Trains, planes, hotels, transfers and more. What to book and when? 

I’m not talking about the weekend jaunt, I’m talking about the long haul trips. Two weeks in Europe, bouncing from France to Spain, and more. The getaway to Asia through Thailand and Vietnam. Or perhaps the coastal drive of Australia. The big ticket trips that require a lot of time and preparation. 

As I’m amidst planning a trip for November of this year, I want to share the way I’ve gone about planning and booking for my husband and I’s trips for the past five years — without the headache.

Do research, decide what you’re interested in, and stick to an itinerary. 

Step 1: International Flights
This is always the first one. We’ve often used points for our bigger trips that we take, and typically book the international flight 6-8 months in advance. For instance, our trip in September to Italy, I booked the tickets in February with points (8 month mark). I’ve found the flights to be well priced, and even better if you’re purchasing with points.
*Book 6-8 months prior to travel

Step 2: Domestic Flights
This is the hopper flight. For instance in our SE Asia trip we took 5 domestic flights within the trip. I booked these flights the minute they went online. If you can’t get to where you want to go, it can affect your entire trip. 
*Book 4-6 months prior to travel

Step 2a: Hotels
With travel becoming incredibly impacted, and peak seasons blending into almost year round in the popular places, I find that I’ll snag a hotel room when I know the exact hotel I want to be in. I’ll do it months in advance when it’s important to be at a specific hotel, for instance if that’s the whole reason I’m going to a destination, like an all-inclusive in Mexico. Somewhere like Krabi, Thailand, if it wasn’t true peak season, I’d book 2-3 months in advance. Another example: I’m currently trying to book an Airbnb for Venice in September (peak season), and I’m incredibly limited to choices in my preferred neighborhood. 
*Book 2-5 months prior to travel

Step 3: Any other transportation
Trains and cars come in after the larger lengths of transportation. When traveling in Europe I’ll book the trains up to 2-3 months prior to travel when they come available, and can even get away with the month or week of for the more popular routes (i.e: Barcelona to Girona). 
*Book 2-3 months prior to travel

Step 4: Tours & such
If there’s a certain tour you want to go on, like the Vatican in Rome, these tours can book up pretty fast during peak season. If you know something you absolutely don’t want to miss, then book it immediately, otherwise I’ll often wait until the month of before squaring down reservations. 
*Book 1-2 months prior to travel

Step 5: Dinner and tickets
Reservations for dinner I’ll most certainly wait until the two weeks before I travel as I want to be sure of my plans. Sometimes I’ll even book the night of. For popular restaurants, like Tickets in Barcelona which requires months in advance to be booked, then it’s a different situation. I usually don’t sweat the reservations because in a new city there’s so many choices. 

Step 6: Planning the days
My husband and I have always done the same thing. For each destination, we right out a “must-see” list and “would like to see” list. The must-sees have the highest priority, and anything else falls into the spare time. We give room in our itineraries to explore as need be, and try not to plan out each minute as I’ve found the best memories have been from spontaneous experiences.


The timing of when you book trips isn’t always going to be at this length, this is just how we’ve utilized our points and found best pricing for travel. The most important takeaway is the priority of what needs to be booked first and last. 


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    Excellent tips! Booking times for flights in particular make a HUGE difference. I try to book everything as early as possible 🙂

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