Booking a big trip is exciting—but it also comes with pressure. Whether you’re traveling overseas for the first time, taking time off for a long-awaited adventure, or planning a multi-stop journey, there’s a lot to think through. The more intentional you are at the beginning, the smoother (and more meaningful) your experience will be.
Here’s what to consider before you hit “book.”
Start with your why
Before you choose a destination, get clear on your purpose. Do you want rest or adventure? Connection or solitude? Are you celebrating something, or just in need of change?
This kind of reflection shapes your entire trip. If you want to reset, a week at sea or a quiet cabin in the mountains might be more impactful than a fast-paced city tour. If you crave inspiration, maybe it’s time for a trip that takes you out of your comfort zone—like a hiking trek, a cultural immersion, or an expedition cruise through Alaska.
The clearer your purpose, the easier it is to make decisions that support it.
Understand your travel style
Not everyone likes the same kind of trip. Some people thrive with a detailed itinerary, others want room to wander. Are you energized by being around people, or do you need lots of quiet? Do you want structure or spontaneity?
Be honest about what you actually enjoy—not what you think you should like. If you prefer having everything handled, a cruise or guided tour could be perfect. An Alaskan cruise, for example, bundles lodging, meals, transportation, and unforgettable views into one seamless experience—with optional excursions for every energy level. If you prefer freedom, maybe you book one-way flights and leave space for the unknown.
There’s no right answer—just the one that feels good to you.
Build a realistic budget
Your big trip doesn’t need to be extravagant to be incredible—but knowing your limits early helps you prioritize what matters most. Break down your estimated costs by category: flights, accommodations, food, transportation, activities, travel insurance, and extras.
From there, identify where you’re willing to splurge and where you’re happy to save. Maybe you’ll skip the five-star hotel so you can take a private wildlife tour. Or opt for a bundled cruise package to stretch your dollars further.
Don’t forget to include the “little” costs—luggage fees, airport transfers, visas, tips, and data plans. Those can add up quickly if you’re not prepared. If you’re flying into Greece, you can easily book an Athens airport taxi in advance and check rates to ensure a hassle-free arrival, saving you time and avoiding unexpected costs.
Research entry requirements and travel documents
This one’s easy to overlook in the excitement. Before you book anything nonrefundable, check if your destination requires a visa, vaccinations, or special documentation. Make sure your passport is valid for at least six months beyond your return date.
Some countries also require proof of onward travel, health insurance, or pre-arrival forms. If you’re traveling by cruise—especially to places like Alaska that might include Canadian ports—make sure your documentation covers every country the ship visits.
Taking care of this early can save a lot of stress later.
Choose the right time to go
Your dream destination might look very different in July than in October. Consider weather patterns, high vs. shoulder season, local festivals, and daylight hours.
If you’re planning something like an Alaskan cruise, for instance, peak season runs from June to August—but May and September offer fewer crowds, lower prices, and still-plenty-of-scenery. If you’re visiting the tropics, avoid hurricane season. For skiing, check snow forecasts. Timing shapes both your experience and your costs.
Compare trip types before locking in
It’s tempting to fall in love with a single idea—but take time to compare a few different options. What are the pros and cons of an independent trip vs. a tour? Would you enjoy a road trip more than flying between cities? What about train travel, cruises, or even a combination?
Sometimes, the style of travel makes all the difference. You might find that a route you assumed needed flights is better explored by rail. Or that a cruise, like the kind that hugs Alaska’s dramatic coastlines, opens up access to places you can’t reach by road.
Don’t overbook your days
It’s easy to fill your calendar with must-see attractions—but try to resist the urge. Leave room for rest, wandering, and the unexpected. Some of the best travel memories happen when you’re not rushing from place to place.
Instead, focus on anchor experiences—those core moments you want to build your trip around. Everything else can flow around them. If you’re cruising, that might be a glacier-viewing day, or a port you’re especially excited to explore. Let the rest breathe.
Thoughtful planning leads to better travel
Your next big trip isn’t just a getaway—it’s a chance to reset, reconnect, and expand your world a little. Planning it well doesn’t mean micromanaging every detail. It means making intentional choices that support how you want to feel.
Start with why. Follow what excites you. And when in doubt, let nature and movement guide you—like a slow train, a long hike, or the quiet glide of a ship through Alaskan waters. You’ll arrive more present, more open, and more yourself than when you left.
