Five Steps to Make Planning a Trip Easy

One of questions I am asked the most, especially when people find out I often travel solo, is “Do you plan your own trips?” Yes! It has taken a little trial and error and I am always refining as I learn, but I have developed good method to my trip-planning madness. In the age of infinite information it is easy to get overwhelmed by the sheer amount of choices and advice and reviews out there. Decision paralysis can result and you are no closer to going on your fabulous vacation.

You have some cash set aside and some vacation time. Stop over-researching and over-planning and follow these guidelines for a low-stress experience planning a trip that will result in you having a wonderful, fun-filled, low-stress experience. Each of these guidelines could really be individual, detailed posts but this is just to get you started.

Note: Most of my travel has been within North America and Europe so this advice may not apply as well in other geographies.

Step 1. Book your flight.
Now you are committed! No backing out now. You are going on vacation!

First things first in planning a trip- getting there. I start my flight research on Google Flights. Sometimes I know when I want to go but I have not settled on a destination. Sometimes I know where I want to go but I have not settled on the timing. Google Flights gives you a lot of options to play with and you can even set up alerts for specific times and destinations. You can also specify how many connections, what cabin you prefer (I am a fan of premium economy), etc.

When it comes to booking your flight book DIRECTLY WITH THE AIRLINE! When you book through a third party site you risk a customer service nightmare if something goes wrong. You save little, if anything at all, booking through a third party vendor. Generally, to get the best price book domestic flights a month or two in advance and, for international, two to five months in advance. When you find the routing and dates you want, book it. Humming and hawing over whether the price will go up or down does little good. Typically flights are not going to get significantly cheaper as your travel date draws closer. If it is what you want and is in your budget Just. Book. It. Some airlines will do price adjustments if the fare changes but it generally is not worth it. See this nice summary here.

It is also worth noting that in Europe it can be much cheaper to fly into major city like Paris or Amsterdam and take the train or an inexpensive internal flight on a separate itinerary to get to your final destination. For example, for a trip to southern France it was significantly cheaper (to the tune of $700) to fly into Paris-CDG than Nice-NCE. I am staying a couple of days in Paris as a bonus and taking the TGV (high speed train) to the south of France.

Step 2. Book your accommodations.
Rad! I am going on vacation! Uh, where should I sleep?

This is one area where I have seen people get lost down a rabbit hole. The Ritz or Four Seasons is nice and all but you are going to be spending most of your time out exploring, so how about clean, safe, and comfortable for a reasonable price? First things first, Alice, figure out what the best neighborhoods are based on what you want to do and what vibe you are looking for. There are loads of blog posts out there for every destination. Read a few of them. Just a few. Like six, tops. Not two dozen. Scroll down a ways in your search results and give some of the smaller blogs some love too. (Hi!) You will find they are all going to tell you mostly the same thing- X is the best neighborhood for first-timers, Y is the best neighborhood for nightlife, etc. Find those areas on Google Maps and start looking at hotels. I like to narrow the options down by price-point and star rating. When I read reviews, I sort by “most recent” and see what people have to say. I look for common themes particularly about staffing, safety, and cleanliness. Close to public transit is important, too. Boutique/independent hotels, especially in Europe, are much cheaper than the large US brands we are all familiar with. I also like that I am supporting a local business.

In the US, I am a Marriott and Hyatt person because I travel for work and have status with both of these chains. I tend to stay away from VRBO and AirBnB for a multitude of reasons, the main one being a short-term rental takes housing out of the housing market for locals, contributing to housing shortages and increased rent. Oh, and I am not cleaning a house on vacation.

Step 3. Book internal transportation.
How are you getting from City A to City B if you are visiting more than one place?

In Europe:
This is for the Americans- you do not need to rent a car unless you are specifically going on a road trip or somewhere that cannot be reached by the extensive public transportation network. The trains are clean, smooth, and fast- sometimes faster than flying by the time you factor in going to the airport and getting through security. If you are not sure what would be best, look at both and do the math with the timing. Keep in mind that budget airlines have restrictions on size and weight of baggage (which is smaller and lighter than US baggage rules), so that $37 RyanAir flight might not be as cheap as you think it will be. Rome2Rio is my favorite site for researching transportation options. For long-distance train travel, you want to book your ticket as soon as you can for the best fares and seats.

In the United States:
This is for the non-Americans – the US is huge and the public transport, excepting of a few cities, is abysmal. You will need a car, especially if you are going anywhere outside a major city and definitely if you are wanting to visit any of the national parks. It takes ~16 hours to drive from San Diego at California’s southern border to the California/Oregon border in the north, for some context. Flying is usually fastest to get between big cities, unless you are somewhere between Boston and Washington DC (called the Northeast Corridor), then Amtrak is also an option.

Step 4. Doing Things.
So you are going and you have somewhere to sleep. How should you fill your time?

One mistake I see a lot of people make when planning a trip is over-scheduling themselves. You spend all your time running yourself ragged to see All The Things, but have no time to sit in a cafe or pub and soak in where you are, catch up on your travel journal, or check something out that was recommended to you by a local.

How do you like to spend your time? Do you like museums? Exploring local cuisine? Music? Shopping? Exploring nature? A boat ride? (I’m a whore for a good boat ride.) Do not feel obligated to do something just because that is what “everyone” does in your destination city. But on the other side of the coin, it is okay to do touristy things- they are popular for a reason. I research activities by reading blogs, watching vlogs, and reading travel guide books (I love Rick Steves books, personally). Once I have a good idea of what I want to do, I start filling in my itinerary…. but not too much. Rome has been around for thousands of years. If you don’t see everything, it will still be there the next time you are in the neighborhood.

The best thing to do when you get to a new destination is a walking tour! This is the perfect way to orient yourself to the city, chat with some fellow travelers, and get a few tips from the guide. One of my favorite questions to ask is if they had a friend visiting for the first time, where are they going for dinner? What do you show them?

There are loads of free and paid options for walking tours. For free tours, where the guides work on tips, Sandemans New Europe and Free Tours By Foot are fantastic. For paid tours of any kind, Viator is my go-to. I really love pub tours and food tours- they are a fun, social way to learn about the local food and drink traditions. Unless you want a guided tour of a museum, it is best to book directly through the museum website. Some popular museums, like the Louvre or the British Museum, have timed entry tickets. Book these in advance, especially if you are going at a busy time to ensure you get the ticket time you want.

Step 5. Staying Organized.
This should probably be Step 0.

In your note-taking program of choice, write out each day and what you will be doing. I use OneNote but I think I may start experimenting with Apple Notes. I include flight, train, and hotel information with booking confirmation numbers, times I have tours or any other reservations scheduled, et cetera. This gives me a bird’s eye view of what I have going on. I also copy links to relevant blog posts, tours, and anything else that may be useful to me in my planning and travel.

In your map program of choice, create a list for your destination. Mark your hotel, places you want to see, restaurants, meeting locations for tours, and places people recommend you go. Make a note about why you are saving it, especially if it something that was recommended to you.

A few more things to do when planning a trip

Check your passport expiration date! In many countries, it cannot be within 6 months of expiring. Research visa and vaccine requirements for your destination. If you are traveling to the EU, as of 2025 you are required to apply for travel authorization, called ETIAS. It costs 7€ and can take up to 96 hours for approval, but it usually takes about an hour. Click here for a list of countries and and the application.

Are you ready to start planning a trip?

By following these guidelines and not over-researching you are going to have a low-stress, fabulous vacation. Remember, have a plan but don’t overplan. You are not there to just check boxes, you are there to experience life in a different place. That is the part of travel that makes us richer- connecting with other people and cultures, not seeing one more painting of baby Jesus. Go Boldly!