How To: Plan a Trip Itinerary

I've booked two semi-spontaneous trips that are coming up in the next few weeks (New Orleans and Grand Cayman Island). A few friends were impressed when I told them that I just jumped at the cheap flights when I had the chance and then figured everything else out afterwards, all without the help of a travel agent.

After being hounded for tips and answering many questions that began with, "But how...?" I thought it would be nice to share some of my tips for planning a trip itinerary. There are some general tips mixed in with some pretty specific tips. The advice I'm sharing is targeted towards anyone who wants to book and plan a trip on their own (sorry travel agents, but we don't need your help) and of course, help you figure out where you want to go and what you want to do when you get there.
As I've mentioned countless times before, I enjoy planning so I find this is one of the most enjoyable parts of vacationing. I find it especially rewarding because planning beforehand makes the actually holiday a breeze and I enjoy myself so much more.

Holiday itineraries start with where you're going, the duration, and the cost.

GOALS. It all starts with where you're going and to figure that out, you want to figure out the goal of the trip. Is this a beach vacation? Is this a city exploration holiday? Is this a skiing holiday? How much do you want to spend? The theme of the trip and the budget need to be decided before you can plan an itinerary. If you don't know where you want to go or what you want to do, you can try spinning a globe and letting your finger land randomly and figure it out from there. If all I have is a budget and a general idea of what I want to do, I love Kayak Explore tab for a visual map and Google Explore and Skyscanner for finding whatever flights work. Or, I like to peruse Instagram and find out what my favorite bloggers are doing and if I find those destinations interesting enough to visit. Pinterest is a great resource for travel inspiration, especially because of the visual component but also because you can type "best snorkeling" and come up a variety of pins to browse through and get excited about.
WEATHER. Consider the weather and season before you book. I don't do well in cold weather. I'm not great in heat either. But I know that I'd rather sweat than shiver. So, I'm okay with visiting a warm destination even in summer but I'm not really keen on heading anywhere chilly if it's already snowing at home and I book accordingly. And before I book anything, I do a little research on the typical expected weather of the destination so that I don't end up booking a trip during a notorious bad weather season like monsoon or hurricane season. Plus, knowing the weather will also help you know how and what to pack.

OFF SEASON TRIPS. Booking in the off season can be a great way to save money. However, some towns will shut down entirely in the off season. For example, Parisians make a mass exodus in August to go on their summer holidays and that means a lot of shops are closed up for the month. If you're into that emptiness, then by all means, go for it. But, more than likely, it's something to avoid, especially if you're keen on patronizing smaller family-owned business and restaurants. (I doubt that the major retailers on Champs-Elysees shut down for holiday.) Shoulder season (a month prior or a month after the high season) is a safer bet. The rates will be cheaper but you'll likely have a v. similar experience to someone who's visiting right in the middle of high season.
MAJOR EVENTS. Find out if there's anything cool going on in nearby towns for your proposed timeline, like festivals or holidays or town celebrations, basically anything that will give your trip a lovely highlight and/or make your trip a little more expensive. If you go to New Orleans during Mardi Gras, you're bound to pay a little more for your flight and your lodging; this might be a deal breaker or the event may be awesome enough that it will be worth it.

MULTI-CITY TRIPS. Once you pick a destination city, you might also consider visiting neighboring and/or easily accessible towns. I like multi-city trips when I'm doing a longer flight and want to milk it for all its worth. Last year, I flew into Paris but also did Lyon, Annecy, and NiceThis year, I flew into Milan and also went to Cinque Terre, Genoa, Alberobello, and Polignano A Mare. One reason that I like multi-city trips is that I love adding to the list of cities I've visited, which is maybe a vain reason but it's true. Really though, it's nice to experience a few days in each city because I'm never bored. Plus, I use trips like this to do a little preliminary research. If I really fall in love with a city, then I make plans to go back.
ROUTE PLANNING. Always be practical and choose a route that makes sense. For a multi-city trip, don't jump north, south, and then back north again. Minimizing time spent on trains, planes, and buses maximizes the time spent exploring the destination. Also, weigh the cost savings of flying to a dinky airport farther from the city center versus the time savings of flying to a major airport with easy access to the city. Plan out the route on a map and calendar simultaneously to imagine the most practical plan and to block out the dates.
ANTICIPATING DELAYS. If you are planning a multi-city trip or the route to your destination requires a layover and/or multiple modes of transportation, make sure to factor in some buffer time. Don't pick a flight where the layover is 30 minutes in a gigantic airport. Don't book a train that departs 20 minutes after you land in a different country where you will have to wait in an immigrations line. And don't assume everything will go perfectly. There's always the looming possibility of missed trains, flight delays, weather events, etc. Relax and make sure that your schedule is flexible enough that a delay here and there won't curtail the entire trip.

NOT OVERDOING IT. Know your limits and be realistic. When you're planning a trip, you're likely to be under the impression that you can do everything because the excitement can cloud your judgment. Realistically, you won't be able to because jet lag, time differences, culture shock; these are energy zappers that will make your feet heavy and your eyelids droopy. Don't try and pack 20 cities into 10 days. Give yourself a little time in each destination. Don't waste an experience by trying to check off a bucket list. Enjoy where you are and what you're experiencing and give yourself time to do that. Don't let yourself get burnt out; it is a vacation, after all.

Itineraries need to be planned for specific city and day-to-day exploring too.

TAKE SOME HELP FROM THE EXPERTS. If you're not keen on making your own itinerary, hop online because there are plenty of free guides with 24-hour, 48-hour, and 72-hour itineraries that you can use. And don't feel like you have to follow them to a T either; cross out things you don't care about and add in things you like.
MAKE A LIST. If you're making your own itinerary, make a list of activities and must-see sites (which I tend to find on trusted travel blogs, through Pinterest, Instagram, or just plain old internet research). It's such a waste of precious time to arrive somewhere only to resort to sitting in the hotel, figuring out what to see and do. If you've planned the trip, it's likely that you'll at least have an idea of what the cool monuments and museums are but it's also likely that your list will consist of just two or three (cliche) ideas. Have a long-ish list of ideas that you can choose from once you arrive. Choosing is much better than sitting-in-a-hotel-researching.

PRIORITIZE. You're never going to be able to see everything so once you've made your list, pick your top sites and activities and prioritize those. If there's still time, you can see the lesser ranked sites.

MAP IT. When you're making a list of your must-see sites, map them out. I love the My Maps feature on Google for mapping my holidays (and you might've noticed that I frequently embed my site-studded maps onto my travel posts - and stay tuned because I'll be sharing a post with how I make my own travel maps soon). Whilst you're away, be practical and plan your day's activities in a prudent route. As I mentioned with the big picture route planning, don't head to the north of the city, then to the south, and back north again. Visit adjacent sites before wandering out of a neighborhood. Mapping out the sites and looking at them beforehand will help you get a sense of the city and help prevent you from doubling back to see something you missed.
USE A CALENDAR TO HELP YOU SCHEDULE. If you're as into food as I am, you'll want to figure out where you want to eat even before you arrive. It's super easy to plan out your meals on a calendar and to write down any reservations you've made. It's also v. helpful to jot down your activities and write in any tours you've booked. I like to do a rough draft on a scrap piece of paper and then I copy down the final choices into my travel notebook.
A photo posted by ra¢h 💋 (@racheerachh) on

BE FLEXIBLE. Don't get too attached to your daily itinerary and have a backup plan. You never know what might happen so always have an alternate plan in case of a weather event or cancellations or whatever the travel gods throw at you. And leave a little room for spontaneity. It's unnecessary to plan everything down to the smallest detail. If you have to follow a strict schedule, then you might have a hard time enjoying yourself because your eyes are glued to your watch; that is not a vacation, that is work. If you're like me, you'll want to have your list that I mentioned above so that you're never wasting time looking for stuff to do but you should also ask the locals for suggestions, leave time to wander around and get lost, and give yourself the ability to have some fun.

THE EARLY BIRD GETS THE WORM. Schedule any tours and excursions (if that's part of your plan) and book them way ahead of time, especially if it's a popular activity because you avoid the risk of spots selling out (e.g. visiting The Last Supper in Milan requires purchasing a ticket months in advance). Plus, some companies will offer early bird discounts so you might save some money. And, if you're visiting a site that requires an admission ticket, check to see if you can buy tickets online. Sometimes there's a discount for buying tickets online - especially if it's a multi-pack type of ticket that gets you into several places - and you can skip the line when you get there.
Give your loved ones copies of your (tentative/rough) itineraries. It's a "just in case" measure, especially if you won't be reachable by telephone. You never know.

Go forth and enjoy your well-organized and perfectly executed holidays!