How to Plan A Weekend Trip that Will Reset Your Soul

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If you want to plan a weekend trip, you don’t need weeks of research or a giant itinerary. In fact, some of our favorite getaways have been the spontaneous ones that came together with just a little bit of planning. The trick is knowing what actually matters when you only have a few days, so you don’t waste half your weekend getting there, overpacking, or arriving with a list of 25 things you somehow think you’re going to fit in.

A weekend trip should feel like a break, and we’re here to help you do just that. That’s why we like to keep the planning simple: figure out when you can go, choose somewhere that makes sense for the amount of time you have, pick a few things you really want to do, and leave yourself some room to actually enjoy being there.

In this guide, we’ll walk you through exactly how to plan a weekend getaway from start to finish, including choosing your dates and destination, checking the weather and events, packing light, building your itinerary, and creating a plan that’s fool-proof. By the time you’re done, you’ll have everything you need for a fun and stress-free weekend away.

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What to Consider When Planning a Weekend Trip

Before diving into how to plan a weekend trip, let’s take a quick peek at what a successful weekend getaway looks like, and the main things you should consider when organizing your travels.

📆 What Should a Weekend Trip Look Like?

A weekend trip should give you enough time to actually experience somewhere without making the travel itself the biggest part of the trip. That means being realistic about how far you can go and how much you can fit into a couple of days. I used to try and squeeze 3 destinations into a weekend, but my favorite weekend getaways were ones where I fully focused on one place.

For us, the ideal weekend getaway has a few things we really want to do, some flexibility around them, and enough downtime that we’re not constantly watching the clock. You don’t need to see every attraction in a destination to have a successful trip (although I’m notorious for forgetting this). If you come home having enjoyed yourself and experienced the things that mattered most to you, the trip did its job.

The biggest thing for us is balance. Not every meal has to be a long and fancy one, and we don’t need to be doing back to back hikes. Balancing a bit of good food, a night out, some sightseeing, and an activity or two is our key to having a truly epic weekend.

👀 Things to Consider When Planning a Weekend Trip

Before you start putting your itinerary together, there are a few important things to consider. Since you’re working with limited time, making these decisions first will make the rest of the planning much easier.

Here’s a bit of what planning a weekend trip will look like:

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How to Plan a Weekend Trip Step-by-Step

Now let’s get into the actual process. These steps are designed to keep you organized without turning a two-day getaway into a three-week research project.

📆 Step 1: Choose Your Dates

The first thing you need to figure out is when you can actually take the trip. Start by looking at your work schedule and seeing whether you have any PTO available, a holiday to connect your trip to, or ways to extend your weekend longer than just 2 days.

💻 Working Remotely

If you work remotely, you may be able to turn a normal weekend into a longer trip by working from your destination on Friday or Monday. We are actually usually working while traveling, and simply taking your laptop to a cute cafe or beach club allows you to feel like you’re already on vacation even if you have a bit of work to do.

You can also opt for working at the airport or on your flight – doubling your work time into travel time as well. Just make sure you know your company’s rules about working remotely before booking anything.

🎅🏻 Working with the Holiday Calendar

You should also look at the holiday calendar, as there might be days you have off that you didn’t know about! A holiday that falls on a Friday or Monday can give you a three-day weekend without using any PTO, while taking one extra day off around a holiday can turn a regular weekend into a four-day getaway.

Step 2: Choose a Destination That Makes Sense

Once you know when you’re going, it’s time for the fun part: deciding where to go.

The biggest mistake we see with weekend trips is choosing somewhere that takes too long to reach. Remember, your trip doesn’t start when you arrive. If you’re flying, you need to account for getting to the airport, security, connections, potential delays, and getting from the airport to your accommodation. If you’re driving, think about traffic, stops, and how much time you’ll actually spend behind the wheel.

A destination that looks close on a map can eat up most of your Friday and Sunday if the transportation is complicated. For a short trip, getting there easily is often more important than getting somewhere far away.

🎉 Planning Around a Specific Activity

If you want to plan a weekend trip around a specific activity, concert, sporting event, festival, attraction, or other experience, check availability before committing to the destination. There’s nothing worse than building your entire weekend around something only to discover that tickets are sold out.

And if you’re booking close to the travel dates, check the weather before you finalize everything. Weather can impact events greatly, and we’ve had several weekend trips we had to pivot last minute due to the anticipated event being postponed or cancelled.

Step 3: Check What’s Happening

Before you start putting your itinerary together, check what’s happening at your destination during the dates you’ve chosen. Look for festivals, concerts, sporting events, markets, exhibitions, holidays, local celebrations, or anything else that could be happening while you’re there.

This can help you find something you wouldn’t have otherwise known about, but it’s also important for planning around crowds and availability.

A major event could mean that hotels are more expensive, restaurants and activities are booked up, or certain areas are much busier than usual. On the other hand, finding out about a local festival or event could end up being one of the highlights of your weekend.

Step 4: Book the Important Things First

Once you’ve decided on the destination and dates, book the things that could sell out or become significantly more expensive.

For most weekend trips, this means transportation and accommodation first. If your trip revolves around a specific event or activity, book those tickets first and foremost.

You don’t necessarily need to have every hour of your weekend planned before you book anything. In fact, we recommend the opposite. Lock in the things that are essential, then build the rest of your weekend around them.

Check out excursions on Viator

Explore transportation options on Omio

Step 5: Pick Your Main Things to Do

Now it’s time to figure out what you actually want to do once you arrive. We you plan a weekend trip, don’t try to see everything (yea this is a hard one to stick to). Pick the handful of things that would make you feel like the trip was worth taking and use those as your anchors.

Maybe there’s one restaurant you’ve been dying to try, a hike you really want to do, a museum you’ve always wanted to visit, or a neighborhood you’ve been curious about. Those are the things you build your weekend around.

Think of these as your must-dos, rather than creating an enormous itinerary where you’re constantly checking the clock. Once your main activities are chosen, you can fill in the spaces around them with food, sightseeing, shopping, or whatever else interests you.

📋 Make an ABC List

This is one of our favorite ways to organize a short trip without overplanning it, and makes planning a weekend trip much easier for flexibility. You know exactly what matters most, but you’re not beating yourself up because you didn’t make it to every single place on your list.

Instead of creating one rigid itinerary, divide your ideas into three categories:

Step 7: Build Your Weekend Around Your Anchors

Now you can actually put the trip together! Start with your A-list activities and place those into the days based on location, opening hours, reservations, and any other timing restrictions. Then look at what’s nearby and add a few B-list options around them.

This is where grouping things geographically can save you a ton of time, which is why learning how to make itineraries in Google Maps is a total game-changer.

Use your anchors with a rough timeline – that way you can see how the day is going and add/subtract B & C choices according to the flow of your itinerary.

Step 8: Pack Light

For a weekend trip, we recommend sticking to a personal item whenever possible. You really don’t need a million outfits for a couple of days. We recommend bringing a few pieces that work together, comfortable shoes, and the basics you’ll actually use.

Just make sure you pack for any specific requirements at your destination. For example, knowing what to pack depending on the weather, culture, and religion are key. Before you zip up your bag, do a quick check that you have what you need for the plans you’ve already made, along with important documents.

Step 9: Make a Backup Plan

You don’t need a backup itinerary for every single minute of the weekend, but you should have alternatives for anything that could easily get ruined by weather, closures, or sold-out tickets.

If your A-list activity is outdoors, know what you’d rather do if it rains. If you’re planning around a restaurant, have another option nearby. If you were hoping to visit a specific attraction, check whether you need reservations and know what else you could do instead.

Your backup plan doesn’t have to be elaborate. In fact, we prefer having a short list of alternatives rather than creating an entirely second itinerary. The goal is simply to avoid that moment when something falls through and everyone stands around saying, “So…what do we do now?”

Step 10: Do a Final Weekend Trip Check

A few days before you leave, go through your plans one more time. This is when you’ll catch the little things that are easy to overlook when you’re planning several weeks in advance.

Double check your transportation times, accommodation, reservations, activity tickets, weather, and anything that requires advance booking. If you’re driving, check the route and parking situation. If you’re flying, make sure you know how you’re getting to and from the airport.

Then take one last look at your packing list and make sure you have the essentials. You don’t need to keep researching once everything is confirmed. At this point, you’ve done the work. Save your confirmations somewhere easy to access, make sure your phone is charged, and get ready to actually enjoy your weekend getaway.

Final Tips for Planning a Weekend Trip

A successful weekend trip isn’t necessarily about seeing as much as humanly possible. It’s about choosing a destination that makes sense for the time you have, prioritizing the experiences you actually care about, and leaving yourself enough flexibility to enjoy them.

The whole point of planning a weekend getaway is to come back feeling refreshed, not like you need a vacation from your vacation. Keep the planning simple, give yourself a few priorities, and don’t be afraid to change your plans when something isn’t working.

Before you leave, remember:

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👀 What’s Next?

Now that you know how to plan a weekend trip, it’s time to help you with some other planning and budget-travel tips.

Here are some other guides to help you plan your trip:

Ready to plan the the most epic weekend trip? Let us know if you have an questions in the comments below!

Looking for some other travel inspo for a particular time of year? We have monthly travel round-ups to help you decide where to go depending on the time of year. Also, don’t forget to subscribe to our newsletter for our weekly article updates, and for exclusive discounts on our shop!

Need more help planning your weekend trip? We can plan your travels for you, or you can sign up for a one-on-one consultation where we spend time walking you through anything you need.

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