How far in advance should I plan my vacation? A luxury travel advisor’s guide
One question that I am asked on a regular basis as a luxury travel advisor is, “How far in advance should I plan my vacation?” The answer to this question varies for each type of trip, as seasonality, availability, and pricing all change from trip to trip. Cruises, luxury hotels, and certain destinations and seasons require different pre-planning windows.
Over the last decade of luxury vacation planning, I have worked with all different types of travelers. Some want to plan their trips last minute (I’ve had clients ask to plan a trip to Bali just four months out). On the opposite end of the spectrum, there’s clients with more of this vibe: “I’d like to go on an African safari in three years, can we get this booked next week?”
Depending on the type of experience, I have different recommendations on how far in advance to plan a trip. While my personal sweet spot is 6 months, I also know that for some trips, that isn’t enough time. Keep reading for the planning windows for cruises, holidays, high seasons, weekend getaways, and more.
Table of Contents
How far in advance to book a cruise
How far in advance book holiday travel
When to book travel during high season
How far in advance to book a cruise (small ship, big ship, river cruise, expedition)
Book your cruise or expedition 12-18 months in advance. Sometimes 24. Wait, what?
Most companies will offer early booking incentives when they release their dates each year. They may also offer some perks such as shipboard credit or an airport pickup with early bookings.
Each room category can vary greatly in price and amenities. In order to secure not only the room type that you prefer, but also the location on the ship where your room is located, it’s essential to book early. The best room types will sell out quickly!
PRO TIP: Purchase travel insurance* for your cruise deposit that will roll over to your final payment. For example, if you pay $400/person as a deposit, you can insure this amount. The cruise company will likely tell you that this deposit is non-refundable, but with certain levels of travel insurance, you can receive this deposit back if it falls within your coverage. Assuming all goes well and you’re ready to make your final payments for the upcoming cruise, that same travel insurance can simply be increased rather than purchasing a new coverage plan. The original amount that you paid doesn’t go to waste, it is applied to your increased coverage.
How far in advance book holiday travel
Book your trip 12-15 months in advance when you’re traveling during holiday season.
This is high season on steroids. Prices are already high. With each booking, prices will continue to increase because most hotels, tour operators, and suppliers that are popular during holiday season expect to sell out.
What holiday seasons does this apply for? Christmas and Easter in majority Christian/Catholic countries; Spring Break in warm-weather beach areas. Summer generally everywhere. Kids are out of school, families have more flexibility. This is why many places are crazy busy even when it’s not the best time to go there! (ie Europe can be insanely warm in the summer, yet this is when most tourists travel to Europe).
PRO TIP: Keep in mind that if you’re heading to the southern hemisphere (Australia, South America, South Africa, etc), their summer is over Christmas and New Years. This is also summer break for students. This is essentially summer season + holiday season, so choose your travel dates to the southern hemisphere wisely!
When to book travel during high season
Book your trip 8-12 months in advance when you’re traveling during high season.
When is high season wherever you’re going? Here are some quick references:
Popular European destinations: June–August
Japan: Late March–May and October–November (secondary peaks: late December–early January and mid-August)
Caribbean: December–April
Bora Bora / French Polynesia: June–August
South America / Patagonia: December–February
European river cruises: May–September (December for Christmas market sailings)
Antarctic cruises: Mid-November through mid-March, peak mid-December through mid-February Read more: How to choose an Antarctica Expedition Cruise
African safari: June–October (Great Migration in Kenya/Tanzania peaks July–September) Read more: Which safari destination to choose
PRO TIP: If your schedule is flexible, avoid high season if at all possible, and travel during shoulder season instead. High season = an insane number of tourists, highest prices, not always favorable weather….
Best timing to book shoulder season travel
Shoulder season (the months before and after high season) = good weather, fewer tourists, slight decrease in prices. Book your shoulder season trip 6-12 months in advance and in most cases, you should be golden!
PRO TIP: If you have a specific resort or hotel in mind, I recommend booking it “just in case” 6-9 months in advance with cancellation.
How far in advance to book a weekend getaway
Book weekend getaways or staycations at least 1-3 months in advance. Depending on where and what season, you may need more time for popular hotels and resorts.
Go into this planning early with a little flexibility. You never know when a city is going to be uber expensive simply because a big conference or event is in town. If you wait too long, you will already have made arrangements with work, friends, family to take care of kids, etc to then find out that your favorite hotel is 3x more expensive than normal.
Choose a 2-3 weekend timeframe, check prices to see if any weekend is cheaper than another, book rooms, then make arrangements with friends, family, work etc.
PRO TIP: If you book in advance, many hotels will offer an “Advance Booking” rate, but these rates are non-refundable. If there is any chance that your travel plans may change for these quick getaways, don’t be lured by their advance booking promotions (they’re usually 10% or less, anyways).
Don’t want to figure out these logistics yourself? That’s where I come in! My team at Undiscovered Sunsets can turn your quick email, “Whitney, we need a mid-winter getaway. Where and when should we go?” into a reality. Ditch the planning stress with ease and knowing that every detail is in good hands.
*While I advise all of my clients to purchase travel insurance to protect their investment, I am not licensed to sell nor advise on the specificities of individual coverage plans nor different travel insurance providers. In most cases, we provide a trip protection quote and you will receive all the details you need to look into it further.
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Use the link below to design your vacation together with us.
Whitney Shindelar
Undiscovered Sunsets was a long time in the making, even if I myself didn’t realize it. During my time at the University of Northern Iowa, I studied abroad in New Zealand. Upon graduating, I bought a one-way ticket to France, lived with a French family and studied with classmates from Turkey, China, Russia, Germany, Italy, and everywhere in between. In 2010 I began teaching English as a foreign language. This job quickly took me to China, where English teachers were in high demand and within three years, I began working in a 5-star hotel, speaking Mandarin throughout most of my day. In total, I lived abroad for 7 years.
I consider Undiscovered Sunsets to be the perfect mélange of my personal experience traveling the world and my professional experience working in the hospitality industry.
I look forward to designing your next adventure!
Frequently Asked Questions
How far in advance should I book a luxury resort? Book peak season or holiday travel 10–12 months in advance. The most sought-after properties — overwater bungalows, intimate safari lodges, boutique European hotels — have limited rooms and fill well before standard hotels. If you have a specific property in mind, that's your signal to start sooner rather than later.
What trips require the most advance planning? Antarctic expedition cruises and African safaris require the most lead time, often 12–18 months, sometimes more for peak season. These experiences have very limited availability by nature: small ships, remote camps, and tightly regulated destinations mean there simply aren't many spots to go around. European river cruises and holiday season travel to popular destinations follow closely behind.
When should I contact a travel advisor to start planning my trip? The earlier the better, ideally as soon as you know you want to travel, even if the details aren't figured out yet. A travel advisor can help you work backward from your ideal dates to make sure nothing gets away from you, especially for trips that require early deposits or permits. For complex or high-demand trips, reaching out 12–18 months ahead gives you the most options.
What is high season in Europe? High season across most of Europe runs June through August, when long days, warm weather, and school holidays bring the largest crowds. If your dates are flexible, late April through May or September through early October offer nearly the same experience with fewer people and more availability.
