Your Travel Cheat Sheet, Part 2
Let’s Talk About Those Bucket-List Trips…
Destinations like these live on some people’s wishlists their whole lives: Japan during cherry blossom season, a Greek island escape, the wild landscapes of Australia and New Zealand, Antarctica at the edge of the world, and Africa for the ultimate safari. When the location is this coveted, timing and thoughtful planning make all the difference—and our advisors know how to make all the pieces come together. Here’s our guide to when to start, when to book, and why it matters.
JAPAN
Start planning: 9 to 12 months in advance, or 12-plus months for cherry blossom season and peak fall foliage periods.
Why timing makes a difference: Japan has become incredibly popular, and certain times of year are especially busy. Cherry blossom season and fall foliage are beautiful but also bring significant demand. The best luxury hotels and ryokans, preferred room categories, private guides, and special experiences have limited availability. Japan also has major domestic travel periods, including Golden Week, Obon, and New Year, when demand increases significantly.
WhirlAway tip:
Do not build your entire trip around seeing the cherry blossoms on one particular day. Bloom timing varies, so we prefer to create an itinerary that gives travelers a wonderful experience regardless of exactly when they appear by incorporating multiple opportunities to enjoy the blooms throughout the vacation.
GREECE
Start planning: 9 to 12 months ahead. Many resorts and experiences release the following summer only after the current season ends, sometimes not until September, so you might not be able to book your villa or yacht for next summer until September.
Why timing makes a difference: Greece's summer season is short and extremely popular. July and August bring the greatest summer demand, while the shoulder season can offer a very different experience. The luxury hotels, villas, and private boats that we like to recommend to clients can book well in advance, particularly on the most popular islands. Each island has a different feel and vibe, so starting early also gives us the opportunity to choose the right islands for you rather than simply choosing from what is still available.
WhirlAway tip:
Starting early still matters even when reservations have not yet opened. Your advisor can help determine the right itinerary and options so you are ready to act when the next season is released. We can also secure accommodations at current-year pricing with the understanding that there may be an increase when the rates for the new year are set.
AUSTRALIA & NEW ZEALAND
Start planning: 9 to 12 months ahead is ideal. Consider 15 to 18 months when a specific luxury lodge or resort is a priority, and for festive season and peak summer season travel. Summer season varies by region: December through February for southern Australia and New Zealand, while Australia’s tropical north is most popular during the dry season, from May to September. Cruise itineraries here are in especially high demand so we’ll want to book those as soon as the reservations open—sometimes 24 months out. That’s when availability and pricing is the best.
Why timing makes a difference: These are destinations where the itinerary itself takes some thought. Distances are significant, and flights, transfers, lodges, activities, and accommodations all need to work together. Some of Australia and New Zealand’s most distinctive luxury lodges and resorts have very few rooms, creating significant demand for limited inventory. Starting early gives us more flexibility to create a trip that feels enjoyable rather than rushed.
WhirlAway tip:
We advise clients not to try to see everything. We prefer to help you create a well-paced itinerary with time to actually enjoy each destination.
ANTARCTICA
Start planning: 18 to 24 months before traveling.
Why timing makes a difference: This is a seasonal destination so the travel window is much shorter (November through March with peak season being late December through January). There are more restrictions around landings, so ship size matters. Itineraries vary as well with some including South Georgia/Falklands, crossing the Antarctic Circle, fly-cruise options, and longer routes. Choosing when to go can also change the experience—from the amount of ice and daylight to the wildlife you are likely to see.
WhirlAway tip:
Start by thinking about what you want to experience, not just when you want to go. Penguins, whales, ice, photography, and the overall expedition experience can all influence the best time and sailing for you.
AFRICA
Start planning: 12 to 18 months early is ideal, though some trips (including multi-generational and small groups, or high-season with specific lodges), are best 18 to 24 months in advance.
Why timing makes a difference: Planning can be done closer to the trip, as long as there is some date flexibility and wiggle room on specific lodging and itineraries. With safari involving multiple lodges, everything has to line up, so when a property only has 5 to 8 rooms, availability can get tricky.
WhirlAway tip: Many lodges only have one family suite and they are usually the first to sell out. So if you’re traveling with kids and prefer that setup, we’ll want to plan together 12 to 18 months out.
