Select Dynamic field

How To Book An Upcoming Trip

Posted July 25, 2022 in Engineering Around Travel - Last updated May 26, 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 make sure 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 need to 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 in 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 that you’d be able to use to book yourself. These are likely to be the tools others use to assemble a pre-packaged deal or a travel agent making a custom booking for you.

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

Featured Image Credit


Booking flights can be difficult and sometimes the most costly part of a trip. As a trip leader, picking the arrival and departure times at the destination is the most crucial piece to establish. It is often more accessible for everyone to book their flights in most groups. If members of the group are co-located, 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.

Once you have well-established group arrival and departure times, you need to consider your bookings. Remember that the earlier you book, the better rates you can achieve. There are all sorts of theories into airline ticket pricing, which I won’t dive into there, but 3 to 6 months in advance is usually a reasonable price. In booking, consider the flight length, how many stops there are, 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 for you. 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 tend to be one of the more accurate tools we’ve found.

Hotels & Stays

During the trip, you can expect every night you’ll need to stay somewhere. I do not recommend winging it to foreign areas and where you will stay. There could be events or unknown elements 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 that your group can handle, you’ll have a better handle on what kind of 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., all have various tools you can book directly through. This can be painful as you’ll need to track each of these separately. However, there is hope! has been a great resource as it does have a good database of your options, and it works reasonably well internationally!


Transportation options vary widely depending on what you plan on doing, where you are going, and how big your group is. For large groups, it may make sense to charter a whole private bus to drive you through to your destinations. For smaller groups, hiring a private driver or local guiding companies with shuttles may make sense. 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 with 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 even come with you to your destinations and be active local guides.

If you plan to rent your vehicle, make sure you 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 size of the vehicle 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 very 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 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 out. Some rules or failures to file some paperwork may lead you to ultimate disappointment.

Where Travel-Wise Is Heading

Travel-Wise does not have a booking component yet built in. However, it is in our vision to make booking more accessible and integrated into your travel plans built on Travel-Wise. As we get more power to work with affiliate booking agencies and services, we hope to be able to present you with automatically produced packages for your travels that give you the flexibility and options specific to your travel plans.

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 who live in these places. 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 at hand with the cheapest and most desirable packages presented quickly and accurately.

Success message!
Warning message!
Error message!