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How to Plan the Best Staycation Ever

  • Writer: Devyn
    Devyn
  • Jul 3, 2019
  • 7 min read

I'm in a bit of a travel lull at the moment. After a busy spring, my PTO balance is basically nonexistent, and I'm gearing up for a busy end of the year when it comes to trips. That means I'm trying to lay low this summer and resist the temptation to book another flight to, well, anywhere. While I could just sit back and settle into the normal routine that makes up the "real world" in Real World Wanderlust, I decided this was the perfect opportunity for a staycation!


So what is a staycation? It's your solution to having an incredible getaway experience without actually needing to book a trip across the globe. Staycations are little vacays you take right in your hometown - but trust me, it's still very much the relaxing getaway you'd hope for!


Today, I'm sharing my recent staycation experience to show you why these are the best things ever, along with my tips for planning the best getaway (minus the actually getting away) possible!

Let's start with all my staycation planning secrets!


Find a Boutique Hotel

Just because it's called a staycation doesn’t mean you should stay at home. To make your R&R experience the best it can be, book a hotel! The key is to seek out a boutique hotel - these are smaller with more unique or upscale accommodations or amenities. It will feel more special than staying in a "standard" hotel room. My stay at HotelRED (more details on that later) included a suite-style room, a view of the famous Camp Randall Stadium, locally made sweets and treats, and a fully-stocked mini bar.

Venture to a New Side of Town

Part of the fun of traveling is getting see and experience new things. Make sure you take a step out of your normal neighborhood and explore a new part of town. Opting to stay in a place you don't get to visit often will make your staycation more of a getaway experience. Come from a (really) small town? Try turning it into a mini road trip and hop one city over!


Hit Up a Specialty Store

Most cities come with at least one charming store or block with specialty shops you usually have no reason to go to. Make an effort to linger and explore the wares. When I'm playing tourist, I love to pop into random little stores and check out the interesting gifts and trinkets. You might just find a unique souvenir to remember your staycation by - or some yummy treats to try out during your experience.

Enjoy that "Can't Miss View"

Think of the iconic views or "must-sees" in your hometown. For Madison, it's the Capitol building and the twin lakes. Once you've got your shortlist, pick one and try to experience it through a tourist's view. While I pass our lakes all the time, I spent an evening sitting along the water (with a cold adult beverage) watching the sunset. Sure, it's a view I see all the time, but rarely do I stop to really enjoy it. I'm sure you've got something in town that you haven't fully appreciated - now's your chance!


Try a New Restaurant

Food is (in my opinion) the best part of a traveling. Use your staycation as an excuse to hit up that restaurant or café you've been dying to try but haven't had a chance to yet. Again, exploring new things will make it feel less like just another day in town. You can also splurge on your meal to make it extra special - fancy drinks, apps, dessert - go wild!

Take a Special Class or Tour

Check out your town's events calendar to scope out what's going on. Pick out a class or event that sounds interesting and make it the highlight of your staycation. Any other trip you would take would likely include activities - so why not do the same for this? Whether it's a walking food tour, a bar crawl, sunset yoga, or a cooking class, give something (anything) a try.


Treat Yo Self

Vacations are about resetting and recharging. Make sure you give yourself some "me" time! Pack some bubbly or vino and chocolates and watch your favorite junk TV in your hotel room. Slather on a face mask and soak in your in-room tub for a DIY spa session. Order that room service in the morning and have the best breakfast in bed. You do you - you've earned it!


Still unsure on what to do or how to swing it?


If a friend or family member was visiting you, what would you tell them to do?

That's usually the best mindset to have when it comes to planning your staycation. We usually want the loved ones in our lives to see our city for what it has to offer. You wouldn't tell them to shack up at the Motel 6 off the interstate or grab a sandwich from a chain. You'd want them to hit up the best restaurants, stay in a cool part of town, see a show, or walk around that really scenic park that makes for the best picnic stop, right? Use the list you'd give to a friend as your itinerary for your epic staycation.

Take advantage of your proximity!

Weekends and holidays can mean booked up restaurants or higher room rates at hotels. Take advantage of being in your own backyard and opt for a staycation during a less popular time. Take Friday or Monday off to do a Thursday or Sunday night hotel stay. Go out to a fancy local restaurant for lunch instead of dinner - the prices are usually cheaper during the day, too.


Treat it like a vacay and go completely out of office

If you were jetsetting on a first-class, all-inclusive getaway to Fiji, what would you do? Would you pack in advance, get all excited, and definitely turn on your "out of office" at work? I'm guessing yes. Why should your staycation be treated any less? It's still a getaway! Make sure you leave work at work and enjoy your time off. Don't let yourself minimize the amazing experience you're about to have - staycations are just as fabulous.

Rediscover your hometown and see it from a "tourist's" point of view

After a while, our daily routine makes home feel, well, a little boring. We stop looking around, marveling at the views or the buildings or the little things that make it unique. We overlook the things that once drew our eyes and attention. A staycation allows you to see your city through a visitor's perspective and rediscover your town. You might just find yourself falling in love with what makes your hometown charming.

Want the details on my staycation?


Chucking my to-do list aside and leaving the pets with a sitter, I headed to the other end of town to experience my hometown in a new light. First things first? Finding the best place to rest my head! Thanks to my lovely friends at HotelRED, I got to stay in style at this AMAZING boutique hotel. My suite was decked out with a spa-like shower, had tons of spacious areas to hang out, and featured amenities like slippers, robes, in-room treats and drinks, and a patio overlooking Camp Randall.

I usually hit up Madison's famous farmer's market each weekend, but it's more for stocking up on weekly produce and other essentials. In true vacation style, I left the grocery list at home and spent my time wandering the stalls I usually skip over. I ended up treating myself to some amazing fresh bread, gourmet chocolates, and a gorgeous bunch of flowers (just because).


I normally stroll around while traveling, so I decided to stick with it and peruse the blocks of shops I never have an excuse to visit. It's not every day you need to visit the craft olive oil maker, an eclectic shoe store, or the high-end cheese monger. But as a temporary tourist, it seemed like the perfect excuse to just, well, browse. I ended up enjoying more than my fair share of samples at the cheese shop and walked away with a seriously special gouda. At this point, I realized I had all the makings for a little cheeseboard spread and stopped for a bottle of wine for later before continuing on.

When I travel, I like to book activities to keep me occupied. Keeping with the theme, I signed up for a local class that caught my eye - a bitters bootcamp, where I could sample bitters-based drinks and even whip up my own bottle to take home. It was a seriously boozy event, but hey, that’s how most great vacation stories start. It was great to learn about something so special to our home state (bitters are a key ingredient in our unofficial state drink, the old fashioned).

The rest of my day was spent relaxing in my hotel suite and walking around the parts of town I don't spend much time in. It was a great way to unwind, forget about the chores I had to do at home, and just enjoy my weekend. I did go out with a bang with dinner at a nicer restaurant I rarely get a chance to eat at, given its distance from where I live.


After dinner, I decided to play tourist one last time and take in a local sightseeing stop - watching the sunset over the lake at the college's outdoor terrace. With a drink in hand, I watched the sun go down and just marveled in the gorgeous colors. It's not everyday I appreciate the sunsets in Wisconsin - usually I think of the amazing ones I've seen in the Gulf Coast or the Mediterranean - but dang, this was a sight to see.

Nearing the end of my one-night staycation, I treated myself to my DIY cheeseboard (remember my farmer's market haul), slipped into a cozy robe from HotelRED, and tucked in with a movie. I can't remember ever having such a relaxing weekend at "home" - there was no thoughts of yardwork or house-y projects. I ran zero errands, disconnected from the world, and just soaked up every second of my staycation. It was bliss.

A huge thank you to HotelRED for the gifted stay in such a fabulous suite - it truly made the experience as amazing as it was! If you ever find yourself in Madison, WI, I would HIGHLY recommend this boutique hotel!




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