How to Plan a Staycation You’ll Actually Look Forward To with Jenn Neilson
A step-by-step guide to turning your own backyard into your next favorite destination. We spend so much time dreaming about far-off destinations that we completely overlook the magic sitting right in our own backyard. But with flight prices climbing, limited PTO, and life getting more expensive across the board, staycations are regaining popularity.
I sat down with Jenn Neilson, travel blogger from Will Save For Travel and co-host of the Travel Mug Podcast, to talk through exactly how to plan a staycation that genuinely feels like a getaway. Jenn lives in Nova Scotia and has turned local exploration into an art form. Here’s everything you need to know, step by step.
Continue reading or listen to the full podcast episode below.
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1. Redefine What a Staycation Actually Means
Before you plan anything, let go of the idea that a staycation means sitting on your couch for three days. The definition is much more flexible than that, and that flexibility is exactly what makes it so special.
“I think the definition can be fluid, and it can mean whatever you want it to mean. I don’t know if there needs to be a rule.”— Jenn Neilson, Will Save For Travel
What is a staycation?
Jenn considers her entire province of Nova Scotia to be within her staycation zone, an area about the size of West Virginia.
For me? Anything in Connecticut counts. And yes, sometimes that looks like booking a hotel 45 minutes away just for a change of scenery.
Your staycation could be a day trip to a nearby city, a one-night hotel stay, or a full weekend getaway exploring towns you’ve driven past a hundred times without stopping.
What matters is the intention to explore, not the distance.
Helpful Tip: Draw your personal staycation boundary — your city, your county, your state. Anything inside that circle is fair game. There are no wrong answers.
2. Build Your Running List of Ideas Before You Need It
The best staycation planners don’t start from scratch.
They keep a running list of things they’ve been meaning to check out and pull from it when the moment is right.
“I keep a running list of things I want to do that are close to me, and I’m just gathering those over time. Mostly I’m getting those from friends posting things on Instagram and Facebook.”— Jenn Neilson, Will Save For Travel
You don’t need a fancy system. A note in your phone works perfectly.
The goal is to capture ideas as they come up: a restaurant someone mentions, a hike you see on a friend’s story, or a festival on a community flyer.
Here’s where to look when you’re building that list of things to do:
- Social media like TikTok, Instagram, or Facebook — what are people near you actually doing on weekends?
- Tourism Facebook groups for your region — full of local tips and visitor questions
- Travel bloggers who’ve written about your area — they find hidden gems locals overlook
- Community center bulletin boards and local newsletters
- Billboards on the highway (seriously — they advertise events you’d never think to search for)
- Food truck festivals, carnivals, and local event pages
3. Use the Anchor Activity Method
This is Jenn’s go-to staycation planning framework, and it works just as well for a day trip as it does for a full weekend away. The idea is simple: pick one “anchor activity,” then build a loose itinerary around it.
“Say there’s a hike I really want to do or a restaurant I really want to try. Then, I research what else I can do while I’m in that area. I approach it the same way as a big trip.”— Jenn Neilson, Will Save For Travel
Research local attractions near your anchor activity for added fun and discovery.
Is there a brewery or a museum nearby?
Could you do a ghost tour in the evening or even a cooking class?
The key is to think about what you enjoy most and then look for the local version.
Tired of reading? Listen to this podcast episode on Spotify.
4. Treat it Like a Real Trip
A staycation only feels like a vacation if you treat it like one.
That means planning ahead, getting intentional, and actually committing to the experience.
A staycation breaks the weekend chores-and-errands cycle, turning downtime into adventure.
It’s a deliberate choice to break that cycle.
5. Balance Staycations with Your Bigger Travel Goals
The whole point of a financially savvy travel lifestyle isn’t to choose between a staycation and a trip abroad — it’s to have both, sustainably, all year long.
Staycations keep your sense of adventure alive without draining your big-trip budget.
Jenn takes two or three longer trips per year, which leaves plenty of room for local adventures in between.
“We have a savings account that is only for big trips. Local trips, we tend to just take out of our fun money. It’s a pretty fluid situation.”— Jenn Neilson, Will Save For Travel
Another trick? Turn necessary errands into mini adventures. If you have to drive 90 minutes to a Costco or Home Depot, research what’s fun in that area and make a day of it.
Helpful Tip: Spread errands across the week so weekends stay free. For example, I do grocery runs on Tuesdays or Thursdays, which frees up my weekends for exploring.
Lastly, here are some fun and affordable staycation ideas to get you started.
Staycation Ideas Worth Trying
Mix and match these based on your anchor activity.
Hike a trail: Jenn has a provincial park not too far from her house, which she’s never visited. Bet you have one too.
Visit a local museum or historic site: Most areas have at least one, and many are free or discounted on certain days.
Book a ghost tour in a nearby town: History, walking, a little drama, and a great story to tell. Perfect anchor activity for an evening out.
Explore a local brewery or winery: An easy half-day or full-day activity. Great vibes, built-in social atmosphere, and usually locally owned.
Get a resort day pass near home: Great for couples and friend groups.
Attend a food truck festival, carnival, or street fair: Check community boards and local event pages. Summer is especially packed with free or cheap events.
Drive to a lighthouse, overlook, or scenic point: This is the kind of thing tourists travel hours to see. Bring the entire family.
Catch a local theater show or concert: Supporting local arts is both a cultural experience and a community investment, especially as funding cuts threaten small venues.
Visit an ice rink, apple orchard, or seasonal spot: Staycation ideas shift with the seasons. Winter brings ice rinks, ski slopes, and cozy stays; fall brings orchards and foliage drives. Rotate your list year-round.
Your Homework
A staycation is the perfect opportunity to break free from routine, spend quality time with those you love, and rediscover the magic in your own backyard.
Search “things to do in [your area].”
Write down two or three things, then make an actual plan to do them by marking your calendar.
Whether you want to sleep in your own bed or don’t mind a hotel stay, make space for adventure and relaxation in your everyday life.
When planned with intention, it can feel just like a traditional vacation, refreshing your mind and filling your days with new memories without venturing too far from home.
Read Next: Trips vs. Vacations – What’s the Difference?
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Danielle Desir Corbett is an award-winning and 6x grant-funded travel writer and podcast host who went from financial struggle to visiting 27+ countries all without waiting until retirement. Her story is proof that budget doesn’t limit adventure. Tune into The Thought Card Podcast for practical strategies to travel smarter and live on your terms. Say hello: thethoughtcard (at) gmail (dot) com.
