Hilton Head 2025/2026: Day 1

I made the 5-hour drive to Hilton Head, South Carolina yesterday afternoon after spending five days in Florida visiting my family and playing hide-and-seek and “phones” with my 2-year old niece. Hilton Head Island has been my favorite vacation destination for the last 20+ years and crossing the bridge over the Intracoastal Waterway feels like coming home.

Calhoun Street Dock, Bluffton
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A Day in Newport, Rhode Island

Newport, Rhode Island was on my summer to-do list, but I didn’t make it there until the very last weekend of official summer. I know I was in Newport years ago, but I don’t remember much about it so it felt like visiting for the first time. With blue skies and temperatures around 70 degrees, the day couldn’t have been more picture-perfect for exploring the Gilded Age mansions and rocky coastline of this small New England city.

The Breakers
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Cape Ann in a Day

You don’t have to go far to feel like you’re on vacation. Even though I was in Gloucester (MA) just three days ago, today I was back playing tourist in my own backyard. Gloucester is about a 20 minute drive from home, but today it felt like being much further away as I explored an old castle, took a boat tour, and ate some delicious seafood.

Gloucester, Massachusetts
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Chicago 2025: Day 3

Welcome to Chicago! As I returned my rental car at the airport this morning, I was thinking that I would just like to jump on a plane and go home. By the end of the day, I remembered why I love Chicago and am happy to be here again. I blame my desire to go home on not having had a good night’s sleep in over a week and just wanting to sleep in my own bed. Anyway, a few sprinkles didn’t keep me from wandering around Chicago, having some cider, and enjoying a delicious pizza dinner.

Chicago
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