“Where do I start?”
If you have a traveling itch, you want to get out of town, or you simply want a new experience, my advice to you is DON’T BE PICKY.
1. Pick dates. This is the first step whether you have a destination or not. I found traveling somewhere Wednesday through Sunday works “best” because you get to experience the Friday/Saturday nightlife and Wednesday through Friday means shorter lines at tourist attractions.
*I like to buy the major things (flight, car, hotel, etc.) more than 2 months in advance. The closer you buy these things to your departure date, the more expensive it is (look at how much I unnecessarily spent in the Caribbean). The sooner you pick a destination, the sooner you can begin!
2. Buy your plane ticket. I typically use Expedia and Orbitz to book my hotel and flight, and I try to do them both together (increased likelihood of saving money!). This is a large category so let’s break it down:
Airlines: I LOVE SOUTHWEST. You get a ridiculous amount of drinks and snacks, it’s amazing. Their seating arrangement has its downfalls but it’s absolutely made up for by their prices (and two free checked bags!). The only airline I’d prefer to never fly again is Spirit. They had EXCELLENT prices but the seats were uncomfortably small/close together and they provided no beverages/snacks.
Flight Times: I prefer arriving in the late afternoon. It gives you time to get settled/explore the hotel, grab dinner, and go to bed early so you can begin your adventures early the next day! Arriving at 6am in a new place tends to suck. Most hotels’ checkin isn’t until 3pm, you’re jet lagged and want to nap/shower, and now you have to explore your new surroundings the whole day because you don’t want to waste a day.
Which Airport: Sometimes smaller airports are cheaper. The downside is that less airlines fly in and out. Check out your local airlines prices to your destinations’ various airports and compare! For example, flying from LA International to Chicago O’Hare was more expensive than flying from Ontario Airport to Chicago Midway. Both were smaller airports so no Southwest, but the prices beat the larger airports.
3. Make your hotel reservations. Again, I usually do this in conjunction with my flight reservations as Expedia and Orbitz tend to have a larger amount of savings. This is also a larger category so we’ll break it down again:
Location: I hate renting cars. More on that later. I usually end up walking and taking taxis wherever I go so location is very very important. Google “Cool things to do in ______” and look at the options on a map. Compare this map to the map of hotels on Expedia/Orbitz. You want something central. Accept that you may have to use the subway or taxis to get to the furthest points, but the more you walk the more you save (and burn calories, so it’s really win-win).
Breakfast: I like free breakfast. Hot and lots of it. If your hotel doesn’t have free breakfast, I’m sorry. Some don’t, some do, and it’s definitely a plus.
Chain Hotels: For example, Marriott, Ramada, Hyatt, etc. They all pretty much have breakfast and wifi (a HUGE plus).
Non-Chain Hotels: When I go somewhere new, I like to experience local things. Some hotels in your destination have a history to them that cannot be replicated anywhere else. These are the places I want to experience. They’re usually pricier, but they’ve always been worth it to me.
4. Renting a car. I already said I hate renting cars, here’s why: I’M NOT 25. Anyone under 25 renting a car will have to pay an exceedingly ridiculous amount of insurance. I understand their point so I don’t fault them for it, but it sucks. Anyway, try to find a coupon. Costco memberships and AAA always help. My dad usually rented cars from Hertz and he’s a very astute man. I prefer cars from Avis and Budget. Avis always has some sort of “upgrade” deal last minute and they both always provide reasonable prices. Keep in mind you can always rent a car for just one day at your destination instead of having it for the entire time.
Obviously there is so much more to planning your perfect adventure but these reservations are an excellent place to start. I can’t stress how important it is to make these reservations as soon as possible once you decide your date and destination.