DRIVERS LICENSE
If you intend to make Madeira your main or permanent home, there are a number of very good reasons for exchanging your licence for a Portuguese-issued one. These are: - If lost, stolen or damaged, the licence can only be renewed or replaced by the original issuing authority. - When the licence eventually expires, the Portuguese authority cannot renew it as you will have to take (and pass) a driving test in Portugal before the Portuguese authorities can issue you with a licence. In order to exchange your driver's licence, you should apply to the nearest office of the IMTT - Instituto da Mobilidade e dos Transportes Terrestres (Portuguese Driver and Vehicle Licensing Authority). You will be required to surrender your original licence in exchange for a locally-issued one. 

VEHICLE INSURANCE
If you are planning on driving you will need the correct insurance.
Requirements vary among countries, so select an insurance provider with the expertise and resources to ensure the policy is appropriate.

PROPERTY INSURANCE
International personal property insurance, which can include transit and destination coverage, protects items damaged during the relocation process.
Some insurance providers specialise in relocation and expatriate insurance.

HEALTH INSURANCE
Even if the destination country has a socialised healthcare system, not everyone may be eligible for coverage. This may require an individual policy to protect the insured worldwide, including medical protection and evacuation services.

BANK ACCOUNTS
Review accounts and notify banks of the relocation. Also consider online international banking, which makes it easier to transfer and manage funds between countries.

PRESCRIPTION DRUGS 
If you or a family member takes prescription drugs, purchase additional quantities and obtain a copy of the medical file related to the condition. Keep them in your carry-on luggage in the event any bags are lost in transit.

TAX OBLIGATIONS 
Each country has distinct tax rules for foreign earned income. Determine the tax obligations and gather the necessary paperwork.

PETS 
If a pet is being moved, ensure it receives proper vaccinations and identification microchip. Find a pet carrier. If a pet is not being relocated, allow enough time to find it a new home.

PHONE SERVICES
Consider using VOIP (Voice over Internet Protocol) phone service, otherwise known as broadband phone service. It is an affordable way for expatriates to make local, long-distance and international calls, all for a monthly fee.

HEALTH CARE
To access free medical benefits under Portugal’s National Health Service, you’ll either need to have EU citizenship or be working and paying contributions into the country’s social security (segurança social) system.
Retirees from non-EU countries generally need to have private health insurance. You will be expected to provide proof of this when applying for a residence card.

COST OF LIVING
Obviously much depends on your  lifestyle. It is possible for a couple to enjoy life in Madeira for around 800€. This does not include rent.
Rental accommodation prices depend mostly in the location. A two bedroom apartment in Funchal could cost you an average of 500€, monthly. The same price will rent you a house in the outskirts of Funchal.
Utilities such as electricity, gas, water and garbage should run somewhere between 80€ and 100€.
Here are the prices of some everyday grocery item:
Litre Milk 0.80 cents 
12 Eggs 2.00€
Sugar 0.60 cents

Whole wheat bread 1,20€

The cost of living in Madeira is considerably lower than the rest of Europe.  This fact is reflected by the cost of living. The majority of goods are much cheaper than in the other European Union countries, including the price of property, renting, food, drinks and entertainment. The fact of the matter is that the majority of foreigners living in Madeira coming from Western European countries consider the cost of living to be up to 50% lower than in the country of their birth.