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One day, while chatting with my best friend about travel, she started asking me questions about logistics and the order of doing things when it comes to trip planning. “I never know what I should do first,” she told me. “So I just don’t do any of it and never go on any trips. But I want to go places. I just get overwhelmed by the planning process. Should I book my flights or hotel first?”

If I’m being honest, it had not occurred to me that someone would want my advice about how to begin trip planning – probably because in my mind, I’m always planning a trip so there is no beginning or ending to my processes, ha! 

“Can you just tell me where to start?” my best friend asked me. “Just tell me if I should book my flights or accommodations first.”

Okay, chica. Here you go. 🙂 

How to know whether to book your flights or your accommodations first. 

What type of accommodation will you stay in?

My first question would what type of accommodation do you plan to stay in? Do you want to find a free place to stay via home exchange or housesitting? Or do you want to pay for accommodations, such as a hotel, hostel, or VRBO?

A home exchange would give you a free place to stay and let you live more like a local. 

Paying for accommodations gives you more flexibility and control over where you stay.

Paid accommodations 

If you plan to pay for accommodations, such as at a hotel, hostel, or VRBO, then go ahead and focus on your mode of transport first. Book those flights – and chase a good deal if you can! Set up flight alerts with Google Flights or your travel site of choice.

Depending on the level of flexibility, you may be able to plan your trip around the best price rather than another priority (such as weather or a special occasion). If you have firm dates that can’t be changed, focus on getting those flights booked first — or however you plan to arrive whether via rental car, ferry boat, train, etc. For domestic US travel, you’ll want to book flights 1-2 months out; I usually find that 6 weeks is a sweet spot for prices. For international travel, you’ll want to book 2-5 months out.

Home Exchange

If you want to find a free place to stay through home exchange or house sitting, then I would ask you a followup question: Do you have firm travel dates or are you flexible in the timing of the trip? The answer to this question will influence the recommended action. 

Are your dates firm or flexible?

How firm or flexible are your dates?

Having firm dates, such as a school break or holiday weekend, means that you are limited in when you can go to your destination. 

Flexible dates means you have some wiggle room in the timing of your travel. 

Flexible dates

If your dates are flexible, then get started looking for a home exchange. This process can take time so you want to get an early start and keep as open a mind as possible. Be ready to say yes to the unexpected! 

If you are part of the HomeExchange.com Facebook community or forums in the app, then you could go so far as to post looking for an adventure: list what you’re looking for in terms of space, number of travelers, type of destination, time of year, general duration… and see what comes back to ya! We see all sorts of listings, ranging in specificity and flexibility. Sometimes folks are looking for a specific duration or location but any time of year; sometimes they are more focused on the type of house, especially if they have kids, but are more open to region and duration. 

We’ve posted many times, often without any interest. And that’s okay! We either pivoted to paid accommodations or taking a different trip. Sometimes the home exchange thing doesnt work out. But when it does, it can be magical. Let me share an example from a recent summer, we were searching for a 2-4 week exchange somewhere so we could take a workcation. None of my dozens of proposals had been accepted, and no one was responding to the postings in the forums. But then we received a message from someone who had seen our post in the Facebook group from a region not explicitly mentioned in our post – but one that was included in our Preferred Destinations list on our profile. And we said yes! We negotiated dates, and agreed on a date by which we’d all buy our plane tickets. That’s how we ended up spending two weeks in Montreal, which turned out to be one of our favorite family trips ever!! 

Firm dates

If your dates are firm and can’t move, you will have a hard time finding a home exchange. Remember that other people also have firm dates and prior commitments as part of their lives, so your spring break dates might not line up with my spring break dates. We often get requests from users who don’t check our availability calendar first, but we can only travel during school breaks. We also get last minute requests but we plan our trips 6-12 months in advance and usually can’t vacate our house with only a few weeks notice. Preparing your house for a home exchange also takes time – and it takes the same amount of time for a week long exchange or a month long exchange, so longer exchanges are usually preferred. 

Having said all of that, it is still possible to find an exchange with firm dates! We have done it multiple times using GuestPoints. Most home swapping sites offer two ways to exchange: reciprocal and non-reciprocal. Reciprocal exchanges are one-to-one: you stay in my house while I stay in your house, either simultaneously or at another time. Non-reciprocal exchanges are one-way: you stay in my house but I dont stay in your house. On the site where we are members, we use GuestPoints for non-reciprocal exchanges, earning them when people stay in our house and spending them to stay in someone else’s house. This was how we did our lovely spring break trip to Florida! 

If you can not find a free place to stay with firm dates, then be prepared to pivot in one way or another: either paying for accommodations or looking in another location.