Things to Consider Before Your Next Vacation - Cupcakes & Cashmere

Things to Consider Before Your Next Vacation

How to plan the trip of your dreams.
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People who don't list "travel" in their top five interests are few and far between—whether that means driving an hour away to go camping, or taking a trans-Atlantic flight. But for such a popular hobby, it's an investment, even with aggressive saving and budgeting tricks, so it's important to ensure the memories that come out of it are worthy dividends. Here are five things to consider before committing to a trip: 

1. Are you looking for adventure or relaxation?

This may seem obvious, but it’s a goal we often forget to identify from the get-go. You may want to see every city in the world, but sometimes you have to be honest with yourself and accept that site-seeing for 10 hours, while rewarding and educational, isn't what you're really craving for your next trip. It's your time and money, so if you want to sit on a beach with a book for a week, do it. If you want the thrill of pounding-the-pavement-tourism, do that. Be real about what you're craving. 

2. When’s the next opportunity you'll have to travel?

If you have a finite number of vacation days or won't be able to swing another trip for a few years for work or personal reasons, consider prioritizing location over any other factors. Ask yourself, "What's my number one dream trip with reason? And if I don't take it now, or this year, when is the next realistic time I'll be able to?" If it's now or never, metaphorically speaking, do whatever it takes to make it happen. 

3. How long will it actually take you to make the most out of this trip?

While five days may be plenty of time to visit one city, it may feel like the blink of an eye in another (especially if you're flying half-way around the world to get there). If you're flying to Tokyo from the west coast, it's probably not worth it if you only get 48 hours to explore the diverse city. The prospect of asking for additional time off may seem daunting, but consider having an honest conversation with your boss about squeezing a few days in if it means taking a more memorable trip or making it worth the money. Or, plan a trip somewhere that better fits into your time allotment, and save a place like Tokyo for a time when you do have the time to really do it justice. 

4. Who do you really want to go with on this trip?

Just because you're in a relationship, have a family, or live with your best friends doesn't necessarily mean you have to travel with them. Some trips are infinitely more fun solo (you get to do whatever you want), while others benefit from a large group (you get to share in the experiences, like group wine tasting), or the right one person. Paris with your mom may sound amazing to some people, while others may want to save their first time in the infamously romantic city for a significant other one day. Who you bring can drastically change the mood of the trip, so make it count. 

5. What is the most you can spend on this trip?

Money is one of the biggest limitations of travel, so it helps to be brutally honest with yourself when you start planning. Prioritize what matters (Would you rather stay in a beautiful hotel or save money by sleeping in the cheapest accommodations possible? (We're not recommending this, but for the record, Leslie did sleep in a car in New Zealand to save money on other things that mattered to her more). Is eating expensive meals important to you, or can you survive on grocery store sandwiches instead, to save all your money for shopping?) Whatever you decide, make a rough budget before you book anything so you don't end up spending more than you bargained once you're there, which can leave you with a sour feeling toward traveling again.