Flying to Canada is actually a fairly simple process, you can do so IFR or VFR and you can do it with a regular US private pilot certificate and US medical in a US (N) registered aircraft.
Before doing so, there are a few bureaucratic steps you must take, and there are a couple restrictions to who can go.
To start you need at minimum a US Private Pilot Certificate, a student pilot certificate or sport pilot certificate will not suffice, meaning don’t try soloing into Canada when you are learning. Additionally you will need an actual FAA Medical Certificate of any class but Canadian regulations do not recognize basic med.
Aside from these things your aircraft will need a couple of certificates, you will need to be carrying a couple of documents, and you will need to complete a couple of regulatory steps before you depart and reenter the US. Below you will find a list of all the things you need for each, and links to where you can obtain them as well as short explanations if they are not self explanatory.
Aircraft
Customs Sticker
Your airplane (whether you own it or not) will need a customs sticker to fly into another country and back. These are $35 and are valid for 12 calendar months. it takes about a week to obtain the actual sticker, but the receipt should be good enough if you are on a time crunch.
https://dtops.cbp.dhs.gov/main/#%20
Radio Station License
Your aircraft needs a radio station license to operate internationally, the license is easy to obtain from the FCC and it cost $135.
To obtain the Aircraft Radio license:
Get an FCC Registration Number (FRN) here: (you will need this for the operator license below)
https://apps.fcc.gov/coresWeb/publicHome.do
Once you have that go to the application page here:
https://wireless2.fcc.gov/UlsEntry/licManager/login.jsp
Click new license on the top left and pick AC – Aircraft
Owner Letter
If you are flying someone else’s plane you will need a letter from them stating that you are authorized to fly the aircraft internationally, I have never been checked for this, but it’s always a good idea.
Pilot Requirements
Pilot Certificate
Self explanatory, but make sure you have it.
Medical Certificate
Self explanatory, but make sure you have it.
Passport
Self explanatory, but make sure you have it. Also make sure you have a book, the card is not valid for air border crossing.
Radio Operator License
You will need an FCC Radio Operators license, these are easily obtained from the FCC website by filling out the form and paying a small application fee. They last forever, and if you plan on becoming an airline pilot you will need one anyway.
to obtain the restricted radio operator license
Get an FCC Registration Number (FRN) here:
https://apps.fcc.gov/coresWeb/publicHome.do
Once you have that go to the application page here:
https://wireless2.fcc.gov/UlsEntry/licManager/login.jsp
Click new license on the top left and pick RR – Restricted Operator
Filing information
US
eAPIS The Electronic Advance Passenger Information System is what the US uses to keep track of people entering and leaving the country. You will need to create an account here to file entry and exit information for you and all of your passengers. As the pilot you will create a profile and you can use it every time you go, for your passengers you will need their passport information to complete the process.
Once logged in you will need to create manifests by going to
Create a new “Notice of Arrival” and traveler manifest
https://eapis.cbp.dhs.gov/eapis/auth
Departing
Create a new “Notice of Departure” and traveler manifest
You can leave from any airport in the US as long as you have a flight plan filed (IFR or VFR) work just make sure you activate your VFR flight plan before you cross the border and if at all possible get flight following.
Returning
Some airports have full time customs services, so all you need to do is tell them you are coming. Other such as Manassas VA, Rome NY do not have full time customs agents, so you will need to call to make sure an agent will meet you at the plane. Most of the time at smaller airports you will need to request the agent at least 24 hours in advance, and then update them with a precise ETA within a couple of hours of landing.
DO NOT EXIT YOUR PLANE UNTIL AN AGENT HAS MEET YOU!
Canada
Entering Canada is usually a little easier than the US, you will need to go to the customs ramp at the port of entry, but most of the time they just have you call them, confirm your passengers and arrival time, then they will give you an entry confirmation code.
If you plan on going multiple times you should apply for CANPASS, this will streamline the entire process.
https://www.cbsa-asfc.gc.ca/prog/canpass/privateair-eng.html
Or you can do things over the phone:
Call this number and file your information before you take off, and after you land
(888) 226-7277
you will need passenger passport information to do this
DO NOT EXIT YOUR PLANE UNTIL YOU HAVE SPOKEN TO AN AGENT!