10 days

Magical Tuscany & the Portofino Peninsula

Magical Tuscany & the Portofino Peninsula

Cinque Terre's Lover’s Walk

Florence - the birthplace of the Renaissance

Portofino Peninsula walk

UNESCO World Heritage-listed medieval Siena

Trip rating
  • Spend six days among the splendour of Tuscany and complete your journey with a few days walking on the famous Cinque Terre and the elegant Portofino peninsula.

    Why we love it

    • We start in Florence, the city that gave birth to the Renaissance
    • Visit Montepulciano, with it’s labyrinthine cobblestone streets lined by boutiques and wine cellars
    • Discover charming villages such as Monticchiello and Bagno Vignoni, hidden to mass-tourism by their location and tiny size
    • Stay for a couple of days in Siena, a Tuscan city of refinement and class
    • Uncover the secrets of the hilltop village of Volterra, famous for its magnificent sunsets and Etruscan ruins dating back more than 2000 years
    • From our base in charming Santa Margherita, we make excursions to Portofino and the Cinque Terre


    Day 1 - Florence

    • Your trip will start today with your arrival in Florence, the cultural capital of Italy and the gem in Tuscany's crown.
    • No activities are planned for today so you may arrive at any time. Please make your own way to the joining hotel that is centrally located (details will be in your travel documents).
    • Whilst at your discretion, we recommend arriving/ departing by train where possible within Europe, as this method of transport has minimal carbon emissions.
    • There really is so much to see in Florence, so if you are arriving earlier, plan to make a few discoveries of your own.
    • In the evening you will meet your tour leader and fellow travelling companions at a welcome meeting (this is usually at 6 pm, but you will be advised as to the exact time and place in a notice, located near the reception at our hotel), where the leader will give you a briefing on what lies ahead on the tour.
    • This evening you will enjoy a group dinner together at a local restaurant in Florence.
    Hotel La Fortezza or similar

    Day 2 - Arezzo - Montepulciano

    • From your hotel you will walk into the heart of Florence with your tour leader and take some time to explore the outstanding works of art preserved over the centuries in this captivating city. Florence is considered the birthplace of Renaissance, as well as the cradle of the Italian language.
    • You will stroll along its fascinating streets, and enjoy the essence of Italian history and culture. You will also pass along the Ponte Vecchio Bridge, visit Piazza della Signoria and gaze up at the landmark of Florence, the Duomo.
    • At around midday you will drive to the town of Arezzo, the setting for the movie 'La Vita è Bella' and in Roman times, the most important city of the Etruscan federation.
    • You will be free to wander around this interesting town and enjoy lunch at your leisure.
    • In the late afternoon you will travel on to Montepulciano, one of Tuscany's most attractive hill towns. You will settle into your hotel in the historical centre, and have some time to walk through the old town and perhaps have a drink before enjoying a group dinner together.
    La Terrazza Di Montepulciano or similar
    Breakfast | Dinner

    Day 3 - Montichiello - Montepulciano

    • After breakfast you will walk to the impressive Chiesa di San Biagio, a 16th century Church nestled at the edge of the village walls overlooking the winding valley below.
    • From here you will commence your walk into the picturesque valley and through vineyards, olive groves, past pastel coloured villas and across rolling hills.
    • This is a morning of delightful Tuscan scenery enjoyed and experienced at its best - by foot.
    • You will then reach the restful village of Monticchiello, where you will enjoy a flavoursome lunch under the welcome shade of creeping grapevines, with a stunning view out upon Monticchiello's ancient main village gateway.
    • After lunch the bus will pick you up from Monticchiello and you will drive back to Montepulciano and then enjoy a sightseeing tour of its labyrinthine maze of alleyways and laneways and imposing defensive walls.
    • You will then be treated to a wine tasting in a local cellar, sampling this region's fine nectar.
    • The rest of the afternoon will be at leisure to explore and enjoy some shopping in Montepulciano's classy boutiques. (Walking time: 3-4 hours, walking distance: 10 km)
    La Terrazza Di Montepulciano or similar
    Breakfast | Lunch

    Day 4 - Pienza - San Quirico d'Orcia - Siena

    • This morning you will be transferred to the beautiful village of Pienza for a short sightseeing walking tour.
    • Part of the tour will include views from Pienza's city walls that are quite simply mesmerising.
    • You will take time to pause and enjoy the captivating vistas afforded to you. The epitome of Tuscan landscapes rolling expansively before you - burnt orange villas, tightly wound hay bails, meandering country lanes and fields of barley.
    • You will then depart for the charming village of San Quirico d'Orcia, where you will buy lunch.
    • The distinctive landscapes of the Val d'Orcia, flat chalk plains interspersed with almost conical hills topped by fortified settlements have inspired many artists.
    • It is in this bucolic setting that you embark on your next splendid walk, which takes you to the unique Spa town of Bagno Vignoni. Here the main town 'square' is actually a picturesque ornamental pool built by the Medici family!
    • You can also cool your heels in the many Etruscan water channels that surround the old watermills just outside of the centre. This is a truly unique attraction in the Val d'Orcia, all but unknown to mass tourism.
    • You will complete this fabulous day by arriving in Siena in the late afternoon.
    Locanda Di San Martino or similar

    Day 5 - Siena

    • After breakfast you will walk directly from the hotel to commence your morning sightseeing tour of Siena, a fascinating chance to discover the best of this most celebrated medieval city.
    • Its heart, in every sense, is the famed 'Piazza del Campo', a grand fan-shaped piazza built on the site of the old Roman forum. Bordering the southern flank of the square is the 14th century Palazzo Pubblico, with some fine early Renaissance frescoes.
    • Also of interest is the beautiful main church, the Duomo, a wonderful mixture of Gothic and Romanesque architecture, with a particularly splendid façade.
    • Your guide will show you the most interesting monuments as well as the hidden corners of this 'red city' before some free time to explore.
    • The afternoon will be at your leisure to shop or further explore the multitude of museums on offer. Many may just take a seat in the Piazza del Campo, sip on a local glass of sangiovese and partake in another fine Italian tradition - the art of people watching.
    Locanda Di San Martino or similar

    Day 6 - Monteriggioni - Colle Val d'Elsa - Volterra

    • After breakfast you will journey towards ancient Volterra.
    • On the way you will pay a short visit to Monteriggioni (already mentioned in historic manuscripts from the time of Dante) and the charming small town of Colle Val d'Elsa.
    • Monteriggioni, sitting atop a small natural hillock, is a completely walled medieval town in the Siena Province that dates back to the 13th century.
    • Its splendid fortifications were ordered by the overlords of Siena to command the Cassia Road running through the Val d'Elsa and Val Staggia.
    • Your next stop at pretty Colle Val d'Elsa is equally worthwhile in terms of scenic appeal, and this small Tuscan town is responsible for close to 15% of the world's fine crystal glassware production.
    • In the early afternoon you will arrive in beautiful Volterra, full of Etruscan history, and famous for its alabaster.
    • You will enjoy a guided tour through the town, the Roman theatre, and the Etruscan ruins.
    • At the end of the day you may stroll through the restful parklands or catch Volterra's famed sunset from the town walls, before having dinner in a fine local restaurant.
    Hotel Cavallino Blu
    Breakfast | Dinner

    Day 7 - Volterra - Cinque Terre - Santa Margherita

    • You will bid a fond farewell to Tuscany and enter the province of Liguria and your next destination - the Cinque Terre.
    • The vehicle will bring you to La Spezia, and from here you will take a train to the village of Riomaggiore, the last village on the Cinque Terre.
    • Riomaggiore is a tiny collection of pastel shaded houses clinging unfeasibly to cliff faces spilling down into the sea.
    • The postcard perfect harbour, populated with tiny rowboats painted in a kaleidoscope of colours, is where you will begin the world famous walk.
    • You will walk the most scenic section of the 'Lovers Walk' to the village of Manarola, and enjoy lunch looking out to sea.
    • In the early afternoon - as a group - you can also opt to continue the walk towards Vernazza, arguably the prettiest of the five villages.
    • In the late afternoon you will board the train for an hour ride along the dazzling coast to your pretty base in the village of Santa Margherita Ligure. (4 hours walking/ 10 - 12 kms depending on route taken)
    • PLEASE NOTE: Due to recent landslides in the area some sections of the Lover's Walk may be closed to the public due to safety concerns. Should this still be the case at the time of your visit we will be choosing an alternative walking route instead.
    Hotel Jolanda or similar
    Breakfast | Lunch

    Day 8 - Portofino - Santa Margherita

    • After breakfast you will begin a scenic stroll to glamorous Portofino. En-route you will spend time exploring the best of charming Santa Margherita including its wonderfully coloured historic heart and the awe-inspiring harbour.
    • You will walk through a pleasant agricultural landscape, dotted with beautiful fin-du-siècle villas and monasteries.
    • Along the intriguing 'Valley of Mills' you will reach the pleasant beach of Paraggi, where you will make a short stop.
    • You will walk on along a beautiful footpath along the coast to Portofino itself.
    • As you approach Portofino proper you will take time to visit its impressive castle and lighthouse, which are not be missed!
    • The tiny hamlet of Portofino is arguably Italy's finest residential address and titles to properties here pass from generation to generation with the utmost of care and security.
    • Its hillsides and picture-perfect harbour are an enclave for presidents and movie stars. A visit here is truly something special.
    • The afternoon will be at your leisure, or perhaps you may wish to do the optional walk back to Santa Margherita along a pleasant coastal route (in about an hour you are back in Santa Margherita). Otherwise you can take an optional powerboat ride or local bus back to your base for the evening. (3 hours walking/7 km)
    Hotel Jolanda or similar

    Day 9 - Camogli - Santa Margherita

    • This morning, a short train ride will take you to Camogli, one of the prettiest towns of Liguria. Its name has a double meaning in Italian.
    • The first translation, ''houses close together,'' is apparent when you stroll through the town's narrow streets, which are lined by tall columns of pastel-coloured homes.
    • The second meaning, ''houses of wives,'' is not so obvious; it refers to the fishermen's wives, who traditionally spent their time at home while their husbands were out at sea.
    • From here you will undertake a short scenic walk onto the western part of the Portofino Peninsula.
    • A short climb will bring you up to the hamlet of San Rocco, from where a very scenic path leads you to the southern end of the peninsula. Here, you can enjoy views that embrace the whole Gulf of Genova, from Corsica to France.
    • You will then descend towards the small harbour of Punta Chiappa.
    • A picnic lunch can be had either in the shade of the Romanesque church of San Nicolò, or in the sun at the sea shore of Punta Chiappa.
    • You will then take the boat to the Abbey of San Fruttuoso - an 11th-Century 'jewel' that is set in a secluded cove and is reachable only by boat or on foot.
    • You will have over an hour to visit the monastery, make a short stroll to the charming fishing village, or just relax on the beach or on a terrace with a drink, before returning by boat to Camogli. In Camogli, you will take your time to wander around through the colourful historic centre and have a relaxed drink or grab a gelato on one of the many terraces.
    • You will then have a 5-minute train ride back to Santa Margherita. At night you will walk to a good local restaurant for your farewell dinner. (2.5 hours/ 6 kms)
    Hotel Jolanda or similar
    Breakfast | Dinner

    Day 10 - Santa Margherita

    • Your trip will come to an end this morning after breakfast in Santa Margherita. There are many regular train connections to cities such as Milan, Pisa, Florence and Nice from Santa Margherita station.
  • What to Know

    What's Included

    • The services of Peregrine's expert English-speaking local tour leader
    • Sightseeing (including entrance fees where relevant): Montepulciano, Pienza, Siena, Monteriggioni, Colle Val d’Elsa, Volterra, Riomaggiore, Santa Margherita Ligure, Portofino and Camogli
    • Walking tour of lesser-known parts of Florence
    • Walks from Chiesa di San Biagio to Monticchiello, Val d'Orcia to Bagno Vignoni, La Via dell'Amore in the Cinque Terre, Santa Margherita to Portofino and Camogli to western Portofino Peninsula
    • Boat ride to 11th century Abbey of San Fruttuoso
    • Free time to explore Florence, Arezzo, Montepulciano, Siena, Volterra and Portofino
    • Gratuities for essential services in tour package

    Not Included

    • International flights
    • Arrival and departure transfers
    • Departure taxes
    • Visas
    • Travel insurance (compulsory on all trips)
    • Meals (where not listed as included in the itinerary)
    • Optional additional tours or activities during free time
    • Gratuities for tour leader
    • Items of a personal nature
  • Past Travellers' Ratings & Comments

    At the end of each trip, we ask our travellers to provide feedback. We publish the positive, negative and neutral feedback on this page to give you an overall idea of what to expect on this trip.

    Magical Tuscany & the Portofino Peninsula

    Peter - Australia, 22 Jun, 2012
    Overall Rating

    We were very pleased with the trip and particularly our guide

    Magical Tuscany & the Portofino Peninsula

    Craig - Australia, 22 Jun, 2012
    Overall Rating

    Exceptional. Great timing, excellent tour leader, excellent itinerary, good accommodation, great food. Difficult to fault.

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Trip at a glance

Trip Code PEMT
Start City: Florence
End City: Santa Margherita
Style: Small Group

What to know

This trip can be enjoyed by just about anyone with a reasonable level of fitness.

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