Small Group Tours by STORY

Story Land & Sea®

STORY WALKS: Best of Tuscany

The Best of Tuscany Walking Tour awaits you on this hand-crafted Story Walks' adventure through Italy.

STORY WALKS: 8 Day Best of Tuscany Walking Tour

This Story Walks Adventure Features

Journey Overview

“Very likely the ‘perfect walking tour through Tuscany.’ We didn’t realize exactly how “best” it was until we experienced the luxurious hotels, and those unique “Story surprises” along the way. Oh my! Story Land & Sea® has it right!”

WALKING TOUR CHARACTER: Easy to Moderate, 2 to 5 miles daily on average. Group size: no more than 16 guests.

 TRIP COMMENCES: Gaiole in Chianti, Italy with included airport or train station arrival transfer to Gaiole in Chianti.

 TRIP FINALE: Fiesole, Italy. Located near Florence, with included airport, train station or hotel departure transfer to Florence.

ADD AIRFARE:Check with our Air Service Department to inquire about competitive airfare rates. Visit Air Service for an airfare quotation with your walking tour.

WALKING TOUR SUMMARY:Explore Tuscany from a completely different perspective with our Best Of Tuscany Walking Tour. Walking Tuscany’s countryside through rolling hills, vineyards, olive groves and farmhouses. It’s Tuscany “up close and personal” as we journey through the paradise that is the regions of Chianti and Siena with visits to Montalcino, Monteriggioni, Siena, Gaiole in Chianti, and the hills above Florence in Fiesole.


Itinerary at a Glance

DAY 1: Departure Board your Transatlantic flight overnight bound for Tuscany. We can assist you with your international airfare. Inquire with us here.

DAY 2: Gaiole in Chianti Idyllic location in Tuscany and voted as one of Europe’s most idyllic places to live.

DAY 3: Walking Chianti Vineyards, pristine forest, home-cooked cuisine paired with vino. Can a day get any better?

DAY 4: Walking & Tasting San Gimignano. Of towers and perspectives, San Gimignano continues to impress.

DAY 5: Walking Siena. Narrow, picturesque streets culminate in a medieval town center.

DAY 6: San’t Antimo Abbey Bagno Vignoni, the thermal baths await you after your walk today.

DAY 7: Walking Fiesole The Fiesolean hills are alive with the sounds, sights and scents of Tuscany.

DAY 8: Arrivederci Day Transfer to the airport or extend your stay. It’s your choice.

Daily Itinerary

Flight Day

Day 1: Your Overnight Transatlantic Flight

Fly from your home airport to Florence International airport.

Note: Day 1 is the published tour date and is the date you will arrange your air travel. Your small group tour commences on itinerary Day 2 upon arrival into Florence.

Can we help you with your Airfare? 
Yes, we can arrange your air travel from the STORY Land & Sea air department. We'll work with you to get the absolutely lowest fare available based on your travel preferences. Remember, airfare is a completely separate arrangement from your land tour. It is your responsibility to arrive at the point of tour origination on time regardless of whether STORY Land & Sea has arranged your air.

At the end of the Tuscany Walking Tour you should set your flight to return from Rome or Florence. Inquire for details on your trip planning.

 Travel Protection
Story Land and Sea® recommends that you purchase a travel protection plan to help protect you and your travel investment against the unexpected. A Protection Plan can include coverage for Trip Cancellation, Trip Interruption, Emergency Medical and Emergency Evacuation/Repatriation, Trip Delay, Baggage Delay and more.

For more information on available plans or to enroll, go to or contact Travelex Insurance Services at 800-228-9297 and reference location number 06-0051.


Day 2: Welcome to Tuscany

Gaiole in Chianti
Chianti Region, Italy

food icon   Story® Way Dining: Welcome Dinner Tonight

Upon arrival to the airport, you clear customs and are met by our Story Representative for your included transfer to Gaiole in Chianti, home to our castle estate for the next two evenings.

Join your Story Adventure Guide for our Orientation Walkabout on your arrival day. 

Gaiole in Chianti is a community in the province of Siena in Tuscany and was named by Forbes as one of “Europe’s Most Idyllic Places to Live.” Our estate is located nearby and upon arrival we will celebrate the beginning of the week-long walking and hiking journey with our special reception.

Story Way Dining: Welcome Dinner - Dining at the Estate's Private Cellar
Tonight, you will feast at the estate with our included welcome dinner.

About the Story® Way of Dining
Our approach to dining is truly unique: Our favorites dishes represent the region we’re traveling through. We call this, parla come mangia or ‘speak the language of your food.’ From our unique, off-the-beaten-path restaurants we visit for each included dinner to the variety of hand-crafted dishes, it’s truly an immersion into authentic Italian food and wine. No buffets here. Your Tour Captain is there to make sure your dining experience goes smoothly and will help you interpret any menu item. Your Tour Captain will select a variety of appetizers, featuring regional cuisine, and will select your vino from the estate ~ a variety of red and white wine from the very heart of Tuscany ~ and yes, “the wine flows.” It’s an intentionally slow evening of delight so you can savor the experience.

Accommodation: Castello di Meleto or Similar, 2 Nights






food icon   Dining: Included Breakfast and Dinner
star icon   Story Land & Sea® Exclusive: Winery Estate Lunch

Today’s Walks in Bella Tuscany: The Picture-Perfect Tuscan Landscape springs to life as we consume its aesthetics with our senses of sight, sound and taste.

Character of the Morning Walk: Gaiole in Chianti to Estate Dievole: About 3 Miles with a walk-rating of Easy to Moderate. After breakfast (included daily), we begin our walk through olive groves, vineyards and pristine forest bound for another villa estate in Vagliagli.

Story® Exclusive: Enjoy a scrumptious home-cooked lunch and wine-tasting.

After a fantastic visit to our villa we continue with our walking journey as we make our way back to the castle.

Character of the Afternoon Walk: Dievole to Villa via unique route: 3 Miles with a walk-rating of Easy to Moderate.


food icon   Story® Way Dining: Enjoy another unique dining experience in our beautiful castle!




San Gimignano
San Gimignano

food icon   Included Breakfast

food icon   Story® Way Dining: Welcome to San Gimignano

Today’s Walk in Tuscany: Experience the San Gimignano tourists never see as we enjoy spectacular views of the city and region.

Character of the Walk: This morning after breakfast we transfer to San Gimignano and begin our trek nearby. About 2 miles with a walk-rating of Easy to Moderate. Enjoying the land around San Gimignano on our walk today culminates with a visit to the towered medieval town. We also will enjoy walking the cobblestone streets of San Gimignano and discover much of the town that is truly hidden from the average tourist. We enjoy time for lunch on your own in San Gimignano and the balance of the day is at leisure. Our home for the night is our hotel in San Gimignano.

food icon   Story® Way Dining: Tonight enjoy an included dinner at one of our favorite local hangouts.

Accommodation: Leon Bianco or Similar, 1 Night





Torre del Mangia Tower, or Clock Tower, Siena Square

food icon   Included Breakfast and Optional Dinner

Today’s Walk in Tuscany: The medieval town of Siena is full of discoveries we’ll find on our guided walk.

 Character of the Walk: Our exclusive walking tour of the medieval city is 1-2 Miles with a walk-rating of Easy.

We depart San Gimignano this morning bound for Montalcino. Along the way we’ll enjoy a stop and time in Monteriggioni and a walking tour of Siena.

Siena boasts narrow, picturesque streets, and is famous for its twice-annual horse race called Il Palio. A rival with Florence through history (and still today!), we’ll enjoy discovering this town along with its secrets along off-the-beaten-path routing. The atmosphere of Siena is a blend of gothic and Romanesque architecture spreading over three hills.

After taking our time in Siena, we continue on to Montalcino, our home for the evening.

Montalcino is a walled hill town and the birthplace of one of Italy’s finest wine varietals, the Brunello. The hill upon which Montalcino sits has probably been settled since Etruscan times.

Optional Dining in Montalcino: Join the Tour Captain for an optional dinner or enjoy exploring the quaint town of Montalcino on your own.

 Accommodation: Hotel Vecchia Oliviera or Similar, 2 Nights




food icon   Included Breakfast, Story Exclusive: Tuscan Farmhouse Lunch, and Optional Dinner

Today's Walk in Tuscany: Enjoy our hike from Montalcino to San’t Antimo Abbey.

 Character of the Walk: Montalcino to San’t Antimo Abbey: 5 1/2 Miles with a walk-rating of Moderate.

San't Antimo Abbey
San't Antimo Abbey

We will depart Montalcino on our walk bound for San’t Antimo Abbey arriving around noon. The gentle rolling hills complemented by the vineyards that produce the Sangiovese Grosso grape that is grown for the Brunello will only make your walk through the olive groves, wineries, and farmland more exhilarating. Truly a beautiful trek.

food icon   Story® Exclusive Dining: Lunch in a Tuscan Farmhouse

Enjoy an included lunch at an old Tuscan farmhouse at Locanda Antimo. Our hosts will welcome us with an assortment of typical Tuscan favorites including cheeses (like the local Pecorino made from sheep’s milk), to a taste of salami from the Cinta Senese – a very ancient Tuscan breed of pig that nearly went extinct until it was discovered in a painting and the breed was resurrected. Cinta means belt and are characterized by a black body with a white “belt ” on their shoulders and forelegs.

We continue on our journey to the Bagno Vignoni, the thermal baths. Enjoy them just like the Romans did for an afternoon at leisure.

Bagno Vignoni Thermal Baths
Bagno Vignoni Thermal Baths


Return to Montalcino for a free evening or join your Story Adventure Guide for an optional dinner.





food icon   Included Breakfast, Story® Exclusive Dining: Farewell Dinner

We transfer to Fiesole above Florence. The view from the Fiesolean hills provide a spectacular perspective. The remains of ancient Etruscan walls help historians date Fiesole back to around the 9th century BC.

Today’s Walk in Tuscany: Upon arrival, we freshen up and set out for our last hike in the hills above the capital of Tuscany.

Character of the Walk: Walking the hills above Florence: 5 Miles with a walk-rating of Moderate.

Afternoon we return to our wonderful Villa Fiesole Hotel to relax and reminisce before our farewell celebration set in a wonderful Tuscan Ristorante.

Story® Way Dining: Included Farewell to Tuscany Dining Experience

One of our favorite nights of fun and celebration, as we toast one another to a wonderful journey together. The venue and activity we have designed for you tonight will make for the perfect finale to your Italian walking tour. It is a night of great cuisine and, of course, vino from Tuscany along with your new friends.

Our days have been filled with new sights, tastes, and discoveries – tonight enjoy reflecting on the incredible journey we’ve had together!

 Accommodation: Villa Fiesole Hotel or Similar



food icon  Included Breakfast, time permitting

A complimentary departure transfer to Florence Airport, or to your hotel in Florence if you are extending your stay, is included.

### TOUR END ###

Inquire with reservations for pricing and details.

Call toll free 1-877-865-6711


Deluxe Hotels & Relais

Gaiole in Chianti Hotel - 2 Nights

San Gimignano Hotel - 1 Night

Siena Hotel - 2 Nights

Fiesole Hotel - 1 Night


Story's Best of Tuscany Walking Tour

A Luxury Walking Tour through Italy

Story's Small Group advantage means you are not waiting to get on and off big traditional sized tour buses, and you get to interact with our Story Adventure Guide and local Expert Guides more easily (not to mention our boutique hotels, skip-the-line sightseeing experiences and Story's signature Story® Way Dining and Story® Exclusives. See the world more easily and continue your Story of Travel with our small groups in Italy.

2020 Trip Departures

True Small-Group Walking
Prices are per person, based on double occupancy. Single Supplement: $2,100

Published Date

True Small-Group®

Pricing Guarantee

May 11
Jun 15
Sep 12
Oct 12

Published prices are based on a guaranteed departure with at least six (6) Story guests — Inquire with reservations to find out your preferred departure's current tour size and pricing and our Book with Confidence program!

Or do these dates not work for your schedule?

Call us: 1 877 865 6711

Take over a departure for your own private group.

Inquire for details.

Prefer to travel with just the two of you?
Enjoy STORY's Tuscany package with as little as two guests for $6879 per person.

2021 Trip Departures

True Small-Group Walking
Prices are per person, based on double occupancy. Single Supplement: $2,100

Walking Tour Published Date

True Small-Group®

Pricing Guarantee

May 22
Jun 19
Sep 12
Oct 14

Published prices are based on a guaranteed departure with at least six (6) Story guests — Inquire with reservations to find out your preferred departure's current tour size and pricing and our Book with Confidence program!

Or do these dates not work for your schedule?

Call us: 1 877 865 6711

Take over a departure for your own private group.

Inquire for details.

Prefer to travel with just the two of you?
Enjoy STORY's Tuscany package with as little as two guests for $6879 per person.



Story's Tuscany Walking Tour
A world-class tour of Italy's Tuscan Countryside in the company of a few new friends and travelers...Why Story Land & Sea Tours for Italy?
  • All Breakfasts, 2 Gourmet Lunches, 4 Dinners with premium wine and beverages
  • 5-Star luxury hotels (upgrade to a suite if available, call for details)
  • Professional Story Adventure Guide throughout your journey.
  • Two complimentary lightweight, telescoping Trekking Poles.
  • Complimentary waterproof travel backpack and transformable multi-functional Waist Bag and Lightweight Daypack
  • Admissions, entrances and events while on tour.
  • All transportation from tour commencement to finalé.
  • Magic Portage from commencement to finalé.
  • Customary gratuities included. Story Adventure Guide gratuities optional.
  • Story®’s Unique Perspective Experiences



Services of a full-time Story Adventure Guide.

Comprehensive daily sightseeing per itinerary via private transportation with experienced, local driver. Admission & entrance fees to all sightseeing as detailed per itinerary.

Full, hot breakfast daily. Lunches and dinner included per itinerary. Coffee or tea included with breakfast only; all other beverages are extra. Select dinners with Wine and cocktails are included at unique restaurants.  

Portage (one suitcase per person) and all tipping (driver, restaurant, hotel and guide staff) included. Extra bag portaged for $130 per bag. Story Land & Sea luggage tags given upon arrival at your first hotel.

Single Supplement applies. See Dates & Rates Tab.

International Airfare is not included.

PASSPORTS: A valid passport is required and must be obtained in person by each tour member at a local passport office. Travel documents are your responsibility including compliance with customs' regulations.

Tour prices are per person, based on two persons sharing double or twin-bedded room with private bathroom with tub or shower. Single rooms subject to availability and at an additional cost (tour participants without a roommate will have to pay the single room surcharge). Hotels used are Deluxe class categories (4 and 5-Star) you choose based on your preferences.

SERVICE CHARGES AND TAXES: All departure taxes and tipping are included. 


Get Started: Ask a Question, Schedule a Call, Request a Trip Quote, or Have us Craft Your Trip




What questions do you have?:


Let STORY Air book your flights!

Story Air
  • Discounts on most fares
  • Fly dates seemlessly coordinate with your tour dates

Airfare is a completely separate booking from your land tour.



We recommend some form of travel protection to help provide coverage for trip cancellation, trip interruption, emergency medical and emergency evacuation, lost or delayed baggage and more. You may purchase this coverage from the provider of your choice. For your convenience, we offer plans through Travelex Insurance Services For more information on the available plans or to enroll, go to TRAVELEX (click here)


The product descriptions provided here are only brief summaries and may be changed without notice. The full coverage terms and details, including limitations and exclusions, are contained in the insurance policy. Travelex Insurance Services, Inc CA Agency License #0D10209. All products listed are underwritten by, Berkshire Hathaway Specialty Insurance Company NAIC # 22276. 11.17 83IT

For questions call 888-989-7390, option 3


Airfare is not included but it can be quoted here. Remember, you are responsible to arrive at the point of your small group tour origination. If you are delayed for any reason, your vacation may be at risk even if STORY Land & Sea® made your airfare arrangements. Airfare is a completely separate booking from your land tour vacation. You can cancel your vacation with a 100% refund up to 90 days prior to departure. Within 90 days you will begin receiving penalties per the terms of the Tour Application should you have to cancel.


Guest Reviews

"...loved our 'story host' and was blown away each day by what we experienced. thanks!"

“Very likely the ‘perfect walking tour through Tuscany.’ We didn’t realize exactly how “best” it was until we experienced the luxurious hotels, and those unique “Story surprises” along the way. Oh my! Story Land & Sea® has it right!”

“We were not avid hikers per se but enjoy walking a lot. The pace of the Story itinerary was just perfect. We enjoyed meeting new friends and are looking forward to walking with them on your Italian Lakes trip. Truly, a special thank you to Dan – stellar Story Adventure Guide!"
Grazie Danino!