An insider’s guide to becoming a digital nomad

For many, living the life of a digital nomad (someone who can travel around while working virtually) is a dream. You can experience exciting places, change your zip code every month, all while staying connected. And in a year as strange as 2020 (has anyone checked on the murder hornets, by the way??), it’s nice to think that work-from-home has given some travelers the opportunity to change their scenery.

If you’re considering that digital nomad life, here are tips from KAYAK employees who are hitting the open road within the US.

What you need to do to get started

  • Check with HR. If you’re currently working remotely full-time, check in with your company’s HR department and detail your plans. For some companies, there may be tax implications or work registration needed before they can give you the A-OK to work from the road.
  • Stay up to date on travel restrictions. Use KAYAK’s Travel Restrictions map as a starting point and research requirements of each destination on your list. Be prepared to pivot if restrictions change by booking flexible travel options. Pro tip: Use flexible travel filters when you search on KAYAK.
  • Make a plan. Whether you want to roam, settle down in one place or something in between – do your best to write out your itinerary. Include the towns or states you plan to travel to, the best way to reach you at each stop, and approximately how long you’ll be staying. If you’re working for a company, you’ll need to share this with your manager and/or HR department to ensure they can keep your file up to date.
  • Budget, budget, budget. Use your rent and utilities as a budget guideline for accommodation and don’t forget to include storage in expenses. KAYAK Trips can be a great way to save and organize your options before you book, while calculating total expenses.
  • Rent a car. Roadtripping between destinations? Renting a car can save you money – here’s why.

Choosing where to stay

  • Choose a place that feels like home. Home rentals and unique stays (castles, cabins and chalets, oh my!) may provide private access to outdoor features, which can be a sanity saver if lockdowns move forward again. KAYAK has over 450,000 properties in the US to search from.
  • Embrace spontaneity. Book your lodging closer to when you go and be spontaneous. With things changing so quickly, it’s easier to plan closer to your trip. And hotel rates can sometimes decrease if you book last minute as well.
  • Unlock those deals. Check for discounts on long-term stays. Sometimes adding in another night or two could actually save you a ton (especially on rentals!).
  • Check out self-check-in. Many rentals have self check-in options or are willing to be flexible. Don’t be afraid to call in advance and see if there’s a way you can arrange for one even if it’s not advertised.
  • Put safety first. If you’re staying in a rental, these tips may make you more comfortable in your home away from home.

Working on the road

  • Set your hours. Take advantage of time differences. Staying on an East Coast schedule while working on the West Coast can free up your afternoon to explore or relax, and vice versa if you’d rather get your hike in before work.
  • Plan out your downtime. If you do plan on getting out of your apartment to explore, try to do so during off times. Working while traveling gives you the flexibility to stay longer, so rather than trying to cram things into one weekend, spread things out. Checking out that popular hike after work on Tuesday can make it a lot easier to social distance and explore safely, than hitting it on the weekend.
  • Buy a hotspot (or see if your IT department has one to lend out). If you’re planning on working from destinations that are heavy on the nature scene but light on WiFi, invest in a portable hotspot that can give you a few hours of connectivity, wherever you go. But before buying one yourself – reach out to your IT person to see if the company has one to spare.

Things to bring

  • Get a cooler. Road snacks are a must. Find a well-made cooler that’ll fit easily in your trunk and is also easy to transport. Store perishables (like pre-made sandwiches, breakfast foods and easy meals) that you can take from town to town. The less you have to go grocery shopping – and the less you have to stop on your travels – the better.
  • Stock up on water bottles. If you’re green-conscious, you don’t want to buy plastic bottles if you need a refill – but you’re also probably not super comfortable filling your water bottle up at a fountain due to COVID-19. And, as an added complication, for sanitary reasons many companies that would usually be happy to refill a reusable container are no longer willing to do so. So, make sure you take multiple full bottles for travel days, or buy a larger (we’re talking gallon+) with a dispenser that you can use to fill up as you go.

Sold on digital nomading but not sure where to start your trip? We rounded up some of the top trending spots for longer stays according to our data. See our Top digital nomad destinations for inspiration and resources. And, wherever you’re headed, be sure to put safety first and practice safe travel.

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