I find that as I've grown older my need to stay in cheaper, hostel like accommodations has diminished severely. Yes, I will admit it, I have become a lodgings snob. I don't mind paying for nice views, quaint surroundings, a whirlpool tub, and a big flat screen when they are available. Yet despite my new found willingness to pay for the better things, I do want to make sure I maximize the return on my hard earned money. So when I look for lodgings, a few things are absolutely critical for me, cleanliness, WiFi, and a quiet room. I want to be able to sleep, stay connected to the outside world, and not worry about getting sick from unsanitary conditions.
Once I have decided what city or cities I will be traveling to, I like to use several options for identifying what lodgings would be most suited to my personal taste. The first task is to see what accommodations are available in the subject city using a review site such as TripAdvisor or Fodors. TripAdvisor has a great feature that allows you to view all the available hotels, B&Bs, and restaurants on an interactive map. To use this feature, type in the name of the subject city, then click on View Map of... option beneath the map on the right side of the page.
Once I have all of the hotels displayed, I start to look at specific areas of the city near major sites or features such as train stations, palaces, or specific streets. I then note which hotels look interesting, have received high rankings, and are in areas I want to stay in (this requirement might need additional research on your part before you get to this stage of planning). Once I have a list of the hotels I like, I then try to locate websites for each one. I tend to only stay in lodgings with websites. I know this limits me, but it is one of my personal preferences and it increases the chance that the place has some level of tech savvy staff or owners. Once I have located their website, I look into the pricing for the given season (high versus low) and use this to further reduce the size of my list based on my budget.
At this point I have should have several locations that I want to find more information about, so I return to TripAdvisor and look up the reviews to each of the entries on my list. Customer service is an important consideration of mine, if I read a lot of recent reviews bashing a hotel for lack of customer service I tend to move on. I also like to look at the pictures provided by the reviewers. Hotel provided pictures tend to promise a lot more than they really can deliver on, but the average TripAdvisor reviewer is one of us and therefore has no qualms about showing cracks in the bathroom tiles or dust on top of a window ledge. Likewise, you can usually trust a fellow reviewer when they show off a great view from their window or balcony.
Once I have been through all the reviews and pictures, I make my selection. I also identify a backup (number 2) because while I may have my mind set on one place, other travelers may have had the same idea before I did and there might not be any vacancy. The identification of a backup allows me to still proceed with my planning process without having to make definitive reservations until I am absolutely ready. I have used this strategy in the past, only to decide to change cities in my itinerary. Had I made my reservations from the start, I might have been stuck our lost out on a deposit. Waiting until I am happy with the entire itinerary and having backup options ensures flexibility during planning and reduces the risk of losing suitable lodging choices for my trip.
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