How Far in Advance Should You Plan a Big Holiday?
When you are planning a major holiday—whether it’s a European summer adventure, a multi-city itinerary, or a once-in-a-lifetime family trip—the key to reducing stress (and often reducing costs) is timing. Knowing what to book and when can make the difference between seamless travel and last-minute panic. Over years of planning itineraries for our family trips, we’ve learned which bookings need to happen months out and which can wait until just a few days before departure. That’s not to say that you can’t enjoy an amazing spur-of-the-moment holiday, but it will often come with a much higher price tag.
This guide lays out the ideal timeline for planning a big holiday, along with practical tips, the tools we use, and reminders you won’t want to miss.
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10–12 Months Before: Choosing Your Itinerary and Booking Flights
The first step in planning a major holiday is determining your itinerary. Start by deciding where you want to go, how long you want to stay, and which cities or regions you’d like to explore. For longer trips, we often fly into one city and out of another so we can cover more ground without backtracking. This works particularly well in Europe, where multi-city flights are common.
When to book flights
We typically book flights around ten months before travel. Because we usually have specific dates and travel as a group, booking early ensures the best routing options—particularly mid-week flights, which are often less expensive. We also look for flights that are as direct as possible to minimize travel fatigue, especially after long-haul journeys. We use Google Flights to compare prices, routes and dates. The price tracker helps monitor fluctuations so you can secure a good fare without guessing.
Pro Tip: Check your passport expiry date the moment you start planning. Many countries require at least three to six months’ validity beyond your return date.
6–10 Months Before: Booking Accommodation
Once flights are set, the next priority is accommodation—especially if you’re travelling during peak seasons like European summer or school holidays. In recent years, we’ve noticed that many vacation rentals, especially well-located properties, book far earlier than expected. We typically book through Airbnb or directly with property owners who have their own websites. Holiday rentals give us the ability to cook meals, do laundry, and spread out comfortably as a family, all of which help keep travel costs down.
When to book
For peak summer destinations abroad, we now aim to book accommodation 8–10 months in advance. With free-cancellation options, it’s easy to secure a place early and adjust later if needed.
How we choose
We read a lot of reviews and always look carefully at the location, saving favourite neighbourhoods on Google Maps so we can compare them. Proximity to grocery shops, public transport, and key sites can make a huge difference in the overall experience.
4–6 Months Before: Cars, Ferries and Trains
Car rentals
Car hire can fluctuate dramatically in price and availability, especially in popular summer destinations. Booking 4–6 months ahead usually secures the best rates and selection. Look closely at insurance coverage and any rules around international driving permits.
Ferries and long-distance trains
If travelling between islands or countries, book ferries and national or regional trains as early as ticket sales open. Some release bookings six months ahead, others three. Popular routes (especially summer ferries) sell out fast.
Local trains and urban transport
These are often available closer to your travel date or bookable on arrival, but it’s worth researching options in advance so you don’t waste valuable holiday time deciphering transport systems.
Airport transfers
We often use Welcome Pickups when arriving in a new city, particularly when travelling with a larger group. Having a friendly local meet you after a long transatlantic flight is infinitely easier than facing public transport immediately, and the travel tips they share often help shape our stay.
1–3 Months Before: Tickets, Attractions and Special Experiences
Attractions all have different release dates. Some museums and events release tickets months ahead, while others only allow bookings within a tight window.
Where we book
Get Your Guide is an excellent starting point for tours, skip-the-queue access and local experiences. Check the tour as they often offer good cancellation and payment closer to your visit. For the best rates, we book directly with museums, amusement parks, and cultural sites whenever possible.
Timing varies
Some attractions open bookings 3–6 months ahead, while others—particularly popular or limited-entry venues—may only release spots seven to thirty days before. Add booking dates to your calendar and be prepared for middle-of-the-night alarms to account for time zones. We’ve had more than one 02:00 booking session to secure must-see experiences. Even some free venues require advance tickets. The Sky Garden in London, for example, should be booked ahead.
Pro Tip: If you are visiting something special, particularly during peak holidays, be sure to book tickets for opening, when crowds and lineups are much lighter.
Special add-ons
If it’s a milestone holiday, consider a Flytographer photoshoot. These often require early planning, especially in iconic cities or at sunset. For more on our experience with Flytographer, check out this post.
1–8 Weeks Before: Restaurants and Dining Reservations
We like to choose one special place to eat in each destination and do a bit of research to see what others recommend. Most restaurants can be booked close to your visit, but some require serious planning. One example is the Big Mamma Group in Europe, known for fun, energetic Italian dining. Their restaurants are incredibly popular and often require booking months ahead, especially if you want a specific date.
We also bookmark cafés, bakeries and family-friendly restaurants so we have options ready when hunger hits. You can also build your own food tour in a Google Map to try a few local favourites.
The Final Checklist: Insurance, Documents, Money and Packing
As your holiday approaches, there are a few more essentials to tick off, including a countdown calendar.
- Travel insurance:
- Purchase comprehensive travel insurance early, ideally shortly after booking your flights. This ensures coverage for cancellation, medical needs and lost luggage.
- Driving permits:
- Check whether you need an International Driving Permit for car rentals.
- Money matters:
- Compare currency conversion rates and consider ordering currency in advance. We prefer a mix of cash and cards with no foreign transaction fees, we use the Wise card for the whole family.
- Phones and SIM cards:
- Research local SIM cards or eSIM options. Many travellers now use local services for easy international data.
- Packing and preparation
- Restock your travel first aid kit, check your walking shoes, and ensure you’ve got weather-appropriate clothing. Confirm luggage allowances for all flights, including regional carriers, which often have stricter rules. For a packing guide, see this post.
A High-Level Timeline for Planning a Big Holiday
Here is a quick summary of when to book what:
- 12–10 months: choose itinerary, book flights, check passports
- 10–6 months: book accommodation
- 6–4 months: book car rentals, ferries, long-distance trains
- 3–1 months: attractions, tours, national rail tickets
- 8–1 weeks: restaurant reservations, final confirmations
- 2–1 weeks: insurance checks, SIM cards, currency, packing
- Travel week: print or download tickets, charge devices, check in online
Final Thoughts
Planning a major holiday doesn’t have to feel overwhelming. With the right timeline, a few trusted tools and a system for organising bookings, you’ll give yourself more choice, better pricing and a far less stressful countdown to departure. Whether you’re travelling as a family, a group or on your own, starting early sets the stage for an unforgettable adventure.
What’s your favourite travel planning tip?