Your journey begins in Rome. Eternal and ever-evolving, Rome is a city where layers of history rise effortlessly into modern life. Ancient ruins stand beside bustling cafés, Renaissance palaces open onto lively piazzas, and everyday moments unfold in the shadow of monuments that have shaped the world.
In the afternoon, you will meet at your hotel for a brief orientation and introduction to the journey ahead. To conclude the evening, we gather for our first dinner together at a traditional Roman restaurant, sharing local flavors and conversation as we begin to get to know one another, in quiet anticipation of the adventure that lies ahead.
Overnight in Rome
Dinner included
Today, we discover the highlights of Rome on a guided walking tour with a local expert, bringing the Eternal City to life through its most iconic landmarks. We stroll through centuries of history as we visit the Pantheon, the Colosseum, the Roman Forum, Trevi Fountain, and Capitoline Hill, among other treasures, covering approximately 4 km on foot. Along the way, ancient ruins, grand piazzas, and lively streets reveal the layered story of a city that has shaped Western civilization for millennia.
After time for lunch and a final taste of Rome’s vibrant atmosphere, we depart in the afternoon and leave the city behind as we journey into the heart of Tuscany. The landscape gradually transforms from urban sprawl to rolling hills, cypress-lined roads, and open countryside as we travel toward Pienza, a Renaissance hill town set in the Val d’Orcia.
Overnight in Pienza
Breakfast and dinner included
Driving distance:
Rome to Pienza 190 km / 3 hr
Today we set out on a full-day hike through the rolling green landscapes of Tuscany, following quiet country paths that wind between cypress trees, scattered farmhouses, wheat fields, and distant hilltop villages. Departing directly on foot from Pienza, we walk into the heart of the Val d’Orcia, a landscape shaped by centuries of agriculture and beautifully balanced between nature and human cultivation, where every ridge reveals another sweeping view.
Our route leads us first toward the iconic Chapel of the Madonna di Vitaleta, standing alone among the fields, before continuing across gentle hills and open countryside toward Bagno Vignoni. Here we conclude our hike in the unique atmosphere of this historic thermal village, where warm waters fill the central square and steam rises gently from ancient stone basins that have drawn visitors since Roman times. The evening is at leisure, allowing you to explore and dine wherever you choose.
Overnight in Pienza
Breakfast and lunch included
Hiking distance: 12,8 km / Hiking duration: 4 hr
Elevation gain & loss: 228 m & 480 m
Say farewell to the Val d’Orcia and set off toward Siena, a magnificent medieval city that once rivaled Florence in wealth and influence, built on centuries of banking, trade, and artistic patronage. Upon arrival, we explore the historic center on a guided visit, wandering through its atmospheric lanes and discovering highlights such as the striking Piazza del Campo, famously home to the dramatic Palio horse race held twice a year, as well as the impressive cathedral, a masterpiece of Gothic architecture and craftsmanship.
In the mid-afternoon, we continue by a short drive into the heart of Tuscany to San Gimignano, a beautifully preserved hill town renowned for its medieval skyline of stone towers, once symbols of wealth and power, now rising above vineyards and olive groves in the surrounding countryside where we settle in for the next two nights. As the day winds down, we gather for dinner in a local restaurant, sharing regional dishes and a final glass of wine as the town slowly settles into its evening rhythm.
Overnight in San Gimignano
Breakfast and dinner included
Driving distance:
Pienza to Sienna 55 km / 1 hr
Sienna to San Gimignano 41 km / 50 min
Today we set out on a scenic hike through the rolling countryside surrounding San Gimignano, leaving the town’s towers behind as we follow quiet paths through vineyards, olive groves, and open Tuscan hills. The trail unfolds through classic wine country scenery, with cypress trees and scattered farmhouses marking the rhythm of the landscape, until we arrive at a family-run organic winery nestled among the vines. Here, the hike concludes with a wine tasting experience paired with a light lunch, showcasing the estate’s wines alongside local seasonal dishes, all enjoyed in the relaxed setting of the Tuscan countryside.
After returning to San Gimignano, the afternoon is left free to explore at your own pace, whether wandering its historic lanes, visiting a museum, or simply enjoying a gelato in one of its lively squares.
Overnight in San Gimignano
Breakfast and lunch included
Hiking distance: 10 km / Hiking duration: 4 hr
Elevation gain & loss: 274 m & 317 m
Leave the rolling hills of Tuscany behind as we journey toward the Ligurian coast, driving approximately three hours to Levanto, a relaxed seaside town just north of the Cinque Terre. Here, we take time to wander its laid-back streets and perhaps sample local specialties such as fresh focaccia or farinata, a traditional chickpea flatbread, before setting off on foot along the coastline.
Our hike follows a scenic trail climbing above the sea toward Monterosso al Mare, the largest of the five villages and our base for the next three nights. Along the way, panoramic views open over the rugged coastline and the colorful villages perched between cliffs and sea. By late afternoon, we arrive in Monterosso, where the pace softens and, as the day visitors depart, a quieter side of the Cinque Terre begins to emerge.
Overnight in Monterosso
Breakfast and dinner included
Hiking distance: 8 km / Hiking duration: 3 hr
Elevation gain & loss: 563 m & 556 m
Driving distance:
San Gimignano to Levanto 190 km / 3hr
Spend the day hiking the scenic trails of the Cinque Terre, moving between its iconic villages along historic coastal paths. We begin directly from Monterosso al Mare, following a beautiful trail to Vernazza, often considered the most picturesque of the five, where there is time to wander the harbor or pause for a coffee by the sea.
From here, the path continues to Corniglia, perched high above the water with sweeping coastal views and a quieter atmosphere. After some time to explore, we return to Monterosso by train. In the evening, we gather for dinner at a local restaurant, enjoying fresh regional dishes and the relaxed ambiance of the Ligurian coast.
Overnight in Monterosso
Breakfast and dinner included
Hiking distance: 10 km / Hiking duration: 4 hr
Elevation gain & loss: 700 m & 689 m
This morning, a short train ride brings us back to Corniglia, where we resume our journey along the coast. The trail leads us high above the sea toward Manarola, crossing a landscape shaped by centuries of human effort, steep slopes carved into narrow terraces and planted with vines that seem to cling to the cliffs. The path offers sweeping views over the coastline before descending into Manarola, where there is time to pause, explore, and perhaps enjoy a gelato or a relaxed lunch by the water.
After the day’s hike, we return to Monterosso al Mare by ferry, offering a different perspective of the coastline from the sea. In the evening, we gather once more for a final dinner, celebrating the journey and the landscapes we’ve explored together.
Overnight in Monterosso
Breakfast and dinner included
Hiking distance: 6,5 km / Hiking duration: 3 hr
Elevation gain & loss: 370 m & 319 m
Breakfast is at your leisure at the hotel. Following this, you will transfer independently to the nearest airport for your onward flight home, or choose to extend your stay and continue exploring Italy at your own pace, perhaps returning to a favorite city, discovering a hidden corner, or simply allowing a little more time to linger in la dolce vita.
Breakfast included
We are constantly updating our unique itineraries based on new information and experiences available. The walks, accommodations, and visits listed may be adjusted. The itineraries presented are subject to modification and change by Tripin Adventures. We reserve the right, without penalty, to make changes in the published itinerary whenever, in our judgment, conditions warrant, or if we deem it necessary for the comfort, convenience, or safety of participants, anything not mentioned in above program.
