I get a lot of questions about how far out to book a trip and how to create an itinerary.
There is no right or wrong answer of course (despite what you read online, flights aren’t always cheaper on Tuesdays, for example), but my trips to destinations further afield tend to follow a similar booking pattern:
For a long-haul flight, like my recent trip to the Benelux region, I typically begin by choosing dates and booking flights around three months in advance. Hotels and other long-distance forms of transportation come next, one or two bookings at a time to ease the pain of the costs. Finally, I really dig into my itinerary, checking to see what events are happening and deciding what sights I simply don’t want to miss.
So for the sake of authenticity, I’m sharing my exact timeline of when I booked transportation, lodging, and attractions for a trip dated September 15 – October 2, as well as a snapshot of my travel itinerary.
Note: This post is not necessarily intended to be a guide. In an ideal world, I would have dedicated more time earlier on to purchasing our sightseeing tickets and performing other research a month earlier – but as I took two weekend flyaway trips and several other road trips over the course of the three months depicted here, this left a smaller amount of time for planning than I would have liked. Instead, consider this a real-life example of what it is like to book a trip while considering work and other obligations, helpful for new travelers approaching their very first long trip.
Early June: Start dropping hints to Michael about wanting to take a trip. Also begin dropping hints to my boss about wanting to take a trip.
Mid-June: Insist that Michael and I must take a trip, and begin looking at the calendar and doing some airfare research. Also, corner my boss with calendar printouts of all of the important working days and (gently) demand to know which dates are acceptable to be away.
June 22: Panic and book a flight to Mexico City over Labor Day weekend just in case we don’t end up booking a trip to Europe (you know, a normal thing to do).
June 23-24: Spend lots of time watching TV shows about the locations we are considering (Finland/Estonia; Czech Republic/Austria; The Netherlands/Belgium); really, truly begin searching for flights.
June 25: Finally decide where to go (!). Compare prices, dates, and times once again. Determine that driving to an airport that is further away yet will provide a direct flight is preferable to flying out of a closer airport with a long layover and more expensive ticket. Verify passport will still be valid six months after the flight dates. Purchase tickets. Immediately begin telling all family members so no one has to claim they heard it from anyone else.
June 26: Begin placing guidebooks on hold at the local library, and begin reading in snippets.
June 28 – July 11: State “Today is the day” we will begin planning our itinerary and booking our Airbnbs. Fail and repeat the following day.
July 12: Tentatively plan dates to spend in each city; research train itineraries and prices. Contact six Airbnb hosts in our first city (Amsterdam).
July 14: Book an Amsterdam Airbnb. Book train from Brussels Airport to Amsterdam. Begin looking at Luxembourg Airbnbs.
July 23: Message Airbnb hosts in Luxembourg. Book train from Amsterdam to Luxembourg.
July 24: Book Luxembourg Airbnbs.
July 25: Book two one-way rental cars (total cost $67) from home to the airport and back after calculating the cost of parking at the Miami Airport ($272) and other off-airport parking lots.
July 26: Save Bruges Airbnbs to a Wish List
July 31: Decide to stay in Ghent based on what we’ve read online & responses to Instagram and Twitter polls.
August 3: Message Ghent Airbnb hosts.
August 4: Book Ghent Airbnb.
August 5: Panic and book a trip to St. Louis, Missouri.
August 9: Message Brussels Airbnb hosts.
August 10: Book Brussels Airbnb.
(August 11-12: Fly to St. Louis)
August 13: Book train tickets from Luxembourg to Ghent and from Ghent to Brussels.
August 14: Buy tickets to the Anne Frank House.
August 17: Purchase seats on first flight, as they are now available.
August 20: Book a hotel in Miami for the night before our flight.
(September 1-3: Fly to Mexico City)
September 6: Purchase seats on second flight, as they are now available. Purchase tickets to the Van Gogh Museum.
September 11: Purchase tickets to the Rijksmuseum.
The trip begins! You can read about each destination by clicking the link, but here’s a general outline of where we went and how long we stayed in each place:
September 14: Pick up a rental car after work and drive to Miami. Stay overnight.
September 15: Explore Miami and head to the airport. Return the rental car, pick up tickets, and board the plane.
September 16: Arrive in Brussels and immediately board the train for Amsterdam.
September 17: Explore Amsterdam.
September 18: Rotterdam day trip.
September 19: Explore Amsterdam.
September 20: Day trip to Delft and Den Haag.
September 21-22: Explore Amsterdam.
September 23: Take the train to Luxembourg City and check in to Airbnb.
September 24: Explore Luxembourg City.
September 25: Take the train to Ghent and check in to Airbnb.
September 26: Explore Ghent.
September 27: Day trip to Bruges.
September 28: Explore Ghent.
September 29: Take the train to Brussels and check in to Airbnb.
September 30: Explore Brussels.
October 1: Day trip to Antwerpen.
October 2: Take Uber to Brussels Airport (due to train strike); get tickets and board the flight. Arrive in Miami, pick up the rental car, and drive home.
That’s it! That’s the condensed version, at least. Have you ever planned a long trip? What is your travel-planning strategy?
See you tomorrow for the first post on Amsterdam!
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- How to Spend a Few Days in Ghent, Belgium
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- Traveling Light: Two Weeks in the Netherlands, Luxembourg, and Belgium Packing List
