5 Tips for planning your first vacation
Congratulations! You’ve decided it’s time for a well-deserved break—but now comes the big question: how do you even start planning your first vacation?
Don’t worry if you don’t have every little detail figured out yet. Vacation planning is a building process, so think of this as laying down the foundation before diving into the nitty-gritty.
In this post, we’ll walk through the key steps to get you on track, one simple step at a time. By the end, you’ll have a solid plan in place and the confidence to bring your travel dreams to life.
Tip 1: Dream
The first tip in your travel plans? Dream big! Before diving into details, take some time to imagine what kind of trip feels right for you. Start exploring Instagram, Pinterest, and Google searches to get a sense of the places and experiences that catch your eye. Think of this as “window shopping” for your dream vacation—no commitments yet, just saving ideas that spark excitement.
To make things easy, focus on these three basics: location, style, and duration.
- Location – Get a general idea of where you want to go. Are you craving a beach getaway, a mountain retreat, a big-city adventure, or even a relaxing staycation close to home? Start by narrowing down if you’re looking for something domestic or international, urban or remote.
- Style – Think about how you want to spend your time. Are you the “live like a local” type, eager to explore hidden gems? Or maybe you want a fully touristy experience with guided tours and museums. Not sure? Try taking an online quiz to get a feel for your traveler type—it’s a fun way to narrow down options.
- Duration – For your first trip, 4-7 days is the perfect amount of time. It’s long enough to unwind and explore but not so long that you feel overwhelmed.
Need some help organizing your ideas? Check out VRBO and Expedia for inspiration and to get a sense of costs. And don’t forget to save your finds to a Pinterest board so you can easily revisit and refine your ideas later. With these basics in mind, you’re ready to start building a dream vacation that fits you perfectly!
Tip 2: Plan
You’ve got your big three sorted—location, trip style, and duration! Now it’s time to start filling in some details and shaping your travel plans. Remember, this phase is about building a solid framework, so let’s break it down step-by-step.
- Who’s Coming Along?
It’s tempting to invite everyone you know, but for a first-time trip, keep the group small. Pick friends or family you have a solid track record with. A vacation isn’t the best time to test the waters with a new friend! And large groups? They can add layers of complexity you just don’t need for your first travel planning adventure. Start with a reliable, tight-knit group and avoid the added stress of managing a big crowd. - Set a Realistic Budget
This one can feel tricky—how do you set a budget if you don’t know how much things will cost? But remember, everyone has a budget, whether it’s $500 or $5000. Be honest with yourself about what you’re willing and able to spend. Starting with a realistic budget helps prevent disappointment down the road. If you’re aiming to keep it affordable, that’s okay too! There are plenty of ways to make the most of a smaller budget. Ultimately, this is about you telling your vacation what to do, not the other way around. - Ask for Time Off Early
Once you’ve got a rough time frame, start thinking about requesting time off from work. Ask early, get it in writing, and make sure it’s locked in. For more tips on how to do this effectively, check out our blog post on How to Ask for Time Off. Timing can also affect costs—peak travel times, like spring break, can mean sky-high prices. If you’re flexible, look into less popular travel dates to help your budget stretch further.
With these foundations set—your group, budget, and time off—you’re now ready to start thinking about the next exciting steps in planning. This groundwork keeps your vacation planning process stress-free and fun!
Tip 3: Book
Now that you have your dream trip sketched out, it’s time to lock in the details and make it official! But before you dive into the booking process, let’s cover some essentials to make sure everything goes smoothly.
Before you press purchase!
- Double-Check with Your Crew and Work
Before booking, confirm that you’re fully approved for time off. If you’re traveling with friends or family, check in to make sure everyone’s still good to go. Plans change, so you’ll want to avoid any last-minute surprises! And a quick tip: keep your money separate—don’t cover others’ tickets or rooms. If someone backs out, you don’t want to end up chasing them down for refunds. - Start with Flights
Your flights are often the biggest booking expense, so tackle this first. If you find a great deal, make sure you know the cancellation policies. The cheapest fares can be non-refundable, which could cost you if plans shift. Sometimes, paying a little more for flexibility is well worth the peace of mind. For any trips where you might need to change dates, I’d always go with the cancelable option. Booking.com is a great place to start! - Use and Earn Miles
If you have a points or rewards program, compare options across travel sites (like Priceline or Expedia) and the airline’s own website. Even if you don’t have points yet, it’s never too late to start earning! Sign up for free mileage programs with airlines—it’s a win whether you book directly with them or through a third-party site.
With flights booked, your trip is starting to feel real. You’re well on your way to the ultimate getaway!
Reserving Accommodations
With your flights secured, it’s time to find a cozy spot to rest your head. Booking accommodations is the second step in the booking process, and just like with flights, there are a few tricks to help you get the best deal.
- Check Sites Like Expedia and VRBO for Deals
Start your search on popular sites like Expedia and VRBO to get a sense of pricing and availability. But don’t stop at a single search—check back over a few days. Prices can fluctuate, and sometimes the perfect spot pops up at a lower rate. - Book Sooner Rather Than Later
While prices can go up and down, waiting too long can lead to higher prices as your travel date approaches. Once you’ve found a place that fits your budget and needs, go ahead and book it to lock in the rate. There’s nothing worse than seeing a perfect place disappear because you waited too long! - Consider Cancellation Policies
Like with flights, make sure you know the cancellation terms. Sometimes, a flexible option is worth the extra peace of mind, especially if you think plans might shift. This way, you’ll avoid any last-minute charges if things change.
With your accommodations in place, the major parts of your trip are officially booked. You’re now that much closer to making your travel plans a reality!
Tip 4: Prep for the Trip
Now that the essentials are booked, it’s time to prep for your time away. Think of this stage as a chance to make sure everything back home is handled so you can fully enjoy your vacation without worries. Here’s how to get things sorted:
- Handle Bills and Appointments
Check your calendar and see if any bills will be due while you’re away. If so, schedule them for autopay or pay early so you’re not stressing about them mid-trip. Also, check for any automatic appointments—no one wants to miss an eyebrow wax or dental appointment they accidentally set for vacation week! - Arrange for Plant and Pet Care
Your pets and plants need a plan too! For plants, find a friend or neighbor to water them while you’re gone. For pets, arrange for a pet sitter, a neighbor to pop in, or set them up at a reputable doggy daycare. If you have other pets that can stay at home, make sure someone checks in on them. - Do a Walk-Through with Your Helpers
Make sure your house-sitter or pet-sitter has a quick walk-through of your home with you the week before you leave. Show them how to get in, where to find your pet’s favorite toys, and any other essentials they might need. This prevents those last-minute calls wondering where to find Fifi’s toy stash or how to unlock the side door!
With all these details taken care of, you’re ready for a smooth, stress-free trip. You’ll be able to fully relax knowing things are handled back home!
Tip 5: Live in the Moment
You’ve planned, prepared, and now you’re finally here—enjoy it! This is your time to fully disconnect from the stresses of everyday life and leave work behind (yes, they’ll survive without you, I promise). Here are some ways to make the most of each moment and embrace the adventure:
- Take Photos—but Not Too Many
Photos are a great way to remember the trip, but don’t let capturing the moment keep you from living it. Snap a few pictures and then put the phone away. Give yourself time to enjoy the view with your own eyes, not just through a screen. - Embrace the Bumps in the Road
Not everything on your trip will go according to plan, and that’s okay! Maybe the tour you booked didn’t live up to expectations or the weather threw off your beach day. Instead of letting it bring you down, look at it as part of the experience. Sometimes, the “fail” moments make for the best stories later on! - Let Go of the “Perfect Trip”
Perfection is overrated. You’ve spent a long time planning and dreaming about this trip, so don’t let little hiccups stop you from having a great time. If something doesn’t go as planned, roll with it. This is your time to relax and have fun, so soak it all in and enjoy the moment.
This is what all that dreaming, planning, and prepping was for—so let yourself unwind and embrace every part of the journey.
Ready to Make It Happen?
There you have it—your step-by-step guide to planning that first vacation like a pro! Sure, there might be a few bumps along the way, but that’s all part of the adventure. You’ve got your dream destination in mind, your plans in place, and now it’s time to enjoy the journey. Remember, it doesn’t have to be perfect—it just has to be yours. So go out there, make memories, snap some photos, maybe get a little lost, and soak up every moment.
Bon voyage and happy travels!
