If you’ve been following along for awhile now or if you know me personally, you already understand that I’m pretty Type A. When we plan a vacation, this personality type becomes extremely apparent. Thankfully, this works for Sasha, and some people like to wander lackadaisically around new cities with no itinerary – I honestly cannot wrap my head around that, as I land with a printed agenda and have plans down to the minute as to what we’ll do and see. The most important thing for me (and others like me) to remember is that if something goes awry, just let it be. If we have ten things planned, but end up spending lots of time at one museum, it’s okay to let the other things not happen. But I do need plans just in case!

When we went to Turkey, Athens and Paris, I printed a book out that had our flight confirmations, passport info, and day-by-day itinerary. I’ve wiped out personal information, but you can get a good idea of the plans we had by reading it here. I created a very similar document/folder when we went to Bali last year for our honeymoon (see the custom map here). I think it’s very important to be well-prepared before you travel to a new city in order to absorb as much culture, sightseeing and delicious food as possible.

Praying in the Tirta Empul Temple in Bali

We’re currently planning our trip to Paris and St. Petersburg in May. I spent almost four months living in Paris in 2009 and have been back twice since then, so planning that portion requires much less research. St. Petersburg is an exciting challenge, as we’ve both never been, don’t speak any Russian, and don’t have any friends who have visited before. Fortunately, my best friend’s boss is from St. Petersburg, so I’m going to ask her for advice once I’ve done more research, as well as use Tripply (more on that below).

Picking your destination(s) is the most important step early on in the travel discussion. Perhaps you’ve got a bucket list of places that you’re dying to see (like me!), or maybe you’re open to any country. If you fall into the latter group, then it’s best to do some researching. Are you looking for a cultural experience? Or a relaxing beach getaway? Once you know what kind of vacation you’re interested in and have decided on a budget, I recommend scouring the following sites for city inspiration.

• Entouriste: This travel photography site features jaw-dropping pictures from cities all around the world (all of the photos on this post are from Entouriste except the header and second photo!).
• Atlas Obscura: This travel blog has an inspiring section called Places, which highlights cities and sites from all around the world and includes a bit of background and some photographs.
• Conde Nast Traveller: I am obsessed with this site. You can browse destinations or get inspired by ‘Types of Trips’ – whatever you’re looking for, you’ll find on this site (to be referenced later on in the process too). Their travel guides are phenomenal too.
• Trip Advisor: I am a huge Trip Advisor nerd. Like huge. I swear that you can plan the most incredible vacation by reading other people’s reviews. When you’re trying to pick a city or cities, I highly recommend looking at their Top Destinations in the World listings.