After arriving and checking in, start your day with a leisurely Greek coffee and pastry at Taf Coffee in the lively Psiri neighborhood before heading to the hill of Filopappou (Philopappos Hill) for sweeping, less-crowded views of the Acropolis and city-perfect for stretching your legs and snapping photos. Continue with a gentle wander through the tree-lined paths to the historic Arcadian Gate (Philopappos Monument) and end the morning by exploring the nearby Anafiotika quarter's whitewashed alleys and charming balconies for a quiet introduction to Athens' layered history and local life.
Stroll down to the vibrant Monastiraki Square to browse the weekend flea market and hunt for unique souvenirs among antiques and handmade goods, then duck into Little Kook for a whimsical themed coffee and dessert break. Continue with a relaxed guided visit to the nearby Roman Agora and the atmospheric Hadrian's Library, where you can soak up ancient Athens before an early evening aperitif at a rooftop bar overlooking the illuminated Acropolis.
As twilight falls, wander to Anafiotika Viewpoint for a quieter sunset perspective before heading down to sample meze at the convivial Taverna Saita in the nearby Plaka lanes. Finish the night with a nightcap at A For Athens rooftop bar, where the illuminated Acropolis Museum and the glowing Parthenon create an unforgettable Athenian skyline to toast your first evening in Greece.
Begin with a guided early visit to the hilltop Acropolis, where you can walk the Parthenon terrace, admire the Erechtheion's Caryatids, and enjoy city panoramas before crowds arrive. After descending, explore the nearby classical treasures at the Acropolis Museum, then sip a cappuccino on the museum's terrace overlooking the ruins as you plan the rest of your Plaka wanderings.
Wander down to Monastiraki Square to explore its lively stalls and antiques market, then follow Ermou Street to the peaceful Anafiotika Steps for tucked-away photo spots and traditional island-style houses. Pause for a late lunch of grilled seafood and chilled retsina at the waterside tavern Kuzina (or a nearby Plaka meze spot), then climb to the terrace of Areopagus Hill for golden-hour views before drifting into the labyrinthine lanes of Plaka to shop for ceramics and handmade jewelry.
As dusk settles, take a relaxed stroll through the ivy-draped lanes of Psyri, stopping for inventive small plates and local wines at Oinoscent to sample contemporary Greek flavors. After dinner, head to Lycabettus Hill by funicular for a panoramic night view of the city and the glittering Acropolis below, then finish with a late-night coffee or cocktail at the intimate rooftop bar Couleur Locale to soak up the Athenian nightlife atmosphere.
Catch an early ferry from Piraeus and, after arriving at Mykonos Port (Chora Harbour), drop bags at your hotel before strolling to Matoyianni Street to browse boutique shops and enjoy a late Greek breakfast at Lena's House. Continue with a relaxed walk toward Alefkandra (Little Venice) to sip espresso by the sea and watch fishermen mend nets, then climb up to the windmills near Kato Mili for classic Cycladic views and photos as you map out the island for the afternoon.
After a relaxed morning in Chora, head to the quieter north coast for a swim and sun-soaked lounge time at Agios Sostis Beach, where a barefoot taverna like Kiki's Tavern (no reservations, rustic charm) serves charcoal-grilled seafood. Later, explore the island's rural heart with a scenic drive to Ano Mera to visit the 16th-century Monastery of Panagia Tourliani, then sit down for a late-afternoon meze and local loukoumades at a village kafeneio as the light softens over the countryside.
As dusk falls, wander to the quieter waterfront of Psarou Bay for a cocktail at a chic beach club terrace, then continue to the atmospheric fishing quay of Fokos to sample fresh grilled octopus at a seaside taverna while listening to waves. Finish with a leisurely after-dinner stroll through the twilit lanes toward Manto Square, pausing for a gelato or single-origin espresso as whitewashed houses and lanterns cast a soft island glow.
Start the day with a relaxed seaside breakfast at Fokos Taverna (arrive early for peaceful views) before heading to the sheltered cove of Kalafatis Beach for windsurfing lessons or a calm swim in crystalline waters. After a few hours of sun and water sports, explore the nearby fishing village of Ornos for a mid-morning coffee at Spilia Seaside and a stroll along the marina to watch local fishermen and luxury yachts juxtaposed against classic Cycladic architecture.
Head south to the sheltered cove of Paraga Beach for a relaxed seaside lunch at Alemagou-lounge on sunbeds, swim in clear water, and try a chilled rosé as DJs spin mellow afternoon sets. Later, return toward Chora to wander the cobbled lanes of Little Venice (alternate quay areas around Alefkandra) for golden-light photos, then climb to the quieter terrace of The Windmills viewpoint opposite the famous mills to watch the light soften over the Aegean before an early evening aperitif.
As twilight deepens, head to the hillside terrace of Panagia Paraportiani Viewpoint for a peaceful sunset vantage away from the busiest quays, then descend to the waterfront of Drafaki Bay to dine on grilled seafood and island mezes at Sea Satin by Giorgos while lights shimmer on the water. After dinner, wander the charming backstreets toward Manto Square for a lively late-night coffee or ouzo at a local kafeneio, then finish with drinks and dancing at the intimate cocktail bar Caprice overlooking the marina.
Board an early ferry from Mykonos and arrive in Santorini with time to drop bags and stretch your legs at Perissa Beach, where you can stroll the volcanic black sand and grab a relaxed breakfast at Tranquilo (try their fresh fruit bowls and Greek yogurt). Afterward, head inland for a gentle exploration of Pyrgos Village-wander its maze of alleys, visit the hilltop Profitis Ilias Church for sweeping island views, and pause at Karamolegos Bakery for a pastry before your afternoon ferry arrival routines.
After dropping bags, wander the cliffside paths from Fira toward the quieter hamlet of Imerovigli, pausing at a cliff-top cafe like Avocado for a late lunch and panoramic caldera views as the light softens. Continue with a short hike to the dramatic Skaros Rock for a close-up of the volcanic cliffs and seabirds, then unwind with a sundowner and small plates at the intimate La Maison terrace while watching ferries slip into the caldera.
After settling in, wander from your hotel down to Firostefani Promenade for an easy cliffside stroll and catch the first glow on the caldera; pause at 1800-Floga for a cocktail on their terrace while the island light deepens. For dinner, head to Metaxi Mas in the nearby village of Exo Gonia for hearty Cretan-Cycladic dishes and local assyrtiko wine, then finish the night with a digestif and live bouzouki at the intimate Kira Thira Jazz Bar, soaking in the island's relaxed nocturne.
Wake with a leisurely breakfast on the terrace of Café Loulou in Oia, sampling fresh local honey, white cheese and a perfectly pulled Greek coffee while watching fishing boats glide below. Spend the morning exploring the quieter lanes toward Ammoudi Bay, descend the stone steps for a seaside stroll and fresh seafood tasting at Dimitris Ammoudi Taverna, then return via the coastal path to pause at the sculptural viewpoint of Byzantine Castle Ruins for sweeping caldera vistas and early light photography.
Stroll from Oia's center toward the quieter terraces of Mikri Vlychada (the scenic viewpoint near the fortress ruins) and pause for a light seafood mezze and chilled assyrtiko at Roka Restaurant while watching the caldera's shifting colors. After lunch, take a short boat excursion from Ammoudi Bay Marina to the volcanic islet of Nea Kameni for a guided walk across fumaroles and black lava fields, then return in time to relax with a coffee at Pelican Kipos before preparing for the famed Oia sunset.
As twilight deepens, wander down the quieter lanes toward Amoudi Bay's cliffside tavernas for a pre-sunset meze of grilled scorpionfish and a chilled glass of Assyrtiko while watching fishing boats return. After dinner, take a moonlit stroll along the caldera edge to Fira Lighthouse Viewpoint for a peaceful panorama of illuminated villages across the crescent, then finish with cocktails and live acoustic music at the intimate terrace of Skala Bar to cap a magical Santorini evening.
Begin with a relaxed tasting at Santo Wines, where a guided flight of local Assyrtiko, Nykteri and Vinsanto comes with sweeping caldera panoramas and an introduction to Santorini's volcanic terroir. Afterward, head inland to the ancient site of Akrotiri Excavations for a morning guided tour of the well-preserved Bronze Age ruins, then pause at the nearby Venetsanos Winery for a cellar tour and a light paired mezze on their cliffside terrace to connect the island's vinicultural history with its archaeological past.
After a morning of tastings and Akrotiri, spend the afternoon exploring the volcanic vineyards around Megalochori, beginning with a guided cellar tour and tasting at Gavalas Winery to learn about traditional basket-trained vines and sample their crisp Assyrtiko. Continue with a scenic walk through the village to Armeni Bay for a seaside late-lunch of grilled fish and tomato keftedes, then visit the small on-site exhibition at Megalochori Folklore Museum to connect local agrarian life with the island's winemaking traditions.
As dusk falls, head to Exo Gonia Square for a relaxed pre-dinner drink at Anogi Wine Bar, where small plates of local cheeses and tomato keftedes pair perfectly with a late-harvest Assyrtiko while village life drifts by. For dinner, reserve a table at Selene, famed for its modern take on Cycladic cuisine and tasting menus that highlight Santorini produce; finish the night with a short walk to the clifftop Prophet Elias Chapel viewpoint for a quiet panorama of the illuminated caldera and distant ferry lights.
After your ferry or flight back to Athens, enjoy a relaxed final morning with a breakfast of koulouri and freddo cappuccino at Mokka Specialty Coffee near the port, then stroll the nearby seaside promenade toward Piraeus Marina for a last look at Aegean boats and island-bound life. If time allows before your transfer, visit the compact but fascinating Nautical Museum of Greece for a quick dive into Greek seafaring history, then pick up a final selection of regional olive oil and honey at the artisanal stalls of Pasalimani Market to pack as souvenirs before heading to the airport.
After settling any luggage at a left-luggage service, take a leisurely stroll through Kastella (Pireo's elegant ridge) for seaside views and a late brunch at the waterfront bistro To Koutouki tou Marathonithi, sampling grilled sardines and a chilled local white. If time allows before your transfer, pop into Peiraiki Agora to pick up last-minute snacks (olive tapenade, regional spoon sweets) and then enjoy a tranquil seaside coffee at Kalamaki Café while watching ferries come and go-an easy, relaxed final taste of Athenian coastal life before heading to the airport.
For a final relaxed Athenian evening before your flight, wander the modern waterfront of Mikrolimano to sip a chilled ouzo or draft beer at a seaside terrace and watch luxury yachts drift by while enjoying a plate of grilled calamari. Continue with a short taxi to the sheltered neighborhood of Koukaki for a cozy dinner of charcoal-cooked souvlaki and seasonal salads at Thanasis Kouzina, then finish with a nightcap at the laid-back cocktail bar Drunk Sinatra to toast a memorable Greek week before your transfer.
| Place / Activity | Cost |
|---|---|
| Taf Coffee (coffee & pastry) | €4 |
| Filopappou (Philopappos Hill) | Free |
| Philopappos Monument / Arcadian Gate | Free |
| Anafiotika (neighbourhood walk) | Free |
| Monastiraki Square & flea market | Free |
| Little Kook (themed coffee & dessert) | €8 |
| Roman Agora | €6 |
| Hadrian's Library | €6 |
| Rooftop bar with Acropolis view (aperitif) | €12 |
| Anafiotika Viewpoint (sunset) | Free |
| Taverna Saita (meze dinner) | €25 |
| A For Athens (rooftop nightcap) | €12 |
| Acropolis (guided early visit) | €25 |
| Acropolis Museum (entrance) | €10 |
| Kuzina (waterside/Plaka lunch) | €30 |
| Areopagus Hill | Free |
| Plaka shopping (ceramics/jewelry) | €20 |
| Oinoscent (dinner, small plates & wine) | €30 |
| Lycabettus Hill funicular (roundtrip) | €7 |
| Couleur Locale (rooftop drinks) | €10 |
| Ferry Piraeus to Mykonos (fast ferry, per person) | €45 |
| Lena's House (breakfast) | €10 |
| Alefkandra (Little Venice) walk | Free |
| Kato Mili (windmills viewpoint) | Free |
| Agios Sostis Beach / Kiki's Tavern (lunch) | €20 |
| Ano Mera / Monastery of Panagia Tourliani (visit) | Free |
| Village kafeneio (meze & loukoumades) | €12 |
| Psarou Bay cocktail (beach club) | €15 |
| Fokos seaside taverna (dinner) | €25 |
| Manto Square (gelato/espresso) | €5 |
| Fokos Taverna (seaside breakfast) | €10 |
| Kalafatis Beach windsurfing lesson | €50 |
| Spilia Seaside (coffee) | €4 |
| Paraga Beach / Alemagou (lunch & sunbeds) | €35 |
| Windmills viewpoint (sunset photos) | Free |
| Panagia Paraportiani Viewpoint | Free |
| Sea Satin by Giorgos (dinner) | €30 |
| Caprice (cocktail bar) | €12 |
| Ferry Mykonos to Santorini (standard ferry, per person) | €35 |
| Perissa Beach / Tranquilo (breakfast) | €12 |
| Pyrgos Village & Profitis Ilias Church (walk) | Free |
| Karamolegos Bakery (pastry) | €3 |
| Fira to Imerovigli cliff path & Avocado (lunch) | €25 |
| Skaros Rock (hike) | Free |
| La Maison (sundowner & small plates) | €20 |
| Firostefani Promenade & 1800-Floga (cocktail) | €14 |
| Metaxi Mas (dinner) | €35 |
| Café Loulou (Oia breakfast) | €12 |
| Ammoudi Bay & Dimitris Ammoudi Taverna (seafood) | €30 |
| Byzantine Castle Ruins (viewpoint) | Free |
| Roka Restaurant (lunch) | €25 |
| Boat excursion to Nea Kameni (guided walk) | €25 |
| Pelican Kipos (coffee) | €5 |
| Skala Bar (cocktails & live music) | €15 |
| Santo Wines (guided tasting) | €18 |
| Akrotiri Excavations (entrance + guided tour) | €12 |
| Venetsanos Winery (cellar tour & mezze) | €25 |
| Gavalas Winery tasting & tour | €15 |
| Armeni Bay (late lunch) | €25 |
| Megalochori Folklore Museum (small entry/donation) | €3 |
| Anogi Wine Bar (pre-dinner drink & small plates) | €20 |
| Selene (tasting menu dinner) | €85 |
| Prophet Elias Chapel viewpoint | Free |
| Mokka Specialty Coffee (breakfast koulouri & freddo) | €4 |
| Nautical Museum of Greece (entrance) | €6 |
| Pasalimani Market (artisan shopping) | €10 |
| To Koutouki tou Marathonithi (brunch) | €18 |
| Peiraiki Agora (snacks) | €6 |
| Kalamaki Café (seaside coffee) | €4 |
| Mikrolimano waterfront (ouzo/beer & calamari) | €20 |
| Thanasis Kouzina (souvlaki dinner) | €12 |
| Drunk Sinatra (nightcap cocktail) | €10 |
| Estimated Total (per person) | €1,112 |