How to Make Planning Epic Itineraries Easy

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The more trips I go on, the better I’m getting at figuring out how to create the perfect travel itinerary for me. While I like having a bit of free time to just explore a new place, it pays to have some interesting things planned out ahead of time to make sure you’re making the most of your experience. This post will walk you through how I plan an epic travel itinerary, complete with food options, driving routes, and helpful resources to stay organized so that you don’t experience things like this (all of which I learned from experience):

• You ended up in a less exciting area of town eating pizza because you wandered into a residential area around dinnertime and couldn’t find a better option.
• You wanted to try a new restaurant but you didn’t realize you needed a reservation.
• You didn’t know that the parking lot at an attraction gets full before noon and you’ll be waiting or walking from farther away to get there.

Preventing these things take some level of planning. I certainly do not plan every aspect of every trip down to the letter, but I am a project manager by trade and tracking all the little things is what I’m trained to do. Luckily for you, I’m going to share how I’m planning epic itineraries with an example from my upcoming trip to Denver, Colorado.

Step 1: Deciding Where You’re Going

If you ask me where I want to go on my next trip, my response is usually “anywhere”. Ok, so maybe there are some places that rank higher on the list than others, but I love visiting new places and exploring new terrain and cultures. It may sound silly to include this as part of your itinerary planning, but sometimes its one of the hardest things for me. If you aren’t traveling for a specific obligation, (i.e. wedding) where you go depends a lot on your budget, the time of year, the length of your trip, and what types of things you’d like to do.

Sometimes my travel is even completely impromptu if I can’t pass up a good deal. This trip to Denver actually happened because Frontier Airlines was having a promotion for their new direct route from my local airport to Denver. If anyone lives near a small regional airport, you know how difficult it can be to find direct flights anywhere. My boyfriend and I had no intention of visiting Colorado this year, but for $250 round trip for 2 people it was hard to resist! We made the decision to book the tickets in 48 hours and now I think it will be my favorite trip of the year. If you can find a good deal I say go for it, even if you don’t have a specific reason for visiting. You never know what you might find!

However, if I’m looking for inspiration on specific places I’d like to visit, my first stop is typically Pinterest or Instagram. Pictures make for some of the best wanderlust inspiration. If you’re looking for a cheaper all-inclusive, Groupon is great as well, but I’m not one for cookie cutter tours as much. I’d rather explore and plan my own itineraries. So once you pick a location, it’s time for some itinerary planning sessions!

2. Researching Your Destination

One of the first things I always consider is how much I’m looking to spend on the trip. I want to have a good time and really experience a place, but I also don’t want to unnecessarily spend a lot of extra funds on vacation. It’s so easy to say “I’m on vacation, I’m going to treat myself” and that’s completely ok! Just make sure you plan that extra spending money out ahead of time and give your budget some wiggle room. Once that’s set you can start picking places to stay and things to do.

First Things First: Your Epic Itinerary Doesn’t Have to Be Packed

Some of my best advice is don’t overplan and try to cram too many activities into your days. You’re on vacation to relax and explore after all! You’ll notice in my itineraries that I have something planned for each day, but it’s never centered around a specific time or location unless it’s necessary (like a reservation / tour time slot). I have restaurants or bars I would like to visit but I don’t actually plan where I’ll go for each meal.

Tripadvisor

You may recognize several of the tools I’m suggesting from my useful travel apps list. Tripadvisor is one of them. I almost always use Tripadvisor to look for things to do in the area. But did you know that Tripadvisor also has forums for travelers to ask questions and share advice?

I found a couple of great forums for traveling in Rocky Mountain National Park with experts that live in the area to answer some basic questions. One of the forum questions on there basically helped me plan where I wanted to stop in the park! Half my planning for that day was done for me! Locals can also give you tips about which roads to take. The forum gave me a heads up that we would want to avoid a particular road in the rental car because it’s a toll road, and provided instructions to get to the scenic byway that is a bit longer than a GPS might take you, but has way better views. This is the type of information you want to get from people directly, instead of tourist sites.

Blogs

If you’re here, it probably means you are familiar with searching travel blogs for information to plan your trips. Checking out what my favorite bloggers have posted about a place often carries more weight than a random person reviewing a restaurant on Yelp and they’ve typically done their research when they visit an area. Visiting a new place as a travel blogger you see things differently and make notes of it.

Referrals from Friends / Coworkers

My last method for planning itineraries comes from my friends and coworkers who have previously visited the location I’m going. This especially works out great for day trips, like a Mexican food recommendation in Montreal from one of my coworkers that was one of the best meals I’ve ever eaten. It’s always better in my opinion to take suggestions from someone you know and who knows your preferences!

Location, Location, Location

Once I know what types of things I’d like to do and check out some recommendations, I start looking for accommodations in that area. This cuts down on transportation needs during your trip and gives you more time to enjoy the area. You’ll thank yourself when you book a hotel close to the airport for your early Monday morning flight instead of being stuck in traffic in the city. The one exception I make to this rule is that if it is much cheaper to stay on the outskirts of the city, I may decide it’s worth the extra trip into town.

Food & Beverages

Once I’m finished picking a location, the next step is to find places to eat and drink. Since my boyfriend and I love craft beer, we always try to look for some local breweries or wine tasting opportunities. With Denver, I’m actually planning a DIY craft beer tour with several breweries I found with a quick Google maps search since there are multiple in the same general area. Tripadvisor and Yelp are also great for searching great places to eat, along with websites like Eater.

Read: How to Use a PTO Calculator for Vacation Planning

3. Booking Your Trip

In a previous post I wrote about how to choose an airport to fly out of for your next trip. In the case of our Denver trip this was quite easy to plan out since the flight deal was for our particular airport, but in most cases I do a lot of research on times, locations, and pricing before I pick a flight.

In general, I typically book flights first, then accommodations, then transportation (like a rental car), and lastly any tours or attraction tickets we may need. I personally like using sites like Expedia along with a rebate service like Swagbucks to get some cash back on my bookings. For the trip I took to New York City a few weeks ago, I ended up getting over $100 in cashback just from my hotel room that I turned into an Amazon gift card!

Another method I use to save some money is through my credit card’s travel rewards program. Much has been written about the best credit card reward programs, but having only one main card I can’t comment on anything but the one I own: Chase Sapphire Preferred. Chase Sapphire Preferred gives you 2% cashback on any dining or travel you do (which are what I spend a large portion of my discretionary money on) and if you purchase something through their travel booking service you get 1.25x the points. So if their 50,000 point bonus for sign-up is worth $500, you can actually buy up to $625 worth of trip with those points. I particularly like to use these points for rental cars or hotel rooms.

4. Tying it All Together With Helpful Tools

Downloadable Itinerary Planner

Once I get a bunch of ideas together on what I want to do and make all my bookings, I try to lay it out more visually in an itinerary planner, that way I have all of the information I need whether it’s an address to plug something into my GPS or the name of a restaurant to try. The itinerary is definitely subject to change at any time during my trip based on anything from the weather to what type of cuisine I’m craving. My itinerary planner looks something like this:

If you’d like to use my itinerary planner for planning your trips, feel free to download!

Google Maps Creation

My new favorite thing though has to be creating personalized Google maps with all the locations pinpointed on them prior to the trip. I’m absolutely terrible with directions so having a map that I can pull up (or screenshot for when there isn’t service) with locations on it is super helpful. Unfortunately, they won’t actually provide you driving directions, but it can be super helpful for you to tag that cool Mexican restaurant near your hotel that looks delicious, or that little museum downtown you want to stop at. Check out my Denver Itinerary Map for an example of the route I picked from our hotel up to Rocky Mountain National Park and some of the things I’d like to stop and see there.

While I’m searching the map to add pins to each of the locations I’m interested in, it helps me see where everything is in relation to each other and helps me find unexpected spots I may want to stop at along the way. This is another great way to add items to your itinerary and a little detour can be such a fun part of your travels that you otherwise may never have known was there.

5. After You’ve Booked Everything for Your Itinerary

In today’s digital age, sometimes it doesn’t make sense to print out all of your travel confirmations, but it’s something I still like to do to keep myself organized and ensure I have all the right information. I also make sure I have all of my information in my helpful apps like my flight reservations. Most of the time I never really need it, but I like knowing I have all my tickets and information in one place.

If you are planning to go abroad, there are some additional steps you should take to prepare for an international trip, like packing power converters, checking for any necessary immunizations, or check any visa requirements for visiting the country.

6. Enjoy Your Epic Itinerary Customized for You!

Congratulations, you’re all done planning! Now you can enjoy the fruits of your labor with an amazing trip tailored perfectly for you. Everyone is looking for different things out of a trip, and while it’s great to take suggestions and hear from others, not everyone’s experience needs to be the same. Planning your own itinerary like this is perfect no matter what your goals are and who you’re traveling with. To check out how my trip went, see some of my posts about Colorado!

If you found this post helpful in planning your trip, let me know in the comments!

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