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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 luxury 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, we're already reserving 2029 cruise itineraries for some of our clients. By reserving early, we can secure their preferred ship, itinerary, and suite, while monitoring the cruise in case of any subsequent fare reduction, which we could rebook them with.
Similarly, certain Four Seasons Private Jet itineraries book quickly, so it's best to reserve when new expeditions are announced; for example, the 2027 Unchartered Discovery private jet journey which includes Antarctic, Machu Picchu, and Buenos Aires, among others, and the 2027 Timeless Encounters journey that includes Bora Bora, Bali, Chiang Rai, Sydney, and the Taj Mahal are both waitlisted.
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1 Year in Advance: Yacht Charters, Award Flights with Frequent Flyer Miles and Points, Luxury Hotels, Some Michelin Restaurants, African Safaris, All 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. Also see our Superyacht Charter Guide and Tips.
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, spring break, ski season, 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.
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4-8 Months in Advance: International and Hawaii Airfare (Paid), Private Guides, Certain New Year's Eve Reservations
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, particularly in this time of rising fuel prices. 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.
Places with extremely high demand (and high pricing) for New Year's Eve, for example restaurants with great vantage points to view the fireworks in Sydney, Australia, should also be reserved many months in advance.
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2-3 Months in Advance: Popular Upscale but Non-Michelin Restaurants
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.
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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).
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