a beautiful sunset over the sea in Santorini Greece

2026 Itineraries Worth Planning Right Now

We believe every adventure should feel like a dream — effortless, immersive, and beautifully tailored to you. And the secret to crafting these unforgettable experiences is booking early. When you secure your trip months ahead, you unlock the very best destinations, the most charming boutique hotels, and the rare experiences that turn a vacation into a lifelong memory.

Why Booking Early Matters

Planning ahead means you can design your trip around the exact experience you’re hoping for rather than scrambling for what’s left. Early booking:

  • Guarantees availability in the most sought-after destinations.
  • Locks in the best prices.
  • Ensures you can stay in authentic, lovely accommodations and boutique hotels.
  • Gives you the luxury of time to get excited, research hidden gems, discover tiny restaurants, and savor the anticipation.

Most importantly, early planning delivers the greatest luxury of all: a perfectly crafted adventure, where every detail suits your style and every moment feels effortless.

Which Trips Most Warrant Early Planning:

Sun-Soaked Summers in the Greek Islands

June through August brings the Greek Islands to life in full technicolor. July and August are traditionally considered “peak season”, but in recent years, June and September also have crowds soaking up the good weather, swimmable seas, and buzzing energy. If you’re dreaming of that sun-soaked classic Mamma Mia vacation, summer is the time to go, and booking now is essential.

A family at a wine tasting table with views overlooking the sea in Santorini Greece

Summer is ideal for long beach days, island hopping under sapphire skies, and vibrant nightlife in the warm evenings. But ferries, hotels, and car rentals book up fast. We recommend securing your trip 4–6 months in advance (or more) for the best options and rates. With many islands offering mostly small-scale, charming accommodations, early planning is even more important for families or groups needing multiple rooms.

[Photo Credit: Alyssa & Jay via Shared Adventures —read about their Greece family Adventure here!]

Fall in the World’s Great Wine Regions

Autumn sweeps across Tuscany, Bordeaux, and Mendoza like a painting come to life. Featuring golden vineyards, crisp air, and beautiful boutique wineries that offer intimate tastings. But their charm comes with limited space, and they fill up fast.

If you want a fall wine getaway, the time to book is now so you can sip, savor, and stroll through the vines of your dreams and not just the ones that remain available.

[Photo Credit: Bucelleti Casali and Catina via Shared Adventures — read about Ann’s Tuscany adventure here!]

Wineries and hills in Tuscany Italy

A Fairytale River Cruise Christmas Escape

There’s nothing quite like Europe’s Christmas Markets in November and December. And to experience these on a river cruise delivers pure serenity. Picture yourself gliding past glowing cities while enjoying seasonal events and crisp, cool weather. These unforgettable moments are in high demand, and booking early ensures you get the best cabin, the ideal route, and every activity you’ve been dreaming of.

Christmas Markets cruises are limited to just a few short weeks of the calendar. And, but their nature, space is also limited. These aren’t the giant cruises of the high seas. The best cabins on prime sailings book up more than a year in advance, so you do need to plan ahead.

[Photo Credit: Ann via Shared Adventures – read our guide to River Cruises here!]


Are you ready to plan a year of extraordinary travel? Let us know! We’re always ready to begin planning your next great adventure – the earlier the better!

SHARE THIS

You provided excellent guidance for us. I appreciated that you really had us think about what was most important to us when we were selecting the right cruise – and not to totally focus on what other people had to say. THANK YOU for helping to make this a memorable trip for our family! It really was a trip of a lifetime!

Clare and Mark (family cruise to Alaska)

The level of service we experienced was out of this world (and we did NOT make it easy on Ann). We weren’t quite sure where we wanted to go, when we would be able to go, or what “vibe” we were going for. After asking us some key questions (what we liked, didn’t like, why, etc.) Ann helped us narrow down our trip details and planned the honeymoon of our dreams. She helped book some of our excursions, answered some emergency questions while abroad and was always available/willing to help. I think it’s safe to say we won’t be using anyone else for future travel planning – Ann is a rockstar!

Carli (Italy and Spain)