Central Italy Journey

An unforgettable journey through the Archipelago Toscano and countrysides of Umbria and Tuscany.

Duration: 7 - 14 Days Available: May through October Group Size: 2 to 10 guests (always private) | Price Request

An adventure for each sense...

This is an opportunity to live as a temporary resident in central Italy’s most serene regions.

You’ll traverse the pristine and rugged beaches of Tuscany's hidden archipelagos and travel through the misty countryside of Umbria (The Green Heart of Italy) and world renowned wine regions of Tuscany.

We’ll witness the magnificent history, enjoy the world renowned cuisine and taste the many vintages of these incredible regions!

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Here’s the plan:

Day 1:

Arrive FCO airport in Rome. Private car transfer to Todi, Umbria - the green heart of Italy. Settle into our hilltop villa overlooking the splendid green valley. Take some time to acclimate to the time difference in the midst of this incredibly peaceful environment. We’ll enjoy a house cooked meal of Umbrian specialties and local wine on the terrace this evening.

*Easy / Dinner / Sleep: Todi, Umbria

Day 2:

We’ll head out this morning to explore the narrow lanes and shops of Bevagna, a medieval hamlet. Then onto the historic, hilltop town of Assisi where we’ll enjoy a private tour led by an active friar. You’ll witness the peaceful grounds and learn about the priceless artwork of the Basilica of St. Francis. We’ll end our day with an unforgettable private dinner and wine tasting in the town of Spello.

*Moderate / Breakfast, Dinner / Sleep: Todi, Umbria

Day 3:

After breakfast this morning, we’ll visit hilltop Orvieto. Take the afternoon to self-explore this wondrous commune including the beautiful duomo di Orvieto and ancient rock-carved subterranean city. Following our visit, we’ll travel to one of Tuscany’s most amazing natural wonders - Cascate del Mulino, a series of natural thermal pools that run warm year round. You’ll soak in the waters as the Romans did thousands of years ago and enjoy the beauty of this natural setting. Once you’re ready, we’ll travel to our boutique B&B in picturesque Pienza Tuscany where we’ll drop our bags and freshen up before dinner at a local trattoria.

*Moderate / Breakfast, Dinner / Sleep: Pienza, Tuscany

Day 4:

We’ll head out early this morning for a peaceful moment (and incredible photo opportunity) in misty hills of Val d’Orcia! Following our brief stop, we’ll continue north for lunch and wine tasting at a historic winery in the hills of Tuscany. Depending on the time of year, you’ll have the opportunity to participate in the grape harvest before learning about the production of this regions most special wines. We’ll be sure to pick up some of the famous Pecorino di Pienza (sheep's milk) cheese from this region! We’ll end our day with another spectacular dinner over looking the peaceful Val d’Orcia.

*Moderate / Breakfast, Lunch / Sleep: Pienza, Tuscany

Day 5:

This morning we’ll head to Siena and enjoy a private tour of this incredible city with Costanza, a local, passionate guide. After lunch, we’ll make a brief stop at a surprise location before heading to the magical island of Elba! Known for its crystal clear waters and beautiful beaches, Elba is one, if not the most beautiful island in the Archipelago Toscano. We’ll board a ferry from the town of Piombino on Italy’s mainland to Elba’s main port and capital - Portoferraio. Take some time to admire the “Old Town”, wander among the historic tenements before checking into our seaside villa.

*Moderate / Breakfast, Lunch / Sleep: Elba

Day 6:

Today is your day to make your own discoveries! Explore the island, go snorkeling or just relax at one of the many incredible beaches like Spiaggia di Sansone, Archipelago Toscano National Park or Padulella Beach. I’ll be available all day to arrange transportation, provide suggestions and offer assistance in the planning of your day’s activities.

*Up to you / Breakfast / Sleep: Elba

Day 7:

Today we island hop over to the small, remote island of Pianosa. Only 330 daily visitors are permitted on this island, allowing nature to be left mostly undisturbed. Visit the white sand beach of Cala San Giovanni, where you can discover the remains of a nearby Roman villa. Snorkeling in the island’s waters is an unforgettable experience, a chance to observe groupers, lobsters, bass, snappers and moray eels and many more Mediterranean species in shallow waters (additional fee will apply).

Once our time is up, we’ll return to the island of Elba where you’ll enjoy dinner on your own this evening.

*Moderate / Breakfast, Lunch / Sleep: Elba

Day 8:

On this day, we’ll drive to the northwest coast, Elba’s wildest corner, popular with divers and hikers. We’ll visit the sheltered, seaside village of San’Andrea. Follow the rock-cut footpath or, better still, swim around the cliffs to the hidden cove of Cotoncello. Here you’ll come face to face with solitude amongst the rocks and crystalline waters.

*Moderate / Breakfast, Lunch / Sleep: Elba

Day 9:

After breakfast this morning, we’ll board a ferry from Elba back to the mainland. Depending on your departure flight, you may either be taken directly to the airport or I can help you find accommodations in Fiumicino for the night and take you to the airport in the morning!

*Easy / Breakfast

All itineraries are fully customizable and may or may not include all items listed above.


Where You’ll Stay!

Todi, Umbria

Pienza, Tuscany

Elba Island, Tuscany


Journey Details:

What’s Included: Private airport transfers and journey transportation by van, 4 ferry crossings, 15 incredible meals, all journey accommodations, entry and activity fees.

What’s not Included: Airfare, activities, transportation and meals not listed in the itinerary along with travel protection and insurance.

*Activity Level: Our journeys are physically active. This is an important part of traveling like a Sojourner! On our Journeys — among other things — you'll need to be ready willing and able to 1) Carry/roll your luggage over uneven pavement (several blocks if necessary) and up stairways to reach your lodgings; then up several flights of stairs to reach your room. 2) Be on your feet, walking, standing and sometimes hiking for three to eight hours, indoors and outdoors, in all weather conditions, on varying types of terrain and elevation. 3) Sleep with street noise and no (or weak) air conditioning. After orientation and transportation lessons, be able to navigate through the city on your own.

Accommodations: Your Journey Pass includes one double room with one queen size bed or two twin size beds for 2 guests. We stay in small, boutique B&Bs and not hotels. A single supplement will apply if you require an additional room.

Meals: Travelers must make Sojourn Italy aware of any dietary restrictions and allergies 96 days prior to departure. 13 outstanding meals are included on this journey. All included meals are listed in the detailed itinerary.

Cancellation / Transfer Policy: Deposits for journeys are 100% refundable for 30 days from the date they are received. After 30 days your deposit becomes non-refundable, and will be forfeited should you decide to cancel your reservation. Cancellation Fees: 96+ days prior to trip start - $200 per person (including the contest winner). 61-95 days prior to trip start - 30% per person (including the contest winner). 31-60 days prior to trip start - 60% per person (including the contest winner). 0-30 days prior to trip start - 100% per person (including the contest winner). If you must cancel your reservation, your cancellation fee will be determined according to the policy outlined below. Exceptions to our cancellation policy cannot be made for any reason, including weather, terrorism, civil unrest or personal emergencies. There is no refund for arriving late or leaving a trip early. Percentage charges are calculated on the total trip cost, including the value of the contest winner’s free journey pass. Cancellations must be in writing: sent via email to anthony@sojournitaly.com. Cancellations become effective on the date received by Sojourn Italy. You may transfer from one date to another, for this journey only, up to 96 days before the trip departure without penalty, after which time our cancellation policy applies. New journey dates are subject to the availability and full discretion of Sojourn Italy, LLC. When transferring to a new date or trip, if the new trip costs more than the original trip, you must pay the difference in cost. Your transfer request must be approved by Sojourn Italy, LLC.

Traveler Protection: Sojourn Italy, LLC. does not offer a Travel Protection Plan. It is your responsibility to research a plan (if you wish) that covers: trip cancellation for medical reasons, trip delay, medical expenses, accidental death, lost baggage and medical evacuation.

Other: All guests will be required to sign a travel waiver before departure. Passport required for all guests traveling outside their home country. most countries require that your passport be valid at least 6 months beyond your trip dates.

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