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Sithonia is the least internationally known of Halkidiki's three peninsulas, and that's exactly why it works as a finale here; the pine forest running down to small coves around Kalamitsi and Toroni is genuinely undeveloped, and the shift from Thessaloniki's Byzantine density to that coastal silence is one of the sharpest contrasts this itinerary delivers. In Thessaloniki, the Modiano and Kapani covered markets deserve an hour before lunch: the city's food identity as a distinct market culture lands differently from anything in Athens, and it's worth experiencing even briefly. The port wine tasting in Porto earns more when you cross into Vila Nova de Gaia by the lower bridge and enter the caves from the riverside; the barrel scale and the temperature shift read completely differently from that lower level.
Sithonia is the least internationally known of Halkidiki's three peninsulas, and that's exactly why it works as a finale here; the pine forest running down to small coves around Kalamitsi and Toroni is genuinely undeveloped, and the shift from Thessaloniki's Byzantine density to that coastal silence is one of the sharpest contrasts this itinerary delivers. In Thessaloniki, the Modiano and Kapani covered markets deserve an hour before lunch: the city's food identity as a distinct market culture lands differently from anything in Athens, and it's worth experiencing even briefly. The port wine tasting in Porto earns more when you cross into Vila Nova de Gaia by the lower bridge and enter the caves from the riverside; the barrel scale and the temperature shift read completely differently from that lower level.
Day 1
Located in northern Portugal along the Douro River estuary, the old sailing port of Porto is a World Heritage Site and the second-largest city in the country. While retaining the timeless charm of a small town, Porto also has many of the modern advantages of a metropolis. Browse the expansive art collection at the Soares dos Reis National Museum, view the ornate interior of the Church of Sao Francisco, and explore the medieval maze of stairways and terraces in the old quarter of Ribeira. Don’t miss the chance to visit the Vila Nova de Gaia area to sample some of Porto’s famous Port wine. Other popular attractions include the 12th-century Porto Cathedral, Clerigos Tower and the Harry-Potteresque Livraria Lello bookshop, showcasing some magnificent neo-gothic architecture.








Experience the melancholic sounds of traditional fado in an atmospheric venue in the heart of Porto. Let yourself be enchanted by the emotional music and enjoy a selection of exquisite Portuguese wines at an exclusive wine tasting. A perfect combination of culture and enjoyment!
Day 2 - 3
The beautiful city of Lisbon lies draped across a string of seven hills on the western Iberian Peninsula and is the westernmost and oldest city in western Europe. Its long and tumultuous history has resulted in an aesthetic characterised by a haphazard combination of old and new; however, the aesthetic chaos of Lisbon only adds to its appeal and its undeniable charm. Bright yellow centenarian trams rattle their way up steep, tree-lined, cobbled streets; ornate ironwork balconies overrun with bougainvillaea sit above elegant outdoor cafes housed in ancient whitewashed, red-roofed stone houses; and a flurry of detailed mosaics decorate the sidewalks. Ancient statues adorn grand squares and hidden gardens. A diverse culinary scene, a plethora of fascinating museums, and numerous castles make it easy to see why Lisbon is one of Europe’s most misunderstood and underrated cities.









The Hop-on Hop-off 48-hour river cruise offers a flexible way to discover the city from the water. You can hop on and off at various stops and explore the sights at your own pace. Ideal for anyone who wants to experience a relaxed and varied tour.
Day 4
The port city of Thessaloniki enjoys a waterfront location at the Thermaic Gulf of Macedonia in northern Greece. This tourist favourite offers a wealth of cultural sights, vibrant cafe culture and exciting nightlife. Explore the ancient archaeological sites, including the remarkably well-preserved Roman Agora in the heart of town, the Rotunda Monument and the Arch of Galerius, among many others. The iconic architectural style of the Byzantine empire is evident throughout the city, most notably at the Agios Demetrios church and the Byzantine Baths, both protected UNESCO World Heritage sites. The White Tower - the well-preserved 16th-century structure - is the city's most emblematic landmark. The Archaeological Museum of Thessaloniki is a must-visit, as is the Museum of Byzantine Culture. Find a mix of esteemed shops and fabulous boutiques in the shopping district surrounding Tsimiski Street, or enjoy the myriad restaurants, cafeterias and nightlife on the lively seafront promenade.







Day 5 - 7
Situated in the Chalkidiki region of Northern Greece, the peninsula of Sithonia is sandwiched between the cosmopolitan city of Kassandra to the west and Mount Athos to the east. Also known as Longos, Sithonia is known for its wonderfully mild climate and offers a land of dramatic cliffs, pine forests, countless secluded coves, and over 100 pristine white-sand beaches lapped by crystal-clear turquoise waters. Visitors can enjoy a wide selection of fun-filled activities: rent a boat to explore remote and secluded beaches, cycle along the spectacular Sithonia Circuit, bike, or hike through Sithonia’s magnificent mountains. The crystalline waters of the Aegean Sea are perfect for diving, snorkelling and swimming. History and culture enthusiasts should make sure to visit the traditional villages of Parthenonas and Palia Nikiti.






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200+
Plan with professionals who are explorers themselves.
20+ hours of time saved
Our experts plan and book for you.
9+ Bookings managed
Everything is bundled in one place and perfectly planned.
7+ Transfers coordinated
For optimal transport and comfort.
Excellent
One night in Porto, two in Lisbon, one in Thessaloniki, and two in Sithonia — a compact week that covers more genuine cultural range than its brevity suggests. Portugal's fado-tinged Atlantic character and Greece's northern Byzantine identity are rarely placed in the same itinerary, and the contrast between them is exactly what gives the week its distinctiveness.
A detail a lot of travelers miss about Thessaloniki: the White Tower promenade at dusk, when the city takes its evening walk along the waterfront, gives you the social character of a Greek city in a way that Athens' more monument-heavy atmosphere doesn't provide. One night is lean, but the city rewards the time.
Hotel: TURIM Oporto Hotel
One night with the Ribeira district, a port wine tasting in a lodge cellar across the Dom Luís I Bridge, and the riverfront in the evening. The lodge cellars are best visited in the late afternoon when they're cooler — a short walk from the hotel. The view back across the river from Vila Nova de Gaia, with the Porto skyline stacked above the Ribeira, is the one worth stopping for.
Hotel: Portugal Boutique City Hotel
Two nights with the hop-on hop-off city exploration, the Alfama and historic district walks, and the fado experience. Book the fado venue before you travel — the intimate Alfama houses fill up on weekends, and the performance lands differently when the neighborhood you've spent the day walking is the one the music is about.
Hotel: Anatolia Hotel
One night with the Byzantine landmarks and the waterfront promenade. The Rotunda and Hagios Demetrios together cover the most historically significant ground. The Ladadika district behind the port, where the restaurants and bars fill the old warehouse streets, is the right place for a final Greek evening before the coast.
Hotel: Acrotel Athena Pallas
Two nights on the quietest of Chalkidiki's three coastal peninsulas. The smaller coves on the eastern coast of Sithonia — reachable on unpaved roads — have water clarity that rivals anything in the Cyclades. After the cities, having nowhere particular to be for two days is its own reward.
The best time for this multi-country trip is during the shoulder seasons of spring and fall. These seasons offer a perfect balance of pleasant weather, ideal for exploring cities like Lisbon and Thessaloniki, while also enjoying the coastal beauty of Sithonia and Porto before the intense summer heat.
The cost for this multi-country trip can be tailored to various budgets. On a mid-range budget, you can expect to spend around $140 per day in Portugal and around $160 per day in Greece, excluding flights. A budget-friendly trip starts at approximately $55 per day in Portugal and $65 per day in Greece.
This trip is a rich blend of cultures, art, and coastal landscapes. Highlights include a boat trip on the Douro River in Porto, the Byzantine churches of Thessaloniki, and the coastal beauty of Sithonia. For activities, you can take a culinary walk in Lisbon or a cooking class in Paros.
➔ Things to see Portugal | Activities Portugal | Activities Greece | Things to see Greece
7 Days
4 Stops
Private transfer
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4.4 of 5
5,368Reviews

4.4 of 5
5,368Reviews


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Top travel company—we’d book again anytime. My travel consultant was very friendly: I shared what we had in mind, and she planned the trip for us. She was also able to make adjustments when something didn’t quite fit—everything went perfectly. Afterwards, customer service took care of us and was quick to help. The trip itself was a dream. It’s also worth mentioning that we had a local guide we could message with any questions. Excellent support, and the Tourlane app was perfect—everything we needed right at hand on our phone. Many thanks to everyone who supported us on this trip.
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