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Overnight On The Eastern Shore

An overnight trip doesn't give you a lot of time away, but it does give you the opportunity to pack a bunch of outfits in a weekender or carry-on bag! This is not license to throw items in your bag willy-nilly. You can still be strategic about what you pack so that you are prepared and feeling your best for any activities (or relaxing) you plan to enjoy.

Here are a few tips for making the most of your luggage and preparing looks ahead of your arrival so that you can take advantage of every minute you're on location. I've also shared examples of the looks I packed for a recent trip to St. Michaels, Maryland - a picturesque harbor on Maryland's Eastern Shore.


Location - The most important thing to consider about the location is the vibe. A night away in Miami would look very different than in the Smoky Mountains. In my example, I'm considering a historic, out-of-the-way, bayside town where you can have an elegant dinner, but you could also be picking a table full of crabs. Did I consider a new LBD I've been itching to wear? Yes. But that will have to wait for a more cosmopolitan night out, because it's just not right for St. Michaels. Of course, you'll also consider the weather forecasted for your getaway.

Possible activities - You also need to consider what you might be doing during your trip. You don't need to have a detailed itinerary - it's usually enough just to make guesses based on the intent of the getaway, be it romantic, relaxing, adventurous, etc. If there are plans that would involve very specific items (e.g. hiking boots or a cocktail dress) you will want to nail those down ahead of time.


Looks by activity - Once you have a rough idea of your plans, you can turn to your closet. The objective is to pack a look for each possible activity or "event". I 100% write this out and recommend you do too. For the St. Michaels example, I used the following headings for my "events":

Travel To




Travel Home

Then build your looks under each heading, including undergarments and accessories.

Strategic overlap - Especially if you're not certain about a particular activity, it's not necessary to build a look with completely unique pieces. Shoes and bottoms are typically the easiest items to get multiple wears out of and it will result in a lighter bag. You'll see that I wasn't sure about our sightseeing plans so I figured it would be safe to re-wear a pair of shorts for that potential event and the drive home. And one hat would work for the pool and a tour boat ride.

St. Michaels Packing Plan

Travel To - fun mixed prints and neutral sandals for the mid-day drive

Pool Time - easy but cute ;) for the hotel pool and some QT with a magazine (and my husband)

Sightseeing - uber casual for a few tasting rooms and a boat tour

Dinner - not getting into the nicest places and may do some walking around downtown after dinner

Travel Home - early morning departure to get the kids to swim practice

All items in the looks are J. Crew Factory except the black Capri sandals which are from Old Navy.

Give this strategy a shot for your next trip so you can enjoy every minute of the getaway!

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