Certain destinations—like Tuscany, Machu Picchu, or Paris—are perennially popular with travelers. And for good reason! But sometimes, the most enriching travel experiences are found a bit more off the beaten path. 

That’s often been my experience on my own journeys. Today, I’m recapping three of my favorite lesser-known destinations that are definitely worthy of adding to your bucket list. As a bonus, they come with far fewer crowds, a more authentic feel, and an atmosphere that encourages you to truly slow down and savor your time there.

Madeira, Portugal

Portugal has become a hugely popular destination in Europe—but most people still skip Madeira in favor of sticking to the mainland and cities like Lisbon and Porto. But I absolutely fell in love with this island about 600 miles off Portugal’s coast (it’s actually closer to Africa, and comes with the sunshine and Moorish influences to prove it). 

It’s a resource-rich island made up of mountains and long swaths of beach, great for hiking, boating, swimming, and more. One of the best things to do there is take a cable car ride up to the top of the mountains, soaking in all the coastal views, and then ride a toboggan down the steep streets—it’s a thrill! Don’t skip the picturesque fishing villages that hug the coast; Winston Churchill used to spend time in one of them, painting the scene on canvas. 

My favorite thing about Madeira, though, is its incredible food scene. Of course, there’s tons of beautiful wineries producing Madeira wine (the island’s answer to the mainland’s port wine). The food, though, is extremely fresh and showcases the abundant produce on the island–we dined at one of Madeira’s Michelin-star restaurants one evening and were blown away by the creative courses.

Milos and Sifnos, Greece

If you’re dreaming of a Greek Island idyll, consider skipping Santorini and Mykonos and head to these gems instead. Milos is a gorgeous island in the Cyclades known for its numerous beaches, each more stunning than the last. From lunar-like landscapes carved out of limestone to powder-soft golden sand, you can spend an entire week on Milos just exploring different hidden coves.

But my favorite part of our Greek isle vacation was a day trip we took to neighboring Sifnos. This tiny spit of an island is actually considered the culinary capital of the Cyclades. On Sifnos, we toured a farm owned by a young couple, collecting ingredients along the way. We cooked a meal together, enjoying our bounty al fresco—and then topped off our indulgence with a hike featuring the most incredible Mediterranean views. This more intimate, authentic cultural exchange is definitely harder to come by in the more popular Greek islands!

Valle de Guadalupe, Mexico

Bypass the coasts and head inland for your next Mexico escape, to a region that totally stole my heart. The Valle de Guadalupe is an agricultural region in northern Baja made up of rolling hills of vineyards, posh BnBs and boutique resorts, and picturesque mountains rising on three sides. 

This is the heart of Mexico’s wine country; I loved visiting the family-owned wineries and enjoying a glass in the cool breeze—the region stays relatively temperate year round. The food, too, was incredible, and the desert-like landscape studded with olive groves was captivating. Valle de Guadalupe is just about two hours from San Diego by car, and not far from the Sea of Cortez; you could easily combine a trip here with a relaxing stint at a luxury resort along the Pacific Coast.

Ready to discover an “under-the-radar” destination for yourself?

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