Through a travel agency, you can book flights and hotels together. It’s not that these companies have greater access to packages—although some do—they just have more experience coordinating activities, lodging and transportation. DIY travelers are fully capable of doing the same, though the concept stresses some out. After all, you can’t have a trip without a place to stay or a way to get there, so which should you prioritize?

Why Transportation Often Comes First

Most commonly, people start with transportation because it sets the start and end dates. That said, some modes of transportation are more flexible than others, making them less necessary to book first. For example:

• Flights—airfare fluctuates more than lodging rates. Thus, a good deal on flights may prompt a trip.
• Rentals—while vehicle rental rates do oscillate, the change is never dramatic. Plus, there are so many companies these days that the competition keeps prices in check. Worst case, you’ll pay extra for an upgrade if all economy vehicles are sold out.
• Buses and Trains—rail and road transportation remains steady in price; however, the schedules can be restrictive. Unless visiting a major metropolis, you may find buses run only a couple times a week.

When assessing transportation, consider how many ways you can get somewhere. If you can reach a destination by car, bus, train or plane, then focus on accommodations first.

Cancellation Policies Matter

Airlines dole out refunds less liberally than hotels. While you can add cancellation insurance, getting out of a flight can be a big headache. Other modes of transportation are not as painful. In fact, buses and trains often promote refundable tickets for travelers buying in advance.

Most hotels grant guests a 24-hour window within which they can cancel without financial repercussions. For this reason, many travelers prefer to book first with a hotel and then cancel should transportation fall through. Most hotels will also accommodate changes to the reservation if flights fly out on different days.

So Does the Purpose

Almost always there will be somewhere to stay. If not a hotel, there are hostels and Airbnb properties (to name a few options). Flights, trains and buses, though, do sell out. Thus, it’s sometimes safest to arrange transportation first, unless the trip centers around a destination.

When the trip orients a specific event, then the reverse logic applies. Finding accommodation for a big event will be harder.