ALPINE TO AMALFI

ITALY

Italy rewards travelers who resist the urge to cover too much ground. This journey moves deliberately from the Dolomites' limestone towers and alpine air to Tuscany's vineyard-draped hills and then south to the Amalfi Coast's sheer cliffs above the Mediterranean. Three landscapes, three distinct rhythms, and twelve nights to let each one settle. The kind of Italy that takes longer to plan and considerably longer to forget.

Note that everything you see here is an example of what your trip could look like. Your adventure will be tailored specifically to you.

WHEN TO GO

DURATION

MAY - SEP

12 NIGHTS

LANGUAGE

ITALIAN

CURRENCY

EURO

ESTIMATED COST

$13,600

per person, excl. int'l flights

(based on two adults sharing)

Why this adventure

Italy's north-to-south range is extraordinary, and most people experience a fraction of it. This journey traces the full emotional arc: crisp alpine mornings in the Dolomites, where the light on the limestone at dawn is one of the better arguments for getting up early, to the slower, more deliberate rhythm of Tuscany, where the food and wine are not amenities but the point, to the Amalfi Coast's operatic combination of cliffs, sea, and the particular Italian talent for making excess look inevitable. Each region asks something different of you. The connecting thread is a pace that allows the asking.

Journey flow

The journey opens in the Dolomites, where the UNESCO-listed limestone peaks of South Tyrol rise above forests and alpine meadows, and the air at 1,800 meters has the quality of something that should be bottled. Days here move between guided hikes and the restorative rituals of a lodge that takes its relationship to the landscape seriously. Tuscany follows: a softer, warmer landscape of rolling hills, medieval hilltop towns, and estates where the food comes from the same ground you're walking on. The Amalfi Coast closes the journey in the way only the Amalfi Coast can, with cliffs that drop sheer to the water, boats that reach coves the roads can't, and evenings that refuse to end at a reasonable hour.

Take it farther

A truffle hunt in Tuscany with a local tartufaio and his dogs is genuinely worth building into the Val di Merse days, particularly in autumn when the white truffle season peaks, and the dinner that follows at Borgo's Michelin-starred Saporium is a logical extension of that morning. Extending the Amalfi section to include Capri, reached by boat from the coast in under an hour, adds a different register of Italian coastal experience. And for those who want to go deeper into the Dolomites, guided via ferrata routes through the high-altitude terrain above Forestis open up terrain that the standard hiking trails don't reach.

Customize this itinerary

Every trip we design is built around you: your pace, your curiosity, your definition of a good day. No set departures, no group tours, no one-size-fits-all anything. If this itinerary sparks something in you, let's talk about what that could look like for you specifically.

START YOUR JOURNEY

Adventure highlights

DOLOMITES ALPINE EXPLORATION

Guided hikes through UNESCO-listed landscapes at 1,800 meters, where the Dolomites' jagged limestone towers catch the light differently at every hour of the day and the Puez-Odle Nature Park stretches across some of the most dramatic terrain in the Alps. The mountain refuges along the trails have been doing this since before anyone thought to photograph it.

TUSCAN ESTATE LIVING

Three hundred acres of organically cultivated Tuscan estate, a Michelin-starred restaurant sourcing from the property's own farm, and a spa that takes the phrase "farm-to-table" into skincare as well as food. The Abbey of San Galgano, six minutes away, is the kind of place that arrives without warning and stays with you for a long time afterward.

AMALFI COAST BY BOAT

The Amalfi Coast's most interesting geography is below the road. Private boat excursions cover the sea caves, hidden coves, and cliffside villages that the winding SS163 can't reach, including the Grotta dello Smeraldo, where the water turns an improbable shade of green from the light refracting through underwater openings.

ITALY BY CONTRAST

The Dolomites, Tuscany, and the Amalfi Coast share a country and almost nothing else. The contrast between alpine silence, Tuscan pastoral warmth, and Mediterranean drama is not incidental to this itinerary. It's the point.

How it unfolds

DAYS 1-4

THE DOLOMITES

The journey opens on the slopes above Brixen/Bressanone, surrounded by dense forest with the Dolomites filling the horizon. Guided hikes cover UNESCO-listed terrain: the Puez-Odle Nature Park, the alpine meadows above the treeline, and the traditional mountain refuges that have been feeding walkers on these trails for generations. Evenings return to a lodge where the spa draws on forest-based therapies, the restaurant sources within its immediate landscape, and the bar uses herbs and berries foraged from the surrounding woods.

DAYS 5-8

TUSCANY

The Val di Merse sits 40 minutes south of Siena in the quieter, less-visited part of Tuscany, and the days here take on the rhythm of the land: vineyard walks, wine tastings, day trips to Siena, San Gimignano, and the roofless nave of the Abbey of San Galgano open to the sky. This is Tuscany at a pace that allows it to register as something more than a series of postcards.

DAYS 9-12

AMALFI COAST

The coast closes the journey in its own terms. Private boat excursions reach the sea caves and hidden coves that the coastal road misses entirely. Positano, Ravello, and the Grotta dello Smeraldo are all within reach. The final evenings are for cliff-side terraces, the sea view, and the particular satisfaction of a journey that covered Italy's full range without rushing any of it.

Where you could stay

FORESTIS DOLOMITES

A summit-perched sanctuary at 1,800 meters above sea level in South Tyrol, built on the site of a 1912 Austro-Hungarian sanatorium, its clean-lines architecture of stone, glass, and local spruce wood designed to frame rather than compete with the surrounding Dolomites. No clocks in the resort, days measured instead by the twice-daily drama of sunrise and sunset washing the limestone peaks in shades from salmon pink to deep red. A Small Luxury Hotels of the World member running on 100% renewable energy, with a spa built around forest-based therapies and a restaurant sourcing from within its immediate landscape.

BORGO SANTO PIETRO

A 300-acre organically cultivated estate in the Val di Merse region of Tuscany, 40 minutes south of Siena, where medieval pilgrims once stopped to heal and rest. Twenty-two individually styled rooms and suites in a 13th-century villa, a Michelin-starred restaurant, holistic spa, organic skincare range Seed to Skin, and a working farm whose output appears on the table each evening. A Michelin-starred treehouse restaurant built around a magnificent oak, and a spa team that takes biodynamic cultivation as seriously as the kitchen does. The kind of Tuscan property that makes leaving feel like a minor tragedy.

MONASTERO SANTA ROSA

Originally a Dominican monastery built in the 17th century, perched on a cliff in Conca dei Marini between Amalfi and Positano, striking the balance of seclusion without solitude. Twenty ocean-view rooms named after herbs grown in the property's gardens, a Santa Maria Novella-stocked spa, and a cliffside infinity pool that blends into the Bay of Salerno below. The Michelin-starred Il Refettorio serves alfresco on a terrace overlooking the Gulf of Salerno. Prince Albert of Monaco was among the first guests when it opened, which tells you something about the crowd this place attracts and absolutely nothing about why it's worth staying here. The cliff, the pool, and the view do that on their own.

Ready to start planning?

All Peregrine trips include:

Every trip we design starts from scratch, built around how you travel and what you're actually after. No fixed routes, no shared departures, no compromises. If something on this page resonated, that's a good place to start a conversation.