When should I start planning my next vacation?

One of the most common questions I hear from travelers is: “How far in advance should I begin planning my vacation?” 

The answer, of course, depends on the type of trip you’re taking—and that's likely why it’s such a frequently asked question.

Below, I break down ideal planning windows for different types of vacations.

Personally, I plan trips that will last more than 5 days about 6 months in advance.

That works great for short getaways, but anything longer should be 6 to 12 months out, even 24 months for certain cruises.

Cruises:

Plan 12-18 months ahead—and sometimes up to 24 months.

Why so far in advance?

Cruises, especially the more popular ones, can book up quickly, particularly in desirable room categories or cabin locations.

Early booking often comes with perks like shipboard credits or complimentary airport transfers, and securing your preferred cabin type can be easier when you plan ahead.

Additionally, booking early lets you take advantage of early bird promotions that cruise lines often offer when they release new itineraries.

The best cabins and room types tend to sell out fast, so the sooner you book, the more options you’ll have.

Pro Tip: Consider purchasing travel insurance for your cruise deposit. Many cruise lines offer non-refundable deposits, but with the right insurance, you can get that deposit back if it falls within your coverage. Plus, if you upgrade your coverage later, the amount you paid for the deposit will be credited toward your new plan.

Holiday Season Travel

Book 12-15 months in advance.

Holiday season travel—think Christmas, Easter, Spring Break, and summer—can be a high-stress, high-cost affair.

With peak demand comes peak prices, and if you wait too long to book, your options will be limited.

This is the time when many destinations are at their busiest, and popular hotels, tours, and excursions will likely sell out months in advance.

To secure your spot and avoid sticker shock, it’s best to plan well ahead of time.

Pro Tip: If you’re traveling to the Southern Hemisphere (e.g., Australia, South America, South Africa), remember that their summer season coincides with the Christmas and New Year holidays. So not only are you dealing with summer demand, but the added rush of holiday travel. Timing your trip carefully is crucial to avoid high costs and overcrowding.

High Season Travel

Book 8-12 months in advance.

High season varies depending on the destination.

Popular spots like Europe or ski resorts may experience their busiest periods during specific months, and if you're aiming to travel during peak season, you’ll want to secure your accommodations and tours well ahead of time.

Not sure when high season is for your destination?

Lonely Planet is a great resource. Here’s how you can use it:

1. Go to LonelyPlanet.com.

2. Search for your destination.

3. Navigate to the “Survival Guide” and then “Best Time to Go.”

4. Check the months highlighted in green, which indicate high season.

   
   
   
   

Pro Tip: If you can, avoid high season altogether. Instead, opt for shoulder season travel. Shoulder season offers the benefit of good weather, fewer tourists, and often lower prices. If you plan for shoulder season, aim to book 8-12 months in advance for the best results.

Independent Travel (Non-Cruise, Non-Group Itinerary)

Book 6-9 months ahead for shoulder season travel.

If you're planning a more flexible trip, like a self-planned road trip or independent journey through Europe, I recommend booking your accommodations and major activities 6-9 months in advance if you're traveling during shoulder season.

This window gives you plenty of time to lock in the best deals without the pressure of last-minute bookings.

Pro Tip: Before booking flights, ensure your hotel choices and itinerary are finalized. Sometimes, after booking flights, you realize you need to adjust your plans because a favorite hotel is sold out for part of your trip, or you decide to stay longer in a particular location. Having your itinerary settled first gives you the flexibility to book flights that best align with your plans.

Weekend Getaways or Staycations

Book 1-3 months in advance.

Weekend getaways or staycations can usually be planned on shorter notice, but you’ll still want to book early to avoid the inevitable price hikes that come with last-minute planning—especially if a big conference or local event is happening.

Aim to book your hotel 1-3 months out, and if you’re flexible, compare prices for different weekends to see if one is cheaper than another.

Pro Tip: Some hotels offer “advance booking” rates that are cheaper but non-refundable. If there’s any chance your plans could change, don’t be lured by these discounts—they’re usually only a small percentage off, and the non-refundable nature of the deal could end up causing more hassle than it’s worth.

While the above guidelines are a great starting point, every trip is unique.

If you're planning a more complex or specialized trip (like a destination wedding or luxury safari), the planning timeline may differ.

Regardless of your travel style, I always recommend purchasing travel insurance to protect your investment, especially when booking long-term trips or cruises.

However, I’m not licensed to provide specific insurance advice, so if you have detailed questions, we can always work together to contact the provider and get the answers you need.

Happy planning!

Whether you're booking a relaxing weekend retreat or an epic cruise, the earlier you plan, the better the options—and the less stress you'll face.

Safe travels!