity to Duval, and a walkable route to restaurants and bars.

Restaurants & celebratory dinners

Key West dining ranges from high-end contemporary to relaxed seafood spots and iconic bars. For a 30th birthday dinner, aim for a fine-dining reservation on the first night (or the night you want to celebrate), and then keep one casual/fun meal.

Café Marquesa — Frequently ranked among the best fine-dining experiences in Key West; elegant tasting-style menus and a great choice for a birthday dinner. Reserve early.
Dorada (or similar contemporary bistros) — Contemporary seafood/creative plates — good for a classy but less formal night out.
Louie’s Backyard / Southernmost or other waterfront venues — If you want ocean views plus refined food, prioritize booking these ahead — they fill fast around the holidays.
For a fun, lively night: Sloppy Joe’s, Green Parrot, or one of the Duval Street cocktail spots — great for celebratory drinks and a local vibe (not formal dining but iconic Key West nightlife).
Breakfast / brunch: The Breakfast Club and local cafés near Duval are popular — reserve or arrive early on busy days.

Drive-there suggestions (Gulf-side → Key West scenic route)

If you’re driving from the Gulf side, the classic and scenic route is the Overseas Highway (US-1) once you reach the Keys — it’s the highlight of the drive with iconic bridges and island stops. Recommended stops to break up the drive and add experiences:

Key Largo: For an early coffee or short nature stop (John Pennekamp Coral Reef State Park / quick snorkeling or a short kayak), especially if you’re arriving from the mainland.
Islamorada: A great mid-point for lunch, art galleries, and famous seafood shacks or tiki bars (Lazy Days, Robbie’s). Perfect for a relaxed meal and stretch.
Marathon / Seven Mile Bridge: Walk a portion of the Old Seven Mile Bridge or stop at the Marathon area for beaches and photo ops; Bahia Honda State Park (on Big Pine Key) has famous beaches and is worth a detour for postcard views.
Sunset stop: If you time it right, plan for a pre-Key West sunset at one of the western keys or arrive into Key West in time for the Mallory Square sunset festivities — that’s a quintessential Key West welcome.

Practical tips for a 2-night birthday trip

Book at least your hotel and one special dinner reservation in advance (Christmas → New Year → post-Christmas remains busy). For a 30th birthday, try to secure the celebratory dinner (Café Marquesa or equivalent) early.
Aim to stay in Old Town or very near it — walking to dinners and bars keeps the weekend relaxed and avoids parking hassles.
If you want an extra-special touch request a room upgrade, a corner room with a porch or private garden, or ask hotels about small celebration packages (some B&Bs help with surprises).
Allow time on the drive for unplanned stops — the Overseas Highway *is* the attraction. Plan one relaxed stop (Islamorada or Marathon) to break the journey and keep the vibe vacationy rather than rushed.

Final short sample plan (2 nights)

Day 1 (drive in): Scenic stops (Islamorada or Marathon) → arrive Key West, check in, relaxed dinner / rooftop cocktails.
Day 2 (celebration day): Breakfast in Old Town → day to wander, shopping, beach or pool time → special birthday dinner at Café Marquesa or similar → drinks on Duval or a sunset sail (if you prefer a private group option).
Day 3 (drive back): Brunch, last stroll, then leisurely drive back with a stop at Bahia Honda or Marathon if you didn’t earlier.

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