What’s in My Travel Bag Chesapeake Bay Edition

Happy Wednesday! I am heading to the Chesapeake Bay for a sailing excursion and stay at a timeless resort right on the water. I can’t wait to share it with you! As I was packing for my trip, I saw temperatures in the 70’s in the forecast. It will be cooler on the water, and of course aboard the yacht, but the warm up is happening!


Layers are going to be key for this trip. Knowing that we will be sailing, I am bringing all the essentials. Sunblock, sweaters, sunnies, ball caps, jackets, and deck shoes. Also, we have some receptions and dinners to attend, so I’m bringing some resort worthy dining options. Really hoping for a good old Maryland crab bake too!

Here’s what is in my travel bag…Chesapeake Bay Edition!

Dinners & Resort Wear

I’m bringing out the summery dresses, fun earrings, and bags! That blue Vineyard Vines dress is so flattering on! I love how easy breezy it is and that shade of blue is lovely. Also, I wanted a little prep in my step and that classic gingham from Draper James fits the bill.

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For a Day Sailing the Bay

The place we are staying at and featuring is classic Americana. We are covering the “Return of the Fleet” and will be sailing aboard one of their Hinkley Yachts for the day. Bringing out the red, white, and blue layers!

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I’m really looking forward to a day on the water. What a great way to kick off the travel season! Also, I’m excited to share who will be joining me on this trip.

I’m going to keep packing and getting ready…See you in Maryland!

Until next time,


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