With the rise of remote work and sabbatical leave, more people are able to travel for extended periods (more than 30 days). Certain professions also allow for flexbility either with a school calendar or the ability to trade shifts and build lengthier time away. Extended travel take a bit more planning, especially with rentals, medical requirements, and tax implications.
Paperwork
Visas requirements vary by country. Many cap a tourist stay at 90 days. For the Schengen block, you may visit for tourism purposes for 90 days within a 180 day period. Before you pick a destination, ensure that you can work legally during your holiday if needed. Check the state department site for details on your destination. and confirm plans with HR for tax implications. If you will exceed 90 days, more countries are beginning to offer digital nomad and self-employment visas. Requirements vary, typically that your employer is based outside of the visiting country and that you can prove sufficient funds for your stay.
Even for shorter stays, be prepared to show border control sufficient funds to cover your stay such as a recent bank statement. You may also be asked to show a return ticket within the allowable period. This has only happened to us once in the UK to cover a month long stay.
Rentals
Accommodations become much more important over a long stay, both ammenities and pricing. Look at home rental sites like VRBO or AirBnB and filter by length of stay. Many are listed on multiple sites. Reach out to the property owner to decide which platform is best for booking, discuss a discount for length of stay, and confirm a suitable deposit and payment schedule.
Most car rental companies do not allow leases longer than 28 days. This is typically the max duration for credit card insurance. Non-EU nationals may lease a car directly from some manufacturers at major European airports. Insurance, roadside, unlimited miles, and warranties are included in a lease. Family members can usually drive the vehicle as well without a fee.
Health
Call your health insurance to confirm what is covered and for how long when on the road. Look at supplemental coverage, especially if there is an underlying health condition within your party. Be sure to check duration of your supplemental coverage as some time out after 31 days.
Classifications and approvals for medications change noteably by country as well as names. To avoid issues, keep these three things in mind.
Identify if medication is available for refill where you are headed. Confirm the name that it is sold under and whether a prescription is required. Some over the counter medications in the US are not available in other countries without a prescription.
If possible, bring enough for your stay. Some insurers only cover a month at a time. Check with your doctor if they can provide a script for a 90-day supply. If not, request an exception from your insurer to allow you to buy what you need prior to departure.
Always carry the paper prescription with your doctor's contact information on it. Be sure to use original containers for medications with your prescription information attached.
Language
One of the best parts of extended travel is meeting locals. This can be challenging without learning at least a little of the local language. Find a resource that works for you. Apps are great. My personal favorite is Babbel, but Duolingo is good as well. Check with a community college to audit or attend a language class. Universities with online offerings may also provide continuing education classes in language. Join a local language group to practice your skills.
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