How to Plan a Weekend Getaway



This weekend I’m visiting my sister in Western Massachusetts. She lives near Northampton; a fun, quirky little college town that has amazing restaurants and a cool shopping scene. While it’s important to be open to anything while traveling, it’s also important to get a good sense of what you want to do while you’re there. So whether you’re headed to NYC or hitting the beach this weekend, here’s a step-by-step guide on how to prep for a great weekend getaway.

Arrival Time

First, figure out how you’re going to get to your destination and when you’re going to leave. I actually couldn’t leave until Saturday morning, so I looked for early trains/busses that would get me into Northampton around lunch time. Arriving to your destination at either lunch or dinnertime is a great way to kick off a vacation. You can order a glass of something bubbly, cheers to a great weekend, and get started with the real reason you’re visiting that town: the food!


Make a Wishlist

I always make a list of the restaurants I want to go to, the bars I want to check out, and the museums or sites I want to explore whenever I go to a new place. There are only three meals in a day, 2 nights in a weekend, and a small amount of daylight so it’s important to plan out and optimize your time. However, you don’t want to fill out a timetable. Making a tentative list is a much more flexible, easygoing way to hit all the places you want to see without rigidly assigning them to specific hours of the day. I googled ‘best restaurants in Northampton’ and made a list of all the ones I hadn’t been to, giving myself plenty of options. I also googled ‘best bars’ and ‘things to do.’ Yelp, TripAdvisor, and Google reviews will give you a good sense of what’s fun and what’s not, but you can’t trust these reviews entirely. I’ve found plenty of good restaurants that only get 3 stars on Yelp and I’ve been disappointed by places that get rave reviews. Take the reviews as a guide, and then let your instincts dictate the rest of your plan.

Organize the List 

Now that you’ve got a dream list of everything you’d like to do, assign them to different days. You’re not going to hit all 3 bars in the same day. If you’re having a fancy dinner on Saturday night, consider a less-expensive lunch spot. If you’re going to a museum on Sunday (which your travel companion might hate) make sure you do something she wants to do on Saturday.

Diversify the Activities

It can be exhausting to go to museums, go out to dinner, and then hit the bars both Friday and Saturday night. For Saturday, consider a wine tasting or cocktails before dinner then get to bed early. Or, if the town you’re visiting has a famed pizza joint, you can get take-out one night and enjoy a laid-back dinner before going out later (just make sure you’re properly caffeinated). Don’t spend more than an hour at any one place, and schedule afternoon coffee breaks or even naps if you can swing it! It’s okay to take some down time, even if you are only in town for the weekend. Vacation is about relaxation as much as it’s about discovery.

Consider Everyone’s Opinion

It’s a waste of time to argue with your travel companions about what everyone wants to do while your at your destination, so get a sense of everyone’s expectations well before you go. Send out an email with your wish list, and ask everyone to add to it, veto certain items, and help assign the activities to certain days. If someone is driving, make sure you buy them a bottle of something and if you’re staying at someone’s house get them a gift, too. Starting the weekend off with generosity, gratitude, and a good idea of what everyone wants to do is a foolproof plan for fun. It’s going to be the best weekend ever!


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