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GoWithGuideFind your perfect tour guide at GoWithGuide. Relax and cherish unforgettable tours with loved ones. Create personalized tours for a truly memorable trip!

How to plan a trip: 5 Essential Steps

Naoaki Hashimoto

by GoWithGuide travel specialist:Naoaki Hashimoto

Last updated : Aug 07, 202413 min read

Travel Tips

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I managed to get a two-week vacation this year, so I decided to go on a trip with my family.

This is where the travel planning began.

Which country shall we visit? Once deciding on the country we've always wanted to go to, the first step was to book the plane tickets. Of course, there's no point in reserving hotels if we can't secure flights.

Next, we chose the areas we wanted to visit within the country. After deciding on the number of days we'd stay in each area and the order in which we'd visit the areas, we booked our hotels, planned our daily itineraries, and decided on what food we'd like to try.

This is a rough outline of my process in planning a trip. Some people enjoy planning every detail in advance, while others prefer to keep things flexible and make decisions on the go once they arrive at the destination.

While many don't dislike planning, they may often feel the burden of it because they don't want their trip to go wrong.

So, do you enjoy planning your trips? Or do you find it to be a hassle? After planning many trips, I've experienced some common mistakes that tend to be the source of frustration for many travelers...

Common Travel Mistakes

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  • Feeling like you've wasted time and money because your trip wasn't well-planned.
  • Missing out on must-see attractions.
  • Seeing other people enjoying the same itinerary much more than you.
  • Making your family feel unsafe.

To avoid these mistakes, plan an itinerary that suits you and your family, and make the most of your trip. You want your family to be happy and create the best memories of your lives.

Yes, planning is crucial to the success of your trip.

So, how exactly do you go about planning a trip? We've put together a simple overview to help you out. From picking the country to visit, to planning your daily activities, follow these five steps to create the perfect vacation.

The Travel Planning Process: 5-Step Plan

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1. Choosing The Country

How do you decide which country to visit? Are you overwhelmed by too many choices, or do you struggle to find somewhere that really excites you?
Let me share my method for finding the perfect travel destination:

Listing Countries of Interest

Begin by listing countries that come to mind based on memories from TV shows, videos, or recommendations. Don't worry about budget at this stage. Think about places you've seen and been curious about. If you love UNESCO World Heritage sites, check out their list. You can also search "recommended countries for overseas travel" on Google, consider destinations based on safety, or find relevant keywords on social media. Asking AI assistants like ChatGPT about destinations tailored to your preferences can also be helpful. Browsing through travel guidebooks at a bookstore is a classic way to find inspiration. If you have friends who are avid travelers, ask them for direct recommendations, or ask your followers/friends on your social media accounts to gather suggestions from a wide range of people. Personally, I often ask fellow travelers I meet during trips about their list of top countries they have visited to find my next destination! 

Refining by Ideal Season

Once you have a list of countries, the next step is to refine it. Check if your travel dates align with the best season to visit each country. It's best to skip the rainy season—it can make getting around tricky and spoil the scenery. Exclude destinations where the weather might hinder your enjoyment.
Also, consider if there are special seasonal attractions such as famous festivals or unique natural phenomena like the cherry blossom season in Japan. If you have the opportunity to visit a country for the first and perhaps last time, it's worth planning your trip during the best season possible.

Considering Trip Duration

Another important factor to consider is the duration of your trip.
If you're fortunate to have nearly a month for your vacation, you can likely explore all the places you desire in any country. Some countries have so many attractions that you may need more than two weeks to see everything. If you have the possibility of taking a longer holiday in the future, save that country for when you have a two-week break. For now, let's choose a country that suits the duration of your current holiday.

Trust Your Instincts When Making the Final Decision

Once you've narrowed down your options to two or three countries, trust your instincts to make the final decision. There's no one-size-fits-all answer. Think about which destination excites you the most. Remember that unforeseen events, such as pandemics or personal life changes, could impact your ability to travel in the future. Choose the country that speaks to you the most to ensure a trip filled with unforgettable experiences.

Oh, and don't forget the most important part! If you have a travel partner, make sure to discuss and decide together. It'll help avoid any future disagreements and keep the trip smooth and fun.

2. Finding and booking the best deals on flights

Once you've decided on your destination, book your flight right away. The earlier you book, the cheaper it will be. Conversely, the longer you wait, the more expensive it gets. Flight prices fluctuate based on dynamic pricing, which means they change depending on the number of available seats. When there are plenty of seats, prices are lower, and as seats fill up, prices increase.

Now, let's talk about where to buy your tickets.

Start by using comparison websites to check prices, layovers, and flight times. There are several flight comparison sites out there, so try a few and see which one you like best. My personal favorite is SkyScanner.

When selecting your flight, here are some important factors to keep in mind:

Narrowing Down with Mileage

If you're earning frequent flyer miles, choose flights within the same airline alliance. If you're not yet earning miles but travel abroad often, it's a good idea to start collecting them. The advantages of earning miles and which alliance is best are big topics I won't cover here. By the way, I collect mine with Star Alliance.

Direct or Connecting Flights

If you want to reach your destination quickly and conveniently, opt for a direct flight. The advantages of connecting flights often include lower prices compared to direct flights, and sometimes you can enjoy a stopover to explore the connecting city.

Flight Schedules

Key points to consider include:

  • Arrival Time: Avoid arriving late at night if possible, as navigating unfamiliar territories with bulky luggage in the dark isn't ideal.
  • Day or Night Travel: For long-haul flights, deciding between traveling at night or during the day is crucial, each with its own pros and cons.
  • Scenic Views: Daytime flights offer breathtaking views from the window, while nighttime flights limit visibility. Viewing landscapes from the air is a unique experience not to be missed—I always book a window seat for this reason.
  • Financial Aspect: Night flights can save on accommodation costs for that day.

Preferred Airline

Different airlines vary in amenities such as seat monitors, size, onboard entertainment, seat quality, meals, and service levels. Search "airline rankings" to gather information on these differences.

Price

When comparing similar layovers and flight schedules, price becomes a crucial factor. Once you've selected your airline and flight through comparison sites, check the airline's official website for the best prices—often the most reliable and user-friendly option. Be cautious as additional fees like seat selection may increase the final cost from the initially quoted price on comparison sites.

3. Planning Your Itinerary by Area and Day

Once you've purchased your flight tickets, your travel start and end dates are set. Manage your itinerary using Excel or a spreadsheet.

Here's an example of the actual itinerary I used when traveling to Norway:

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First, enter the dates of your vacation, from the first day to the last day, in the leftmost column.

Next, fill in the "Area" column. You can immediately enter the area where you'll arrive from your country on the first day, and the area where your return flight departs on the last day.

Now, let's add the areas you plan to visit. The goal here is to decide which areas you'll visit, how many days in each, and the order of your itinerary.

Start by listing the areas you're interested in. Similar to choosing a country, this will involve extensive online research.

Use keywords like "Top COUNTRY sightseeing spots" to list popular areas first. Learn about the main sightseeing spots in each area and decide if you want to visit them.

Once you've chosen an area you want to visit, search for terms like "AREA itinerary model course" to find out the ideal number of days to stay and the best way to explore that area. Given that you might not have another chance to visit this country, it's important to explore all the must-see spots to avoid any regrets later on. Missing out on places you wished to see during your previous visit would mean having to travel again, which could be quite expensive and inconvenient.

Also, checking the itineraries offered by travel agencies selling package tours can be very helpful. Package tours from travel agencies efficiently line up must-see spots. However, prioritizing efficiency too much might mean you end up seeing famous tourist spots only through the bus window, so it's better not to rush through them without experiencing them fully.

A common mistake is cramming too much into a day's itinerary. Planning to visit one sightseeing spot every hour limits your experience to just the basics of each place, leaving little time to stumble upon local gems or unexpected delights. Also, squeezing too much into an itinerary is more tiring than anything! I recommend planning a reasonable schedule with breaks and determining how many days you should stay.

Once you've finalized your daily itinerary, start looking for restaurants and cafés for lunch and dinner. Exploring local cuisine, including specialty dishes from the country or region, adds an extra thrill to your trip. Make reservations ahead of time for popular spots, as some places may fill up quickly. Since plans can change, always review the cancellation policy before confirming your booking.

4. Methods of Traveling Between Areas and Booking Transportation 

Once you've chosen your destinations, verify if reservations are necessary for transportation between them. For flights, booking in advance is crucial as it ensures lower costs. Traveling to minor areas may affect the itinerary time due to the limited number of flights. If seats are fully booked and reservations aren't possible, it could disrupt your itinerary significantly.

5. Booking Accommodations Economically

Once you've locked in your travel plans between places, go ahead and book your hotel in that area.

Picking a hotel can take time, especially with so many options to choose from. Certain booking sites may display "only 1 room remaining," creating a sense of urgency. Prices can vary between sites and change depending on when you search. Even if you find a good deal, rooms might fill up, so it's wise to book sooner rather than later.

With so many booking sites out there, I think the longer you take, the better deal you can secure on a hotel. But trying to find that sweet deal can really eat up your time and stress you out, right?

I’d like to share with you my method for future reference.

First, search these four sites: Booking.com, Agoda, Trip.com, and Airbnb to find the accommodation you want. Once you've narrowed down your options, compare the prices with the official website of the accommodation to see where you can get the best deal.

Honestly, hotel reservations can be quite exhausting for me. That's why I like to stick to just these four sites and skip the others.

Private Tour Guide Proposal for Itinerary Planning

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It's tough to planning a trip yourself, with so much you don't know taking up time and stress.

If your budget allows, I would recommend for you to use a professional private tour guide who lives locally. Tell the guide your needs and consider receiving suggestions for your  itinerary from a half-day tour to a multi-day tour.

Private tours guides will efficiently incorporate must-see spots and hidden gems known only to locals into your itinerary based on your needs.

Even with multiple people, you can customize a private tour entirely tailored to your needs at a price that isn't much different from, or even cheaper than, joining a one-day group tour offered by a travel company!

GoWithGuide allows you to compare and consider professional local private tour guides. You can message the guide before purchasing a tour to customize your itinerary, which is our standout feature.

You can watch the guide's introduction video, then communicate your travel needs to the guide you feel suits you best. Based on your requirements, you’ll receive a customized itinerary proposal, and if you like it, you can purchase the tour.

With major sites, it's often the case that you can't choose your guide beforehand, so you only find out who your guide is on the day of the tour. Moreover, there are situations where you can't discuss the itinerary before purchasing, leading to last-minute planning with the guide on the morning of the tour (resulting in less time for sightseeing!). This can also lead to issues where it's too late to visit the places you originally wanted to go. Even though it's a private tour, there are cases where the itinerary is fixed from the beginning and cannot be customized.

Professional guides are your partners in ensuring a great vacation. Traveling with a guide means experiencing hospitality, entertainment, cultural exchange, and authentic connections. Finding a good guide can exceed your expectations for the trip.

Why not give GoWithGuide a try and message a guide today? Before purchasing a tour, get to know the guide through their videos, reviews, and message responses. Once you find a guide you like, purchase a customized private tour. You'll eagerly look forward to meeting your guide on the day of the tour. Rest assured, your tour will either meet or exceed your expectations, ensuring a highly satisfying experience.

Now, let's start planning a vacation that will create the best memories of your life and your loved ones.

Wishing you a truly wonderful vacation ahead!

Written by Naoaki Hashimoto

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Naoaki Hashimoto is the CEO of GoWithGuide. To date, he has visited over 70 countries. Since his student days, he has wandered the world as a backpacker. For his university graduation trip, he traveled from Tokyo to Morocco using only land and sea routes, without flying. After working for ten years as a corporate employee at companies operating travel booking sites, he embarked on a nine-month journey around the world. Upon returning to Japan, he founded Travelience Inc. in 2013, which develops and operates GoWithGuide. He has also contributed articles to various travel and tourism media and has appeared on TV and radio channels in Japan.

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