How to Plan a Weekend Getaway (Without Overcomplicating It)

If you’ve been thinking about getting away for the weekend but don’t know where to start, you’re not alone. Weekend trips can feel like they should be easy to plan, but somehow they get complicated fast.

Here’s the thing: they don’t have to be.

Carlos and I take weekend trips all the time, and we’ve gotten pretty good at making them happen without the stress.

Whether it’s a quick trip to St. Augustine with a Hop-on Hop-off Trolley Tour or a spontaneous road trip to New Orleans, we’ve figured out what actually works when it’s time to plan a weekend getaway.

So let me walk you through how we plan our weekend adventures, step by step.

Quick Tips on How to Plan a Weekend Getaway

• Start by picking a destination from your bucket list and setting a realistic budget that covers transportation, accommodations, food, tours, and activities before you book anything.

• Decide on the style of your trip first (relaxation vs. adventure) because this will determine what kind of accommodations to book and how packed your itinerary should be.

• Pack light by choosing versatile clothing items you can mix and match, and always check the weather forecast so you're not scrambling for last-minute essentials.

Start With Your Destination (Not Your Budget)

I know this sounds backwards, but hear me out.

Before you start crunching numbers, figure out where you actually want to go. Carlos and I keep a running list of places we want to visit, and when the weekend trip itch hits, we pick something from that list.

Why? Because if you start with the budget first, you’ll end up talking yourself out of places you actually want to see. Pick the destination, then figure out how to make it work.

That said, once you know where you’re headed, it’s time to estimate costs. Look at flights (or calculate your road trip gas costs), check accommodation prices, and get a rough idea of what food and activities might run you.

This way, you’re not blindsided when it’s time to book.

Set a Budget That Actually Makes Sense

Here’s how Carlos and I budget for weekend trips, and honestly, it’s a game-changer.

We divide everything into categories:

• Travel (flights, gas, tolls)
• Accommodations
• Museums and attractions
• Tours
• Restaurants and food
• Activities
• Souvenirs

We keep tours, museums, and activities separate because they each require different planning and can vary a lot in cost. A 90-minute walking tour is a lot different than a 3-hour adventure excursion.

The reason this works so well is that it gives you flexibility. If you get to your destination and decide you’d rather skip that museum and do something else instead, you can easily move money around without blowing your whole budget.

Decide What Kind of Trip This Is

This step is huge, and most people skip it or don’t even realize it.

Before you start booking accommodations, talk about what you actually want this trip to be.

Are you looking to relax and recharge? Or are you cramming in as many hikes, tours, and adventures as possible?

Why does this matter? Because it completely changes where you should stay.

If it’s a laid-back trip and you’ll be spending more time in your room, invest in a nice hotel with good amenities or a VRBO that’s within walking distance to the main attractions.

But if you’re planning an adventure-packed itinerary where you’ll be out the door early and back late, save your money and book something comfortable but affordable. You’re basically just sleeping there anyway.

Carlos and I always have this conversation at the very beginning of our planning process. It makes everything else so much easier.

Book Accommodations Strategically

Once you know the vibe of your trip, you can start looking at where to stay.

Here’s our system: before we look at a single listing, we decide on one non-negotiable feature we need in the room.

For us, it’s a decent-sized bathroom. If the bathroom situation looks cramped in the photos, we move on. For you, it might be breakfast included, city views, or premium cotton linens.

Start with your non-negotiable, then compare options based on price and what fits your budget.

And please, don’t take reviews too seriously. Where you stay is a personal preference, and what bothers one person might not bother you at all. Yes, pay attention to any red flags like cleanliness issues or safety concerns.

But a guest who leaves 2 stars because the lights were too dim or the decor wasn’t contemporary enough? That’s not something I’d let sway my decision.

Also, check the cancellation policy before you book anything. Some places have strict policies that could cost you if your plans change last minute.

Figure Out Your Transportation

Your transportation will depend entirely on the type of trip you’re taking and how far you’re going.

Carlos and I prefer driving anytime we can. Road trips are exciting, and if we’re heading to Georgia, South Carolina, Virginia or even New Orleans, we’d rather hit the road than deal with airports.

Plus, you can pack more, stop whenever you want, and have your car with you once you arrive.

If you’re driving, map out your route ahead of time and plan for rest stops. And make sure your car is in good shape before you leave.

If flying makes more sense for your trip, book your tickets as far in advance as possible to get better deals. Same goes for buses or trains.

Whatever you choose, give yourself plenty of time to get there. Weekend trips are short, and you don’t want to spend half of it stressed about travel logistics.

Plan Your Itinerary (But Leave Room to Breathe)

When Carlos and I start to plan a weekend getaway, the first thing we figure out is how many activities we want to cover and whether anything requires any extra driving time.

Then we think about the main focus. Are we chilling? Are we adventuring? That shapes everything.

One thing to keep in mind: if you’re planning tours, be strategic about timing. Some walking tours run 90 minutes, but adventure tours can take 3+ hours. Build that into your schedule so you’re not rushing from one thing to the next.

And don’t forget to leave some free time. Some of the best moments on a trip happen when you’re just wandering around, stumbling onto a local cafe or a street you didn’t plan to explore. Leave room for nothing at all.

Pack Smart (Not Heavy)

Packing for a weekend trip should be simple, but somehow it never is.

My rule: pack items that can be worn more than once and mix and match with different outfits. A pair of black casual shorts, for example, can work with multiple tops and shoes. White sneakers go with just about everything.

Here’s a quick checklist of what to consider:

• Sunscreen
• Bug spray
• Hat or sunglasses
• Toiletries
• First aid kit
• Camera
• Comfortable walking shoes or sandals
• A few easy layers, depending on the weather

Also, check the weather a week or two before your trip. It’ll give you a good idea of what to expect and help you avoid packing things you won’t need. But always have a backup plan just in case conditions change.

And if you’re flying, make sure everything fits in your luggage and check for any size or weight restrictions.

Safety Considerations

Before you head out on your adventure, think about safety.

If you’re travelling solo or going somewhere remote, let a family member or friend know where you’re going.

If hiking is on your agenda, tell them the trail names and how long you expect to be out. Most trails don’t have cell reception, so it’s a good idea for someone to know your plans.

Familiarize yourself with the area and bring a physical map in addition to your GPS or trail apps. Knowing where you are and where you’re going is key, especially if you’re venturing into the wilderness.

And always pack essential supplies: food, water, shelter, and a first-aid kit. Better to have them and not need them.

Final Thoughts

A successful weekend getaway doesn’t require complicated planning. It just takes a little intention.

Pick your destination, set your budget, decide what kind of trip you want, and pack smart. That’s really it.

Most of our travel is based on weekend trips since Carlos and I both work full-time jobs. It’s absolutely possible to see amazing places and have incredible experiences without taking weeks off.

So start researching destinations, make your lists, and book those accommodations. Your next adventure is waiting!

Estimate Your Gas Costs

Carlos and I always calculate this before a road trip, so we can get an idea of what we’re working with. Plug in your numbers and see an estimate of what your drive will cost.

Road Trip Gas Calculator 🚗

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*Results are only estimates and are for informational purposes only. Road trip calculator created by Next Stop Adventures.

Need help planning your next getaway? Contact me for my travel planning services.