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Your initial maximum stay is only 30 days and then you have to get an extension. Since you know you are going for more than 30 days you can get a visa for up to 59 days at the Philippine embassy in Washington, DC. Then in the PI you can get an additional 29 days. So basically you are limited to just under 3 months.
Go to this link to see more about visas
U.S. citizens may enter the Philippines for purposes of tourism without a visa if they present their U.S. passport valid for at least six months beyond the date of their entry into the Philippines, and a return ticket to the United States or an onward ticket to another country. Upon your arrival, immigration authorities will annotate your passport with an entry visa valid for 30 days. If you plan to stay longer than 30 days, you must apply for an extension at the Philippine Bureau of Immigration and Deportation's (BI) main office at Magallanes Drive, Intramuros, Manila, or at any of its provincial offices. If you know you will stay in the Philippines for more than 30 days, you can obtain a fifty-nine (59) day visa at the Philippine embassy or consulate closest to you before traveling to the Philippines. Once in the Philippines, you can apply for a twenty-nine day extension. If you are coming to the Philippines for purposes other than tourism, please check the Embassy of the Philippines website for visa requirements. You may be denied entry or be given a fine if your purpose for entry is other than tourism and you do not possess the correct visa.
U.S. citizens may obtain a multiple-entry transit 9(b) visa to permit travel from one country to another via the Philippines. Travelers must obtain a transit visa from a Philippine embassy or consulate prior to traveling to the Philippines—transit visas are not issued upon arrival in the Philippines. The transit visa generally is valid for one month and allows the traveler to remain in the Philippines for up to three days. The transit visa is not convertible to any other type of Philippine visa and cannot be extended. U.S. citizens holding an approved transit 9(b) visa should possess the following to qualify for entry to the Philippines: a passport valid for at least six months beyond the date of entry into the Philippines, a confirmed onward ticket to another destination, and a valid visa for the country of final destination, if a visa is required.
Persons who overstay their visas are subject to fines and detention by Philippine immigration authorities. Please remain aware of your visa status while in the Philippines and strictly follow immigration laws and regulations. Travelers departing the country from international airports must pay a Passenger Service Charge in Philippine pesos. Visit the Embassy of the Philippines website for the most current visa information.
There are also consulates in other cities that you can contact which may be closer to you.
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