How to Plan the Best Weekend Getaway, Ever

Plan now, sit back & relax later.

October 16, 2018
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I readily admit I’m an overly organized traveler. Some people like to fly by the seat of their pants when traveling, but honestly, that mentality is just stressful for me—and traveling shouldn’t be stressful. For that reason, I tend to do a lot of research and planning before any trip, even if it’s just a weekend getaway.

Thanks to my have-to-plan nature, I’ve discovered a LOT of helpful travel tools over the years. Whether you need help picking a destination, finding a place to stay, planning a road trip, or managing your itinerary, there’s an app or online service that can help—and the vast majority of them are free!

Even if you’re a more relaxed traveler than me, the following tools will help you put together an amazing weekend getaway that’s completely stress-free.

Picking Your Destination

First thing’s first: You have to pick your destination. (If you already know where you want to go, you can skip this section, but bookmark it for your next trip.)

There are many websites that will provide you with fun, exciting travel destinations for your next weekend trip. For instance, we absolutely adore browsing Fathom’s destination and inspiration sections, which provide helpful intel about the must-see spots and hidden gems in cities around the world.

I don’t remember how exactly I discovered The Discoverer, but boy, am I glad I did. This email newsletter sends out weekly travel guides, highlighting amazing global destinations. Each guide includes tips on when to go, where to stay, and what to eat, as well as firsthand experiences from fellow travelers.

Want to plan a food-focused getaway? You have to check out the travel section of Edible Communities. They have a whole list of foodie road trips, including ones for Nashville, Santa Fe, Cape Cod and more.

Prefer to do your planning via an app? Then you should definitely check out Guides by Lonely Planet. Lonely Planet, perhaps best known for its wanderlust-inducing Instagram, offers more than 200 inclusive guides to cities around the world. In addition to attractions, restaurants, bars, and shopping destinations, each guide offers a budget tool that shows you what to do each day to stay within your spending range.

Booking Lodging

Once you know where you’re going, it’s time to find a place to stay. Everyone has their own favorite sites for finding hotel rooms, but a few good ones are Kayak,, and Expedia. Personally, I even like to use the Google Hotel Finder, which lets you filter by price, location, ratings, and hotel class.

And, of course, who can forget about good ol’ Airbnb. Some people think of Airbnbs as awkward rooms in a person’s house, but you can find a lot of affordably priced apartments and homes that are private and luxurious. I’ve found some truly wonderful, welcoming, pristine accommodations via this site, including ones in Denver, Vermont, and even Paris. All that to say: Don’t rule it out if you'd like to explore beyond traditional hotel lodging.

Finding a Flight

If you plan on flying to your destination, there are a few tricks you can use to score a good deal. Hopper is an awesome app if you’re planning your flights in advance, as it tells you the best time to book in order to get the lowest price.

I’m also a big fan of Google Flights, which lets you compare flight times and prices from pretty much every airline. It also allows you to track flight prices, similar to Hopper. The only downside is that it doesn’t include flights from Southwest.

This next app doesn’t help you find a flight, but it does help you monitor them after you book. App in the Air keeps track of your boarding and landing times, and it even lets you know the current wait time at security so you know when to head to the airport.

Planning a Road Trip

Hitting the open road for your weekend vacay? Roadtrippers will help you plan the ultimate road trip, mapping out the best route, helping you pick hotels, and finding fun activities, restaurants, and attractions along the way.

It’s always a good idea to have Hotel Tonight on your phone when you’re taking a road trip, as well. This app finds you great deals on last-minute hotel rooms, just in case you get sidetracked and don’t make it to your destination as planned.

Sorting Your Itinerary

Once your trip is all planned, you condense and simplify all your documents and reservations using an itinerary app. TripIt has been the gold standard in this category for years, thanks to its ability to automatically pull reservations from your emails.

However, Google Trips is giving TripIt a run for its money. This newer app lets you store all your travel info in one place, as well as recommending local attractions and mapping out your days. Try them both and see which one fits your needs better. Either way, you’ll have an impeccably organized weekend getaway.

What are your best tips for getting the most out of a weekend trip? Share them with us below!

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Carolyn Rabideau

Written by: Carolyn Rabideau

1 Comment

N K. October 21, 2018
Thx. Can’t say I learned a lot here – but just wondering how it’s possible that you don’t use TripAdvisor?