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How to Staycation

By: Leah Rosenbaum

As we get into September, or as I call it, a month of Sundays, I’m always hit with a wave of summertime sadness. How to beat them? Why not take a staycation and soak up all of the relaxation and excitement of a vacation without the hassle of hours on a plane, train, or car? Here’s how to plan the perfect in-town get away.

Where to rest your head?

Image by Leah Rosenbaum

The great thing about a staycation is that it can be as lavish or simple as you like and since you know your home, you can easily figure out how to budget (plus there’s no currency exchange or foreign fees – VAT what?!)! Where you want to sleep is the biggest decision. Do you want to be home or in a hotel? Would Airbnb be more your style? Perhaps there’s a house-sitting opportunity in a part of town you’d like to explore. Once you know how much you want to spend on lodging, it’s pretty easy to start narrowing down your options.

Sites for hotels/where to stay:

Paint the Town Red or Keep It Chill?

I’m awake, now what? How do you want to spend your days? When it comes to an itinerary, I think there are three ways you can take this:

  1. Tourist – Do everything, see everything, pack your days and nights

  2. Chillax to the Max – The name of the game is slow and relaxing, think spa appointments, leisurely walks, movie nights

  3. Everything I never get to do – Are you always having to forgo museum exhibits, food festivals, seeing friends, etc. for work or other obligations? Not anymore!

I suppose option 4 is to do a mix-and-match but you get the idea.

Once you’ve settled on the kind of vacation you want, it’s time to plan. Just as you would on a normal vacation (or is that just my family?), make a list of what you want to do. Check times, transportation (i.e. is the [insert subway/bus/train] running on a different schedule), and if any of your to-dos are outdoors, the weather. After you have the info, you can map out your days. Of course, you’ll need to be willing to adjust, you never know when there will be a passing shower, you might be exhausted come lunchtime and need to knock something off the list, or you might learn of something new to replace one of your activities. That said, flexibility is NOT the same as being open to just blowing off everything and working from home or spending your days filled with house chores and TV, there’s a time for that and it’s called “the weekend.”

Looking for inspiration? Some great places to start are your local paper/magazines. For example, if you’re in NYC, check out TimeOut New York or the New Yorker. Look at the websites of local concert venues/performance spaces or town hot spots, even city government (ex: nycgo.com). Many cities also host fun events in public places like parks or beaches. Keep an eye out for signs in stores- a la the Lululemon or Whole Foods community boards. I also love to explore the hidden gems or quirky sites if you will. A good way to find these is simply resorting to the interwebs and searching for unique/hidden/quirky [city]. I am also a huge fan of the Instagram account @withthelocals. Every week they feature a different person and his/her city. Whoever is in charge that week takes you on a virtual tour of their favorite haunts. It’s a great way to discover places a little off the beaten path, and figure out which brunch line is actually worth your time.

I’m SO Hungry!

Image by Leah Rosenbaum

I could spend all of my money on food and more or less do. The way that you eat on your staycation will have a lot to do with where you’ve chosen to sleep. If you’re home or at an Airbnb, you can cook some meals, easing the tension on your wallet. That said, even in my home city of NYC, you can make it through a day without needing to call in a favor from the bank of Mom and Dad.

Once you figure out how you’ll be eating (cooking, take-out, restaurants), figure out a game plan. Approximately how much are you looking to spend each day on food? Maybe you want to have one or two splurges or maybe you want to use this time to dig into a new meal-delivery service and get your hands dirty. If you’re in a hotel, remember that Room Service while heavenly (IMO) is expensive. Prices are ridiculously marked up and the bill is laden with fees, and, although a service fee is often included, you feel awful for not also giving a tip. Many hotels offer packages that include breakfast or a certain dollar amount in food each day. Additionally, beware of the mini bar. Mini bars are so tempting, particularly at night. Again, this is another place where prices are astronomical. Go to a nearby store and buy your own water, snacks, and essentials. Even when traveling with my family, I often go to a local market or drug store and stock up on yogurts and fruit to have on hand for easy and cheap breakfasts and easy snacks like nuts, bananas, baby carrots, and dried fruit.

It’s also worth seeing if there are any deals going on a la a restaurant week or perhaps a particular restaurant has a burger and beer special from 5-7pm on Wednesdays. Have a favorite food truck or one you’ve been wanting to try? Go to its website or social feeds and find out where it will be. Food trucks have some of the best food these days and at very reasonable prices. Also look to see if there are any food festivals, street fairs, or the like which often mean lots of food at great prices. (You can usually find this info in the same places I listed for activities.)

Staycation On, World Off

The trickiest thing about a staycation is how to replicate the distance from work, real life, technology, etc. that you have when you are somewhere else. What I’ve found works the best, is to replicate how you would/wouldn’t use technology and communicate when you’re away. What does that mean?

Pack up your computer, power cords, etc. and anything work-related that you would normally take on a trip. Get everything zipped up in their cases just as you would pre-plane. When you need something, take it out. When you’re done, put it away again. If you’ve chosen to stay at home, this is particularly challenging but trust me, do it.

Next up, email. Put on your “out of office” response. It doesn’t matter that you could theoretically pop into your office. You are away. Vacation days are important and you owe it to yourself to honor your time off.   

Phones are trickier. You need your phone for safety, navigating, making reservations, looking up train times, and taking pictures of all the awesome stuff you’re doing so going without isn’t really an option. Depending on your activities on any given day, you have a few options, you can turn off your data and rely solely on wi-fi when you need it (remember to be safe when it comes to unsecured networks), set times during the day/night when you will not use your phone, or, try using airplane mode.

Image by Leah Rosenbaum

Chances are when you mention taking a vacation, everyone will want to know where you’re going. Navigate this question with care. You don’t need to lie, but you also don’t want to make it seem like you’re just playing hooky/around and able to help with whatever. As with anything, I think a direct approach is best. Let people know that you have chosen to do a staycation and will be treating it as if you were away. If a friend plans something or you get an invite to an event that you want to go to, feel free to go if you want, but don’t feel like you have to jump on a conference call that if you were away, you wouldn’t be needed for. It might feel selfish, but it isn’t.

Tips or tricks I missed? Taken any staycations recently? Leave a comment below or email me!


-Leah Rosenbaum_Six Degrees Contributor_Headshot.jpg

Leah is a fourth-generation New Yorker, lover of brownies, and sweat enthusiast. After graduating from Brown University with honors in Literary Arts, she earned her JD from NYU School of Law, and holds a Certificate in Online & Social Media Marketing from Pratt Institute. Through co-running a popular Instagram account, Leah discovered that social media was the perfect way to combine her analytical and creative sides and has never looked back.  She is a social media/content strategist and writer. Leah loves puns, pop culture, and has zero regrets about any song in her iTunes Library.

Instagram: @whatleahloves

Website: www.glitterforbreakfast.com