How To Book An Upcoming Trip

Posted July 25, 2022 in Engineering Around Travel - Last updated November 9, 2023


You’ve planned out your trip, but now it is time to start thinking about how to book an upcoming trip. Your plan this far will help ensure you can reserve and book the segments of your trip accordingly. If you book far enough, you can save quite a bit on the costs! The plan will give you the primary outline of what you must account for in your booking. Booking can be a painful process, making some resort to pre-booked packages. From group tours and one-click buy packages to assisted help booking, such as travel agents. This process is painful, but there is help. Let’s explore more on how to book an upcoming trip!

In principle, you will want one person in your group to take the lead and ensure everyone is represented, whether you are driving a packaged deal, working with a travel agent, or booking yourself. A solid plan helps as a communication mechanism and ensures things are not improperly booked. Things like dates and locations can be straightforward to make mistakes on. Further, your group may have various needs from individual to individual, which must be accounted for.

In this article, I’ll focus mainly on the tools you could use to book yourself. Others likely use these tools to assemble a pre-packaged deal or a travel agent to make a custom booking for you.

Also, check out our high-level overview of travel planning and creating an itinerary.

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Booking flights can be difficult and sometimes the most costly of a trip. As a trip leader, picking the arrival and departure times at the destination is crucial to establishing. It is often more accessible for everyone to book their flights in most groups. If group members are co-located, it is even better if flights are shared, but this is optional. Some folk may be leaving the trip early, so they may need to plan their departures.

You need to consider your bookings once you have well-established group arrival and departure times. Remember that the earlier you book, the better rates you can achieve. There are many theories into airline ticket pricing, which I won’t dive into, but 3 to 6 months in advance is usually reasonable. In booking, consider the flight length, the number of stops, and layovers. Layovers are notorious as they can be burning your time somewhere. You also have a slight chance of losing your luggage or a connecting flight due to irregularities. Sometimes, layovers can be nice if you account for them in your plan. We’ve turned some layovers into extended layovers and visited the surrounding area.

Optimize the booking for the shortest total time, with minor stops, in an acceptable budget range. This can be tricky to get right. You may even want to watch ticket prices for several days to understand how much prices fluctuate before committing. Google Flights has been a super helpful tool for us to do some preliminary research on flights and tends to be one of the more accurate tools we’ve found.

Hotels & Stays

During the trip, you can expect you’ll need to stay somewhere every night. I do not recommend winging it to foreign areas and where you will stay. Events or unknown elements could be at play that leave you and your group homeless. As a leader, you must also understand the needs of your group. Some folk might be comfortable staying at cheaper budget options like a hostel. They may prefer the atmosphere. Others may prefer a more comfortable and private housing of a hotel. Airbnb options are also worth exploring if you have a large group. Renting a whole house can be convenient.

Once you establish the minimum tolerable level your group can handle, you’ll have a better handle on what places you will need to look for booking. Also, the place will determine the costs and arrangements you’ll need for the group. For example, some parties may want their rooms while others can group.

From there, it is time to book! Various hotel chains, hostels, Airbnbs, etc., have tools you can book directly through. This can be painful as you’ll need to track each separately. However, there is hope! has been a great resource as it has a good database of your options and works reasonably well internationally!


Transportation options vary widely depending on your plan, where you are going, and how big your group is. It may make sense for large groups to charter a private bus to drive you through to your destinations. Hiring a private driver or local guiding companies with shuttles may make sense for smaller groups. The critical bit is to understand where you are going. Perhaps you won’t need a vehicle if the destinations are close. Then, you can get by by walking and taxing as needed.

In some parts of the world, traffic laws, culture, and the side of the road folk drive on changed vastly. Unless you are very comfortable driving under different conditions, exploring hired drivers might take a lot of stress off your shoulders. Hired drivers also make great individuals for understanding local culture, happenings, language, and more. In many ways, they can make interacting with locals easier, especially those you cannot speak directly with due to language barriers. Local drivers may accompany you to your destinations and be active local guides.

If you plan to rent your vehicle, do it in advance. I often see destinations having limited or out of vehicles to meet the demand. You don’t want to get caught off guard, as it may be a show-stopper. Understand the vehicle size you need and one that meets the needs of the worst terrain you will go to.

There is no one-stop shop for booking transportation, and it will vary worldwide with local companies. So, do your research and contact agencies directly. Be sure to book in advance, whether it is a private guide/driver, a charter bus, or a rental car.

Permits & Events

Depending on your travel plans, if there are important events or places that your trip centers around. Make sure you understand if these places require permits or tickets. These are limited, may only be sold seasonally, and may be hard to acquire. Some trips may be made or centered around the dates. These can be acquired alone. For example, if you are planning a group climb of a famous mountain like Mt Rainier in Seattle, WA. You cannot just show up and climb that thing. Climbing permits are pretty challenging to acquire. Failure to plan and understand these risks may leave you wasting the trip.

Double-check that each critical place on your travel plan requires no planning to attend. Once you understand all the events and permits involved, you can start planning around them. Some permits across the world function off a lottery system, to which now you can utilize your entire group as everyone should play the lotto for better odds. Pre-book these events and keep the permits and event tickets safe. Understand the limits of the permits and event tickets to ensure you don’t miss something that will void them. Some rules or failures to file some paperwork may lead you to ultimate disappointment.

Where Travel-Wise Is Heading

Travel-Wise officially has booking built into our trip planner! Once you finish planning your dream trip, the booking tool is fully integrated to make it easier to keep your booking in line with the tool. You can still book from outside sources and copy the info to your trip planner.

While it may be difficult to replace the human element in booking everything, as noted above, today, there are very few international booking services outside of hotels and flights. This still drives a lot of knowledge down to local agencies and experts living there. They may or may not have websites and be hard to discover. As our community grows, this is something we want Travel-Wise to spearhead. Our users should be able to make their travel plans and have the options readily available, with the cheapest and most desirable packages presented quickly and accurately.

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