Wednesday, October 21, 2026

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Fall break vacation (Key West, FL)

Southernmost point of the continental U.S.

Before I talk about the trip, I need to vent. Southwest sucks. Sucks hard. Unfortunately, I'm pretty much locked in with them since I have the Companion Pass (a friend flies free) and my job requires that I use them when booking work trips. There's not one flight, not one, that's ever flown as originally scheduled. There is always a delay. And for our family trip, it was the absolute worst.

Lies! How can we depart at that time when we haven't even boarded the plane yet?

Our original time to land was at 11:50 p.m. (which was already late) but it got pushed back to an arrival time of 3:01 a.m. The delayed flight was set to depart at 11:36 p.m. but however, we hadn't even boarded the plane yet so who knew when we would actually arrive. WTF. By the time we landed, retrieved our luggage and rental car, and checked into our hotel (which was close to the airport), it was 4:45 a.m. At the hotel, I was greeted with a "good morning." She gave me a confused looked when I said that I wanted to check-in, not out.

It's 3 a.m. and we're still in the air.

On our way from Miami to Key West.

We stopped by Harriette's to try their "world famous" key lime muffin (Key Largo).

Pitstop at Georgie's for coffee and beignets (Marathon).

Fish tacos at Hogfish Bar & Grill (Stock Island)

And drinks.

We made it.

Catching the sunset on our first day in Key West (Smathers Beach).

Breakfast (Cubano benedict) at The Breakfast Club, Too.

Their specialty, the pancake charcuterie.

The default tiers for tipping, yikes.

At the Butterfly Conservatory and someone didn't notice a butterfly attached to them.

Kermit's for a slice of key lime pie and all things key lime: jelly beans, cookies, soft serve, and even peanuts.

Pizza and pasta at White Street Pizza.

Another day, another sunset (Higgs Beach).

Cuban sandwiches at 5 Brothers Grocery & Sandwich Shop.

On our way to snorkeling.

Snorkeling at Rock Key Reef.

Just hanging out on the boat, with unlimited drinks.

Dinner at Moondog Cafe.

Evening walk along Duval St.

Thanks, Trump.

List of restaurants/foods (for my sake):

  • Harriette's Restaurant (Key Largo) - home of the "world famous key lime muffin" (decent)
  • Georgie's Coffee Shop (Marathon) - Georgie signature coffee (good), key lime beignet (meh)
  • Hogfish Bar & Grill (Stock Island) - fish tacos (good), margarita (good)
  • The Breakfast Club, Too - Cubano benedict (really good), pancake charcuterie (fun)
  • Kermit's - key lime pie (good), cookies (really good), peanuts (gross), jelly beans (good)
  • White Street Pizza - Neapolitan pizza (really good)
  • 5 Brothers - Cuban sandwiches (good)
  • Old Town Bakery - pastries (meh)
  • Cuban Coffee Queen - cafe con leche (meh)
  • Moondog Cafe - Big Papa burger (really good), banana cream pie (good), basque cheesecake (good)
  • F-ing Bagels (Islamorada) - bagels, bagel sandwiches, coffee (good)
  • Dasher and Crank (Miami) - strawberry matcha latte (decent)
  • Cluck Face (Miami) - hot chicken sandwich (really good)

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