Long Term Travel

Long term travel can be difficult because of stay restrictions in most countries. For example, the Schengen area of the EU allows a maximum of 90 days at which point you have to leave. If you are planning to move around within the Schengen, there is a handy Shengen calculator that helps keep track of your stay there to avoid overstaying your allowed visit time.

The EU is implementing, what is essentially a digital ID for foreign visa-free travellers in the Schengen Zone known as ETIAS, which stands for European Travel Information and Authorization System. From their website:

It is a completely electronic system that allows and keeps track of visitors from countries who do not need a visa to enter the Schengen Zone....
The legal procedures to pass the ETIAS have started in 2016, and the system is expected to be fully operational in November 2023.

The ETIAS is not yet implemented (as of August, 2022). The EU travel website will post updates on the program and when it will be in operation.

Another handy website is Sherpa which provides information on travel requirements for your destination depending on the passport you hold.

Here is a good video of a couple who travelled in Europe for a year. They detail how to avoid the visitation restrictions in the various areas of the EU. This primarily involves moving within the EU but going in and out of the Schengen area.

Slow Travel

From video from perpetual travellers 2GoRoam on their Youtube channel discussing "slow travel." This is the idea of extended stays in each location. 

They typically use AirBnB for accommodation and have discovered that stays beyond about 28 days provide a significant discount to shorter stays, sometimes up to 50%. 

They also try to stay in great out of the way places that are significantly cheaper to stay. Numbeo's global cost of living index is a good resource.

Cost of Living Overseas

On staying or living in other countries, advice can be found on many expat forums. One I found informative is Expat Exchange. Also, found in International Living, the website Numbeo has a global cost-of-living guide which is very helpful when looking for a place to settle.
On the healthcare side, there are a few indices that rank healthcare quality and each uses different criteria. The WHO rankings are based on quality and overall efficiency. For 2021 the WHO ranks France #1, Italy #2, Malta #5, Spain #7, and Portugal #12 in its world ranking (by comparison Canada is ranked 30th and the U.S. 37th). CEO World bases their ranking more strictly on the quality of healthcare. They rank, from 1 to 10, South Korea, Taiwan, Denmark, Austria, Japan, Australia, France, Spain, and Belgium.

Banking

Non-resident Bank Accounts 

Opening foreign bank accounts in a country if you are not a resident is almost impossible now. Only a few countries allow non-residents to open an account. Georgia and Montenegro do; Singapore and Malaysia also do but require substantial deposits. I asked a person at a bank in Dubai if non-residents can open accounts there. He said yes, but I don't know what the minimum requirements are.

Expat Residence Accounts 

A local bank account is a necessity when living in a new country. A little more research is required to see which bank in each country would be best. Most countries for expats require a local bank account in order to show you have sufficient funds on hand to support yourself.

To start, a survey of best banks for expats in Portugal.

Travel Medical Insurance

I recently purchased travel insurance through CAA (of which I have been a long standing member). They do all of the paperwork, and, interestingly, the insurance company that CAA uses is now owned by CAA.

Medipac Travel Insurance is recommended by the Canadian Snowbird Association and the Canadian Legion as a supplier of travel medical insurance for Canadians. I have not used them.

Safety Wing provide medical insurance for digital nomads and expats. 

Blue Cross travel insurance is available through its Ontario agent.

You should also look at what, if any, vaccinations you will need, and arrange to get them. The Government of Canada travel website has a list of suggested vaccinations by country. You can also contact your physician or local health unit.

Non-resident and CPP & OAS

You can collect both CPP and OAS will living outside of Canada. To qualify for OAS you must have worked in Canada at least 20 years. Both CPP are taxable income. You can receive the full payment due to you or have a portion of your payment withheld to avoid having a large tax bill at reporting time.

In regard to receiving CPP and OAS when living outside Canada see the Canadian government website. One aspect to consider is having your payments deposited in the local currency:

Because your payments will have already been converted into the local currency of the country where you live, you should get a better exchange rate, and you might also pay lower banking fees for cashing your cheques.

To receive your payments directly in your local bank account, see if you live in a country that offers the service of direct deposit.

See the government website listing the countries that accept direct deposit of CPP and OAS into a local bank.

Non-resident and CRA

Below is an excerpt from a September 2018 article from Investors Group entitled "What Happens to Your Assets When You Leave Canada?"

When you leave Canada and sever your residential ties to Canada, you must file a final departure tax return. Let’s say you will be leaving Canada on November 1st. On that day, you will cease to be a resident of Canada and will be deemed to have disposed of all your non-registered investment assets at their fair market value. This is known as a deemed disposition and you will have to report the capital gains or losses that result from it.

RRSPs, tax free savings accounts (TFSAs), registered education savings plans (RESPs) and your principal residence are not subject to this deemed disposition but be aware of the tax consequences in your new country. For example, if you move from Canada to the United States, your TFSA will become taxable by the IRS.

If it is determined that you are a resident of Canada for income tax purposes, you are required to file a Canadian tax return and report your worldwide income on your personal Canadian return. If the Canada Revenue Agency (CRA) determines that you are a non-resident of Canada, you do not need to file a tax return if your only Canadian-source income is investment income, but you will have to pay a withholding tax on the Canadian-source income.

Read the full article for a full overview here.