Tips · Travel

Planning your Perfect Vacation Part 3: Picking your mode of Transportation

Today we’re back again with the third installment of our Planning your Perfect Vacation series!

Now that you have a rough idea of when and where you’ll be heading, it’s time to figure out how you’ll be getting there. My general rule of thumb was always if it’s under 5 hours I might was well drive, but other than that flying is best. Our trip to Charleston, however, made me realize that sometimes the drive can be half the fun. If it’s longer than 5 hours, it’s definitely worth pricing out the difference between driving (don’t forget to include tolls) and flying. It’s also good to factor in whether or not you’ll need a car while you’re there, how difficult/expensive parking will be, and how much luggage you’ll be bringing.


By Air 

If you’ll definitely be flying, it’s time to start scouting out the best flight deals. If you’re planning well in advance, sign up for sites like The Flight Deal or Airfare Watchdog and keep an eye out for any flash sales or deals. No matter when you’re flying, sites like Kayak and Google Flights are going to become your best friend since they give you the most flexibility on searching flights. Be sure to know which airline’s information is being pulled into the search. For instance, Kayak is great but it isn’t able to search for Southwest flights so you’ll need to do that separately if they are an option. Flexible dates can also really help save money, especially if you’re willing to avoid flying on Friday, Sunday, and Monday. If you’re dates aren’t flexible, it may be worth exploring other airport options. For example, if you’re planning a trip to Venice, you may want to consider flying into Milan. Milan is a much bigger hub and in my experience tends to have some of the cheapest fares to and from the Northeast. The best part is, it’s only about a 3 hour train ride from Venice and you’ll get to see some of Italy’s beautiful countryside on the way! If you’re planning a multi-city trip and you’re itinerary is flexible be sure to check flights starting in either direction. While you’ll probably lose some sightseeing time, you may also want to check how much it would cost to go back to your starting city and fly round trip from there, but be sure to factor in all additional costs and what you might have to leave off your itinerary.

Another great tip for getting the most out of your money, is to pick a flight with a long layover. I just did this on my recent trip to Italy. My 8 hour layover in Brussels was just enough time to see the major sites, shop for chocolate and lace, and eat a delicious lunch. The flight was the same price as one with a much shorter layover and so essentially we got to see Brussels for the cost of the train ticket and luggage locker.

By Car

If you’re going to be driving, it’s time to start figuring out what route you’ll be taking. Be sure to map out your stops and any meals. Typically I figure I will need to stop every 4-5 hours and so I try to plan out my route so I’ll be able to see something new along the way and get a great meal. You may also want to see if there are any places on the way that you want to add onto your itinerary. When I choose a route for a road trip, I weigh a number of factors including time, scenery, tolls, and potential stopping points. You may also want to consider staying just outside your destination the night you arrive. This will help you avoid driving into a new city in the evening, plus hotels in the suburbs typically are a bit cheaper and have free parking.

By Train

While in the US we typically defer to driving or flying, taking the train is also a good option. I have to admit, that other than for day trips to NYC, I haven’t really taken advantage of this mode of transportation, but if you’re going cross country or even up and down the East Coast its a great option if time is not an issue. I recently read a post by Derek Low about how, if you schedule it correctly, you can take a train from just outside of San Francisco to New York City for only $213!

Now that you’ve finalized you’re transportation, everything else should start falling into place. In Part 4 of the Planning your Perfect Vacation series, we’ll be sharing all our tips and tricks for picking out hotels while not breaking the bank!


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