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How to Plan a Trip: 10 Easy Steps for Stress-Free Travel Planning

Amy French the Roaming Historian

My day job is as a history professor. Before students read the text or attend a lecture they have far fewer questions than they do after, because they don’t know what questions to ask beforehand…you don’t know what you don’t know. The same is true for travel. How do you know what questions to ask about how to travel if you’ve never gone on (or planned) a big trip before? You don’t. This blog then is meant to provide you with easy steps to follow to plan your next trip. I think you’ll find it useful whether you’re going on your first vacation or you’re an experienced traveler.

  1. Set a budget. You will need to consider duration of the trip (if you’re traveling from the US to Europe, you want to give yourself at least a week.), where you are going, what you plan to do, how you plan to dine, souvenirs you plan to buy, the number of people in your party, transportation and accommodation level (first-class, mid-range, economy), etc.
  2. Pick a place to go.
  3. Research the location. Will you need a passport? Will you need a visa? Are vaccinations required? When is the peak tourism season? What is the weather like? Are there rules for the region you might not like? How is the food? What is the culture like? Do enough people speak your language if you only speak one?
  4. Figure out how you’re going to get there: fly, boat, train, drive…
  5. Choose where you’re going to stay: hotel/motel, inn, hostel, bed and breakfast, farm stay, vacation rental (Airbnb, VRBO, etc), resort…
  6. Think about what you are going to do there. What activities do you want to do? What attractions do you want to see? Are there museums you want to visit? Sporting events you want to attend? Theater productions or concerts? Amusement parks? What attractions do you need to book in advance? Should you book tours?
  7. Consider what you like to eat and places you will enjoy dining. If reservations are needed, make them.
  8. Investigate ways to get around once you’re there: subway, taxis, car rental, buses, ferries, on foot, etc. Some cities have passes that include tickets to big attractions and transportation which might be advantageous.
  9. Check out the weather and think about the places you will be going to and then prepare your packing list. Here are my tips with my packing list embedded in the blog for you to print out: https://roaminghistorian.com/2025/09/07/the-definitive-guide-to-packing-light/
  10. Buy a guidebook! This small expenditure can pay for itself many times over. I prefer Rick Steves books if you’re going to Europe.

Additional items to consider:

  • You may want to consult a travel agent. They are skilled professionals who can save you time, money, and stress.
  • Consider purchasing trip insurance through an independent insurance agency like American Express. Although not exactly cheap, an insurance policy can save you big bucks if you have to cancel, you lose your luggage, or something goes massively wrong. But make sure you read the fine print to know what kind of coverage you are purchasing and when it will actually cover you. Unless you bought an expensive “cancel for any reason” policy there are limitations.
  • Be wary of third-party booking sites. I use them for research, but book my plane tickets directly through the airline. I haven’t found a huge price discrepancy. If I do, I call the airline and see if they will price match. Same goes with hotels. I will occasionally book a hotel through a third-party booking site (if it is fully refundable), but I will first call the hotel and ask if they will price match the third-party site. Sometimes, they not only meet the price but throw in something extra.

I hope you find these tips helpful. They are certainly not exhaustive, so feel free to share your favorite planning ideas in the comments…I would love to hear them. Happy travels! Amy

Amy French, Ph.D., is the voice behind Roaming Historian. A professional historian and seasoned traveler, she shares stories that blend history and travel to give readers a deeper understanding of the places they explore.

Trusted Booking Resource: Booking.com

When planning a trip, it helps to compare your options in one place. Booking.com allows you to search and compare hotels, apartments, vacation rentals, flights, cruises, and car rentals worldwide, making it easier to organize the key pieces of your trip in a single platform. Travelers can review prices, amenities, guest ratings, and neighborhood locations to find accommodations that match their style and budget, and many listings offer competitive pricing, occasional deals, and flexible cancellation policies. Pro tip: when comparing places to stay, focus on guest reviews, location, and cancellation policies—these factors often matter more than the nightly price alone. Browse and compare travel options here: https://www.awin1.com/cread.php?awinmid=6776&awinaffid=1985445

Booking dot com page, hotels, flights, cruises, short term rentals

Tours, Tickets, & Experiences: Viator and Get Your Guide

If you’re planning tours, attraction tickets, or local experiences during your trip, Viator and Get Your Guide are two of the most widely used platforms for discovering and booking activities around the world. Both allow travelers to compare itineraries, prices, reviews, and ratings for thousands of experiences ranging from guided historical tours and museum tickets to day trips and unique local activities. Many listings on both platforms include free cancellation up to 24 hours in advance, which adds flexibility when travel plans change. Pro tip: because these platforms host experiences from many different tour operators, always check recent reviews and overall ratings before booking to ensure a high-quality experience.

Browse tours and experiences here:
Viator: https://www.viator.com/?pid=P00161535&mcid=42383&medium=link&medium_version=selector
GetYourGuide: https://www.getyourguide.com/?partner_id=CMSFGKK&utm_medium=online_publisher

Our Favorite Travel Insurance Site

Protect your vacation with Travel Insurance dot com. This awesome travel site provides quotes from numerous travel insurance agencies and allows you to purchase them with no added increase to you: https://www.travelinsurance.com/?utm_source=pap&a_aid=65590b3a60c44

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Traveling Soon? Trusted Tour & Travel Partners

Planning your trip? Here are our trusted travel partners — thoughtfully chosen for quality, reliability, and exceptional experiences.

We sell fabulous photographic prints from our travels on our Etsy shop! These are great for home decor or as a gift. If you see a photograph on our website that isn’t in our Etsy shop, let me know and I’ll likely be able to add it to Etsy. Disclosure: Roaming Historian may derive revenue from affiliate links and other sources, which helps offset the costs of bringing you the information we do. The blogs and reviews posted on this website are of our own opinion though.

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