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Things like cruises, flights, trains, and even car rentals can be drastically different depending on where you book them. Check the company’s website directly to look for any specials. You should also check at least 4-5 aggregate sites like Kayak.com, Booking.com, or Trivago to get an idea of potential price ranges.  When traveling to a different country, local aggregate booking sites may offer better deals than the ones you find in your home country. Check local listings to see if you can grab a better deal. To get the best idea of how pricing varies, compare itineraries that are the same. Check the same dates and destinations on different sites to see where you can really find the best deals. If you’re traveling as a representative of a particular company or organization, they may have an in-house travel site or travel booker that you are required to use. Check with your company’s administrative department to see if that’s the case. Sites like Kayak.com, Booking.com, and Trivago are great to check for deals on hotels. It's worth considering other accommodations, though, too. Sites like Airbnb and VRBO let you book rooms, houses, and apartments directly from the current occupants. These can be great if you're traveling for long periods or want amenities like a full kitchen to save on meals out.  Likewise, if you're planning on staying in a hostel, hostel-booking sites usually have better offers than hotel booking sites. HostelWorld.com and HostelBookers.com are two options with extensive listings. If you're going camping, check your site well in advance. Popular campsites like Big Bend National Park in Texas can run out of permits months in advance. Don't assume you can just show up at a campsite and set up your tent. You often need to reserve a spot on site. Think about different routes you can take to get to your destination. Flights directly into Washington DC are often expensive, for example, because the DC airports are close to public transportation, hotels, and attractions. Flying into Baltimore is often more affordable, and still puts you a 20-minute train ride away from DC. If you still haven’t booked your transportation or accommodations within 8 weeks of your intended departure date, you need to do so now. The longer you wait, the more expensive these will get. You also run the risk of the flight you want selling out or the hotel being fully booked.  For international trips, you may need to book further in advance, especially if you are flying or taking a cruise. Try to book at least 4 months out from your intended departure date in these cases. Trips taken during popular travel times should also be booked further in advance. If you plan to go to Boston for St. Patrick’s Day, for example, expect hotels to fill up months in advance. Some modes of transportation don’t require you to book as far in advance as others. A train, for example, may only require a reservation the week before your departure. Check your carrier to see their suggested booking time frame. You don't need a restaurant reservation for every meal when you're gone, but you should think about meal plans before you go. Think about how often you want to eat out, and how you want to handle things like snacks. For example, if you have kids, you may want to pack some sandwich bags and get a full-sized box of their favorite snack. That way, you can take these to go instead of spending on snacks every day.  Think about what meals may be included with your accommodations. Does your hotel offer free breakfast? If not, you may need to adjust your budget to include breakfasts. If you're staying at an all-inclusive resort or on a cruise, check with the resort to see if you need to book meals in advance. At some resorts and on some cruises, you have to make reservations for a certain seating time, even if the meal is included in your price. Consider your flight, too. If you have a long-haul flight where a meal is included, let the airline know about any dietary restrictions you may have at least 1 week before you depart. This way, you can ensure you get the right in-flight meal for your diet. You don’t need to plan out every second of every day, but schedule time for the things you really want to see and do. Researching and planning these before you leave allows you to see and do more of what you want. It also gives you the opportunity to make reservations or book tickets and tours for things that sell out in advance.  Your daily itinerary doesn’t have to be elaborate. It may be as simple as “Breakfast: 9-10, Acropolis tour: 10:30-12:30, explore the city after the tour ends.” Just make sure you include those things that are really important for you to see and do. If you’re traveling for business, your itinerary may have to be more formal. Check with your company or client to see if you need to submit a formal itinerary for your meetings and activities. Leave some room in between activities in case things run long or you have any unexpected delays. You don't need to plan every minute of every day, just make sure you have time to fit in those things that are really important for you to see or do.

Summary:
Shop around for deals on transportation. Check the availability for different accommodations. Book transportation and accommodations 2-5 months in advance. Make meal plans before you go. Set a daily itinerary before you leave.