How to Plan an Amazing Weekend Getaway (Without the Stress!)
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Think you’re too busy to travel? Think again. Weekend getaways are a great way to squeeze in some adventure without burning through all your vacation days—and with a little planning, they can be just as unforgettable as a longer trip.
Weekend trips and long weekend trips have seriously helped me travel so much more than I otherwise would have been able to over the past couple of years. This guide will walk you through how to plan the best weekend getaway. Be sure to grab the Weekend Getaway Planner at the end of this post for truly stress-free planning!
You might think a weekend isn’t enough time to truly experience a place and, while I agree you won’t be able to see everything all at once, it’s a great way to get a taste so you know where you might want to return to. I find that, if planned right, weekend trips are not very stressful and can allow you to see so much more of the world.
In this post, I’ll teach you how to plan a weekend getaway, including how to:
- Choose the right destination
- Create an itinerary
- Pack without forgetting anything
- Book your transportation and accommodation
- Stay organized with a printable planner
Step 1: Define Your Getaway Goals
The first step to planning any trip is to think about what you want to get out of the trip and what you want it to look like, while also balancing some more realistic criteria such as budget and travel time.
Envision Your Perfect Trip
Are you looking for a relaxing getaway or an adventure? Who are you traveling with? Do you want to escape to nature or are you looking to see a big city? Think about what you and the people you’re going with want from the trip.
Be Realistic
Once you’ve envisioned your perfect weekend getaway, we need to think a little bit about the logistics. First, consider your budget and what places may fit into that. The second big thing to consider for a weekend trip is travel time. When you’re going somewhere for a short amount of time, the time you spend getting to your destination can take a lot of time away from your trip.
For my weekend trips, I like to think about places I can get to within about 5 hours – either driving or flying. This allows me to leave on a Thursday or Friday evening so I can start fresh on Friday or Saturday morning (depending on if I take Friday off or not). Traveling the night before the official start of your trip is a great way to add more time to your trip at your destination.
Think about places that are just a few hours of driving away or that you can fly to in just a few hours. This one is going to depend on how close your closest airport is and how big it is. People living in bigger cities will probably have a few more options here, but as someone whose closest airport is a small airport, there are still plenty of places that make great weekend trips flying out of my small airport. See my 3-day Estes Park itinerary or my 3-day Edinburgh itinerary for inspiration.
Tip: Knowing your “why” will help you make better decisions about where to go and what to do on your weekend getaway.
Step 2: Choose the Perfect Destination
Now it’s time for the fun part! In this step, you’ll narrow down your weekend getaway possibilities and choose a destination. This is where you’ll really take everything from the previous step into consideration and select the best option for your trip. This is also a great time to get an idea of when you’ll go on this trip.
Narrow It Down
Look at your list of possible destinations and choose one that best fits the criteria defined in the previous step. What fits your vacation style the best? Which destination is nearby and will give you the type of trip you’re looking for?
Do Some Research
This is also a great time to do just a little bit of research into a few different places to see what they’re like at the time of year you’ll be visiting. Look at what the weather is typically like and look for any events that may be happening during your visit and decide if these fit your goals for your weekend trip.
Tip: I love using the explore feature and the map on Google Flights to see which destinations might have the cheapest flights and choosing a time to visit based on that.
Step 3: Plan Your Must-Do Activities
Now that you’ve chosen a destination, it’s time to think a little bit more about what exactly you want to do while you’re there. This is the time to go into full research mode! For a weekend trip, it’s important to be selective. You won’t be able to do everything a place has to offer in just a couple of days so choose either the most iconic attractions or the activities that are most important to you.
List Possible Activities
I like to create a list of all of the possibilities that I might be interested in and put them on a map somewhere. I love using either Google Maps or Wanderlog for this. I tend to save places to my Google Maps just as I see things I want to do all over the world so I usually check to see if I have anything saved there first and then do the bulk of my planning and mapping in Wanderlog.
Wanderlog is a great tool for planning out your itinerary. It’s free to use, although they do have a paid version you can upgrade to for some extra features. When I’m planning a trip, I save activities to a Places to Visit list on Wanderlog, and restaurants and other food I might want to try to a separate Restaurants list.
Wanderlog adds it all to a map for you and color codes the markers by the list each place is coming from. It also lets you add places to each day of your itinerary and maps out a route with travel times between each location.
Choose Your Favorite Activities
Once you have a list of places you might want to go, remember to narrow it down so you’re not packing your itinerary too full. You’ll want a little bit of wiggle room to explore and these weekend getaways are so much less stressful if don’t completely pack each day full of activities. Choose the activities that are most important to you and write them down, throw them on a map, or add them to your Wanderlog itinerary.
Tip: Choose 2-3 activities per day to avoid feeling rushed and overwhelmed.
Step 4: Book Your Transporation and Accommodations
This is the step for figuring out how you’re getting to your destination and where you’ll stay. It’s especially important for weekend trips to minimize the travel time both to and from your destination and in between places you want to see and things you want to do at your destination.
Book Any Transportation
For transportation, decide if you’ll be driving or flying to your destination. If flying, book your flights and figure out how you’ll get around at your destination (public transportation, rental car, Uber). Figure out the logistics around getting to and from airports and arrange any necessary transportation.
Book Your Accommodations
I save booking accommodations for a later step so that the activities are all somewhat planned out. Look at the places on your itinerary and try to choose a hotel or vacation rental that is close to everywhere you want to go. If possible, I like to try to choose somewhere somewhat in the middle of the places I’ll be visiting at my destination. This is why putting everything on a map is so important!
Book your hotel or vacation rental and make sure to save the details and book any other transportation necessary for your trip.
Tip: Book your flights at least a few weeks in advance for better prices. Or better yet – use something like Google Flights to set up price alerts further out so you know if there’s a drop in price!
Step 5: Finalize the Details
This step is your chance to wrap up any of the planning! You have a general idea by this point of everything you want to do and where you want to go, but this is your chance to finalize any details.
Book Activities and Make Reservations
Start by booking any activities you want to book at your destination, plan out your full route for each day, and make any restaurant reservations. This is a good time to find a few places you might want to try to eat at and throw them on your map to keep in mind while you’re exploring your destination. Then, organize all of your trip details in one place to keep track of it all.
Consider What You’ll Need to Pack
This is also a great step in the process to think ahead about what you’ll need to bring with you and make sure you have everything you’ll need so you’re ready to pack it when the time comes. Did your suitcase get damaged on your last trip? This is a great time to buy a new one. I love these travel backpacks for weekend trips and frequently fly with one as just a personal item when flying budget airlines. Some of them can be a little bit too big though so make sure you look at your airline’s rules and use them at your own risk.
Are you traveling internationally and need a plug adapter? Just make sure to get one that matches your destination. Do you live in a warm climate but need warm clothes for a ski trip? This is when you’ll want to do that shopping so you’re not worried about when you’re trying to pack last minute.
Tip: My free Weekend Getaway Planner is a great place to keep track of all of the details! Fill out the form below to grab it!
Now you’re ready to plan your next weekend getaway! I follow these steps for most of my trip planning, but there are extra considerations for shorter trips. Travel time and choosing the activities you are most interested in become even more important when planning a short weekend trip.
If you want to make your planning even easier, download my free Weekend Getaway Planner below to help with the planning process and keep everything organized and stress-free!
