Shopping/Eating local

Question

My husband and I will be there for a long weekend in 2 weeks celebrating my 60th birthday. First trip to Key West.

We will be staying at the Perry Hotel on Stock island.

We will arrive mid-afternoon so will have probably explore around that area. Any good bars/restaurants recommendations around there??

Saving most of walking for Friday and Saturday. Plus our flight leaves late on Sunday so we will have plenty of time that day.

We’re not really outdoorsy sports people. But love good food, culture and art.

And I really like to support local businesses. So with those notes what would a typical free day be like for a local or frequent visitor.

Breakfast/brunch - typical American fare. Hearty and delicious.

We’ll probably do some touristy stuff after that - southernmost point etc.

Lunch- we love good burgers and sandwiches.

After lunch I would love to explore the Old Town area especially any local art shops/galleries and local artisans. (I particularly like photography art.)

Also a book nerd so is there any good local bookshop?

Happy hour with sunset views and good drinks a must. (Bonus points if they have good mock tails as I have to currently watch my alcohol intake due to medical issue.)

We love local bars with friendly and informative bartenders and staff.

For my birthday dinner, we are looking for something a little more special. Price range is open. My husband is a meat and potatoes guy so must have a good filet mignon on the menu. I’m a little more open with my tastes. Love a good steak but also enjoy shrimp and some well-prepared white fish.

My first thought was sunset dinner (no cruise please) and have looked at Hot Tin Roof and Louie’s. But we can also do sunset happy hour and then dinner elsewhere.

Any feedback would be appreciated. TIA

Answer

Congratulations on your upcoming 60th birthday! Key West offers a perfect blend of culture, cuisine, and charm for a long weekend, and staying at the Perry Hotel on Stock Island puts you in a quieter area while still being a short drive from Old Town, which is the heart of shopping, dining, and art.

For your mid-afternoon arrival and exploring nearby Stock Island:

Latitudes at Sunset Key Cottages – Lovely cocktail spot and casual bites right near the water for a relaxed start.
Hogfish Bar & Grill – Local seafood favorite with a laid-back vibe, perfect for a first taste of Keys cuisine.
Lazy Days Stock Island – Friendly local bar atmosphere and casual seafood, sandwiches, and cocktails (they often make excellent mocktails).

Breakfast/Brunch Options:

Blue Heaven – Iconic Key West brunch spot with hearty American fare; don’t miss the eggs Benedict or banana pancakes.
Harpoon Harry’s – Classic breakfast options in a casual setting.
Grand Café – Cozy spot with extensive breakfast and brunch menu, friendly local feel.

Lunch – Burgers and Sandwiches:

Grignano’s Sandwich Shop – Delicious and fresh sandwiches, casual and local.
Five Guys or local burger spots – For classic burgers; locals recommend the “Key West Burger Company” for a local twist.
Glazed Donuts & Burgers – For a quirky, casual option with fun burger creations.

Art and Culture in Old Town:

Key West Art & Historical Society / Custom House – Small but rich in local art and history.
Art galleries along Duval Street and Greene Street – Focus on photography, local artisans, and unique paintings; galleries like The Studios of Key West feature rotating exhibits.
Island Bookstore – Excellent selection of local interest books and photography coffee-table books; friendly staff for recommendations.

Happy Hour with Sunset Views:

Sunset Pier – Classic Key West sunset views, good cocktails and mocktails, lively atmosphere with local bartenders.
Hot Tin Roof – Rooftop bar with panoramic water views; excellent for pre-dinner drinks.
La Te Da – Beautiful spot for sunset cocktails, welcoming staff and great ambiance.

Birthday Dinner Recommendations:

Louie’s Backyard – Elegant waterfront dining, fine steaks including filet mignon, fresh seafood, and excellent service. Highly recommended for a special occasion.
Hot Tin Roof – If you want rooftop sunset first, you could follow with dinner elsewhere.
Seven Fish – Outstanding seafood and fish preparation, local vibe, excellent for pairing a fish entrée with a meat choice if desired.
The Flaming Buoy Filet Co. – Small intimate setting with creative seafood and steak dishes; local favorite for special meals.

Suggested Flow for a Typical Free Day:

Start with a hearty brunch at Blue Heaven.
Mid-morning stroll to the Southernmost Point and nearby photo spots.
Lunch at a local burger or sandwich place, keeping it casual and tasty.
Spend the afternoon exploring Old Town galleries, local artisan shops, and bookshops.
Early evening happy hour at Sunset Pier or Hot Tin Roof for sunset views and drinks/mocktails.
Special birthday dinner at Louie’s Backyard, Seven Fish, or Flaming Buoy for a memorable meal.

This itinerary balances local culture, food, and scenic experiences while keeping walking manageable and supporting local businesses. It offers a mix of classic Key West charm and indulgence for your celebration.

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