A Luxury Greece Trip Worth Returning For: A Luxury Travel Advisor’s Guide to Going Deeper
Photo captured in Meteora, Greece
This luxury Greece trip taken by a travel advisor reveals why returning to Greece opens up off-the-beaten-path regions like Metsovo, Meteora, and Crete; where slow travel, luxury hotels in Greece, and authentic local experiences replace the usual tourist trail.
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What draws you back to a place you've already visited?
For me, I planned my second trip to Greece because my first visit—Athens, Santorini, Mykonos, Paros—left me wanting more in the best way possible. Not just more island views, moussaka, or historical monuments…but more depth. More local connection. More of the feeling that comes from knowing a place deeper, beyond the iconic landmarks.
This second Greece trip was intentionally different because I designed an itinerary that moved luxuriously slowly and ventured into regions that rarely appear on most travelers' radars. What I discovered was a Greece off the beaten path, defined not by what I saw, but by how deeply I experienced it.
This return trip was a reminder that when you travel often, the most memorable experiences come from exploring familiar places in unfamiliar ways.
A Luxury Greece Hotel Worth Traveling For: MANNA
After landing in Athens, we drove two hours west into the Peloponnese, where mountain air meets dense forest and the pace immediately shifts. Our first stop was MANNA, a minimalist luxury hotel tucked into the forest, where every design choice directs your attention outward into nature.
While I know the idea of driving 2 hours after a plane ride sounds less than ideal, this luxury Greek hotel was the perfect ‘reset button’ to set the tone for the rest of the trip. I often recommend to my clients to either start or finish a trip with a few relaxing days at a hotel like this. For travelers juggling demanding careers and family logistics, this kind of intentional slowdown isn't indulgent—it's necessary.
Spa appointments awaited us upon arrival, the restaurant served dishes made entirely from local ingredients, and hiking trails began right outside our door made it easy to relax and start diving into the experience. There were no crowds, no schedules demanding attention…just stillness and space to decompress after travel.
Mana isn't a property designed for constant activity. It's for travelers who understand that luxury can mean permission to do less. To linger over breakfast. To take a walk without a destination. We spent two nights here, and by the time we left, I felt grounded in a way that only nature and intentional quiet can provide.
Photo captured in Thessaloniki, Greece
North to Thessaloniki: Layers of History and the Sea
From the Peloponnese, we traveled north to Thessaloniki, Greece's second-largest city. I expected it to feel busy like Athens, but it didn't. Thessaloniki has energy, yes, but one that felt much more local. Plus, it offers those relaxed ‘close-to-the-sea’ vibes. The seaside promenade is ideal for leisurely walks, and cafés spill onto sidewalks where locals and travelers alike gather over espresso.
What struck me most was the depth of history here. Thessaloniki has been part of both the Byzantine and Ottoman Empires, sits on the ancient Silk Route, and still carries the legacy of Alexander the Great. You walk past ancient ruins nestled beside modern neighborhoods, and the layers of culture feel palpable, not preserved behind glass.
Day trips from Thessaloniki lead to nearby wineries or biblical sites, making this an ideal base for travelers drawn to history, culture, and authentic connection. It's also incredibly practical from a logistics standpoint, with direct flights from across Europe. It’s a perfect starting point for exploring Northern Greece.
For a luxury Greece itinerary that balances urban energy with relaxed seaside living, Thessaloniki delivers with fewer tourist crowds.
A Day Trip to Meteora
Photo captured in Meteora, Greece
One of the most memorable experiences of this trip to Greece was a day-long stop in Meteora, about two hours from Thessaloniki.
It's nearly impossible to describe how surreal this place feels. Narrow rock spires shoot straight up from the earth, and perched atop them are monasteries built centuries ago. The landscape feels otherworldly, and is a destination I’d definitely recommend to rock climbers, photographers, and nature enthusiasts. But honestly, any traveler will be awed by Meteora!
We visited the largest monastery, walking through century-old rooms. From the terrace we could see rock climbers making their way to the summit of a nearby rock tower and a small crowd of us cheered them on as they reached the top. It was one of those unplanned moments that unfolds naturally when you're not rushing and a reminder that some of the best travel memories can’t be planned.
Metsovo and Grand Forest Hotel: Greece's Best-Kept Secret
A couple of hours from Meteora sits Metsovo, a small mountain village that became one of the biggest surprises of the entire trip.
We stayed at Grand Forest Metsovo, a rustic-luxe hotel overlooking Pindos, one of Europe's largest and least visited national parks. The architecture fits seamlessly into the landscape, and every room offers views of either the surrounding forest or the village of Metsovo perched on the opposing hillside.
This luxury hotel in Greece isn't about polished marble or grand lobbies. Its luxury is found in a profound sense of place, with intentional design that blends the lines between hotel and nature. I would send travelers here who love hiking and outdoor aventures.
For example, our days in Metsovo were filled with what I'd call soft adventure: hiking through ancient forests, e-biking along quiet trails, and participating in the most authentic truffle-hunting experience I've ever done. Our guide led us deep into the woods with his dog, and then prepared us a rustic outdoor lunch of local fare that, of course, used our newly found truffles.
Everything about Metsovo felt local, grounded, and genuine. This is Greece off the beaten path in its truest form, and somewhere I would send travelers drawn to untouched nature and meaningful local connection.
Corfu: Lush Greenery and Aqua Seas
Leaving the forests of Metsovo in the morning, we drove a couple of hours to the coast, took a one-hour ferry, and by afternoon, were on the island of Corfu. The contrast from pine forests to aqua blue seas was striking, and another example of curating understated luxury without rushing.
Corfu is part of the Ionian Islands, which are known for being lush, green, and mountainous (different from the drier Cycladic islands like Santorini or Mykonos). It’s such a beautiful island, both nature-wise and through its Venetian-infleunced architecture. I highly recommend planning some time to simply drive around the island and take in the views.
(If you've watched The Durrells in Corfu, you'll immediately understand Corfu's charm!)
And of course, getting out on a boat here is essential. The caves, rock formations, and turquoise waters are some of the most beautiful I've seen. We spent the day exploring sea caves and their interesting geological patterns.
An important note about hotels in Corfu is there are mostly larger hotels and resorts rather than boutique properties. We stayed at Corfu Imperial, a Grecotel Resort, which was beautiful and had delicious food, stunning views, a wonderful spa, and direct access to the beach.
Chania, Crete: The Highlight of a Greece Itinerary
Our final stop was Chania on the island of Crete, and without question, this was the highlight of this entire luxury Greece trip.
Crete is Greece's largest island, and you feel its depth immediately. It's incredibly diverse—from a landscape perspective, yes, but also in terms of what you can experience here. Ancient ruins sit beside Venetian harbors. Thousands of olive groves stretch across hillsides. Mountains rise high enough for serious hiking, with gorges like Imbros and Samaria offering everything from moderate to strenuous treks.
But what I loved most about Crete was the presence of locals. Unlike islands where tourism is seasonal and residents leave during the off-season, Crete is home to people who live here year-round. We saw school groups walking through the old town on field trips. Cafés were filled with locals, not just travelers.
Chania itself is a beautiful town where history layers upon history. In the old town harbor, there's a mosque from the Ottoman Empire. The lighthouse was a gift from Egypt. The waterfront architecture is Venetian. You're walking through centuries of culture—Minoan, Byzantine, Ottoman, Venetian—all still visible, all still present.
From an experience standpoint, Crete offers everything. Olive oil tastings where you learn how production is done sustainably and ecologically. Wine tastings featuring ancient grape varietals you won't find anywhere else in the world. Cooking classes. Boat days exploring entirely different stretches of coastline. Archaeological digs still uncovering new history.
If you travel to the center of the island near Heraklion, you'll find Knossos Palace and more historical sites. Head far east to Elounda, and you'll discover luxury resorts and pristine beaches.
Needless to say, you could plan an entire Greece itinerary just on Crete alone. I am tempted to plan a third trip to Greece just to explore this island!
What a Second Trip to Greece Taught Me
This luxury Greece itinerary reinforced something I've long believed: the most meaningful travel isn't about seeing the most popular sights. When you slow down and curate a trip intentionally, you open up possibilities that many other travelers miss.
By returning to Greece with intention, I discovered unfamiliar regions, stayed in luxury hotels that prioritized connection to place over excess, and experienced a side of the country that felt genuine, unhurried, and deeply rewarding.
If you've already visited Greece (or any destination, for that matter) once, consider going back. But in a different way. Stay somewhere smaller. Leave time each day for unplanned memories. Let curiosity—not checklists—guide your days.
Because sometimes, the richest journeys aren't about discovering new places. They're about discovering what you missed the first time.
Whitney Shindelar
Undiscovered Sunsets was a long time in the making, even if I myself didn’t realize it. During my time at the University of Northern Iowa, I studied abroad in New Zealand. Upon graduating, I bought a one-way ticket to France, lived with a French family and studied with classmates from Turkey, China, Russia, Germany, Italy, and everywhere in between. In 2010 I began teaching English as a foreign language. This job quickly took me to China, where English teachers were in high demand and within three years, I began working in a 5-star hotel, speaking Mandarin throughout most of my day. In total, I lived abroad for 7 years.
I consider Undiscovered Sunsets to be the perfect mélange of my personal experience traveling the world and my professional experience working in the hospitality industry.
I look forward to designing your next adventure!
Frequently Asked Questions
Q: What makes a luxury Greece itinerary different from a typical Greece vacation?
A: A luxury Greece itinerary prioritizes depth over breadth, with longer stays in each destination, boutique properties that reflect their surroundings, and experiences designed around personal interests rather than must-see checklists. It's about seamless transitions, authentic connections, and travel that feels effortless (particularly when you hand over the planning details to a luxury travel advisor like myself).
Q: What are the best Greece off the beaten path destinations to visit?
A: Metsovo offers access to one of Europe's least-visited national parks with incredible hiking and truffle hunting. Thessaloniki provides rich history without the crowds of Athens. Crete's interior regions and mountain villages reveal authentic local life. These destinations offer the luxury of genuine connection and undiscovered beauty.
Q: Which luxury hotels in Greece offer the most authentic experiences?
A: MANNA in the Peloponnese immerses you in nature with forest views and spa treatments. Grand Forest Metsovo overlooks a vast national park and emphasizes rustic luxury with a strong sense of place. While you won’t find many boutique options in Corfu, the Corfu Imperial, a Grecotel Resort is a stunning resort.
Q: How long should I plan for a luxury Greece trip to see multiple regions?
A: A well-paced luxury Greece trip typically spans 10-14 days, allowing 2-3 nights in each region to truly experience the destination without rushing. Crete alone can fill 7-10 nights given its size and diversity, while Northern Greece regions like Thessaloniki, Meteora, and Metsovo combine beautifully over 5-7 days.
Q: What kind of travelers is this type of Greece itinerary best for?
A: I would plan this type of Greece trip for well-traveled people looking for truly unique experiences or those who travel often and don’t want to visit the typical tourist sites. If you haven’t visited Greece yet and want to go to Athens, Santorini, and other popular destinations, I would tailor your itinerary to help you weave in classic staples at your own pace.
