Incognito Tab: Use it when looking at hotels & Flights. Prices will escalate when they know you are looking. Seems crazy but it is true.
Search for Hotel Perks: A continental breakfast or discounted attraction ticket rates. Are there stores near by, if not stop by a store on the way to the hotel. Do not get roped into paying escalated costs due to convenience.
Check for Events in Area: Prices and crowds increase when events take place, festivals, themed days at the park (grad night), the Rose Parade etc. Checking the amusement parks calendar is not enough as many events happening in the city itself will affect your vacation.
Check Expected Crowd Index: Being mentally prepared for peak season is half the battle. Knowing the park will be crazy may open up ideas to explore other things to do in the area in order to prevent burn out from long rides as well.
Coupons: Once you know where you want to visit it’s time to hunt down those deals. Some discounts that I use for vacations are Groupon, AAA, discount tickets from the hotel, discount ticket places at the mall etc.
Plan Itinerary: Rather than saying I want to go to Disneyland, figure out what park tickets best fit your needs. How many days to visit at each place? Even ask the group what rides or shows are a must to add to the to do list. What hours are each place open, does the amusement park have early hours or close early on certain days, while later on other days.
Check Weather: Rain or shine most places are open, however, the quality of the trip declines depending on if it will it be hot or rainy. Create a backup plan for things to do if the weather becomes a damper in the days itinerary to avoid feeling devastated.
Places to Stop: If driving is part of the adventure, take the time to spot out places to stop along the route. Gas stations (diesel especially), restaurants, bathrooms etc. Do not wait for the moment where someone in the car asks for a stop when the next option is 50 miles out.
Have Fun: Planning should not be a drag, it should get the whole party excited. Stressful planning only happens when people wait to the last minute or miss something. If I catch myself getting stressed out while planning, I take a time out to regroup. This is a vacation not a business trip where every minute of the itinerary is planned out. Remember preparation is not fool proof, rather it aids in making the trip a bit better when things start feeling rocky.