There are trips you take, and then there are trips that mark time—the latter deserve a plan made with the guidance of an expert. 

We’re talking the kind of trips that become reference points like “before Patagonia” or “after the Nile,” which ultimately become the adventures your children are still talking about around the dinner table years later. And when it comes to creating experiences that quietly recalibrate how you see the world—and sometimes, even see yourself—we know a thing or two.

In a moment where last-minute bookings have become increasingly common, we’re making a different case entirely: the most meaningful travel of your life deserves a long-term plan. Because landmark journeys—including the ones requiring permits, deploying expedition vessels, or securing private aviation access—reward the early bird. And for these trips, planning twelve, eighteen, or even twenty-four months in advance isn’t simply practical; it’s how you unlock the extraordinary.

What if, instead of thinking about next summer, you started thinking about the next ten years? Mapping out a decade-long roadmap allows you to anticipate mile markers around big birthdays, retirement chapters, and even milestones in your children’s development…

Exclusivity translates to limited availability, and that’s precisely where your SmartFlyer travel advisor comes in. What if, instead of thinking about next summer, you started thinking about the next ten years? Mapping out a decade-long roadmap allows you to anticipate mile markers around big birthdays, retirement chapters, and even milestones in your children’s development—pairing each season of life with destinations worthy of the moment. So how, exactly, do you map a ten-year travel plan with intention? It starts with a conversation—and not about where you want to go next summer. Your SmartFlyer travel advisor will begin by asking you bigger picture questions: What milestones are coming up for your parents, spouse, and children? What pockets does work tend to peak in? What seasons of life do you want to mark in a meaningful way? What experiences would you regret missing if you waited too long?

From there, the plan begins to take shape, following a framework customized to you. Together, you’ll discuss how to: 

• Anchor the decade with milestone moments. Decade birthdays. Major anniversaries. The summer before your oldest leaves for college. A retirement year. Study abroad semesters and graduations. Your advisor helps place these on a long-view calendar first—because those dates aren’t flexible. 

• Match destinations to your children’s ages. This is where experience really matters. Maybe it’s a Galápagos expedition when they’re confident swimmers and still wildly curious. A month of language school in Spain before high school schedules and sports commitments narrow your window. A multi-gen villa summer while cousins still want to share rooms. Your advisor looks at not just where to go — but when it will land best. 

• Plan around limited inventory and ideal seasons. The most sought-after safari camps have fewer than a dozen suites. Prime migration weeks or peak dry-season dates can fill up one to two years in advance, especially for families who need multiple rooms and private vehicles. Mapping these out eighteen months ahead means you secure the right camp, in the right season—not what happens to be left. 

• Balance “pillar” trips with breathing room. A Nile cruise one year. A low-lift Caribbean reset the next.  Your advisor helps pace the decade so it feels intentional—not exhausting. 

• Track fixed-date global events. Olympics. World Cups. Total solar eclipses. These operate on immovable timelines, with hospitality inventory that disappears quickly. With a long-range roadmap, your advisor is watching booking windows and ready to act the moment they open. 

• Revisit the roadmap annually. Kids grow. Careers shift. Interests evolve. The plan isn’t rigid—it’s refined over time, adjusted each year to reflect where your life actually is. 

The result isn’t overplanning—it’s peace of mind. The trips that matter most are protected before life crowds them out. And when charted alongside a SmartFlyer travel advisor, the extraordinary doesn’t happen by accident. It happens because someone was thinking ten years ahead. To get your creativity flowing as you think about some pillar trips to include on your roadmap, we’ve rounded up some epic adventures for consideration.

For the Outdoor & Nature Enthusiast

Some landscapes demand reverence, while others demand perspective. A well-rounded decade of travel for the nature lover should include both cinematic wilderness and remote stillness—places that remind you just how expansive the planet truly is. 

Experience Intrepid Alaska

Alaska is a perfect starting point for the nature lover, and while cruising along its coast is an option that works best for many families, there are other creative ways to explore the United States’ northernmost territory. Instead, imagine a curated lodge circuit that begins in Anchorage and continues by helicopter into Denali’s dramatic terrain. For instance, a heli-adventure to Sheldon Chalet, located on the only privately owned land within Denali National Park & Preserve, becomes a journey that feels deeply personal and wildly cinematic. This is not about checking off “Alaska.” It’s about redefining how you encounter it.

See The Northern Lights

Further north, Norway and Finnish Lapland offer the chance to sleep beneath the Aurora Borealis. The Northern Lights are visible from late August through April, but seeing them well requires thoughtful positioning. Your SmartFlyer travel advisor can help you explore fjord hopping by private yacht, pairing Nordic design-forward hotels with wilderness lodges, and time excursions around snowshoeing, cross-country skiing, or dog sledding to ensure the magic unfolds with ease. 

Connect with Mongolia’s Expansiveness

For travelers craving vastness, Mongolia’s Gobi Desert introduces an entirely different scale. Luxury ger camps allow you to explore fossil fields, ride camels across dunes, and engage with nomadic communities—all within a landscape defined by silence. This is a destination that demands patience and rewards those who plan carefully. United Airlines offers seasonal nonstop flights from Tokyo to Ulaanbaatar, meaning the SmartFlyer Air Team can issue you a ticket from the U.S. to Mongolia through Tokyo. Yet another reason to plan in advance and get this bucket list destination on your travel roadmap.

Scuba in Raja Ampat

For those who feel most alive underwater, Raja Ampat in Indonesia remains one of the most biodiverse marine environments on Earth, making it somewhere that should be catapulted to the top of your list. Chartering a Rascal Voyages vessel in the region allows you to explore remote reefs in privacy, navigating marine seasons and conservation guidelines with precision. Plus, the Rascal way ensures that you can bring along the kiddos, providing invaluable real-life learning about biodiversity, from showing them real-life dragons to brilliantly colored corals and smoking volcanoes.

For the Active Traveler

Movement imprints memory differently. Arguably, some of the world’s most transformative journeys are earned on foot, on skis, or at altitude. 

Hike Through Patagonia

Patagonia feels almost mythic in its scale. Hiking through Torres del Paine National Park or Argentina’s Los Glaciers National Park reveals jagged peaks and glacial lakes that feel cinematic in every direction. Anchoring your stay at Tierra Hotels’ lodges—such as Tierra Patagonia, perched above Lake Sarmiento with uninterrupted views of the Paine massif—adds architectural drama and guided access that elevates the experience beyond a hiking trip. Incorporating Patagonia into a decade-long plan allows you to pair it strategically, perhaps linking it with Antarctica via a fly-cruise from Punta Arenas, reaching the continent in hours rather than spending days crossing the Drake Passage. The goal isn’t extremity; it’s orchestration.

Do A Ski Safari Through the Dolomites

In northern Italy, a ski safari through the Dolomites blends adrenaline with indulgence. Moving between alpine villages, stopping for long lunches in mountain rifugi, and concluding at a spa-forward retreat like FORESTIS transforms a ski trip into a fully realized alpine circuit. Over ten years, you might revisit the Alps in multiple seasons, layering hiking, cycling, and culinary exploration into your version of this dynamic destination, but seeing it by skiing from rifugi to rifugi is something truly remarkable.

Connect To Your Spiritual Side in the “Land of Happiness” 

Bhutan offers another kind of active journey—one rooted in spirituality as much as physical challenge. Hiking to Tiger’s Nest Monastery is physically demanding, but the deeper resonance lies in the country’s philosophy of Gross National Happiness and its “High Value, Low Impact” tourism model. Visa requirements and protective travel policies make advance planning essential. Whether you opt to do a multi-lodge circuit with Six Senses or Aman, you can chart your own path through mountains and valleys that feel both sacred and cinematic.

For the History Buff

Some travelers crave narrative above all else. They want to stand where history unfolded and understand the context that shaped it. If that’s you, we’ve got a few quintessential trips to prioritize. 

Set Sail Along the Nile

Cruising along the Nile offers one of civilization’s most immersive classrooms. From Luxor to Aswan, ancient temples rise from desert sands with staggering presence. Choosing a private or ultra-luxury vessel ensures you’re not merely passing by these sites, but engaging with them alongside expert Egyptologists who provide depth and nuance. Your SmartFlyer travel advisor will be sure to match you with the best suited subject matter experts to ensure you’re maximizing your visit to Northern Africa.

Do the Ultimate Morocco Circuit

A Morocco itinerary weaving through Casablanca, Fes, the Atlas Mountains, the Sahara Desert, and Marrakesh is sure to layer architecture, craft, cuisine, and landscape into one cohesive journey. Exploring medinas with private guides, spending nights beneath desert stars, and retreating to riads that feel more like private residences than hotels creates a narrative arc you won’t soon forget. Be sure to leave extra room in your bag for all the treasures you’ll uncover at the souks.

Embrace the Allure of the Golden Triangle

Delhi, Agra, and Jaipur coalesce to create their own iconic framework known as the Golden Triangle. When paired with private palace stays, exclusive artisan encounters, and wildlife extensions, the journey is sure to engage every sense. India rewards travelers who move thoughtfully, making this a destination well-suited to be planned by travel advisors who understand its beautiful complexity.

For the Epicurian

Food remains a primary motivator for travel, shaping not just where we go but how deeply we connect once we arrive. With thoughtful planning, your advisor can time reservations around seasonal harvests, secure coveted counter seats, and build itineraries that unfold through markets, kitchens, and vineyards rather than just landmarks. 

Dine Your Way Through Peru

Some destinations are tasted as much as they are seen, and Peru stands firmly in that category. Begin in Lima, where one of the world’s most dynamic dining scenes continues to redefine Latin American cuisine, before continuing into the Sacred Valley. From there, your travel advisor will arrange your journey to Machu Picchu aboard the Belmond Hiram Bingham, timing your arrival to avoid peak congestion and heighten the sense of cinematic anticipation as the Andes unfold outside your window. After experiencing the citadel at its most serene, continue on to Cusco, where a stay at Palacio Nazarenas offers quiet refinement at altitude, grounding the journey in both history and understated luxury.

For the Expedition-Minded

For those drawn to exploration by smaller vessels, sailing the Peruvian Amazon aboard Aqua Expeditions’ Aria Amazon offers an intimate counterpoint to traditional cruising. With just sixteen suites and the option for a full buyout, the experience feels less like a voyage and more like a private expedition through the Pacaya-Samiria National Reserve, where pink river dolphins surface at dawn and skiffs glide silently past dense jungle canopy. This is cruising reimagined—design-forward, wildlife-rich, and intentionally small in scale.

For the Wildlife-Driven

Some travelers are pulled toward vast landscapes and untamed ecosystems. They want early mornings on game drives, sundowners overlooking the savanna, and encounters that shift perspective. If that’s you, Africa deserves multiple chapters on your decade-long plan. 

Witness the Great Migration in East Africa

Kenya and Tanzania deliver some of the most extraordinary wildlife spectacles on Earth—and the lodges you select often define how you experience these special parts of East Africa. In Kenya’s Laikipia region, Ol Malo offers a family-owned, deeply personal safari rooted in conservation and community. For front-row access to the Serengeti’s drama, Singita Faru Faru pairs contemporary design with prime migration positioning. And in the Maasai Mara, refined camps such as Angama Mara place you high above the plains with panoramic views that feel almost cinematic. Timing is everything here—river crossings and peak wildlife months follow natural rhythms, not calendar dates—so your SmartFlyer travel advisor secures the right camp in the right region well in advance.

Do a South Africa Circuit

South Africa offers one of the continent’s most seamless introductions to safari, especially when anchored by the visionary properties of The Royal Portfolio. Begin in Cape Town at The Silo Hotel, where art-filled interiors overlook Table Mountain and the V&A Waterfront. Continue into the Winelands at La Residence for vineyard serenity before heading to Royal Malewane for a Big Five safari led by some of the most experienced guides on the continent. This circuit balances cosmopolitan energy, culinary excellence, and wilderness immersion within a single, thoughtfully paced journey. 

End with a Remote Indian Ocean Escape

After days on safari, few finales feel more transportive than Madagascar. A stay at Miavana by Time + Tide offers private-villa seclusion on a protected island off the country’s northeastern coast, where marine life, lemurs, and untouched reefs create an experience that feels worlds away from the mainland. Pairing bush with beach at this level adds restoration without sacrificing a sense of discovery—turning an already extraordinary journey into something truly singular.

Life at Leisure

Not every landmark moment demands exertion. Some are meant to unfold slowly—designed for celebration, restoration, and long afternoons that stretch into golden evenings. 

Charter a Yacht Through the Aeolian Islands

A private yacht through the Aeolian Islands allows you to dictate your own rhythm—swimming off volcanic coves, docking for lingering Sicilian lunches, and anchoring beneath Stromboli as it glows against the night sky. Milestone birthdays and anniversaries deserve settings that feel cinematic, and nothing feels more singular than gathering friends or family aboard your own floating villa. 

Escape to Bora Bora

In Bora Bora, guided shark and manta ray encounters introduce a dose of adventure within crystalline lagoons, while overwater villas provide the kind of privacy that encourages true pause. For an even more secluded chapter, a stay at The Brando elevates the experience entirely—set on a private atoll once owned by Marlon Brando, where sustainability, barefoot luxury, and profound stillness define each day. Over the course of a decade, alternating high-energy expeditions with restorative escapes like these ensures your travel roadmap remains balanced, intentional, and deeply personal.

Take Over a Mediterranean Villa

There is something timeless about a private villa. Whether perched along the cliffs of the Amalfi Coast, tucked into the hills of Mallorca, or overlooking the Aegean in Paros, a fully staffed estate becomes the backdrop for birthdays, reunions, and the kind of unstructured time that families rarely get at home. Days revolve around long lunches, market visits, and spontaneous swims—proof that sometimes the most meaningful travel isn’t about movement, but about staying put.