I’m in the midst of simultaneously planning three trips right now–New York this week, Italy in July and Peru in November–and I’m going a little nuts. Some of them are obviously more urgent than others but all are equally important. I almost never buy a guide book and instead, can probably write my own by the time I am done dissecting and visiting any one destination. Honestly, it’s exhausting work but it’s also exhilarating and makes me anticipate my trip even more. While I’m drowning in Google maps, magazine articles, blog posts and hotel and restaurant reservations, I thought it might be nice to share tips about how I go about planning a trip.

1 – Ask questions

After you’ve decided where you want to go, ask your social media circle (like I do) or close friends and family members to see if anyone you know has been to your destination and if they have any tips that you would only get from someone who has been there before. These can include things like what to bring with you on the trip to a little, out of the way hotel or restaurant only locals know about.

2 – Do your research

I spend a lot of time (and I mean A LOT of time) researching where I’m going and especially were I’m going to eat once I get there. I read magazine articles and blog posts, research Pinterest boards, Instagram feeds and anything I can get my hands on about my destination. I cross reference sources to make sure the places I spot are good. If restaurants, hotels or must see things keep being mentioned, then I know I’m onto something. I usually don’t have a lot of time in any one place so I really don’t want to waste my meal or my night on an average or bad restaurant or hotel. If my trip is a few months away, I bookmark anything I happen to come across about my destination in order to read it when I’m ready to start planning. If you’re going to an exotic or out-of-the-ordinary destination, don’t forget to research any vaccines or paperwork you may need to get before you leave.

2- Google is your friend

Google Maps:

I use Google maps extensively when I plan a trip. I create my own map and place all the spots I want to visit directly on the map. I can create several layers for different items like restaurants, places to visit, directions, etc. I can also use different symbols and colours to differentiate them and for a quick visual reference. As an example, check out the Portland, Oregon map I created where the red dots are cafés, yellow stars are pastry shops, green dots are places to visit, etc. I can also add notes for every item I place. These include where I found this item, who’s recommending it and why. These maps are easy to refer to on my mobile devices and great tools to assess what’s around me when visiting a destination.

Google Docs (similar to Word):

What I look for when I travel is mobile access to my travel notes and Google Drive provides me with that since that’s where you’ll find your Google maps, your Google docs and your Google sheets. I create a Google Docs where I make lists of places I’d like to visit, I take notes, I plan road trip, restaurant recommendations, etc. It is basically a custom-made guide I build for myself containing information that interests me.

Google Sheets (similar to Excel):

I am currently planning a road trip through Puglia in Italy and Google Sheets is coming in very handy. I have my whole trip planned day by day with columns set up for dates, places to visit, restaurants, hotels, distances, scheduled departures and arrivals at any one stop, etc.

3 – Double up on your meals

Too many restaurants, cafés or pastry shops to visit and not enough time? Do as I do and double up on meals! I’ll sometimes have a drink and an apéritif in one spot and a main meal in another. Or I might spend the day snacking at several spots so I can try a few. Or I might have two breakfasts, or two lunches, or a snack and a lunch or a cheese tasting followed by a gelato one. You get the gist of this, right? I eat a lot when I travel, but only so I can report back to you with my recommendations 🙂

4 – Ask the locals

Don’t plan every single minute of every day. Leave room for spontaneity and when you haven’t researched a place for a restaurant or places to visit, or if you diverge from your planned route, ask the locals about the best spots to grab lunch, a show or a swim. After all, they are the experts when it comes to their hometown.

5 – Trip It!

I have been using the Trip It app for a couple of years now and I really love it and rely on it. It stores all my reservation info with one easy click. Once my plane ticket is booked or my accommodation, restaurant or show reservations are made, I forward my confirmation emails to Trip It and they automatically get added to my trip. I can also share the trip with fellow travellers, which is a great option if you’re not the only one making reservations since these will get added automatically no matter who does the booking. It also brings me great satisfaction to look at my Trip It and see all my lined-up trips.