By Brianna Rothman

Some travelers love the thrill of booking a trip six weeks before departure. Others start planning two years out. As I see it, some travelers book a trip six weeks before departure. Others start planning two years out.

And honestly? Both approaches work — especially when you have a travel advisor in your corner.

But certain trips do reward a longer runway. Multi‑generational vacations, bucket‑list destinations, complex itineraries, and seasonal experiences often shine brightest when you have time to secure the best accommodations, plan around ideal weather, and savor the anticipation.

If your 2026 travel plans are already taking shape, now is the perfect moment to start dreaming about 2027. You don’t need to book anything today, but you can start imagining what the year could look like.

Below, I’ve rounded up some of the most inspiring destinations to consider — organized by season, so you can match your travel style to the time of year you want to explore.

🌷 Spring Travel Inspiration

Tulip Season in the Netherlands

When to Visit: April–May For a few magical weeks each spring, the Dutch countryside becomes a patchwork of vibrant tulip fields.

Washington, D.C. Cherry Blossoms

When to Visit: March–April. If Japan feels a bit ambitious for 2027, D.C. offers a beautiful stateside alternative with equally stunning blooms.

☀️ Summer Travel Inspiration

Amalfi Coast, Italy

When to Visit: June–September Long days, cliffside villages, sparkling water — summer is when the Amalfi Coast is at its most iconic. Add a few days in Tuscany for a dreamy Italian itinerary.

Aruba

When to Visit: June–August Located outside the hurricane belt, Aruba is a reliable, sun‑soaked option for summer travelers craving a classic Caribbean escape.

The Great Migration, East Africa

When to Visit: June–October Witnessing thousands of animals move across the Serengeti and Maasai Mara is one of the most extraordinary wildlife experiences on Earth.

Alaska Cruise

When to Visit: May–September Summer is prime time for wildlife viewing and glacier‑filled scenery — and cruising remains one of the easiest ways to explore Alaska.

🍇 Fall Travel Inspiration

Provence, France

When to Visit: September Harvest season brings slower days, golden light, and some of the most rewarding travel moments in France.

French Polynesia

When to Visit: September–November Ideal conditions, dreamy lagoons, and whale‑watching season make fall one of the best times to visit.

New Zealand

When to Visit: September–November As the Northern Hemisphere heads into autumn, New Zealand welcomes spring — perfect for outdoor adventures and road‑tripping.

New England Fall Foliage

When to Visit: September–October. A classic for a reason. Vermont, New Hampshire, and Maine deliver some of the most iconic fall scenery in the U.S.

❄️ Winter Travel Inspiration

European Christmas Markets (One of my favorites to plan)

When to Visit: Late November–December Whether by rail, river cruise, or independent itinerary, Christmas markets offer a festive, cozy way to experience Europe in winter.

Hawaii

When to Visit: December–March Warm breezes, sandy beaches, and a welcome escape from winter temps — Hawaii shines during the colder months.

Antarctica

When to Visit: November–March A short, exclusive expedition season makes Antarctica one of the most extraordinary and remote destinations on the planet.

Ski Season in the U.S.

When to Visit: December–March Colorado, Utah, and Montana offer everything from powder‑chasing to cozy lodge escapes.

Ready to Start Dreaming?

I can’t help with your PTO balance, but I can help you spend it well.

If one of these destinations is starting to feel less like a dream and more like a plan, reach out anytime. Let’s start mapping out your 2027 travels in a way that feels intentional, exciting, and beautifully tailored to you.