How to Plan a Trip: A Month-by-Month Guide

Posted: 4/2/2024 | April 2nd, 2024

Trip planning can be a daunting task. Flights, insurance, gear, itineraries, accommodation, and so much more all need to be considered and sorted out before you go.

It’s easy to get overwhelmed, especially when you haven’t done something like this before.

After over close to twenty years of traveling the world, I’ve planned countless trips and vacations for myself, friends, and family, even group tours. In the beginning, it was trial by fire. I learned a lot of lessons the hard way. However, that helped me develop an efficient checklist that ensures I don’t miss anything important during the trip-planning process.

One big question I get asked a lot is when to start planning. To answer that question, this post breaks the planning process down into month-by-month steps so you can plan your next trip with ease.

Here’s how to plan a trip:

12 Months Out: Decide on Your Destination(s)

A lot of people talk vaguely about travel: they never say where they are going, just that they are going. They might talk about it for years before actually departing (if they go at all). But it’s much easier to reach and plan for the goal of “I am going to Paris for two weeks this summer” than “I’m going somewhere.”

If you already have a dream destination in mind, great! If not, here are some posts to help you get started:

But, this far out, the real thing you want to do is start saving money and figuring out your costs. Accommodation and flights are the obvious ones, but how much do restaurants, attractions, and other activities cost? Knowing these costs will allow you accurately estimate how much money you’ll need. Here is how to research costs:

1. Buy a guidebook
2. Check out my free travel guides (we break down all costs for each destination)
3. Skim the cost of living on Numbeo.com
4. Google prices for major activities you want to do, such as scuba diving, winery tours, etc. (Get Your Guide is a good place to start)
5. Use Skyscanner or Google Flights for flight prices and sign up for alerts to get emails if the price changes
6. Use Discover Cars to price out (and book) a rental car if you need one
7. Use Booking.com and Hostelworld to research accommodation costs

That may seem like a lot but you just want to get a general idea of how much you need to save. You can head to this page to see all my articles on how to save money for your trip.

12 Months Out: Start Collecting Points & Miles

While you’re working to save money,