Tuscany Islands and Val d'Orcia ~ Cultural Walking Tour

TRAVEL AS AN INSIDER

Fall in love with the islands and hill towns of Tuscany, off the beaten path, and immerse yourself in a truly unforgettable journey – designed for anyone who enjoys walking! From the hidden beaches of the lsland of Giglio to the Etruscan cave roads of Pitigliano to the sweeping vineyards of Montepulciano, each marvelous day includes our signature off the beaten path experiences with amazing artisans, delightful local guides and welcoming families who will treat you like one of their own.

While tourists flock to see the most crowded areas, and then quickly leave (without really seeing Tuscany at all) you’ll get to know this spectacular region as an insider – as a traveler. Explore characteristic fishing villages, breathtaking seaside trails, irresistible medieval hill towns, evocative historic sites and meandering countryside strade by day, then return to your boutique hotel and elegant villa accommodations for friendly aperitivo hours, gourmet meals and sweeping Tuscan sunsets.

DATES & PRICES: 7 Days/6 Nights

  • Dates:
    • April 28 – May 4, 2019
    • September 29 – October 5, 2019

SUMMER SALE through September 1, 2018:  Regular Trip Price: $4,195, SALE PRICE: $3,795! Save $400!!! Price is per person, based on double occupancy.

Single Supplement $695 USD solo traveler, single occupancy

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WALKING RATING: Our walks are rated as easy to moderate, with durations on average of 1.5 – 3 hours and distances of 5-10 kilometers (3-7 miles). Although most routes are relatively short, you will encounter cobblestones, rugged pathways, uneven steps and steep ascents and descents in order to reach stunning views and hilltop villages. Our walks ideal for active travelers. No hiking experience is necessary, but we do recommend walking regularly before your trip, including up hills, whenever you can. Although non-walking options are provided throughout the tour, we caution that this trip is not the right fit for those who have difficulty walking or have a health-related condition that would limit participation and/or impede or inconvenience others.


THE UNEXPECTED IS PART OF THE JOURNEY

At Strada Toscana we weave amazing, authentic experiences into every trip, but sometimes unexpected things come up. If Mario calls to tell us they’re pressing olives at just this moment, off we go (I mean, we wouldn’t let you miss his newly pressed olive oil!), and if a site has an unscheduled closing, we improvise to include something equally as wonderful and interesting.

On that note, if our usual boutique hotels can’t accommodate us (which rarely happens), you can rest assured you’ll stay somewhere of an equal or higher level. The quality of our tours is never at risk, as our team is committed to excellence, along with our vast, local, Italian connections.


 REVIEWS : What People Are Saying

“I have to say that this is now the best trip we have ever taken. Pamela is so passionate about Italy, that it’s hard not to fall in love with the beautiful country and all it has to offer. She has some amazing contacts that you are lucky enough to meet, and will soon become their friends too. Thank you Pamela for showing us the Heart of Italy and the Italians that I have come to love!!” —Robyn Smith Raley

“Pamela puts her heart in everything she does. This includes the delightful trips and meals she plans for her guests, who may arrive in Italy as acquaintances but will surely leave as friends. If you are going to tour Italy it would be a mistake to go with anyone other than Strada Toscana!” Sharie Boyle

DAY 1: Arrival

  • Welcome to Giglio, trip orientation, village walk, aperitivo, benvenuto dinner
  • Dinner

Legend tells us that once upon a time when Venus rose up from Mediterranean Sea, seven precious stones fell from her tiara, creating a chain of seven spectacular islands – now called the Tuscan Archipelago. And who are we to argue with legend, as these islands are truly gems of the sea – one is which is our beloved Giglio. Your journey begins here, in the charming fishing village of Porto Giglio, on Giglio Island, surrounded by the beauty of nature and the stunning azure waters of the Mediterranean Sea.

ARRIVAL: Travel from Rome Fiumicino Airport via our private, Mercedes Benz van service, and then via ferry, to your boutique hotel accommodations on Giglio Island.

AFTERNOON: After check-in and a brief tour orientation, you’ll meet your delightful walking guide, Manuele, to enjoy a leisurely walk and to get better acquainted with this ancient fishing village with its colorful houses, adorable shops and historic lighthouses. Not only an exceptional, certified walking guide, Manuele’s friendly manner and outgoing personality will put you at ease right from the start. His passion for his home-region, Tuscany, is nothing short of contagious and this, combined with his vast knowledge and expertise, is a winning combination.

EVENING: Pinch yourself as we gather together for our signature aperitivo hour along the harbor. Spectacular! A delectable seaside dinner follows featuring local specialties, including Mediterranean sea bass and the typical, local pasta.

 

ACCOMMODATIONS: Hotel Saracen0 (3 nights)

Situated on a stunning cliffside overlooking the azure sea, and built upon the ruins of a Roman villa (you can even spot remnants of mosaic floors!), 3-star, boutique Hotel Saraceno is tucked along a picturesque avenue, just steps from the charming fishing village of Giglio Porto. With its fresh, seaside rooms and welcoming atmosphere, it’s the ideal home base for our walking exploration of Giglio Island. And that view!

 

DAY 2: Castello Giglio

  • Castello Giglio ring walk, castle visit, lunch in Castello Giglio, vineyard aperitivo hour
  • Breakfast and lunch

MORNING: This morning you’ll meet up with Manuele for a steeper, but easy to moderate, walk to Castello Giglio – an 11th century fortressed village perched on the highest point of the island – with sweeping views of the sea, and irresistible winding avenues. After exploring the avenues of the town, along with its imposing castle, we’re off to enjoy lunch at our friend Maria’s restaurant in the village’s historic center.

LUNCHTIME: Lunch at our friend’s restaurant

AFTERNOON: After lunch you might join Manuele for a walk back down to Giglio Porto, or opt instead to shuttle back.

LATE AFTERNOON:

  • Option 1: Get an up-close view of Giglio Island’s turquoise coves on small-boat tour along the rocky shoreline. We’ll make a stop in the charming village of Campeggio for a sunset aperitivo along the Bay of Sun, before return to Giglio Porto by boat.
  • Option 2: Take time on your own to explore and shop in the village of Giglio Porto, then enjoy an evening aperitivo at our friends’ port-side bar.

EVENING: Dinner on your own in Giglio Porto

DAY 3: Giglio & Giannutri

  • Scenic coastal and panoramic walk with picnic or boat ride to Giannutri with island walk and picnic lunch, shopping and exploring on your own in Giglio Porto
  • Breakfast, lunch and dinner

MORNING: After a buffet-style breakfast at our boutique hotel, the choice is yours: join Manuele for a scenic coastal and panoramic walk along a centuries-old pathway to the hilly ridge that caps the island of Giglio and a picnic lunch along a panoramic ridge, or instead boat to the nearby island of Giannutri for a guided walk through the pine-laden, protected park that ends with a tour of the ruins of a Roman villa and a picnic lunch alongside the beach. Either way the panoramic views of the Mediterranean are simply stunning, along with the distinct seaside vegetation and terrain. Be sure to have your camera ready for incredible photo ops!

LUNCH: Picnic lunch

AFTERNOON: We return to the hotel for a bit of rest and relaxation

  • Option 1: The best way to see Giglio’s intimate, turquoise coves is by boat, so why not opt for a small boat tour for an up-close look at Giglio’s spectacular, rocky shoreline (optional/extra).
  • Option 2: Take some time on your own to shop in Porto Giglio or dip your toes in the sea.

EVENING: We gather together for our signature aperitivo hour before enjoying one last island dinner together.

DAY 4: Pitigliano & Bagno Vignoni

  • Vie cave (excavated road) ring walk Sovana, snack in Sovana, historic center Pitigliano, welcome tour Relais dell’Orcia and bevenuto dinner
  • Breakfast and dinner

It’s truly incredible how Tuscany’s terrain, landscape and even microclimate changes within a short distance. You’ll experience that today as we leave our coastal world for one of shady forests and gentle rolling hills – filled with Etruscan secrets. This extraordinary, evocative area is irresistible to walkers, so be prepared to explore and discover an amazing ancient world!

MORNING: After breakfast at the hotel, we’re off on an early start to Pitigliano where Manuele will guide you on an unforgettable walk through the unique and evocative vie delle cave, cave roads, that wind their way throughout the countryside and forests that surround Pitigliano. These truly amazing pathways are shrouded in mystery and teeming with beauty. After a stop for a snack in charming Sovana, you’ll make your way to Pitigliano itself to enjoy time on your own for exploring and lunch.

LUNCH: On your own in the historic center of Pitigliano

AFTERNOON: We continue on to the heart of Tuscany’s wine country. After check-in at the beautiful Relais dell’Orcia you’ll have an opportunity to relax and settle in before enjoying a “get acquainted” tour followed by a friendly aperitivo hour.

EVENING: Welcome dinner Relais dell’Orcia

ACCOMMODATIONS: Relais dell’Orcia (3 nights)

The philosophy of the 4-star Relais dell’Orcia of Bagno Vignoni is to surround oneself with the beauty of Tuscany – its landscapes, nature, history and culture – and to enhance the art of hospitality with excellent products from local farms. With its elegant, yet inviting, rooms and proximity to historic walking trails, Relais dell’Orcia rates as our favorite accommodation in the Val d’Orcia for exploring Tuscany on foot.

DAY 5: Montepulciano & Monticchiello

  • Bagno Vignoni to San Quirico, picnic lunch, thermal spa (optional/extra), Bagno Vignoni ring walk
  • Breakfast and lunch

MORNING: After breakfast, join your trip leader for a walk from spectacular Bagno Vignoni – built upon a hilltop rich with hot mineral springs – to nearby San Quirico, a charming medieval village that seems frozen in time. This is classic Tuscany, with sweeping views of the Val d’Orcia that will take your breath away! Take some time to explore on your own, then enjoy a picnic lunch while taking in those views. Walk back to Bagno Vignoni you’ll return to From here you’ll head out on the Anello di Bagno Vignoni (ring walk) with Manuele, a well-traversed trail that winds throughout the picturesque valley, nearby the impressive Castello Ripa d’Orcia, and finally back to Bagno Vignoni where you can explore the tiny shops and choose a place for lunch.

LUNCH: Picnic lunch near San Quirico

AFTERNOON: Walk back to Bagno Vignoni with your trip leader or shuttle back and spend the afternoon as you wish.

  • Option 1: Join your trip leader for a walk along the anello di Bagno Vignoni (ring walk), a well-traversed trail that winds throughout the picturesque valley, nearby the impressive Castello Ripa d’Orcia, and finally back to Bagno Vignoni.
  • Option 2: Soak in the luxurious, mineral-rich waters of the thermal spa in Bagno Vignoni (optional/extra)
  • Option 3: Enjoy free time to visit Bagno Vignoni at your leisure or relax on the terrace at our spectacular accommodations

EVENING: Aperitivo hour followed by dinner on your own at the excellent hotel restaurant or in Bagno Vignoni

DAY 6: Pienza

  • Pienza “passeggiata” ring walk, Chapel of the Madonna di Vitaleta, field of the gladiator, Montepulciano historic center
  • Breakfast and dinner included

MORNING: After breakfast it’s off to the charming village of Pienza, dubbed Tuscany’s cheese capital and famous for its outstanding pecorino (sheep’s milk cheese). The morning begins with the scenic Pienza ring walk, that winds its way past the Chapel of the Madonna di Vitaleta and the “field of the gladiator” before making looping back to the village itself where you can take in breathtaking views of the valley below from its fortressed walls.

LUNCH: On your own in Pienza

AFTERNOON:

  • Option 1: Shuttle to the regal hill town of Montepulciano for a Vino Nobile wine tasting at our friends’ 15th century cantina, followed by free time in Montepulciano for shopping and exploring.
  • Option 2: Return to our elegant accommodations for to relax or take a walk into the village of Bagno Vignoni.

EVENING: Aperitivo followed by a farewell dinner featuring Tuscan specialties

DAY 7: Departure

Transport to Rome Fiumicino Airport.


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WHAT’S INCLUDED

  • Options and flexibility. You’re uniquely you, and we think that’s fabulous! That’s why we provide you options and flexibility each and every day. Prefer a bit of time on your own? Choose an explore-on-your-own option. Wanting more steps? Choose an optional, extra walk. Tailor each and every day to suit your unique desires.
  • Memorable accommodations for 6 nights in hand-selected boutique hotels
  • All breakfasts, 4 dinners served with regional wines
  • Full-time experienced trip leader/walking guide, local guides and experts, behind-the-scenes support staff and support vehicle(s)
  • Tours, visits and hands-on experiences with local residents and artisans
  • Private land transportation throughout the trip
  • Daily guided walks, plus non-walking options: WALKING RATING: Easy to moderate, with durations on average of 1.5 – 3 hours and distances on average 5-10 kilometers (3-5 miles) – ideal for active travelers with or without hiking experience. You can expect hard cobblestones, uneven pavement, steps and steep hills. In addition, elevators are not available at our boutique hotel accommodations. Although non-walking options are provided throughout the tour, we caution that this trip is not the right fit for those who have difficulty walking or have a health-related condition that would limit participation and/or impede or inconvenience others.
  • Gratuities for hotels and meals

Not included: Airfare, ground or water transportation outside of that listed in the trip itinerary, alcoholic drinks, wines or meals ordered “on your own”, gratuities for drivers

The Unexpected is Part of the Journey: At Strada Toscana we weave amazing, authentic experiences into every trip, but sometimes unexpected things come up. If Mario calls to tell us they’re pressing olives at just this moment, off we go (I mean, we wouldn’t let you miss his newly pressed olive oil!), and if a site has an unscheduled closing, we improvise to include something equally as wonderful and interesting. On that note, if our usual boutique hotels or B&Bs can’t accommodate us (which rarely happens), you can rest assured you’ll stay somewhere of an equal or higher level. The quality of our tours is never at risk, as our team is committed to excellence, along with our vast, local, Italian connections.


DOWNLOAD THE ITINERARY

BOOK NOW

WHY CHOOSE a Strada Toscana Tour?

  • YOU’RE NOT JUST A NUMBER. We care deeply about our guests. In fact, we think of our small groups as a kind of family of like-minded travelers.
  • SMALL GROUP – BIG BENEFITS. Our maximum small-group size is 14, which means we’re able to stay in centrally located, boutique hotels (that often have limited rooms), eat in tucked away, family-run restaurants (that are always the best!) and use twin Mercedes Benz vans to reach restricted areas in historic villages.
  • WE’VE GOT YOUR BACK. Our support staff is always at hand to help you with everything from translating a menu to finding that special leather purse.
  • GORGEOUS & COMFY. You stay in upscale, boutique hotels with beautiful sleeping rooms, ensuite bathrooms and lovely touches that reflect the character of the region.
  • BEST VALUE. Because we’re destination experts and operate only in Italy, we know how to get the BEST quality for the very best price – that we then pass along to you. Our tours are an extraordinary value. Period.
  • YOU GET RIGHT TO IT. Spend less time transferring around in vans and more time experiencing. Your accommodations are in ideal locations for stepping outside to walk and explore.
  • PRIVATE DRIVERS. Strada Toscana teams up with exceptional drivers who own their own vans and their own businesses – and are really more like family. No conglomerates and no outside services.
  • AUTHENTICITY. Our trip leaders and guides are locals who are from the areas in which we tour. They know the region, the sites and the people like the back of their hand.
  • EXCEPTIONAL MEALS. The owner-run, top-notch restaurants on our tours are extraordinary, which means you enjoy delectable dinners in a welcoming, friendly atmosphere.

Learn more about our unique approach to traveling in Italy.