10 Steps for Trip Planning

I get weirdly anxious if I can't meticulously plan my vacations. I will spend hours doing online research, reading travel guides, and journaling to make sure that once I'm on holiday, nothing takes me by surprise. Don't get me wrong, I enjoy a little spontaneity while I'm on my trip. Planning doesn't mean I give myself a second-by-second itinerary that I plan to a T. It just means that I like to make the proper preparations ahead of time so that I can relax and enjoy my time away, instead of being holed up in my hotel room trying to hook up to unreliable wifi to solve a problem I could have avoided if I'd just planned ahead. It might sound paranoid, but I just like to avoid disaster, e.g. getting hopelessly lost or ending up in a foreign jail because I was unaware of the local customs.

I wanted to put my neuroses to good use and share my steps for trip planning.
This isn't necessarily everyone's cup of tea because v. few people are as insane as I am (as you may glean from the sheer amount of text I managed to pump out below). However, hopefully, there will be a tip or two in here that will be helpful.

Step 1: Budget
Money is obviously an important for being able travel. I like to do several trips every year (as is evidenced by this blog). I always plan one or two trips with my family and then one or two with friends. To be able to afford all of these trips, I make sure I save up my money and divvy it up well to make all of the trips happen. I previously shared a post on how to travel affordably where I explained what I do to save money and how I book my holidays in a frugal manner.

Before I book anything, I set a hard number that I don't want to exceed and do my best to stick to it. If I do exceed my budget, I'll cut back elsewhere (usually I'll stop clothes shopping and dining out) to make up for it. The number one rule in my (financial) life is, "Don't spend what you don't have." I've never been in credit card debt and I don't plan on ever being in credit card debt.

Once I have my full budget in mind, I like to break up that hard number into categories. In general, I devote 30% on transportation (flights/trains/buses), 30% to lodging, 15% to food, 15% to tourism (e.g. museum tickets), 5% on souvenirs, and 5% as emergency money (for unforeseen circumstances, e.g. replacing a broken umbrella). Obviously, if I find a really good deal on flights, I can divvy a little more money to food or lodging. And if there's any money leftover, it goes right back into my travel fund.

The breakdown above is just my preference; everyone should tailor their spending to their preferences. I don't devote much money to souvenirs because for me, the souvenir is being on holiday. I like to collect experiences instead of trinkets. And I devote a lot to food because I love food. Obviously, if you aren't really into food and you prefer buying souvenirs, you can flip flop the percentages. Do what works for you.

Lastly, I jot down the costs for everything I spend prior to and during the trip (in my journal) because keeping records is the key to sticking to a budget. I also like to flag all of the confirmation emails with a 'holiday' tag and a 'shop' tag so that I can look them up if necessary.

Step 2: Choose a Destination

Sometimes I have a destination in mind. Other times, I just browse flight costs and pick something cheap. And if I'm headed somewhere hub-ish, I'll pick a handful of other cities to make up a multi-city trip.

Kayak's 'Explore' option is great way to get some inspiration.

Multi-city trips are great because you get to see more and get a little more "bang for your buck" and knock a few cities off your bucket list in one go. If I'm traveling in Europe, I like to use Ryanair and Easyjet to see what my options are but otherwise, I just google to see what cheap commuter flights are available in the area. I'm usually 100% flexible about the other cities so I'll just see what routes are possible (because they're limited) and narrow them down by which cities are an appropriate combination of interesting and affordable and I'll just book what works. I also peruse the available routes for traveling by train and by bus. If you're curious about something, just do a web search. It's amazing how many articles have been written by travelers for the most amazing trips and you can learn a lot from someone else's experiences.

Choosing the destination is the definitely the most important step and it should be approached with some caution. Even if you manage to snag a great deal on flights, you also have to consider whether the city you're heading to has a high cost of living, which would mean you'd have to allot more money for lodging and food and shopping. It could also work the opposite way. You might have to fork over quite a bit for your flight but if the cost of living is low in your destination, you'll be able to book a cheap (but great) hotel and spend just a little for tons of delicious food. Just think things through.

And, when I'm planning a multi-city trip, I like to mark up all the possibilities on a calendar. I do my best to make sure I'm leaving an appropriate amount of time in each location, that the available transportation fits into the schedule, and that when it comes time to book everything, I have it all laid out so I can avoid any (costly) mistakes.

Step 3: Plan and Book the Transportation
I like to do a little research and try and find the best deal for the flight/train/bus and choose a time frame that's reasonable and affordable. For example, flying Tuesdays and Saturdays can be cheaper. I've also read that flights are cheapest on Sundays (meaning flights should be booked on Sundays). Traveling in the off-season is also a great way to save money. If it's a place that monsoons in the low-season, I'd say avoid. But if the chance of rain only increases by 10%, then head over because honestly, even in the high season, rain is a possibility, right? Oh, and whenever I'm booking a flight, I check Seat Guru to make sure that I'm not picking a crappy seat that doesn't recline. If I'm doing a road trip, I make sure to figure out how much gas will cost.

It's also important to book early. Yes, it's a bummer to see flight costs go down after you've already booked (though if you register with Yapta, you can sometimes get some money back). However, it's so much worse to not book a trip and then watch the flight costs get more expensive. What's my reasoning? Well, if you're booking a flight, you obviously think the cost is reasonable and it fits into your budget. If you haven't booked yet and the flight just keeps getting pricier, it means you have to adjust the rest of your budget to accommodate a more expensive flight. And, lately, those last minute cheap flights that people used to score are no longer as common. The airline industry suffered some bankruptcies and several mergers in the past decade. The market is smaller so there's less competition, fuel is more expensive so base ticket prices are higher, and the taxes and fees are overwhelming these days. So, booking early is key to getting the cheapest ticket possible. This applies to train tickets and bus tickets with variable pricing also.

If necessary (and possible), I will also book the inter-city travel soon after I've booked my main transportation. Most of the time, I have no idea what my other destinations will be until I've had time to do some research, which can take weeks. However, because the inter-city travel usually involves smaller discount airlines or first come, first serve train rides, booking early is a smart move. It's almost guaranteed to be cheaper, the earlier you book it, and you want to make sure you're getting a seat before all of the spots book up.

And one minor detail to give some consideration to is the departure and arrival times of your transportation. If your budget relies on cheap public transportation, don't take an early morning or late evening flight that requires you to get to the airport during a time when public transit isn't even running.

Step 4: Book the Lodging

If I'm visiting a city where I have friends or family, then the lodging is free! And in those circumstances, my budget is significantly less but I devote some money to treating my hosts to several lovely meals. But free lodging is a rarity and for the majority of my trips, I need to book a hotel. I like to use TripAdvisor to find a hotel with great ratings and I map it to make sure it's centrally located. Then, I do some research to make sure I'm getting the best deal. I compare hotel booking sites as well as the actual hotel site (if there's one available) and book the cheapest option. I also dig around to make sure there aren't any hidden costs.

And, I always take into consideration that there may be some additional fees or taxes that may be required upon checking out. For example, at beach hotels, there are often resort fees for beach chairs and umbrellas (even if you don't use them). And at European hotels, I've often had to pay a city tax at the front desk, even if I've already paid for my room through a hotel booking site. I don't know why it isn't built into the room fee. Hey, I don't run the hotels so don't ask me.

Choosing a hotel is really up to personal preference. Sometimes, I see hotels with beds made with those dated floral-printed quilts and it skeeves me out. But, if the hotel has a great view or an amazing location, I can get over the quilts. For some people, it's worth it to book a cheaper hotel that's not centrally located. For me, I think the time wasted getting into the city center isn't worth the savings and I prefer a hotel that's smack dab in the middle of the action. Weigh your options against your preferences and choose a hotel that's right for you.

Oh, and once the hotels are booked, call or email the hotel to confirm your reservations. There's nothing worse than arriving at a hotel only to find out they don't have your reservation on file.

Step 5: Figure out Public Transportation
Once I have all of the major stuff booked, I like to figure out how I'm going to get around the city. I like to plan ahead and make sure I know how to get from the airport/train station/bus station into the city center and to the hotel. There's nothing worse than wasting time because you're meandering around, unsure of how to get where you need to be.

Then, I try and figure out what modes of transportation I'll use to visit all of the sites, whether it's a metro or tram or bus. And then, I like to find out the costs for the tickets and if there are day passes, multi-ticket packs, and where to buy the tickets. Sometimes it's obvious: buy the tickets at the station. But that isn't always the case. Sometimes, tickets are only sold at certain stops and sometimes, tickets are also available at tobacco shops and newsstands, which can be better because you can interact with an actual human who may help you.

It's also a good idea to get a feel for how the transit systems work. Some systems require you to keep your tickets so you can insert them into the turnstiles as you leave (like in London). If you don't have your ticket (because you threw it out, not knowing any better) you have to pay a fine. Some systems have free transfers; some do not. If you need to transfer and need to pay for that transfer, it's better to know ahead of time and have enough tickets or tokens or what have you, to complete your ride.

Another recent obsession is biking! I've always loved biking and now that cities have public bike shares, it's an amazing way to get around a city. It's faster than walking but more intimate than metros and buses.

Oh, and as a backup, I like to get an idea of the taxi rates because you never know if you'll need one and it's better to have an idea of how much it'll cost so you won't be surprised.

Step 6: Make Restaurant Reservations

Food is extremely important to me. So, I like to plan my meals ahead of time. I look up restaurant reviews (via Yelp, if it's available, or TripAdvisor) and make sure to choose only the best eateries and if possible, I'll make reservations. If I'm going abroad, it's great to be able to use Skype, connected to my wifi, from the comfort of my own home. Or, if emailing the restaurant or booking online is an option, I'll do that. Most of the time, if it's a popular foodie destination (like France), restaurants can book up several weeks in advance so it's a good idea to set up the reservations as early as you can.

I only make restaurant reservations for dinner. For breakfast and lunch, I like to pick a handful of good, cheap eateries. I'll make a list and map them out. Then, while I'm out and about, exploring the city and hunger hits, I'll just pull up my map and see which eatery is nearby and head over. It's stress-reducing for me to know that I'm going to a place that's well-reviewed and won't be a waste of money.

Step 7: List the Must-See Sites & Make a Rough Itinerary
Some destinations are extremely well-known and there are iconic spots that are common knowledge. For example, most people heading to Paris know that they're going to visit the Eiffel Tower, Arc de Triomphe, and the Louvre. London visitors head to Big Ben, Buckingham Palace, and Harrods. Manhattan tourists hit up the Empire State Building, Rockefeller Center, and the Statue of Liberty. Those are the obvious landmarks for those destinations, right?

Wherever I'm going, I make a list of the sites that I really want to visit. If it's a city I've visited previously, I may omit some of the spots I've been to before and only go to my absolute favorites.

When I'm going to well-known destinations, I like to do a web search for underrated sites or hidden gems. When I went to Paris last year, we went to Le Mur de Je T'Aime (which is popular but not super well-known) and Coulee Vert. It was nice to visit bits of Paris that weren't overrun by people and experience life more like a local.

When I go to lesser known, small towns, I have to do a web search to find out what the must-see spots are, as well as the hidden gems (though sometimes the must-see spots are also hidden gems because so few people know about them, at least in the context of tourism). There are several instances where I booked a trip to a place I knew almost nothing about. Istanbul, Belize, and Lyon are three instances where I didn't have much knowledge of the destination and had to rely on the internet to help me plan the trip. And for the upcoming Italy trip, we're going to some cities I'd never even heard of until I booked the trip, so I've had to (and have to) do lots of research.

Once I've got a good list of sites, I map them out (I use the My Maps feature on Google Maps). This way, I can look at the layout and then I can better plan an itinerary by looking at which sites are grouped near each other. Efficiency is really important, especially if you don't have a lot of time to spend in each city. The map also comes in super handy once I'm actually on holiday because I can whip out my phone and navigate without having to deal with a cumbersome paper map (even though a paper map is a great backup).

Oh, and while you're researching, look up the sites with admission fees and find out if there's a discount for booking online or booking early (which often allows you to cut the long lines) or package deals for several sites. Try and find a promo code too, if you can.

Step 8: Learn about the Local Culture

Learning about the local culture isn't quite as important if I'm just going somewhere nearby, but even then, sometimes local customs can be weird. For example, in the US, there are several different regional terms for a carbonated beverage. Cola, soda, pop, coke - yeah, in Florida, for some reason, the generic word for a carbonated beverage is "coke."

Learning about the local culture is super important if I'm going abroad. I like to familiarize myself with the local dress (so that I don't stick out like a sore thumb) and I try and learn a bit of the language. Even if I can't nail down enough to form full sentences, I try and make sure to learn the important keywords: hello, goodbye, thank you, excuse me, that (great for pointing at stuff you want), please, help, how much, yes, and no are my top ten.

Step 9: Figure out Currency
This one doesn't really apply to local travel. But, when I'm going abroad, I like to familiarize myself with the local currency, lest I get ripped off by some scoundrel who tries to slip me the wrong change. I also like to learn about the tipping customs. In some countries, tipping is unnecessary and considered rude. In others, tipping is completely necessary.

I also like to exchange money ahead of time. I just go to my bank (Chase) where I can get money exchanged for a fair rate and without a commission.

And, I set up travel notifications on my credit cards and debit card to make sure I don't get locked out while I'm traveling. Even if I'm going somewhere in the US, I let my bank know because I've had some issues with stores declining my card even when I've just gone up to Boston.

Step 10: Make a Packing List
The last step is to figure out what I need to pack for the trip. I look up the averaged weather patterns for the timeframe in which I'm visiting and make a tentative list. Then, when it gets closer to the actual date of the trip, I look up the actual weather and do a bit of refining. I have a generic list of items I like to work off of when I'm planning.

After all of that planning, go on the trip and enjoy. The planning should make for stress-free smooth sailing.

Oh, and all of that stuff listed above? The information I collect all goes into a travel journal. I like to do my brainstorming, planning, and actual travel documenting in the same journal. It's great because I can write down my hotel confirmations, clip in my boarding passes, and jot down all of that important stuff and refer to it as necessary. It's a great resource during the trip and then it's so much fun to read about my trips afterwards. I think Italy might be the last trip I'll be able to add to the journal; I started this journal in 2010 and have thirteen trips documented already. I'm already excited to start a new one!

Cheers and happy planning!