One of the more frequently asked questions that we get from our clients is about calling home from the Azores or mainland Portugal.
We came up with the following list of the best options, ordered by cost, to call home from the Azores and Portugal:
Pay Phones:
Pay phones are available throughout the major towns and cities in the Azores. 
They are located near town, city centers and near public transportation stops.
Pay phones accept calling cards as well as euros. Calling cards are available at most cafés, corner grocery stores and magazine stands. They are available at a cost of 3, 5, and 10 euros per card, with a 10 euro card letting you call for 376 minutes (€ 0.026 per minute) to call the United States or Canada.
Pay phones also accept coins in 2, 1 euros and 50, 20, 10 cêntimos, they are more expensive then the calling card option, with a rate of more or less 5 minutes per euro (€ 0.20per minute).
Pros: Very inexpensive way to call home.
Cons: You have to search for the pay phones, and some payphones might be out of order.
Buy a Prepaid Cell Phone in Portugal:
You can also buy a prepaid cell phone while out in the Azores. There are two major cell phone companies, Vodafone and TMN, and they have stores located through out the major islands of the Azores. The price of a cell phone begins at about 20 euros, and they usually come with a bonus of 5 euros worth of prepaid calls. The cost to call the United States 2 minutes per euro (€ 0.45per minute), however whenever you receive a call you will not be charged.
Pros: You can call home from anywhere on the islands. Family and friends can call you at any time. Calls that you receive, will not be charged to your balance.
Cons: The cost to call home is a more expensive then using a pay phone. You are investing in a phone that you might only use once and any minutes left on your phone will expire after 6 months.
Personal Cell Phones:
You can also bring your own cell phone out to the Azores, assuming your cell 
phone can work properly out in the Europe. Based on experience, AT&T and T-Mobile phones work out there, Verizon and Sprint not so much. Check with your carrier or your phone manual before bringing your phone. The cost to call the U.S. can be expensive, as most carriers charge $1.99/minute. You will have your personal phone, and friends and family can contact you just as easily.
Pros: Using your personal cell phone it is easy for family and friends to keep in touch with you and you will have your contact information easily available.
Cons: Cost is expensive, when compared with the options above. Phone might not work in Portugal.
My father and I, use the pre-paid option when we are out in the Azores. The reason being it is cheaper then bringing our own personal cell phones, and anybody can get a hold of us.
If you just need to check in once in a while at home,and you do not want anyone calling you, then the calling card option might be the best option. Whatever your choice you can always call home.