Important Things Families Should Understand Before Leaving to Travel Long Term

Last updated on September 10th, 2019 at 11:58 am

Seven years ago (May 2012), Rob and I were sitting in the living room in the house we no longer own; I was on my laptop reading one of my favorite travel blogs. I had been following a couple’s journey as they prepared to travel long term. Kim and Brian of So Many Places.com had sold their home, just left their jobs, and were about to embark on an incredible travel adventure. On that night in May, Rob and I had already listed our house for sale, we had end dates for our jobs, and had begun the process of preparing for long-term travel.

A little over two years after that, we boarded the plane to embark on our expat experiment. That gave us a lot of time to research, figure out the places we wanted to see, and then change our minds about almost everything numerous times!

You’d think we would have had everything figured out to a tee. But, when we arrived at our first destination, Miami, Florida we had only booked one onward plane ticket to Cartegena, Colombia and two weeks total of accommodation.

At that time, we had planned to spend three months in Cartegena. We thought it would better to find a short-term rental apartment once we arrived rather than trying to book ahead from Canada before we left. We did end up spending three months in Colombia but in six different cities. After that time we traveled all over the world, visiting many places we never thought we would.

Our journey to date has ended up nothing like we had planned before we left.

We know changes in plans for long-term travel are not uncommon among other traveling families as well.

The truth is, planning long-term family travel is a very subjective, kind of arbitrary, frequently thrilling and an equally infuriating process.

But, this is not an article about all of the things associated with organizing a ’round the world family trip.

There are questions and comments that come up in Facebook groups and family travel forums from time to time that surprise us and sometimes remind us of mistakes we’ve made along the way. The bottom line is, we understand there are hundreds of things to plan, and organize, not to mention the adversity some people have to deal with when they tell friends and family about their long-term travel plans.

It’s easy to see how critical “need to know” things can fall through the cracks.

You don’t have to research and plan everything down to the last detail. But, ignorance is definitely not bliss when it comes to certain things.

This post includes a few important aspects people seem to forget or tend to overlook altogether before leaving (or even as they are traveling). Paying attention to these key things could help you avoid costly mistakes, even if your travel trajectory is largely unplanned.

Here are important things families should consider while preparing for long-term travel.

1. The cost of transportation in the areas of the world you plan to visit

If where you want to go is difficult and/or costly to get to, it’s probably just as much if not more so, to travel from.

Costs for getting around account for a lot of any travel budget. One of the biggest mistakes for us, and a lot of other traveling families have made was not finding out the costs to travel around a certain area (country or continent).

For us, flying to Cartegena from Miami was reasonable and even flying throughout Colombia wasn’t too bad for the cost. But flying from Colombia to other destinations in South America ended up being a lot more expensive per person than we’d thought it would be.

Taking buses was definitely the cheapest way to get around South America but doing so took a lot of time. Overland travel can be really hard on kids. Long hours and cramped quarters can be a recipe for a major meltdown no matter the age of your kids. Time vs. money for transportation was often a struggle for us early in our travels.

One of the best deals we ever got was a flight from Fort Lauderdale U.S.A., to London, it cost $718.46 for all three of us. That’s $240 per person! While we were in Europe we booked on discount airlines and found it very easy and affordable to fly to different European countries. Getting around was a lot easier and more affordable for the most part than traveling around in South America.

Families should always determine budgets for airfare (or any other mode of transportation) based on individual costs as opposed to picking a set dollar value for the entire family. Then research the area that you’re interested in visiting and see how expensive it is to travel around (get to and from).

If your aim is to see many places on your trip choosing an area that is affordable to travel throughout could help you save a lot of money and frustration.

2. How much budget accommodation will cost based on family size

Cheap accommodation can end up costing you more money than if you’d booked something a bit better. And, finding quality low budget lodging can be more challenging for larger families (four or more). 

We often see questions about how to procure cheap accommodation.

The best deal we’ve found is staying free with house sitting.

But, finding homeowners that welcome families for house sitters can be more challenging. Especially, if your family size is larger than four people.

The key is to filter your house sitting assignment searches to include family-friendly listings and then look for jobs with larger homes and property.

Homeowners with house sits that require more maintenance and/or pet responsibilities often prefer more than one person to look after their place. Enlisting a family can be seen a benefit for homeowners that need more hands to take care of things while they’re away.

House Sitting resources

If you’re interested in house sitting here are some articles and resources that can answer questions and help you get started:

1. This article, “How to Find the Ideal House Sit to Make the Most of Your Trip” outlines important things to insist on before committing to an assignment.
2. Not sure if house sitting is something you and your family would enjoy?  This post will answer questions you may have.
3. We offer a free house sitting e-course, sign up and learn about important things to consider before you start applying for assignments, the benefits of the different house sitting platforms, how to set up a compelling house sitting profile for your family and more.

If house sitting is not appealing, families can stay affordably a few different ways. Airbnb entire place rentals and Hostels are two popular choices.

There are important things families should keep in mind before booking beds in a hostel or an Airbnb apartment rental.

First, hostels can seem like the best cheapest option, but the truth is for a family of four or more a hostel can end up being expensive because of individual costs per bunk.

Make sure you research family-friendly hostel options, costs for family rooms, and/or costs per bed (bunks in a dorm setting). Then, compare your findings to other modes of accommodation like Airbnb or other short-term lease options.

A lot of times, an Airbnb entire place rental will end up being cheaper than a hostel stay for families. An entire place Airbnb rental can often come with other benefits for families as well like washing machines, high-speed internet, and more privacy for everyone.

There are other things to be aware of before booking any Airbnb rental.

1. You need to ensure the listing states it can accommodate the number of people in your family. If it doesn’t you can be charged extra for each additional person or even denied entry on arrival by your host because your family exceeds the number of people allowed in the listing.
2. Make sure you check the “Amenities” state the rental is family/kid friendly. Listings may not state that they welcome families in the Amenities but looking further into the “House Rules” you can find kids are simply not permitted to stay in the apartment.
3. Also, location can be a real budget buster. At the very bottom of the listing, under the reviews and “About the host”,  you’ll see the heading “The neighborhood”. Here you’ll find information about the location of the rental and a map showing the general area. Using Google Maps street view, check to see if necessary amenities like grocery stores and things you want to see (or access to public transit to get to things you want to see) are included in the blue dot area. Also, check proximity to the airport. If you’re staying in a large city, the time, cost, and frustration to get across a new city can be killer.
4. This article, “How We Feel at Home Traveling with Airbnb” outlines more on why we love staying with Airbnb and key things we do to pick the best rentals for our preferences.

We’ve seen family’s struggle to get house sitting gigs because they didn’t search the right kind of assignments. Also, ones who have been turned away at the door because the Airbnb rental was not deemed kid-friendly.

We know first hand how much deciding on an Airbnb based on price vs. location can cost a family. If the rental is far from the airport and inconvenient to necessary amenities your stay can end up being a lot more expensive than you budgeted for.

3. Visa rules and logistical restrictions

It is important to know the visa situation of every location you plan to visit around the world. Every country has different visa requirements depending on nationality, and/or how you plan to enter the country (via an airport or an overland border crossing).

Find out the entry requirements for each country your thinking of visiting, the length of that visa, the price, and any other requirements. Some countries issue free visas on arrival for tourists but others can cost $200 or more. Also, if you plan to visit one region for several months, make sure the local government offers a visa to fit that situation.

When traveling to Europe, you need to be cognizant of time spent in countries included in the Schengen Zone. There are 26 European countries included in the Schengen. Understand, there are stringent rules for the number of days that tourists can spend in the entire area.

For Canadian and U.S. passport-holders, each government offers visas and travel warnings for every country in the world. Consult the applicable list and use it as a resource to map out potential places to visit.

For Canadians:

https://travel.gc.ca/travelling/advisories

https://travel.gc.ca/travelling/schengen-area

For U.S. citizens:

https://travel.state.gov/content/visas/en/general/americans-traveling-abroad.html

Here are three of the most common visa situations:

1. visa on arrival or at a specific border crossing or airport
2. visa by an application at any embassy before you arrive
3. visa by application only within your home country

On some long-term trips, you can get visas for your upcoming countries at an embassy somewhere you are traveling. Some visas expire within months or a year, so you need to plan around having access to embassies or consulates for certain locations on your route. Also, for some countries visa policies are strict. For example, it is next to impossible to apply for a Russian visa outside your home country. These rules and regulations may affect the destinations you ultimately visit andor the order of destinations on your route around the world.

Here are a few more things to be aware of:

1. In most cases, you need to have 6+ months of validity left on your passport to qualify for a visa.
2. Many times, you must have at least two blank pages left in your passport or officials will not issue the full-page visa stickers (which is all some countries offer).
3. You must adhere to the strict time restraints your visa visit allows you to stay in the country, otherwise, you may face fines or more serious consequences.
4. If you lose your passports, you generally lose the validity on those visas as well. Transferring long-term visas is often a hassle if it’s even an option.
5. You may need to prove proof of onward travel for your family before you can enter a country (an outbound flight or bus ticket, for example).

Gaining an understanding of all of the aforementioned points is so important when preparing for long-term travel- especially when you are applying for house sitting assignments. 

4. What travel insurance will cover and steps needed to make a claim

It’s a lot harder to get what you thought you were entitled to with your insurance if you don’t take proper steps before and during making a claim.

It can be hard to decide which insurance company to go with. So many companies have terrible reviews online. Some mention instances where traveler’s circumstances simply didn’t fit within the policy wording so they weren’t covered. That’s really tough to take. It’s so important that you read the requirements for making a claim if something goes wrong on your trip. Be mindful of these things when it comes to your insurance coverage:

1. Document all your valuables.Take photos of all of each of them before you leave. If you need to make a claim, you’ll have to prove you bought the item you’re making the claim for (receipts) and that it was there with you. Also, get physical proof that an item was stolen (a police report). Each of these steps is so very important. Many negative comments we read in family travel forums are people who didn’t get a copy of the police report, or couldn’t provide proof of ownership.Make sure you read your policy and understand exactly what your insurance provider requires to make a claim.
2.  Document your illness should you or one of your kids become sick. Call your insurance company as soon as the illness presents itself, they will help you find the best healthcare providers in the region. Also, keep all paperwork pertaining to the illness! There will be a lot of correspondence as you make your claim and the more information you have the better.
3. Abide by the law. A word of caution, ignorance is no excuse, and it could cost you your claim. Review laws pertaining to roadway safety. We have read about legal loopholes regarding roadway accidents that have prevented families from receiving coverage. Double check laws pertaining to licensing before you assume you’re covered if you’re in an accident on a windy Thai road.
4. Read and understand your policy. Seriously. It will take at least an hour. But read it, highlight areas you didn’t know and really understand what they are covering and what they are not. And if you’re unsure, email or call them. They always answer questions before, during, and after you’re their client.

This article here, Travel Insurance Review covers common things not covered by travel insurance. Everything from pre-existing conditions to extreme sports, there are a few things you just won’t get coverage for in a general travel policy.

Choosing an insurance provider can be tough; who should you go with, what plan will be the best fit for your family, when should you pull the trigger and buy coverage? We have been using World Nomads since we started traveling long term.

Is your family preparing for long term travel?

We know how overwhelming the process can be. With over three years of perpetual travel under our belts, we can honestly say, you don’t need to plan everything down to the last detail when it comes to long term family travel. But, keeping the things discussed in this article in mind will help you save precious time and money, and avoid some of the frustration that goes along with challenges that can crop up during a trip.

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