Italy, Alaska Japan, Costa Rica & More: Don’t Get Left Out

Written By Krista Nannery

The few days after Thanksgiving are a funny time for travel advisors like me. Everyone decides at the Thanksgiving dinner table to head to Costa Rica or Turks & Caicos for New Year’s! Great idea in theory, but sadly there’s very limited inventory and many properties require a five- or seven-night stay. Looking for a two-bedroom or connecting rooms? It’s just so hard.

In these destinations, booking “early” really does mean earlier than you’d expect. By the time most people start looking, the best rooms, guides, and experiences are already spoken for.

So if I can convince you to plan your vacations to these destinations months in advance, let’s do it. Book a complimentary vacation consultation here to talk more.

1. Italy

Italy isn't “busy.” It’s relentless. Tuscany’s prime villa inventory disappears months in advance. The Amalfi Coast? Good luck finding a sea-view room in high season unless you’re booking a year ahead. And don’t even get me started on Lake Como wedding season. If you want Italy in 2026, booking early isn’t a flex—it’s survival. Check out my Virtuoso site for all of the hotels in Italy that offer Virtuoso perks and amenities. Italy is always my #1 seller so let’s connect if you need help planning.

2. Alaska

Here’s the thing everyone gets wrong: Alaska isn’t about availability—it’s about the right availability. The top expedition ships, small-group wildlife experiences, fly-in lodges, and glacier helicopter tours fill a year+ ahead, especially for mid-June to early August.

If you’re dreaming of bears, fjords, and actual serenity (not the 4,000-passenger version), early planning is non-negotiable. But even Holland America and Princess book up early. Cruise deposits are low! Save spots now for a year or two out. Now is a great time to book Alaska 2027. I am not kidding. Let me help you check all the options. Alaska is one of my biggest sellers. Let’s chat.

3. Japan (The New Italy in Terms of Demand)

Japan has become the destination that everyone suddenly needs to experience—food people, culture people, fashion people, even the “I need a cool family trip” people.

The issue? Japan has a finite number of luxury hotels and an even more finite number of licensed Japanese guides who speak English well. True story: Post pandemic, Japan had a shortage of licensed English-speaking guides! So many had retired. So they’ve been gradually training up their new guides. But add in cherry blossom season and…sigh.

If you want the dream version of Japan, you don’t wait. Let’s plan ahead. Luckily pricing seems to have come down a bit since the peak early this year. Check out my Virtuoso site for all of the hotels in Japan that offer Virtuoso perks and amenities.

4. Greece

Santorini and Mykonos aren’t the problem—you already know they’re crowded. The real crunch is on the luxury hotels that are actually worth staying in, plus the private boat captains, sunset cruises, and coastal guides.

Also: villas on Paros and Naxos? The good ones vanish early because there just aren’t that many.

Book early or get stuck with the leftovers. OR…if I can convince you…try somewhere new in Greece! I just put together a honeymoon proposal for Zakynthos and Kefalonia that I am very excited about. I also put together a great trip for clients recently to the Peloponnese.

5. African Safaris (Peak Season Has Its Own Rules)

Safari isn’t like booking a beach resort. You’re competing for a tiny number of tents in camps that cap at 12–18 rooms. The most sought-after camps in Kenya, Tanzania, Botswana, and South Africa will be completely gone 12–18 months out.

And if you’re bringing kids? Family-sized tents are always the first to go.

This is the ultimate “early bird or nothing” destination. Ready to book your safari? Book a complimentary vacation consultation here to talk more.

6. Cruises (Especially the New Ships and High-End Itineraries)

People always assume they can book a cruise “whenever.” That’s… not how cruising works anymore.

Here’s the honest reality:

• The newest luxury ships sell out 9+ months in advance.
Ritz Carlton Yacht, Silversea Regent, Seabourn, AmaWaterways—affluent travelers want what’s new, and the top-tier cabins go immediately.

• World Cruises book up the second they launch.
I’m not exaggerating. Some world cruise sailings have waitlists longer than the itinerary itself. If you’re even thinking about a world cruise someday, you need to be on the early-interest lists before launch.

• Holiday sailings (Christmas/New Year’s) disappear faster than anything else.
Christmas/New Year’s cruises sell a year ahead—sometimes two—because families and groups block the best suites. If you want the itinerary and the cabin category you want, you plan early or you don’t get it.

• Expedition cruises have brutally limited inventory.
Antarctica, the Galápagos, the Arctic—these ships carry 100–200 passengers, not thousands. Combine tiny capacity with high global demand and you get a perfect storm: sold-out seasons.

• River cruises are already tight for late 2025 and 2026.
Europe’s holiday markets, spring tulips, and summer sailings are almost always snapped up by repeat cruisers months before new travelers even start looking. Most river cruise ships only fit about 160 passengers. Remember that Viking isn’t the only game in town, and in fact they squeeze 30 more passengers onto the same size ship as Ama and Avalon. Viking spends $2.8 billion on advertising a year so that’s the brand people know, but there are so many other options!

Bottom line: Cruise inventory is finite, the good cabins go first, and the best itineraries reward the early birds—every single time.

7. Costa Rica Over Christmas (The Single Hardest Week to Book All Year)

Costa Rica is fantastic — but Christmas week? It might as well be the Super Bowl of family travel demand.

Here’s the part travelers don’t realize:

• Every good resort in Costa Rica requires 5–7 night minimums over the Christmas/New Year’s period.
Not “suggests.” Requires. And those rooms are typically released 330 days out — meaning you literally have one shot to grab them before they vanish.

• The luxury eco-resorts have tiny inventory.
Most of the properties your clients actually want (like the Nayara properties and Four Seasons Peninsula Papagayo) have shockingly limited room counts. The suites and villas disappear instantly.

• Families pounce early — they book two or three rooms at a time.
Parents, grandparents, teens, cousins… it’s like family travel bingo combined with a land-grab. If you want two connecting rooms or a suite with a private pool? You’re competing with every other family in North America.

• Flights over Christmas/New Year’s don’t “come down later.”
There’s no strategy here. A good fare to Liberia or San José over Christmas is a unicorn. Booking at 330 days gives you the closest thing to a fair shot.

• Costa Rica is extremely experiences-driven.
The best naturalists, private guides, river float experts, volcano and wildlife specialists? They don’t have unlimited availability. When the resorts fill, the guides do too.

The takeaway: If you want Costa Rica over Christmas, plan a year out for the best options. Not “early.” On time. I can help! Let’s talk.

8. The Caribbean Over Christmas/New Year’s & Spring Break (The Ultimate Availability Minefield)

Everyone thinks the Caribbean is “easy.” It’s not. Not during holiday weeks and not during Spring Break.

Here’s the truth:

• The smaller, more luxurious islands have brutally limited inventory.
Anguilla, St. Barts, St. Kitts, St. Lucia, Grenada, Antigua, the BVIs — these islands don’t have endless beachfront resorts. They have a handful of high-end properties, many with under 80 rooms. Translation: when they’re gone, they’re gone.

• Turks & Caicos is basically a pre-sell situation every single year.
Grace Bay’s top-tier resorts book out 12–15 months ahead for both Christmas/New Year’s and Spring Break, especially for suites and multi-bedroom units. Families lock them in early, and they don’t cancel.

• Mexico is the outlier — in a good way.
Los Cabos and Riviera Maya consistently offer more availability because the resorts are larger and flight access is easier. If you’re a little late to the party, Mexico often saves the day. There’s just so much inventory.

• Direct flights are the choke point most people ignore.
Smaller islands = fewer seats. Those flights get taken by people who booked months before you even started thinking about this trip. If you’re willing to connect through Miami, Charlotte, San Juan, or Panama City, your options multiply — and so do your chances of landing the resort you actually want.

• Villas and suites disappear first.
If you want a plunge pool, separate bedrooms, or beachfront? You’re in competition with families booking almost a year in advance.

The strategy: For the Caribbean during peak periods, flexibility is your best friend. Be open to connecting flights and give me a few islands to play with. The more flexible you are, the more magic I can pull off.

The Bottom Line…The Early Bird Gets the Worm…

If any of these destinations are on your mind for 2026 (or dare I say 2027), a little early planning goes a long way. These places simply book up quickly—especially the special rooms, the standout guides, and the experiences that turn a trip into something unforgettable.

Whenever you’re ready to start thinking through ideas, I’m here to help you get ahead of the rush and secure the pieces that matter most. The difference between a good trip and a truly extraordinary one often comes down to timing. Ready to make your plans for 2026 and 2027? Book a complimentary vacation consultation here.

About Krista

I’m a Virtuoso travel advisor based in West Palm Beach, Florida. I attended the University of Notre Dame for undergrad, and have my MBA from the University of Chicago. Prior to moving to Florida to take care of my elderly mom with Parkinson’s Disease, I spent over 11 years living and working in London, England. My background and 20 year career in the investment management industry have taken me all over the world. To date, I’ve been to 78 countries. Now I bring the joy of travel to others as a Virtuoso travel advisor. I offer a 30 minute complimentary vacation consultation to anyone looking to plan their next trip.

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Krista Nannery
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