Getting Started: Where And When

Every trip begins with a spark — that first moment when the idea of going somewhere takes hold. But turning that spark into a real journey depends on a mix of timing, opportunity, and inspiration. Whether it’s a simple family getaway, a long-awaited dream destination, or an event that brings everyone together, every trip has its own story. Whatever your inspiration, the first step is getting started.

Family Vacation

Family vacations often start with the shared wish to reconnect, rest, and make memories together. The destination might depend on how much time you have — a weekend escape to the mountains or a week at the beach — and what everyone enjoys most. If relaxation is the goal, nature and space often win out over busy cities. If there are multiple generations at play, cruising is a popular choice as there is often something for everyone.

Timing, of course, plays a big role. School calendars shape when families can go, and finding that sweet spot between affordability, good weather, and school breaks can take a bit of planning. But even within those windows, there’s always room for adventure — whether it’s a road trip, a stay in a cozy cabin, or exploring a new national park.

When Life Sets the Date: Weddings, Reunions, and Events

Sometimes, travel isn’t about choosing when to go — it’s about being there when it matters. A destination wedding, a milestone birthday, or a family reunion can set your travel plans in motion. These trips often open doors to places you might not have considered otherwise. We are big fans of taking the celebration and making the most of being in the area. A weekend in Tuscany could lead to exploring Florence or beyond while a kid studying in New Zealand may inspire a trip to visit another continent.

The Pull of a Dream Destination

Then there are the trips we’ve imagined for years: standing before the Eiffel Tower, watching the sunrise over the Serengeti, or walking the streets of Kyoto in cherry blossom season. These journeys take shape slowly, fueled by stories, photos, or childhood dreams.

Choosing when to go becomes part of the magic — maybe waiting for the right season, the perfect light, or the moment when you finally have the time and money to savor it. For many, these trips are often predicated by milestones -- anniversaries, babymoons, honeymoons, graduations, or big birthdays.

Specific Experiences

For enthusiasts of certain activities, timing and seasonality are often what rev the trip planning engines. Here are some examples of timing-dependent trip desires.

• Viewing the Northern Lights or a solar eclipse

• Bike riding through the Alps or anyplace else

• Watching humback whales in Baja

• Skiing, hiking, bungee jumping, rafting the rapids, canyoneering, or camping, etc.

• Viewing gardens or bird migrations

If these are the types of things you want on vacation, congratulations -- you have a starting point!

For those with passions for things which are not seasonal, like wine tasting, gastronomy, art/ architecture/ culture/ museums, the world is your oyster in terms of timing. If you have flexibility, it may be a good idea to go during the off-season or the shoulder season so as to avoid pressing crowds and perhaps save some money on lodging.

Balancing Inspiration and Practicality

Every traveler finds their balance between what’s possible and what’s ideal. Some trips come together because time allows it; others because your heart or pocketbook insist on it. Maybe it’s the only week everyone’s free, or maybe it’s your once-in-a-lifetime chance to see the Northern Lights.

The best trips often blend both — a bit of spontaneity mixed with thoughtful timing.

In the end, travel is about moments — not just the ones you plan, but the ones that surprise you. Whether you’re guided by school calendars, wedding invitations, the desire to experience a beloved activity, or the call of an iconic landmark, each journey starts with a decision to go. And that decision is where every great travel story begins.