I typically go through four steps when planning a vacation. It takes a lot of time, but that’s what you have to do when you don’t want to spend a lot of money.
Find things to do:
Keep an eye on local news: This is how we found the Detroit Canals and the Ohio River Ship.
Links, links, links: You see something cool and there are links to other cool things? Click those. I’m not usually sure how I find things to do because it’s from a link off a link off a link.
Google Keywords: (the state you want to vacay in) + cool/creepy/different/amazing/weird/unique/offbeat + place/river/attraction/museum/festival/town/trail/park OR kayak/canoe/hike/bike/climb
Google Maps: Another way to use those Google keywords. Zoom in on the area you’re interested in and Google those words above.
RoadsideAmerica.com: This website is awesome. It’s a great way to find things to do around where you’re staying or on the way there. There’s a lot of offbeat stuff on there.
Find places to stay:
Craigslist: A good way to find vacation homes. The expensive ones have websites, but the family with a cheap cabin uses craigslist. I haven’t experienced a creepy person yet (knock on wood).
Google Maps: (I cannot express enough how much I use this to plan vacations). Zoom in on the area you’re vacationing and type: campground/campsite OR hostel OR motel OR bed and breakfast OR whatever type of place you’re looking for. We tend to go the camping route.
State/National Parks: Sometimes their campgrounds don’t show up on Google Maps. I don’t know why. So find a park near you and go to their website to find campsites. These are usually pretty rustic but that’s part of the adventure!
Couchsurfing: I’ve never done it because I’m a tiny female but I’ve heard others have had good luck with it. Google couchsurfing and there are a ton of websites.
Figure out how to get there:
Drive: We tend to drive because we have stuff to haul, like kayaks or camping gear. If you’re going far and there’s a bunch of you, you can all take turns driving. I’ve driven across the country six times. It’s horrible. But it’s better when you have a ton of people helping get through the miles. It’s pretty easy to calculate gas cost if you know how many miles per gallon your car gets. Plus, it’s just nice to have your own car to get around.
Train: There are actually a lot of train options if you’re going from a major city to another major city. You can always drive to a major city close by and hop on a train.
Fly: Ahh, flying. There is so much information out there that you can just Google the best time to fly and all. I will say this, however, you can do some creative plane jumping to get the cheapest flight. For instance, one of the cheapest airlines to Hawaii is Alaskan Airlines (weird, I know), but flying from Detroit to Hawaii on Alaskan Airlines is expensive and it layovers in a west coast city because that’s where Alaskan Airline’s main business is. So you can get a flight to the west coast on another airline and then get on an Alaskan Airlines flight directly on the west coast. Just be careful of flight delays – you might want to have a day in between flights or get a refundable ticket. Google: cheapest airline to (whatever city) and you’ll find a lot of information.
Another tip for flying: if your flight has a stop, go back to the main page and select ‘multi-city.’ Put in the first leg, then the second. You will be on the exact same airplanes as before but you will save lots of money. Seriously. I saved $80 by going from Detroit to Denver, Denver to San Diego instead of Detroit to San Diego with a stop in Denver.
Figure out how to get around:
Your own car: Don’t forget about parking!
Rental car: Now that I’m over 25, renting a car is amazing. There are a ton of places online to get cheap car rentals.
Public transportation: Check to see if the city you’re going to has good public transportation. Chicago and San Francisco are good. There are SOOO many cities that are public transportation friendly. You can look around for a passes that let your ride public transportation for an extended period of time for one price.
Bikes: In bigger cities, there are TONS of places to rent bikes. My sister did that in Chicago and loved it.
Taxis: Try to stay away from taxis if you can. They’re expensive. However, I DID have a taxi take me down Lombard Street (the one that zigzags.) in San Francisco for $5 so I could film the ride down.
Uber/Lyft: If you have a smartphone, go for it. I did this in San Diego. It did start to add up but I felt like I was paying for the convenience more than the ride.
These are the four steps I tend to take when planning vacations. I tend to make a Google Map specific to my vacation. I also print out itineraries and maps. I usually travel with a file folder of stuff to do so I never have to worry. I like to over-prepare during planning so I don’t have to worry about anything during the vacation.