10 Easy Steps For Planning the Perfect Weekend Getaway

Need help planning the perfect weekend getaway?

Then you’ve come to the right place!

Going away for a weekend can be a great way to unwind, but sometimes the process of planning a weekend trip can feel overwhelming. As a working mother of two, I get it. That’s why I’ve laid out the steps I follow when planning weekend trips for my family. We’ve used this framework to plan trips across the United States and Europe, making the most of our limited vacation days.

These 10 easy steps to plan a weekend trip will reduce overwhelm and make you feel confident about your next getaway. Read on, and you’ll be maximizing your PTO in no time!

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How to Plan the Perfect Weekend Getaway

1. Decide what you want from your weekend trip

The first step for planning the perfect weekend getaway is deciding what you want to get out of this trip.

Are you looking to relax on a beautiful beach, or soak up the culture of an historic city? Do you want outdoor adventures or vibrant nightlife? Getting clear on what type of getaway you want is a must when planning your weekend travels.

The goal of a weekend getaway is to break away from the usual routine. Your hobbies, interests, and needs all play into what makes the perfect weekend destination for YOU.

The key is to choose a destination and activities that resonate with you and whoever you’re traveling with. 

2. Set a budget

Once you’ve honed in on the type of trip you want, it’s time to talk budget. 

Balancing your weekend getaway dreams with financial reality is important. You want to be able to enjoy your weekend away, not stress the whole time about how much it’s costing you!

Setting a budget early on in your planning process will help you narrow down your options and focus on the destinations you want to visit that you can also reasonably afford. 

Consider all aspects of the trip: transportation, accommodation, meals, activities, and a little extra for those spontaneous indulgences. If you’re a pet owner like me, don’t forget to account for any pet-sitting costs.

Being mindful of your budget doesn’t mean compromising on the quality of your experience. Plan ahead by deciding where to splurge and where to save. For a city break, it can be worth booking a cheaper hotel in order to splurge on a five-star dining experience. Alternatively, if you’re looking for a spa getaway, save on transportation and splurge on the resort. 

With some savvy planning, you can find great deals on accommodations and activities. I like to check flight deals on Kiwi or Google Flights, both of which show the best flights in one easy-to-use dashboard. 

For tours, Viator and GetYourGuide have great deals that will save you time and money if you book in advance. 

Some other budget tips are to look for off-peak travel times, bundle deals, or last-minute offers. Sometimes, the best adventures are those that don’t break the bank but still bring a wealth of new experiences and relaxation.

Remember, the goal is to enjoy a stress-free break, not to return home worried about overspending. A well-planned budget is your roadmap to a getaway that’s both enjoyable and financially responsible.

3. Choose the right destination

Now that we know what type of trip we want and how much we’re willing to spend, our next step is picking the perfect destination.

Picking the perfect destination is like choosing the right outfit for an occasion – it needs to fit your mood, expectations, and budget. With so many wonderful places to explore, this can sometimes be the hardest part of planning your getaway. 

Distance is a critical factor. How much time are you willing to spend getting to and from your destination? When I lived in New York, we would drive to spend weekends in Boston, Philadelphia, or Washington DC. Now that we live in Dublin, we’ve flown out for weekend breaks in London, Berlin, and Amsterdam. How far you go is up to you, but just remember: The more time you spend in transit the less time you have to explore.

When it comes to choosing the right weekend getaway destination, don’t overlook the hidden gems in your own backyard – sometimes the best weekend getaways are quick trips close to home.

In my experience, sometimes the best trips are the ones where the destination chooses you. Stay open to suggestions, do a little digging, and you might just stumble upon the perfect spot for your weekend escape. 

4. Pick your dates

Now that you know where you’re going, it’s time to decide when you’re going.

Timing is everything when it comes to planning a successful weekend getaway. One thing I like to do is combine a weekend away with national holidays. This lets you travel for three days without using any vacation hours. Or, you can add vacation days on top of a long weekend, allowing you to travel longer without maxing out your vacation days.

The one downside to this strategy is that flights and hotels tend to be more expensive over holiday weekends. Destinations are also more crowded as everyone has the same idea – to get away.

Another option is to travel during the off-season. While you won’t be able to double up weekends and holidays, you can save a lot of money by traveling when most people aren’t. This also means fewer crowds and shorter lines getting into major attractions. We went to Cappadocia one winter and practically had the place to ourselves; it was magical!

Just remember, off-season travel can sometimes mean compromised weather or limited availability of some seasonal activities. You’ll need to research your destination and make sure that the experiences you’re looking forward to are available during your potential getaway dates.

In my experience, traveling during shoulder seasons – the period between peak and off-peak – can offer the best of both worlds. You’ll likely enjoy decent weather, fewer crowds, and moderate prices. Websites like Skyscanner can help you track flight prices for different times of the year, helping you decide the best time to go.

5. Sort out Transportation

Your next hurdle when planning a fun weekend trip is figuring out transportation.

Do you plan to drive, fly, or take the train? Will you need to rent a car?

The earlier you book your transportation the better as you’ll save money with advanced planning. Prices on Flights and train tickets tend to increase the closer you get to the departure date. If you need to rent a car, booking in advance will also help you save money and ensure you get a car suited to your needs.

Sometimes the process for booking transportation can be overwhelming, so let’s go over a few tips to help you make the most of your time and money..

Flying

For further away destinations, flying is probably your best bet. 

To get the best deals on flights, start looking early and try to be flexible with your dates and times. 

Websites like Kiwi, Skyscanner, or Google Flights are great for comparing prices across different airlines. 

Train Travel

For a more eco-friendly and scenic option, consider traveling by train when possible.

In the United States, services like Amtrak offer comfortable rides with scenic views. In Europe, train routes span across countries, connecting most major cities. 

Booking train tickets is relatively straightforward, and doing so in advance can often secure you better rates.

Driving

What could be better than a good old-fashioned road trip? If you have a car, driving to your weekend vacation destination is often the easiest and most budget-friendly choice. It’s also very convenient to have a car to explore rural destinations.

If you’re planning a road trip, make sure your car is in good shape. A quick service check – tires, brakes, engine oil, and other essentials – can prevent unexpected hiccups on the road. 

If you’re renting a car for your weekend getaway, be sure to book in advance to save money.

Apps like Google Maps or Waze are the best for navigating new places.

6. Book Accommodation

Choosing where to stay is almost as important as deciding where to go. 

Your accommodation can set the tone for your entire trip, whether you’re looking for luxury, comfort, convenience, or a bit of adventure. 

Think about your priorities for this trip. Do you need a centrally located hotel so you can explore the city on foot? Are you looking for a quaint B&B surrounded by forest? The type of trip will dictate the accommodations. 

I like to use a variety of platforms when searching for accommodations. If traveling with a large group, Airbnb and Vrbo are my go-to’s for finding short-term rentals for larger parties.

Hotel aggregates, like Booking.com, can help you search by location and filter by price or amenities. This is great for if you want a specific amenity, like a pool, or need to cap your hotel costs to stay within your budget.

When booking your stay for your weekend away, my final tip is to always read reviews. There are few things worse than arriving at an Airbnb that looked good in photos, only to find out it smells like a wet dog and hasn’t been properly vacuumed (trust me on this one). Reading reviews closely, and also looking at how a venue or host responds to bad reviews, can be a telling sign of what you’ll be in store for if you book with them.

7. Research your destination

Alright, you’ve got your trip type and budget sorted. Flights and the hotel room are booked. Now, it’s time to dive into research. Trust me, doing the work now means a lot of fun later!

I always like to start by reading the history of my travel destination. Guidebooks are great for this as they often have digestible chapters summarizing local history. Wikipedia is also a great resource to deep dive into people, places, or events you find interesting.

There are so many resources available to learn through – podcasts, movies, books, etc. – that you can find something to suit your preferred learning style. Listen, read, and watch things about your travel destination. Not only will you learn, but it will get you excited to go and see these things in person!

During the research process, think about activities you want to do. Are there any tours that look especially interesting? Write them down and be sure to plan around anything time specific. 

Also, research what’s going on at the destination while you’re there. Are there any festivals or major holidays? For example, Dublin in March hosts the annual St Patrick’s Day Festival, which is important to plan around if you’re visiting that weekend.

Last but not least, don’t forget to check the weather at your destination. I recommend doing this at the beginning stages of planning to get a general sense of seasonality, as well as a week out to get a more realistic weather forecast for your trip. This will help you plan your activities (some of which may be seasonal) and pack appropriately for your trip.

8. Make reservations as needed

Have you ever had your heart set on a specific restaurant or activity, only to find out it’s fully booked? Yep, we’ve all been there. A little bit of planning will help you avoid disappointment and make sure you don’t miss out on any bucket list experiences.

If during your research stage, you come across activities you want to do, be sure to book them in advance in case they sell out. You don’t miss out on that food tour that was calling your name! 

I use Viator and GetYourGuide to browse and book tours when I travel. I love that they have a range of experiences for all interests.

A few weeks before your travels, look into making restaurant reservations. If there’s a place you know you want to dine at, make that reservation so you’re not disappointed. Platforms like OpenTable or Resy are great for snagging a table.

While I love to make a detailed travel itinerary, it’s important to leave time for spontaneity. Not every minute needs to be scheduled. Sometimes the best moments are unplanned.

9. Get packing!

You’re almost at the weekend trip planning finish line… let’s talk packing! Deciding what to pack for a weekend away can be one of the most stressful parts of trip planning. 

But don’t worry, with a few tips and a bit of organization, you can make packing for your weekend trip a breeze.

I’m a fan of the ‘less is more’ approach when it comes to weekend trips. I don’t want to lug around a heavy bag for just a couple of days. It will make your life easier if you stick to the essentials: a couple of outfit choices, necessary toiletries (travel-sized to save space!), and any must-have gadgets – a camera, phone charger, maybe an e-reader for some downtime.

For a long weekend away you’ll need more outfits. I pack one shirt, a pair of socks, and a pair of underwear for each day. I don’t like doing laundry while I travel, but if you really want to pack light you can also wash and re-wear clothes during your trip. 

While packing, keep in mind your planned activities and the weather. Be sure to pack plenty of layers for cooler or unpredictable weather destinations.

Pro tip: Use packing cubes to save space and stay organized.

10. Practice, Practice, Practice

Last but not least, practice. 

The more you plan and execute a successful weekend trip, the easier it gets each time.

Think of each getaway as a learning experience. With each trip, you’ll get better at packing just the right things, choosing destinations that hit the sweet spot, finding great deals, and balancing activities with relaxation. 

Every time you head out, you’re not just making memories; you’re also honing your skills as a savvy traveler. You’ll learn how to quickly adapt to changes, whether it’s a sudden weather shift or a last-minute change in plans. As you keep traveling, planning each trip becomes less daunting. 

Even if things go wrong during your trip, just keep in mind that these mishaps often turn into the fondest memories. 

Some of the funniest moments from our family trips are when things don’t go as planned. The time we bought train tickets for the wrong day and had to run to get new ones minutes before departure? Years later, we still laugh about it!

So, keep planning, keep traveling, and keep enjoying those weekend getaways. Remember, practice makes perfect, and in the case of travel, it also makes for unforgettable experiences and a lot of fun. Here’s to many more weekends filled with adventure, relaxation, and everything in between!

FAQ: Planning a Weekend Getaway

Final Thoughts on Planning a Weekend Getaway

Do you feel ready now to dive into planning an unforgettable weekend trip? I hope these actionable steps gave you the confidence to plan the best weekend away. Keep at it, and soon you’ll be exploring the world, one weekend at a time!

Did this post help you plan a great weekend getaway? I want to hear all about it! Send me an email and tell me all about your amazing weekend away!