Note: All travel is subject to frequently-changing governmental restrictions—please check federal, state, and local advisories before scheduling trips.

The past year has been anything but easy, but a few silver linings emerged from the storm. Many companies are now much more flexible—and prepared—in terms of letting their employees work remotely, plus remote learning continues at many schools, and that’s opened up a lot of opportunity both for spending more time with family and for not being physically tied to the city where your office or kids’ school is located. If you’ve been thinking about making the most of this final stretch of flexible living and taking your work on the road, here’s how to plan your extended stay away, from the nuts and bolts of making it happen to what to pack for a long, long trip.

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Get your supervisor onboard

We don’t mean literally onboard. As much you may like your boss, you probably don’t want them poolside with you. However, explaining to your manager that your work-life balance has been suffering lately and that a change of scenery will actually restore your sense of wellness and increase productivity is always a good idea. Anticipate in advance any concerns she might have and come prepared to address them, and make sure your boss understands that she is a partner in this idea and that the two of you will work together to make it a success.

Pick a destination that makes a longer stay easy

You could keep it simple and book your extended stay in another U.S. city. Or you could up the ante and spend some time in a completely different country. Since the pandemic began, several countries, including many in the Caribbean, have made it easier for remote workers to stay for longer periods via special visa programs. The options are pretty enticing and include nations such as Barbados, Bermuda, Aruba and—on the other side of the world—United Arab Emirates, among others. Be sure to read all the fine of the visa agreement before you apply, though, so you know for sure that you’re eligible and just how long you can stay.

Research how working in a different state/country might affect your taxes

If you’re leaving your home state, ask yourself this: Does the company you work for have a tax base in the state or country where you’re headed? It’s important to discuss this with your employer before you make any big moves. Also, if you move abroad, check to see if you might end up paying income tax twice—once in the U.S. and again in your host country (United States taxes are based on citizenship, not the physical location of the taxpayer). Find out how long can you work in a different state or country before these tax codes start to apply.

Pick a hotel that’s suited for long-term stays

Although it might be fun to brag on social media about the trendy and Instagrammable hotel room you’re checking into for a month, it might not be so fun waking up in that room each day if it’s no bigger than a shoe box, or lacks basic home amenities of home. Likewise, to ensure buy-in from your boss, you’ll want to pick a hotel that offers top-notch perks and facilities for business travelers and excellent WiFi. You may also tire of eating out every day or may in fact need to cook if you’ve booked yourself an extended stay in a remote location so consider a hotel that offers suite or apartment-style rooms. Travelocity even offers an extended stay hotels filter to make your search easier.

Look for vacation rentals with monthly discounts

Here’s the thing about vacation rentals: They’re often independently owned and operated, and it’s enormously appealing for the renter to have the guarantee of a single renter for several weeks or months at a time than having to hope to fill up a calendar with a whole bunch of folks staying for 2-3 days each. (Not to mention the hassle of having to completely clean the entire home or unit after each visitor.) At Travelocity’s sister site VRBO, a filter allows you to search for monthly discounts in a desired destination. Note: The size of the discount is at the discretion of the renter and thus varies from place to place.

Don’t overpack

Yes, you’ll be gone a while, but you’ll be surprised at how much stuff you deem essential that you don’t actually need. An umbrella is always a good idea, but can take up a lot of space and it may make more sense to buy a cheap one once you arrive at your destination and leave it behind for future guests to use. A vacation rental, for example, is also likely to have a washer and dryer and if that’s the case you only need to pack the minimum in terms of wardrobe. We recommending a pair or two of sturdy shoes, a few interchangeable outfits and of course necessary medication. Leave the rest behind. Here are some additional tips on how to pack for a long vacation.

Get your house in order before you go

Will you be gone long enough to make renting your place out an option? While that comes with its own set of tasks like finding someone to manage repairs and other renter’s needs, leaving your house empty will also require someone to check in occasionally, whether that’s to shovel snow, cut the grass, water your plants, pick up any random mail or packages that weren’t forwarded, etc. If you live in a cold climate, make sure you also turn your water’s mainline off in winter to avoid burst pipes.

Set up a way to keep tabs on your home

We recommend a hybrid of human and tech surveillance. Tell your trusted neighbors you’ll be gone a while and leave your contact info, so they can reach out if they see anything unusual going on in or around your home. You may also want to consider a smart-home system like Nest that lets you not only control the temperature of your home remotely, but opt for security add-on that also give you a visual on what’s happening while you’re away. Even better: If you can, rent your place out short term or perhaps you have a friend in another city who would be excited to stay there while you’re away in exchange for bringing in the mail, watering your plants and cutting the grass now and then.


Travelocity compensates authors for their writings appearing on this site; such compensation may include travel and other costs.

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