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I think with two weeks in Ecuador you could spend a few days touring Quito and the surrounding area while adjusting to altitude and then still have enough time to knock off Cotopaxi and Chimborazo with adequate rest time in between. If your physical conditioning and the weather are good you could possibly throw Cayambe in for the trifecta. Accessibility to these mountains is great so you don't kill a lot of time on long approach hikes.
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I did some quick searching on this and you wern't kidding! No crazy flights or multiday long hikes just to get to the base of the mountain. We are looking to go in June/July time frame.....from just the little reading I've done it is the windiest? I know mtns get windy and the weather can turn at the drop of a hat but what would you suggest as the best time to climb? The most I've done is 2 peaks in 5 days and not going to lie, it trashed me pretty bad. He could probably do it b/c he is the stronger/better athlete than I am but this year I plan on having better training and prep climbs.
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I lived a year in Guayaquil, Ecuador. Definitely I recommend visiting Quito (the capital) and nearby Equator line as well as Cuenca (Ecuador's 3rd largest city). Another town that I visited was Riobamba located between Guayaquil and Quito in the mountains. I have also heard that coastal town of Manta is nice, but I have never been there.
As for the Galapagos Islands, the best way to see it is to buy a package deal which includes staying on a boat. It is also possible to buy the airline ticket/s separately and then buy a separate package which includes hotel and full board (3 meals a day) on one of the main islands with day trips (some by boat and some around the island depending which one you are on). The only way to get to see the uninhabited islands is with a guide. In order to make this cheaper for you it might be better to buy these package deals while in Ecuador locally then from the USA before you travel.
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How is the public transportaion between the cities? I don't really fancy renting a car in Ecuador. (Actually, I've never rented a car on any of my international travels).
As far as the Galapagos, I would absolutely LOVE to visit the islands. My first pass on price checking on the packages ran $2,000+ per person, so that is why I didn't think I could fit it in this time around. I just checked and airfare is going to be about $2,300 for both of us. That leaves $3,700 (+/-) for climbing permits, lodging, transportation, food, ect....still not confident that the Galapagos would be doable unless the packages are closer to $1,500 for both, which I'm thinking is highly unlikely.
Ecuador is in the forefront of my interest, thanks to both for so much information.