The frencheetoast Guide to Trip Planning

As I've mentioned before, I am the type of traveler that will research everything. When I was younger, I tried the whole 'let's be spontaneous and figure it out as we go', but it always led to a lot of wasted time spent aimlessly wandering around or dawdling in the hotel/apartment. I know what you're probably thinking right now: you can always stumble upon something cool. But in my personal experiences, this has seldom happened, and in hindsight, I always wished that I didn't just wing it. The way that I see it is: Why leave everything up to chance when you can almost guarantee yourself a great experience? Even though it can be exhausting, I think that the time that you put into planning (and and vetting) is always well worth the investment.  This might make me sound like I'm the type of person who travels with a binder full of schedules and itineraries, but actually, it's more like a fluid list of goals that can easily be rearranged. So, this is my general process for trip planning:

1. Determine your end cap dates, and book your airfare.

2. Determine what days you want to spend in each city or region.

• How big is the city? Are there any day trips you'd want to make off of that hub? Generally, I would suggest 2-3 full days for larger or medium-sized cities and ½ to 1 day in smaller cities and villages, but this definitely depends on your personal values. I like to spend enough time somewhere that at least all the high-priority checks are checked but with maybe a few lower priority places left for the next time. Whenever I'm already in a place and suddenly have extra time to fill up, I've found that I usually do not spend it efficiently, which is great if you want to relax and just soak up the ambiance, but if you're someone like me, it's hard not to have regrets over all the could-have-dones. You can always go back if you feel like you want more time - and on your subsequent visits, you'll be better prepared for what to expect and how to plan.
• What is the travel time between destinations? Remember, trains may take longer, but they almost always pick you up and drop you off right in the city center. Airports are often around an hour commute to get to, plus you have to factor in the amount of time you need to arrive early in order to clear security.
• At this point, I don't usually book the intercity travel, but I do take a cursory glance at the travel routes and jot down travel time estimates/times of departure because it will help in some of the planning down the line.

3. Book your accommodations.

• I tend to prefer Airbnb's to hotels [non-sponsored opinion], and I think that I prefer Airbnb's where you rent out a room in someone's home. Usually this way, the place is quite clean, especially since the occupants have a personal investment in the cleanliness of the location when they're actually living there. [But of course, this is situational, and most definitely scrutinize the reviews.] These listings are also usually more cozy and amenable (like laundry, which is very important!). And the host can give great advice on things to see and do. Sometimes you might even become friends and keep in touch afterwards. 
• If you've never used Airbnb before and are starting out, I would recommend creating a profile well in advance of your departure and messaging the hosts of any places you are interested in. Message as many as possible because before you get a few reviews under your belt, some people may be hesitant to accept you. Also, it would be easier to have too many people accept early on and get to pick your top choice than to have to scramble to find a place closer to your departure, as listings start to dwindle.

4. Make restaurant reservations.

• As you can tell, I love eating, and I have a fondness for the occasional tasting menu. Even if it isn't a fine dining institution, if it's beloved by the public, there's always a chance that you won't be able to get in without a reservation. So if you're passionate about eating and don't want to just stumble into any run of the mill place - when in doubt, reserve. 

5. Start to look up what you want to do.

• Food - Even if you've already made reservations for the big meals or have a general idea of where you want to eat, what about the in-betweens? Where do you want to eat breakfast? Are there any pastry shops? Other specialty food shops like chocolate, spices, ice cream, etc.?
• Cafés - As you can tell, I generally never like to just wander in somewhere. Some countries, you can depend on pretty much any café to serve good coffee, but if you want to try specialty locations or roasters, it still might be a good idea to pre-screen. Also, you will inevitably get tired, so coffee breaks give your legs a chance to rest and give yourself a caffeine boost.
• Shopping - Every city has a street of all those big, international brands, but to me, these aren't that special. I'm not going to tell you to not go there because we may not have the same niche interests, but I will implore you to do a quick search on indie retailers, as these types of shops (a) support local businesses, (b), tend to stock more unique and hard to find items, and (c) will probably give you greater satisfaction when you find something really special and unique to bring home.
• Places of Interest - Landmarks, museums, parks, scenic viewpoints, etc.
• Calendar of Events - Each city should have a website and a tourism website that will list things like concerts, festivals, exhibitions, etc. that might coincide with your stay.
• Art - Museums, galleries, street art, etc. 

Resources

• Websites
• Print Travel Guides
• Newspapers' Travel Sections
• Pinterest - this can be a great resource for directing you to blog posts or articles on off-the-beaten-path sights and activities that you might not find in a general search
• Instagram - Using the geotag feature, you can find a broader and more up to date collection of photos of a location, which can help you get a feel for a place and determine your priority level.

6. Book travel in between cities.

• I like to wait to book this until after I get at least a tentative feel for what there is in each city in case you decide that you want to spend an extra morning in one place.

7. Finish up researching what you want to do.

• Do one final research session, finish looking at any print guides, and maybe do one last general Google search.

8. Make a list of everything you want to do in each location and vet it

• Divide your list into categories ie. Restaurants, Bars, Coffee, Pastry, Shops, Activities, etc.
• For shops, do a quick Google image or Instagram geotag search to make sure that you'll like it beyond someone else's description of it.
• If your list is overwhelmingly long, start to prioritize and maybe even cut out some places. (This is where I sometimes struggle. Be realistic. How much can you conceivably see or do, and leave your list just slightly longer than that.)

9. Move your list over into  Google Maps

• This helps you to visualize where everything you want to do is located so that you can hit up places in the same area at the same time and cut down on transit between locations. Also, if there's a sudden hitch in your plans, you can easily reference your map (which you can access on your phone), to find the next closest location (and spend less time regrouping or discussing where to go next).
   
• Create a map for each city
• Create a layer for each broad category of destination (ie. Food, Shopping, Sights)
• Add pins 
• Add opening times details for each pin (Trust me, when you arrive somewhere to find out that it's an hour before opening or you've come on the day that they're closed, it's extremely aggravating.) 

10. Take a well-deserved break (hopefully you've finished the above with enough time to take a breather before you leave)

11. In the couple days leading to your departure, organize your research in a way that you can take with you

• Make sure you have access to your Maps on your phone 
• Note any restaurant reservations in your calendar (I like to put these in the month calendar widget on my phone and set a reminder)
• Make a note to yourself of any information you might need (or don't)
• Anything last minute that you don't have the time to look over, take a screen shot or copy the link and message or email it to yourself. I will admit that lately, I've gotten complacent and I'm terrible in regards this. I'll often find a list in a guide or some links in my bookmarks that I'd meant to review earlier on. So I'll send it to myself, and when I'm at my destination, I'll look over it before bed (because I'm the type of person who has to read the entire internet both before going to sleep and upon waking). 

12. Enjoy! Have fun on your trip! Don't sweat the small things. You'll have a great time no matter how much you prepped, but hopefully if you took any of my advice, it made it that much better.