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What choices drive you crazy when planning a trip?

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On another thread something the poster said struck a chord with me--about being torn in deciding upon a restaurant between "inventive/creative" and "local specialties" I realized that for me at least there are lots of such generalized "pulls" in planning a trip, i.e. in deciding where to go, how to get there, where to lodge, where to dine, even which entertainment to book.

Because I have somewhat eclectic tastes, I experience these "pulls" within myself, but they seem to multiply when I ask my husband's opinion, or when I consider the interests of others who sometimes travel with us.

Here are some of the pulls and trade offs that came to my mind. Please add those that bedevil you as you struggle to develop plans for the perfect trip.

Large cities with lots of options vs. small villages with lots of charm vs. countryside with charm, peace and quiet

Hotels with lots of services vs. B&B's with lots of personality and opportunity to really get to know the owners

Apartments with space and a feeling of home vs. hotels with conveniences and concierges to make reservations, etc.

Short stays to diminish daily driving distances and provide more opportunity to see more places vs. long stays to minimize packing and unpacking and provide an opportunity to soak up and get the feel for a place

In restaurants and hotels--modern, trendy and design intensive vs. traditional, cushy with a feeling of hominess vs. even antique (which is not my favorite so I can't say what its benefits are)

And the ever popular Cheap to permit expenditure on other things of value vs. reasonable which is that ill-defined but you-know-it-when-you-see-it quality in the middle vs. luxe or even the-sky's-the-limit-over-the-top-because-you-only-live-once

Am I the only one who struggles (and struggles and struggles) or are there others out there, and what are your toughest decision points?

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