Begin your journey at Minneapolis-Saint Paul International Airport with plenty of time to check bags and relax before the overnight transatlantic flight; pick up a coffee and a breakfast sandwich at a local café in Concourse C and confirm your e-ticket and boarding pass. Use the morning to settle in, enjoy duty-free browsing, and stretch your legs before boarding; consider downloading maps and offline guides for Rome so you’re ready on arrival.
Board your flight in the afternoon and settle into your seat for the overnight crossing — use the hours to watch a film, nap, and review your Rome highlights list including the Colosseum, Forum and Trastevere for later in the week. If your flight includes a meal service, savor a light dinner and hydrate well to help minimize jet lag; crew announcements should give you an approximate arrival time in Rome’s morning.
Arrive at Leonardo da Vinci-Fiumicino Airport in Rome in the evening (local time) and take a comfortable airport train or private transfer into the city, passing moonlit views of the Tiber as you approach central neighborhoods. Check into your hotel, freshen up, and if you have energy, enjoy a short stroll to a nearby trattoria for a first taste of Roman cuisine — think classic cacio e pepe or supplì — before turning in to rest for a full day of sightseeing tomorrow.
Wake early and head to the Colosseum to join a timed-entry tour that brings the amphitheater’s gladiator stories to life — consider booking the underground or third-ring access for dramatic views and fewer crowds. From there, walk across to the Roman Forum and Palatine Hill to wander ancient temples and basilicas, imagining republican Rome as you pause at the House of the Vestal Virgins and the Arch of Titus.
After a leisurely espresso and a slice of pizza bianca near the Forum, continue exploring nearby Piazza Venezia and the Capitoline Museums for classical art and panoramic views over the ruins. Meander down Via dei Fori Imperiali toward the iconic Vittoriano monument, stopping for gelato before a relaxed late-afternoon break at your hotel to recharge.
Cross the Tiber to Trastevere for an atmospheric evening of winding cobblestones and ivy-clad facades; start with aperitivo at a small wine bar like Freni e Frizioni, then dine at a family-run trattoria sampling Roman classics such as carbonara and fried artichokes. Finish the night with a stroll up to the viewpoint at Gianicolo for sparkling city lights and a peaceful end to your first full day in Rome.
Start early with a timed-entry visit to the Vatican Museums to beat the crowds — wander through the Gallery of Maps and Raphael Rooms before arriving at the Sistine Chapel to gaze upward at Michelangelo’s breathtaking frescoes. Pause in the Pinecone Courtyard for a coffee at the museum café and take a slower pace through the modern religious art collection if time allows.
Cross into St. Peter’s Square and climb (or take the elevator partway) to the dome for sweeping views over Rome and the Tiber, then descend to explore the vast interior of St. Peter’s Basilica, marveling at Bernini’s Baldachin and Michelangelo’s Pietà. After a reflective moment at the tombs and chapels, stroll across the bridge into the Borgo neighborhood for a relaxed lunch of Roman seafood or a classic panino near Via della Conciliazione.
Return to the historic center as daylight fades and enjoy an aperitivo near Piazza Navona, where the Baroque fountains glow under streetlamps — consider a light dinner at a nearby osteria serving seasonal Roman fare. Finish the night with a gentle walk back across the Tiber to Trastevere or a short detour to the illuminated Pantheon, savoring the sense of continuity from ancient Rome into the spiritual heart you visited today.
Catch an early high-speed train from Roma Termini to Napoli Centrale, enjoying a coffee and cornetto on board while reviewing your Amalfi transfer details; upon arrival, take a private transfer or the Circumvesuviana + SITA bus/drive to the coast, passing Mount Vesuvius and coastal villages en route. Arrive in Positano late morning and settle into your cliffside hotel, then step straight out to wander the steep stairways and pebble Spiaggia Grande for your first views of the dramatic stacked houses tumbling to the sea.
After a light lunch of fresh seafood or a lemon-infused salad at a beachside trattoria, climb up to the chic boutiques along Via dei Mulini and visit the Church of Santa Maria Assunta to admire its Byzantine Madonna and tiled dome. Continue with a relaxed stroll to Fornillo Beach or take the short, scenic hike along the Path of the Gods (or part of it) for sweeping coastal panoramas and postcard-worthy photo stops.
As daylight softens, enjoy an aperitivo on a terrace overlooking the bay — try a Limoncello spritz or local wine — before dining at a family-run osteria such as Chez Black or La Sponda for regional specialties like scialatielli ai frutti di mare. End the night with a leisurely after-dinner walk through illuminated alleys back to your hotel, the sound of waves below reminding you that tomorrow brings more Amalfi Coast discoveries.
Wake to a festive coastal morning and board a private driver or scenic SITA bus for the short, winding ride to Amalfi; begin at Piazza del Duomo to admire the Cathedral of St. Andrew and its striking striped façade, then wander the narrow lanes hunting hand-painted ceramics and sampling a warm pastry and espresso at a café near the waterfront. Pause on the marina to watch fishing boats bobbing against the cliffs before continuing up the coast toward Ravello.
Arrive in Ravello after a cliffside drive and step into a quieter, elevated world—visit Villa Rufolo’s terraced gardens for sweeping views of the Tyrrhenian Sea and the Amalfi coastline that inspired Wagner, then cross to Villa Cimbrone to stroll the Terrazza dell'Infinito for postcard-perfect panoramas. Enjoy a leisurely lunch at a terrace restaurant like Cumpà Cosimo or Ristorante Vittoria, tasting lemon-infused local dishes and a glass of Falanghina as the winter light softens over the sea.
Return toward Positano or your base as the coast lights begin to twinkle, stopping for photo ops at coastal viewpoints along the SS163 and a quick limoncello tasting in a seaside shop. Dine at a family-run trattoria back in town—savor scialatielli ai frutti di mare or fresh grilled fish—and finish with a peaceful post-dinner stroll along the water or a nightcap on your hotel terrace, the sound of waves below carrying you toward a restful sleep after a day of cliffside wonders.
Rise early and depart Positano for a short drive to the archaeological site of Pompeii, arriving when the light is soft and crowds are fewer; wander the remarkably preserved streets to visit the Forum, the House of the Vettii, and the amphitheater while your guide brings the daily life of ancient Romans to life. Pause for a strong espresso and sfogliatella at a café just outside the ruins before heading back toward Naples, reflecting on the juxtaposition of volcanic history and seaside scenery.
Return to Naples in the early afternoon for a relaxed lunch in the historic center — try a classic Neapolitan pizza at Sorbillo or L’Antica Pizzeria da Michele — and, time permitting, take a quick stroll through Spaccanapoli to glimpse artisan workshops and Baroque churches. Collect your luggage and transfer to Naples International Airport with plenty of time for check-in and a last limoncello or espresso at the terminal before your evening flight to Athens.
Board your evening flight and watch the Italian coastline recede as you cross the Ionian toward Greece; upon arrival in Athens, take a private transfer to your hotel and, if energy allows, enjoy a late-night walk in Plaka to admire the Acropolis lit against the night sky and grab a light bite of souvlaki or a glass of Greek wine. Settle into your Athens room knowing tomorrow you'll explore the Acropolis and neighborhoods that connect ancient history with lively modern life.
Start early to beat the crowds with a guided climb up the Acropolis, pausing at the Propylaea, the Temple of Athena Nike and the Parthenon to absorb the marble details and sweeping views of Athens and the Aegean beyond. After exploring the Erechtheion’s Caryatids and snapping photos from the Philopappos Hill viewpoint, descend through the ancient slopes to the Theatre of Dionysus and enjoy a mid-morning Greek coffee at a café near Dionysiou Areopagitou promenade.
Spend the afternoon at the Acropolis Museum, where light-filled galleries place exquisite finds — from friezes to votive offerings — back into their historical context; don’t miss the preserved Parthenon marbles and the top-floor viewing gallery that aligns with the monuments above. Follow with a relaxed lunch in the museum’s restaurant or a nearby taverna in Makrygianni, sampling grilled octopus or moussaka, then wander the adjacent Anafiotika enclave for narrow whitewashed lanes that feel like a Cycladic island tucked into the city.
As daylight softens, stroll through Plaka’s honey-colored streets browsing souvenir shops and family-run ateliers, pausing at a courtyard tavern for an early evening meze and a glass of Assyrtiko or retsina. Finish the night with a leisurely walk up to the Areopagos or a rooftop bar near Monastiraki to watch the Acropolis illuminated against the stars, reflecting on the day’s layers of history before returning to your hotel.
Depart Athens by early ferry from Piraeus (or a short domestic flight from Eleftherios Venizelos) and enjoy morning sea or sky views as you cross the Aegean; on arrival at Athinios port or Santorini (Thira) airport, transfer to your cliffside hotel in Oia, drop your bags, and drink in the first caldera panorama from your terrace. Take a slow walk through Oia’s whitewashed alleys to Ammoudi Bay for a seaside coffee and to watch local fishing boats bob against the volcanic cliffs.
After a light seafood lunch at a waterfront taverna in Ammoudi or a café near the Byzantine Castle ruins, explore Oia’s boutique shops, art galleries, and famed blue-domed chapels, pausing at the Maritime Museum if you’re curious about island history. For broader island context, consider a short drive to nearby Imerovigli or the Archaeological Museum of Thera to see finds from ancient Akrotiri before returning to Oia to prepare for sunset.
Secure a front-row sunset spot at the Oia Castle ruins or a terrace bar like Petra Restaurant for the iconic caldera light show as the sun sinks into the Aegean — arrive early to enjoy a cocktail or local Assyrtiko wine and the changing colors over the cliffs. After the sky fades, dine at a cliffside restaurant such as Dimitris Ammoudi Taverna or 1800 for fresh grilled fish and Santorinian specialties, then wander back through lantern-lit alleys to your hotel, the evening air full of sea-salted calm.
Start the day with a short cliffside drive from Oia to Fira, arriving early to wander the caldera-edge promenade and soak in sweeping views of the volcano and sparkling Aegean; stop for a leisurely breakfast at Naoussa Café or Franco's for coffee and pastries while watching cruise ships nestle in the caldera below. Explore Fira’s whitewashed alleys and the Archaeological Museum of Thera, then ride the funicular down to the old port if you’d like a different perspective of the island’s dramatic cliffs.
After lunch in Fira—try a taverna terrace specializing in fresh grilled fish or fava—join a guided winery tour that visits signature estates like Domaine Sigalas or Santo Wines, where you’ll learn about Santorini’s volcanic terroir and taste Assyrtiko, Nykteri and Vinsanto alongside local cheeses. Between tastings, pause at the vineyards for postcard-perfect caldera views and a cellar explanation of the island’s basket-trained vines, tying today’s sensory discoveries back to the island scenery you admired in Oia.
Return toward Oia or Imerovigli for sunset-caliber viewpoints and a relaxed cliffside dinner—consider Metaxi Mas or Selene for a refined local menu paired with Santorinian wines—then linger over dessert and a glass of Vinsanto while the evening lights of the caldera twinkle below. Finish the night with a gentle stroll under the stars through Oia’s lantern-lit lanes, savoring the lingering flavors from today’s tastings and the sense that Santorini’s volcanic landscape continues to shape each memorable moment.
Sleep in a little and savor a slow Santorini morning on your hotel terrace in Oia or Imerovigli, enjoying an espresso and local yogurt with honey while the caldera light shimmers one last time. Take a gentle stroll to nearby viewpoints or to Ammoudi Bay for a seaside walk, then pop into a bakery for a spanakopita or koulouri before checking out.
Transfer to Athinios port (or Santorini airport) with time to spare — if you’re leaving by ferry, enjoy the short drive past vineyards and the red/black sand beaches; if flying, arrive early enough to browse the small shops at Thira airport and sip a final glass of Assyrtiko. On arrival in Athens, take a private transfer to your hotel, drop your bags, and stretch your legs with a relaxed lunch in Monastiraki or Psiri, sampling a fresh Greek salad and tzatziki at a sunlit taverna.
As daylight fades, reacquaint yourself with Athens by wandering through Plaka’s atmospheric lanes toward a rooftop restaurant with Acropolis views — try a meze dinner at 360 Cocktail Bar or Kuzina to toast your travels. Finish the night with a leisurely stroll beneath the illuminated Parthenon, reflecting on Santorini’s volcanic calm and the lively urban pulse that will carry you into New Year’s Eve celebrations tomorrow.
Wake to a final Athenian morning with a visit to the National Archaeological Museum to catch highlights you haven’t yet seen—marvel at the Mask of Agamemnon and the expansive bronze collection—then stroll through nearby Exarchia for a coffee at Kiki de Grifo or a local boulangerie. Pop into the vibrant Central Market (Varvakios Agora) to sample olives, fresh cheese and loukoumades, picking up a few edible souvenirs and enjoying the lively market atmosphere.
Spend the afternoon shopping for last-minute gifts in Monastiraki and Ermou Street, hunting for handmade jewelry in the flea market stalls and contemporary Greek design in boutiques like Yannis Tseklenis or Zini; pause for a relaxed lunch of grilled souvlaki or a seafood meze at a tavern in Psiri. If time allows, visit the Museum of Cycladic Art or the Benaki Museum for a calm cultural interlude before returning to your hotel to freshen up for the evening festivities.
As dusk falls, join Athens’ New Year’s Eve energy on a rooftop near Monastiraki or in the lively districts of Gazi and Syntagma—book a rooftop table at 360 Cocktail Bar or A for Athens for panoramic views of the illuminated Acropolis and city fireworks. After a celebratory dinner with seasonal meze and Greek wines, mingle with locals at a plaza party or one of the organized countdown events, soaking in live music and fireworks as the city rings in 2026 before returning to your hotel or a late-night taverna for a final toast.
Enjoy a leisurely final Athenian breakfast at your hotel or a nearby kafeneio in Plaka, savoring Greek yogurt with honey and a strong ellinikós coffee while taking one last look at the Parthenon from a rooftop terrace. Pack and check out, then take a private transfer or taxi to Athens Eleftherios Venizelos Airport, leaving time to browse the airport shops for regional treats like olive oil, loukoumi and a bottle of Assyrtiko to bring home.
Complete check-in and security with plenty of time to relax in the departure lounge; enjoy a light lunch of spanakopita or a Greek salad at an airport café and recharge devices before boarding. Reflect on highlights from Santorini’s caldera to the ruins of the Acropolis as you board your transatlantic flight, settle into your seat, and begin the long journey west.
As the flight crosses time zones, rest, watch a film, or nap while the cabin lights dim, and take advantage of inflight meals and hydration to ease jet lag for the final leg home. Arrive at Minneapolis-Saint Paul International Airport in the evening, collect your bags, and reunite with family or local transport — closing out a memorable 12-day Italian and Greek adventure with stories, tastes, and photos to relive for years to come.