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SentieroCustomTravel

Bespoke journeys, considered from the ground up

Trip Inspiration

Every Sentiero itinerary begins as a conversation, not a template. The trips below are illustrative starting points — organized by the activity that anchors them — each one fully customizable in pace, season, lodging, and length. Select one to see a sample built in full.

Food & Culture
Cycling
Hiking & Walking
Golf

family, Food & Culture​

Winding white Strade Bianche near Florence and Tuscany, Italy

Tuscany  Apr-oct

Florence & the heart of tuscany

Renaissance art, architecture, and street food in Florence, then private cellars and long lunches among the cypress ridgelines of Val d'Orcia — vineyard tours, cooking classes, guided e-bike rides, and a hot air balloon ride — from the Four Seasons Florence to a private hilltop castello at Castello di Velona.

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Tower Bridge, London, England, UK

london & english countryside  year-round

london, windsor & stonehenge

A first family trip to London, all from a river-view room at the Savoy: Westminster Abbey and the Changing of the Guard, a private tour behind the glass at the Churchill War Rooms, the Crown Jewels, a speedboat down the Thames, and a day out to Windsor Castle and Stonehenge. Evenings bring afternoon tea, carved roast beef, Harry Potter’s London and a West End show.

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Cliffside villages of the Amalfi Coast, Campania, Italy

rome & amalfi coast, Italy  Apr-Oct

rome & amalfi coast

Ancient Rome for a few days — the Vatican, Colosseum, and a golf cart tour of the centro storico — then the Amalfi Coast: a private boat tour of Capri, a hike along the Path of Gods, and a pizza lover's tour through Naples, from Hotel de Russie to the Grand Hotel Excelsior Vittoria

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Cliffs of Salento coast in southern Puglia, Italy

PUGLIA & MATERA, ITALY  APR–OCT

puglia & matera

A night in a cave hotel in ancient Matera, then the Baroque lanes of Lecce and the olive groves of the Itria Valley: ceramics in Grottaglie, a cooking class with a local chef, a sail along the Otranto coast, burrata made by hand at a family farm, and an e-bike ride through trulli country. Stays run from Sextantio’s candlelit caves to Masseria Torre Maizza.

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Cycling​

Cycling through Nebbiolo vineyards in the Langhe, Piedmont, Italy

Piedmont, Italy  Apr-Jun, Sep-Oct

Langhe Truffles & Wine

Five nights of vineyard roads through Barolo and Barbaresco — rolling hills, traffic-free roads, and manageable climbs — with carne cruda all'albese and tajarin al tartufo on the table, and truffle season adding an optional detour into Alba's autumn market.

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Lake Garda and the Dolomite foothills, Trentino, northern Italy

Trentino, Italy  Jun-sep

trentino Lakes & Mountains

Alpine climbs, valley roads, and river bike paths with the Brenta Dolomites Lake Garda as a backdrop.  Trentino DOC wine and private vineyard tours from our friend and local wine producer host.  Five-star luxury and boutique hotels each evening.

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Hiking & walking​

Hiking trail through the Italian Dolomites — hut-to-lodge adventure

alto adige, Italy  Jun-sep

Dolomites Huts to Lodge Adventure

Alpine meadows and mountain-hut lunches through the Dolomites' finest terrain — Alpe di Siusi, Val Gardena, Sella Pass, Sassolungo, and the Sciliar — moving between five-star Virtuoso alpine resorts with pools and rifugios perched high along the trail.

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Golf​

Ballybunion Golf Club overlooking the Atlantic Ocean, County Kerry, Ireland

southwest ireland   may-sep

Southwest ireland links

Storied links courses across Counties Clare and Kerry — Doonbeg, Lahinch, Ballybunion, Waterville, and Tralee — with private driver transport weaving in iconic sights and experiences around each round and 5 star luxury accommodation each night.  

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The Old Course at St. Andrews, Fife, Scotland — the home of golf

Scotland   may-sep

St. Andrews & East Lothian

Historic links across St Andrews and East Lothian — the Old Course, Muirfield, Kingsbarns, and Dumbarnie among them — with a private whiskey tasting to close out the rounds, and evenings at the Old Course Hotel and the Marine North Berwick.

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