How do you plan a trip, more importantly a vacation? This is how I plan the logistics of our trips/vacations. Granted it's not rocket science and I'm sure everyone has their own method but this is the method to my madness.
First we create a budget, how much do we want to spend on the entire trip; which includes the three main categories of airfare, hotel and meals. We've been lucky to travel a few times with miles so that always helps and allows you to spend more money in other places, but I usually come up with a price I'm willing to spend on a flight first and if it's out of "my price range" we just don't go. For example, I think a ticket from Atlanta to Connecticut should be $200 or less and the same for a ticket from Atlanta to Miami, if I can't find those deals we just don't go.
Once I have the dates and the plane ticket figured out then I can move onto the hotel rooms. I'm rather particular on what kind of hotel we will stay in and mostly because I demand cleanliness over everything else, which I'm sure most people do. For our trip to San Fran it was fun because I played with all kinds of dates and puzzled them together to create a great itinerary. What we did that trip was stay the first two days in San Francisco then went four days to Napa and Sonoma and then back to San Fran for the last two days to see some more and also since we were flying out of SFO. It worked out perfectly we had four awesome days in Napa and then whatever we hadn't covered in San Fran during the first two days we were able to do that when we went back the last few days.
Now how do I look for hotel rooms, again as I mentioned I'm very particular which I think I'm just like everyone else but I don't want to stay in a place where I wouldn't want to take my shoes off and have my feet touch the floor, but in same the token I don't think it's necessary to spend ALL your vacation budget on the hotel room when for the most part you're just sleeping there, not hanging out all day.
We stayed at the Westin Market Street while in San Fran and it was great we managed to get a good rate by booking and paying for the rooms in advance. This can be a little risky if you think your plans may change but it does afford you a good deal. In Sonoma we stayed at a Doubletree which was very nice and friendly. I reserved a rate that was $116 a night and with that we received a complimentary wine tasting the first night we were there. We also received some coupons from the hotel for free wine tastings in Sonoma County. Another great deal.
I tend to use Expedia or Travelocity to find the hotel options in the areas we're traveling too and then I usually make the actual reservation thru the website of that particular hotel. Sometimes you can even get better deals and then you don't have to worry about a third party being involved if you need to make a change.
After the hotel reservations are made I start combing the internet and asking people who have been to the destination before what kinds of things there are to do and what would they recommend. We had a lot of recommendations and helpful information for our trip to San Fran which was great. I set up a tour for the second day we were there so we'd get a good idea of the city and then go back to whatever we were interested in seeing a little more of. I try and do as much research and gather as much information about a place before we get there so I'm not missing out once I'm there and I'm lucky because both Fer and I are laid back and go with the flow so pretty much how ever the day goes we'll have a good time.
Here's a picture from the outside of the Westin Market Street where we stayed in San Francisco
in the lobby