How Far in Advance to Book Travel


One of the questions we're often asked is: how far in advance should I book travel? As with so many things in life, it depends on several factors, particularly the kind of travel being reserved, and the kind of traveler you are. But here are our recommendations for the most common types of travel reservations our clients make.

We also recommend travel insurance to all our clients, and keep in mind that if you want to purchase Cancel for Any Reason travel insurance, it typically must be purchased within 14 days of paying the initial trip deposit and must insure the full cost of the trip. Sometimes it must also be purchased at least 30 days before the trip's start date. Also, if wanting to include a pre-existing medical condition waiver, travel insurance must typically be purchased within 14 days of paying the initial trip deposit.

2+ Years in Advance: Cruises, Four Seasons Private Jet

Cruisers know to plan ahead, particularly for new cruise ships, in-demand itineraries, and special suites. For example, when some of our clients reached out in Spring 2022 about Royal Caribbean's Ultimate Family Suite that accommodates two families and has its own in-suite cinema, private jacuzzi, air hockey table and in-suite spiral slide, most the suite was already booked up for most 2023 dates.

Similarly, certain Four Seasons Private Jet itineraries book quickly, so it's best to reserve when new expeditions are announced; the initial Four Seasons Private Jet 2025 itineraries have already been announced.

When to Book Cruises: 2 Years in Advance


1 Year in Advance: Yacht Charters, Award Flights with Frequent Flyer Miles and Points, Luxury Hotels, Some Michelin Restaurants, African Safaris, Peak Time Travel

While not all yacht charters will know their availability 1 year in advance (as owners can take additional time to decide when they'll use the yacht for their personal travel vs. chartering) it's still wise to reach out to us one year prior, to start the ball rolling and understand the types of options available.

Award flights using frequent flyer miles and points can be booked at the earliest about a year in advance, although some award calendars open later, depending on the frequent flyer program being used.

Peak travel of all kind (think Christmas/New Year's, cherry blossom season in Japan and the like) as well as African safaris, small luxury lodges, and certain popular Michelin star restaurants should always be reserved a year in advance. Even then, there may be other restrictions such as minimum night requirements during festive season or spring break, priority given to returning guests, etc. that make certain luxury resorts impossible to reserve even one year in advance during certain holiday periods.

Even during non peak periods, we recommend reserving luxury hotel and resort stays a year in advance, or as soon as it opens. Why? As long as you reserve a refundable rate, it gives you a free option: if rates decrease, the reservation can be rebooked at a lower rate. And if rates increase, you've managed to pocket nice savings over what you would have paid if you'd reserved later.

When to Charter a Yacht: 1 Year in Advance


4-8 Months in Advance: International and Hawaii Airfare (Paid) Except to Mexico/Caribbean/Canada, Private Guides

If not using frequent flyer miles or points and paying for airfare, we recommend reserving 4-8 months in advance for most ex-U.S. international flights, apart from flights to Mexico, Caribbean and Canada, which can be reserved closer to the travel date (see below). Routes differ in competitiveness, however, so for premium (business or first class) travel during peak holiday periods (think Hawaii over winter break or spring break in flat bed seats) the earlier 8 months in advance timing is likely to be better.

We also recommend reserving private guides at this juncture, as the better ones are booked out months in advance.

Reserve International Flights 4-8 Months in Advance


2-3 Months in Advance: Mexico/Caribbean/Canada and U.S. Domestic Airfare except Hawaii (Paid), Popular Upscale but Non-Michelin Restaurants

Most U.S. domestic travel (except Hawaii in premium cabins) and Mexico/Caribbean/Canada flights can be reserved 3 months in advance, although as always, watch out for peak demand periods, which should be reserved much further in advance.

2-3 months in advance is also when we recommend reserving tables at nicer restaurants (although not the super popular Michelin starred restaurants that require reservations a year in advance or more). This is particularly important for Japan, where small sushi bars and restaurants fill up quickly.

When to Book Flights to the Caribbean and Mexico


1-2 Months in Advance: Transfers, Spa Appointments, Other Dining/Activities for Non-Peak Periods

If you've planned the big items far in advance, you can typically leave it to 1-2 months in advance to arrange airport transfers, spa appointments, resort dining, and other activities (except, as mentioned above, during peak periods).

How far in advance do you make travel reservations?

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