How to Plan a Weekend Getaway

Two women sitting outside with a glass of white wine

[This site is not just about American home cooking, it’s about navigating our busy lives and enjoying them to the fullest. I am passionate about tools and techniques to finding joy and happiness in our everyday experience. On the Advice page, you’ll find planning & organization tips, ideas for living and thinking better, and of course, tips for seamlessly integrating food and cooking into your life.]

It’s important to be open to anything while traveling, right?

Sure, until you arrive at the Airbnb in an unfamiliar city and you and your travel companion play the “what should we do now” game before getting hungry and falling into the closest tourist trap that serves pizza.

It’s always better to have some semblance of a plan, no matter how spontaneous you are.

Whether you’re headed to NYC (me!) or a secluded cabin in the mountains (definitely not me), here’s a step-by-step guide on how to plan a weekend getaway.

Step 1: Arrival Time

First, figure out how you’re going to get to your destination (rent a car, hop on a bus or a train, drive), how long that will take, and when you’d ideally like to arrive. Even if you’re not catching a plane on a schedule, it’s good to give yourself a timeline. Without a deadline, you might spend the first day of vacation still figuring out what to pack.

I like to arrive anywhere about an hour before lunch or dinnertime. That way I have time to unpack and unwind until I’m hungry (hangry). This is a great way to kick off vacation- order a glass of something bubbly, cheers to a great weekend, and get started with the real reason you’re visiting: the food!

Step 2: Make a Wishlist

Two women at a restaurant smiling and looking down at their phone.

Make a master list of restaurants, bars, museums, and sites. Remember, there are only three meals in a day, two nights in a weekend, and a small amount of daylight so it’s important to plan out and optimize your time.

However, this doesn’t mean you should 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.

Google ‘best restaurants in X‘ and make a list of all the ones you’d have a shot of getting into without being Kim Kardashian (unless you’re reading this, Kim).

Google ‘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.

Check out some of the spots that are near where you’re staying and definitely ask for local recommendations when you arrive. Everything you do doesn’t have to be the “best,” but you’ll want a second opinion.

Take all of these reviews as a guide, and then let your instincts dictate the rest of your plan.

Step 3: 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 three 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.

Give yourself a couple different options of restaurants, bars and things to do on each day in case something falls through or you decide you weren’t really feeling Thai food after all.

Step 3(a): 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 takeout 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 museum or tourist attraction, the crowds and lines are enough to make anyone sluggish. Schedule afternoon coffee breaks or even naps if you can swing it.

Remember to take some down time and don’t feel like you have to see everything. Vacation is about relaxation as much as it’s about discovery.

Step 4: Consider Everyone’s Opinion

Two women sitting in a dark bar and laughing

It’s a waste of time to argue with your travel companions about what everyone wants to do while on vacation, so get a sense of everyone’s expectations before you go.

Send out an email with your wish list, ask everyone to add to it or 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.

Is this going to be the best weekend ever or what?

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4 Comments

  • Reply
    Eric
    September 27, 2019 at 2:01 pm

    Yes! It sounds like it’s going to be a great weekend!

  • Reply
    Dodie
    September 27, 2019 at 2:54 pm

    I love your blog! You make me smile and sometimes laugh out loud every time. That’s a good thing and makes for a happy outlook. I also love your photos. This week’s are especially beautiful (and no I am not biased) Thanks for another great read. It is the start to a great weekend!

    • Reply
      Samantha
      September 27, 2019 at 4:04 pm

      I love your comments, they make ME smile!! Thanks for reading, enjoy your weekend 🙂

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