How to plan a vacation

Tips, tools, and technology for your next big trip

Published April 2020


These days, many of us have a little more time on our hands than usual. Our commutes are reduced to mere steps to the workspaces in our homes. We’re cutting back on errands and no longer going out for meals or visits to family and friends. While this new, albeit temporary, reality is challenging for all of us, there is a silver lining to having some extra hours in the day: we can dedicate time to planning that next big trip.

Few things enrich our lives the way travel does, and now is an optimal time to start researching the places that speak to your soul. We’ve rounded up resources to help you find your vacation bliss—since we all need it now more than ever.

Nail down the basics

The first thing you’ll want to determine is who will join you on this adventure, how you plan to get there, and what considerations you’ll need to make. If you’re traveling with friends or extended family, ensure their dates line up with yours and that everyone has the necessary time off work.

Next, make sure you and your travel companions agree about the goals of the trip. After the current environment gives way to open borders, what will you need most? A trip to explore the outdoors? A getaway to relax and let the pool entertain your kids? A retreat to a never-before-seen corner of the world?

Last, get a feel for your fellow travelers’ budget expectations so no one is surprised when plans start coming together. Using simple, shared spreadsheets at the start of planning will help get everyone on the same page and set the stage for an organized planning process.

Select your destination

For selecting your big trip destination, let some visual imagery guide the way. Platforms like Instagram and Pinterest are great places to let yourself go down a rabbit hole of vacation destination inspiration. On both, search for accounts run by destination marketing organizations (like @travelbelize or @discoversouthcarolina). These official handles will have the most up-to-date information and latest attractions. Also, scour online travel publications (and Instagram accounts) like AFAR, Conde Nast Traveler, Outdoor, and Travel+Leisure for “hidden gem” destinations they typically feature. Last, many destinations and attractions have opened themselves up digitally, allowing you to explore virtually and get a feel for the area. Just make sure you don’t spoil all the fun for yourself.

Find the vacation rental of your dreams

Now the really fun part comes into play. Whether you’ll have one place to stay during your trip or multiple, everyone can enjoy pitching in to select the vacation home(s) where you’ll get together for dinners that wind into the wee hours, or gather to appreciate a beautiful sunset from the porch. If you’re traveling in a group, ask each individual or family to pick their top three vacation homes (some of our favorites are below) and send them around for input. This will help surface the features that are most important to everyone and drill down to the best property for the trip. This is also an opportunity to get your kids involved and let them weigh in on their top choices—if nothing else, it’ll distract them for 30 minutes. Once your vacation home has made the final cut, be sure to book early to secure the best rates. Then, take a look into the features and amenities of the home to inform what you’ll need to pack. (Oh, and yes, the same tips apply for hotels, but what can we say? We’re biased.)

Start mapping it out, with tech of course

Now that you have a home and a destination selected, take time to plot out how you might fill your days. If you’re heading to Hawaii where the plan is sun, eat, drink, repeat, then you’re probably all set. For the more detailed planners, there is a tried-and-true tool: Google’s My Maps. With My Maps, not only can you pin and color code museums, attractions, restaurants, and more, but you can also add notes like “restaurant recommendation from Alex” or “must-stop for gelato.” Last, you can add a “layer” of the map for each day of your trip with what you’d like to see and do. My Maps is also mobile-friendly. Once you are done with one stop, check the app to see if any of your other destinations happen to be nearby—a real time-saver for travelers on the go.

Hopefully, it won’t be too much longer before we’re able to hit the road again—we miss it as much as you do. Until then, start planning the trip of your dreams, and if you need even more inspiration, we’re here to help.

A Vacasa home for every vacation

Check out some of our favorite homes for any style of traveler.

Casa del Perezoso
Dominical, Costa Rica

Eagle Ridge Cabin
Mineral Bluff, Georgia

Mountain Luxury
Fayston, Vermont

Lands End 2
Hilton Head, South Carolina

Webb House
Sea Ranch, California

Summer Breeze Villa
St. Simons Island, Georgia

large green lawn of luxury Texas vacation home

The River House
Fredericksburg, Texas

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