SEPTEMBER 1-11, 2027

COASTAL TUSCANY & HARVEST TIME IN UMBRIA

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HIGHLIGHTS

Anchor at Giglio Porto in Tuscany
Tour group eating lunch at Giglio Porto
Boating on Giglio
Cooking lesson - making pasta - kitchen shot
A serene view of a yacht deck during sunset in French Polynesia's Windward Islands.
A serene view of a yacht deck during sunset in French Polynesia's Windward Islands.
A serene view of a yacht deck during sunset in French Polynesia's Windward Islands.

Cruise to Isola del Giglio aboard a private mini-yacht

Enjoy a nature hike on Giglio, with an al fresco lunch in a vineyard

Relax with plenty of swimming, snorkeling, boating, and beach time

Help with the vendemmia (grape harvest) and the first stages of winemaking

Get a cooking lesson in Franca's kitchen, then enjoy lunch with the family

PRICE FROM

$5,899

per person

$500 deposit

Payment plans available


CHECK
AVAILABILITY

📅 DATES

Sept 1-11, 2027 $5899 (10 nights)

🗓 DURATION

11 Days

👤 GROUP SIZE

Max 12

🏅 ACTIVITY LEVEL

Daily walking, stairs, easy to moderate hikes, climbing in and out of boats

📍 LOCATION

Begins in: Rome

Ends in: Rome

JUMP TO SECTION
On a boat Arriving at Giglio Porto

About This Trip

Join us for a fall soft adventure that combines two of our favorite Villaggio experiences: three nights on the Isola del Giglio off the coast of Tuscany, followed by a full week of harvest season in Umbria. We’ll see the glorious Argentario promontory and cruise to Giglio aboard a private charter boat — this trip is offered only in September, the best time to visit, when summer crowds have left but the weather is still warm and wonderful. From there, we settle into our own Six Keys Guesthouse in Allerona for seven nights of grape harvesting, cooking with Franca, hill town exploring, and thermal spa soaking.

This trip is a bit more adventurous than our other tours, though it’s still suitable for nearly all visitors. It includes three nights on Giglio and seven nights in Umbria — 10 nights and 11 days in total.

What's Included?

Meals

Almost all meals, snacks, and ample wine are included

Transportation

We cover all transportation during your tour, including airport pickup and dropoff

Lodging

Stay in a seafront hotel on Giglio, and our own Six Keys Guesthouse in Allerona

Experiences & Activities

We cover everything you'll do with us, from guided hikes to wine tastings and more

Expert guides

We partner with experienced local guides who aren't just reciting from a script

Special moments

Make new friends and family connections that can't be faked

What’s not included:

Airfare or train fare to or within Italy, travel insurance (strongly recommended), tips for hotel staff, optional meals and drinks not included in the tour itinerary, souvenirs and incidentals

Itinerary at a Glance

Day 1: Arrivals and Transfer to Gilgio

Your driver will meet you at Rome Fiumicino airport (FCO) for private van transfer to Porto Santo Stefano, where we’ll have lunch before boarding a private mini-yacht for the hourlong cruise to Giglio.

  • Check into your rooms and have some time to relax, explore Giglio Porto or take your first dip in the sea. 
  • We’ll have a seafood dinner (land-based options available) at a waterfront restaurant.
  • Enjoy an evening passeggiata by the seaside, maybe with a gelato in hand!

Accommodations: Hotel Saraceno or similar

Meals: Lunch, dinner

After breakfast at the hotel, we’ll transfer by taxi to Giglio Castello for a guided tour of the hilltop fortress and town. From there, we’ll hike downhill about an hour to a terraced vineyard.

  • Our hard work is rewarded with a private al fresco lunch in the vineyard, with views for miles.
  • After lunch, we’ll hike down to Giglio Campese, where you’re free to take a swim before we transfer by van back to Giglio Porto.
  • You’ll have some free time to rest or wander before we meet for another lovely seaside dinner.

Accommodations: Hotel Saraceno

Meals: Breakfast, lunch, dinner

On this full day, we’ll experience Giglio by sea

  • After breakfast, we’ll meet our chartered boat for a private cruise around the island, with stops for swimming, snorkeling and beach time, plus lunch on board.
  • Dinner on your own in Giglio Porto, where the waterfront is lined with restaurants and snack bars.

Accommodations: Hotel Saraceno

Meals: Breakfast, lunch

After breakfast, we’ll catch the 1-hour ferry back to the mainland, where our van will be waiting to take us to Allerona, our base for the rest of the week. We’ll arrive around lunchtime.
  • We’ll get you checked our village guesthouse and then we’ll convene for a buffet lunch of local specialties.
  • After some time to unpack and rest, we’ll take an afternoon tour of Allerona, where you’ll learn about the history of the village and some of its special places and hidden corners.
  • Free time to relax, wander around town and take pictures.
  • We’ll enjoy a festive “welcome to Allerona” aperitivo and dinner in a private cantina.

Accommodations: Our own Six Keys Guesthouse

Meals: Breakfast, lunch, dinner

On this full day, we’ll get to know Orvieto, the beautiful medieval city with Etruscan roots and a magnificent 14th-century cathedral.

  • We’ll meet our guide for a tour of Orvieto’s centro storico (historic center) followed by a visit to the Duomo.
  • Lunch at our favorite trattoria in Orvieto.
  • After lunch, we’ll visit one of Orvieto’s many underground caves, carved out over the millennia for storage, shelter and raw materials.
  • Return to Allerona for the evening and dinner at our lovely fine-dining restaurant.

Accommodations: Six Keys Guesthouse

Meals: Breakfast, lunch, dinner

We’ll stay close to home and get a taste of rural life and traditional Umbrian cooking, family style.

  • Depending on seasonal conditions, we’ll get an early start for grape picking. If harvest timing doesn’t align (it changes year to year), we’ll sub this with mushroom hunting or some other outdoor activity, weather permitting.
  • Bring your appetites to a private lunch, prepared and hosted by Paolo’s mom, Franca, and sister, Anna Rita. Friends who’ve visited us recall “lunch with Franca” as the highlight of their stay.
  • Free time after lunch to rest and relax.
  • Private dinner tonight in the home of Allerona friends.

Accommodations: Our own Six Keys Guesthouse

Meals: Breakfast, lunch, dinner

Today we’ll dip into Lazio, one of the regions bordering Umbria, and visit one of the area’s most enigmatic sights.

  • Civita di Bagnoregio (la città che muore, or the dying city) sits on a dramatic tufa plateau just a short distance from Orvieto. We’ll walk across the long bridge — the only way to access the nearly-deserted town — and spend some time exploring and taking photos.
  • We’ll have lunch at Civita, then stop for a fantastic photo op of Orvieto.
  • On the way back to Allerona, we’ll stop for a wine tasting at a cantina with cellars built by the Etruscans.
  • This evening, those who still have some energy and appetite can join us at the bar just outside of town for drinks and snacks (walking, or transport provided). Otherwise, you can just rest and relax with snacks at our guesthouse.

    Accommodations: Our own Six Keys Guesthouse

    Meals: Breakfast, lunch, dinner

Mid-morning, we’ll head to Franca’s kitchen for a cooking lesson. Handmade ravioli, ragu and tiramisu are on the menu!

  • At lunch, we’ll have a family lunch with the delicious food we prepared earlier, followed by a grappa tasting.
  • Your afternoon is free to relax.
  • In the evening, we’ll provide snacks, or you can dine on your own at our restaurant in town.

Weather permitting, we’ll spend most of the day outdoors, learning about the ancient Etruscans, thermal baths and foraged foods.

  • Midmorning, we’ll head up to Parco di Villalba and meet our friend Adio for coffee, followed by a ~2-hour nature hike, where he’ll offer an informal lesson on edible wild plants and herbs.
  • We’ll end our walk at a cozy, wooded osteria for a lunch of traditional Umbrian specialties and local wine.
  • After lunch, we’ll ride about 20 minutes to San Casciano dei Bagni for a tour of the major Etruscan and Roman archaeological site that’s come to light there. Then we’ll head up the hill to take a dip in the thermal pools of a luxury spa, where water bubbles from underground at a constant 104F.
  • This evening, it’s pizza party time!

Accommodations: Six Keys Guesthouse

Meals: Breakfast, lunch, dinner

On your last day in Umbria, you’ll have some free time to shop for souvenirs in Orvieto.

  • Mid-morning, our driver will take you to Orvieto, where you’ll have a few hours to explore and have lunch on your own.
  • Return to Allerona mid- to late afternoon.
  • This evening, we’ll enjoy a festive cookout and say arrivederci to Allerona.

After breakfast, we’ll say our farewells and, depending on your onward schedule, get you transferred to Rome airport of the Orvieto train station.

Meals: Breakfast

Tour Gallery

Boating on Giglio
people at picnic table, outdoor dining
On a guided tour of orvieto - people overlooking wall
Grape Picking at a Vineyard
Woodland Tour led by a guide
Cooking lesson - making pasta - kitchen shot
Group meals - hands serving food dinner
wine tasting, cheers, red wine
On a boat Arriving at Giglio Porto
Sunset at Giglio Porto in Tuscany
Beach at Giglio Porto in Tuscany
Anchor at Giglio Porto in Tuscany
Along the coast at Argentario
Watching the sunset on a dock at Giglio Porto
Vineyard lunch on Giglio
Vineyard at Giglio Porto

Download Liz’s free guide:
5 Roadblocks to an “Authentic” Italy Trip

(…plus how to avoid them, from someone who’s lived here for 17 years).