Obviously any vacation will take time, but I wanted to talk a little about what the general Pennsic schedule is like. First up is Zero Night. This is the Friday night when - historically - everyone camps on the Battlefiled and parties because they have to be up at 9 AM on Saturday to setup their Land and have nothing to do until then. The Land Office has made some changes this year, and it's a little unclear how that will affect things, but I suspect the Zero Night That Was is now over, which is probably for the best -- it was a huge hassle for everyone involved. There will probably still be parties (I know I'm throwing one), but they will no longer be on top of each other.
Land Grab (or Peace Week) is what follows, and it is the most relaxing vacation I've ever taken. We set up camp, sit around the fire drinking, take day trips to visit rosinavs' family, etc. The first battles, the first classes, the first parties, the first performances, all of these things happen toward the end of Peace Week. Opening Ceremonies is on Saturday, this is when the battle lines are drawn and sides are declared. It is the largest gathering of pomp and circumstance in the Known World.
War Week is the most action-packed vacation I've ever taken. There's so much to do, it is all happening at once, and all of it is in walking distance -- which means that even though my day is packed from 8 AM to 10 PM, I still have time to sit and read a book. This is also the most important time to volunteer. Pennsic is run by volunteers and if everyone simply volunteered 8 hours of their time, then everything will be setup on time and organized.
Finally is teardown. Most groups start organizing camp in preparation Thursdayish and do the full teardown Friday or Saturday. There is a penalty for failing to leave your campsite clean and empty by noon Sunday, and most groups are pretty good about doing just that.
To drive to Pennsic from Massachusetts, some people take the Northern Route, which is I-90 to I-79, which has the advantage of being mostly straight with well-lit rest areas. Others take the Southern Route, which is Is 90-84-81-80-79, which is hypothetically shorter. And others fly.
rosinavs and I spend about $700 each for Pennsic. I know people who do it for less. According to legend, you can show up with a sleeping bag and a case of homemade mead and everything will work out. Our budget is roughly as follows:
Site Fee - $170
Camp Fee - $200 (see Encampment)
Hotel & Transportation Costs - $230
Booze, Entertainment, and Souveniers - $100
One obvious way to save money at Pennsic is to not stay in any hotels: it's a camping trip and some people happily camp on the way down and back. Another obvious way to save money is to skip Peace Week: the price drops $40 at 0:00 on the middle Friday. Two years ago, rosinavs couldn't get Peace Week off and flew down. She spent half an hour knitting Thursday Night waiting for the price to drop. If you further need to save money, you can work while at Pennsic. Digging ditches, taking care of children, cooking and serving, toting and hauling, or simply working for one of the many merchants. People can work their desk jobs remotely via Mystic Mail - Pennsic's own internet cafe - or via the McDonald's just offsite.
Note that there is no day rate for Pennsic. The simple truth is that a lot of cool stuff happens overnight and the people who own Cooper's Lake Campground (the Coopers, natch) don't feel it would be profitable or enforceable. Also, the relatively high cost to enter helps deter hooligans from coming onsite and messing with your stuff.
The land distribution system of Pennsic is a unique artifact of its history. The entire campground is broken down into 100 or so blocks of varying size, the borders of which are determined by site features like forests, rivers, roads, etc. Everyone who attends gets approximately 250 ft2 of land to pitch their tent. If you preregister, you have the option of registering with a group, commonly known as an Encampment. Currently, there is plenty of land available at Pennsic, so Encampments usually get land in whichever block they request (which is usually the block they were in the year before). Encampments send a Land Agent to Land Grab to sign the paperwork on how to subdivide the block, though these days most of the negotiation happens in advance.
Encampments are a great way to maximize the utility of your space and your stuff and spend time with good people. Note that you don't necessarily want to share an encampment with your best friend or with your mother. Choosing an Encampment is a lot more like choosing a roommate: You want someone who will handle their fair share of the tasks and with whom you will not get into a shouting match with when it's 100 degrees out and you're pissed off at them. Encampments usually require some form of monetary contribution to handle the purchase and storage of camp equipment as well as using some portion of each person's land to handle communal infrastructure and green space. In the event your encampment needs or wants more space than the aforementioned 250 ft2/person, you will need to register some Ghosts. Ghosts are people who - hypothetically - might show up to Pennsic but in reality probably won't because you registered them only for their land. DO NOT REGISTER CHILDREN AS GHOSTS. Note that you must have a paid preregistration in order to register land with an encampment.
Another important determining factor for your encampment is food. Many people have incompatible food restrictions or preferences or simply differing opinions as to how important communal dining is. Some encampments simply provide you with kitchen space to cook your meal, while others have catered parties with free-flowing alcohol and pantry tents.
People who do not preregister with a group are referred to as "Singles Campers" and when they arrive onsite, they choose a plot of whatever land is still available and that will be where they pitch their tent.