SEPTEMBER 5-12, 2026

COASTAL TUSCANY AND UMBRIA SAMPLER

HIGHLIGHTS

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 seasonal harvests, and get a cooking lesson in a nonna's kitchen

Savor private dinners and receptions, and exclusive tastings of local products

PRICE FROM

$5,199

per person

$500 deposit

Payment plans available

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AVAILABILITY

📅 DATES

Sept 5-12, 2026

🗓 DURATION

8 Days/7 Nights

👤 GROUP SIZE

Max 10

🏅 ACTIVITY LEVEL

Daily walking, stairs, easy to moderate hikes

📍 LOCATION

Begins in: Rome

Ends in: Rome

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About This Trip

Join us for a late summer soft adventure that includes some of our favorite areas of Italy that aren’t Umbria. We’ll see the glorious Argentario promontory and the Isola del Giglio off the coast of Tuscany. This trip is specifically offered only in September, as it’s absolutely the best time to visit: summer crowds have left, but the weather is still just as warm and wonderful as August. (And yes, you’ll see the coastline from the sea aboard a private charter boat).

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 four nights in Umbria.

What's Included?

Almost all meals, snacks, and ample wine are included

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

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

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

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

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

What’s not included:

Airfare or train fare to or within Italy (other than train from Venice), travel insurance (strongly recommended), tips for drivers and guides, optional meals and drinks not included in the tour itinerary, souvenirs and incidentals

Itinerary at a Glance

Day 1: Arrivals and Transfer to Gilgio

Liz and your driver will meet you at Rome Fiumicino airport (FCO) for private van transfer to Porto Santo Stefano, from where we’ll board a private boat (sailboat or mini-yacht, depending on conditions) for the cruise to Giglio, with a lunch stop along the way.

Check into your rooms and find a welcome snack. From there, you have a couple of hours to relax, walk around or take your first dip in the Mediterranean.
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

Day 2: Hiking Across Gilgio

After breakfast at the hotel, we’ll join a local guide for a moderate hike to Giglio Castello, the hilltop fortress town that dominates the island.

Our hard work is rewarded with a private al fresco lunch in a 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

Day 3: Giglio by Sea

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, dinner

Day 4: Goodbye, Giglio & Hello, Allerona

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

Day 5: Cooking with Franca

We’ll spend the morning in Franca’s kitchen, then visit a private noble palace.

Mid-morning, we’ll head to Franca’s for a cooking lesson. Handmade ravioli, ragu and tiramisu are on the menu!
At lunch, we’ll dine on the delicious food we prepared earlier, followed by a grappa tasting.
Your afternoon is free to rest and digest.
This evening, we’ll tour a village palace, the ancestral home of a local family, followed by tasting of local olive oil, wine and other products.

Accommodations: Six Keys Guesthouse

Meals: Breakfast, lunch, dinner

Day 6: Tuscany and the Umbrian Bosco

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

Day 7: Orvieto and Farewell Dinner

Today, we’ll get to know Orvieto, the beautiful medieval city with Etruscan roots and a magnificent 14th-century cathedral. On the 20-minute ride to Orvieto, we’ll explain a little of the city’s history (and maybe a little about how Liz and Paolo met here!).

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, you’re free to explore on your own, though I’ll provide you with some suggestions for sightseeing and souvenir shopping.
Enjoy a festive cookout at night (and sadfly, get ready to say arrivederci…)

Accommodations: Six Keys Guesthouse

Meals: Breakfast, lunch, dinner

Day 8: Goodbyes and Transfers

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