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Why limit yourself to just one trip a year? With a little foresight, it’s often easier than you think to plan two—or even several—journeys that fit naturally into your life.
Rather than saving all your travel dreams for a single, high-pressure vacation, mapping out travel across the year allows for more balance, flexibility, and enjoyment. Early planning opens the door to better experiences, greater choice, and the freedom to travel on your terms. Here’s how to approach 2026 with intention and make room for more meaningful journeys.
Make Travel a Year-Long Priority
The most fulfilling travel doesn’t happen by accident. When trips are treated as an afterthought, they tend to get squeezed into whatever time is left. But when travel is planned early, it becomes part of the rhythm of your year.
Think of travel as a long-term investment rather than a once-a-year indulgence. Shorter getaways and longer adventures both have a place, and together they create a more rewarding travel calendar. Look ahead at the year and identify a few windows where travel fits naturally—perhaps a spring escape, a longer summer journey, and a quieter trip later in the year. Blocking time early helps ensure those plans stay protected.
Federal holidays are a great way to add extra days to your trip, especially when they result in long weekends. Some, like Christmas, can even form the theme of your travels.
Plan Around What’s Happening
Some travelers love to build trips around major global events, while others prefer to experience destinations at quieter moments. Many enjoy a mix of both. Whatever you choose, knowing what’s happening when helps you plan more strategically.
In 2026, major events include:
- Winter Olympics, Milan and Cortina d’Ampezzo, Italy (February 6–22)
- FIFA World Cup, United States, Canada, and Mexico (June 11–July 9)
- Total solar eclipse, visible across parts of North America, Greenland, Iceland, and Spain (August 12)
- Asian Games, Nagoya, Japan (September 19–October 4)
Beyond these, seasonal highlights such as cherry blossom season, Oktoberfest, and wildlife migrations can shape the best time to visit a destination. Understanding the calendar allows you to decide which trips to prioritize now and which might be better suited to another time—making it easier to plan more than one journey in a year.
Book Early to Expand Your Options
Early planning is one of the simplest ways to improve your travel experience. Booking well ahead of time gives you access to the most desirable accommodations and experiences, from intimate safari lodges to iconic train journeys like the Ghan.
It also removes the pressure of last-minute decision-making. With more time, you can refine itineraries, secure preferred dates, and confidently plan multiple trips without compromise. And if circumstances change, adjusting plans early is often easier than missing out altogether.
Mix Longer Journeys with Short Getaways
Traveling more doesn’t always mean traveling longer. A smart travel year often includes a mix of experiences: a longer, immersive journey paired with a few shorter escapes.
A cultural city break or a week in nature can fit neatly into smaller pockets of time, while a longer trip allows for deeper exploration. This approach makes travel feel more accessible and diverse and ensures that all your anticipation isn’t tied to a single departure date.
Take Advantage of Shoulder Seasons
Shoulder seasons (the periods between peak and low seasons) are ideal for travelers looking to fit more trips into the year. With fewer crowds and a slower pace, these periods often deliver some of the most authentic experiences.
While the weather may be slightly less predictable, that unpredictability can add atmosphere and character. Whether it’s fog shrouding the Cliffs of Moher or a European city easing out of summer, shoulder-season travel often rewards those who plan thoughtfully and can make additional trips more feasible.
Check the Practical Details Early
Small logistical details can have an outsized impact on travel plans, especially when you’re planning more than one trip.
Passport validity is a common example. Many countries require passports to be valid for at least six months beyond travel dates. Checking expiration dates early, and renewing in advance, helps avoid limitations later in the year. Taking care of these details upfront keeps your options open as opportunities arise.
Stay Open and Flexible
Flexibility is one of the greatest advantages of planning ahead. When dates, destinations, or events shift, having a broader view of the year allows for creative alternatives.
At Enchanting Travels, our specialists draw on firsthand experience across more than 70 destinations worldwide. Often, a trip begins with a specific place in mind and evolves into something shaped by a theme: wildlife, culture, cuisine, or slow travel. Keeping an open mind can lead to experiences that feel even more personal and unexpected.
Plan More, Travel Better
Traveling more often isn’t about rushing or overpacking your calendar. It’s about planning with intention, thinking beyond a single trip, and making thoughtful choices early.
By mapping out more than one journey per year, booking ahead, and paying attention to key details, you’ll create space for trips that feel seamless and deeply rewarding. As you look ahead to the rest of 2026 and beyond, our experts are here to help you plan smarter, so you can experience more of the world along the way.
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