Went just last weekend on a short road trip to Michigan, My fiance's best friends family owns some land with some cottages. Total cost for us was about $200 or so for gas and food and such.
In a month we are going on another short road trip to my grandmothers house in Wisconsin (about 250 miles 1 way). It will cost less since my grandmother will supply more than enough food, and we will take my car instead of borrowing fiance's mom's Explorer. (my forester has crappy back seats, but just the 2 of us on the road so we get 25mpg rather than 15-20mpg)
In December, we are going on a 7 day cruise from Baltimore to Orlando and then the Bahamas. It's around a 750 mile drive from home, so it shouldn't be too bad to drive all at once. We plan to spend a day in DC and a day in Baltimore. The cruise was about $1000 or so for the 2 of us, gas will be around $250-300 if it stays under $4.50 per gallon. We have about $150 of "credit" on the boat towards drinks and whatever. We will probably buy the maximum amount legal of duty free cigars or cigarettes and booze to bring home. Total budget for this trip is about $2000 given 1 night of hotel in Baltimore area, 1 night of hotel in DC area, cruise, excursions, fuel, food, and discretionary spending. In theory, we should be able to come in about 300 or 400 under budget, but, the money is there if we need it.