Story Land & Sea®

Best of Tuscany Walking Tour

Best of Tuscany Walking Tour

"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 8 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 round-trip airfare rates. Visit Air Service for a quote.

WALKING TOUR SUMMARY: Explore Tuscany from a completely different perspective with our Best Of 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, Fiesole.

Transatlantic Overnight 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 QueensLander air department. We'll work with you to get the absolutely lowest fare available based on your travel preferences. 

  • Airfare is not included but it can be quoted by clicking here. Remember, you are responsible to arrive at the point of your small group Italy 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 Italian 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.

  • Travel Protection is not included. Story Land and Sea recommends that you purchase a travel protection plan to help protect you and your travel investment against the unexpected.

Travel protection companies, such as Travelex, plans include coverage for Trip Cancellation, Trip Interruption, Emergency Medical and Emergency Evacuation/Repatriation, Trip Delay, Baggage Delay and more. Click here to get a quote and purchase on their website.


Story Land & Sea®'s Unique Walking Tour Experience
We do walk on our small group tours of Italy. We walk a lot, but it's unhurried and there are ample opportunities to sit and relax. But you must be physically capable of walking and experiencing the many stairs of Italy. Please inquire with Story Land & Sea® Reservations for more details.


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

Welcome to Tuscany
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.

Tonight, you will feast at the estate with our included welcome dinner.

About the Story Land & Sea ® 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


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 Siena for a scrumptious home-cooked lunch and wine-tasting in the private cellars.

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.

Tonight, enjoy an included dinner at the estate.

Accommodation: Castello di Meleto or Similar


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: Transfer to San Gimignano and begin 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 in San Gimignano and the balance of the day is at leisure. Our home for the night is our hotel in San Gimignano.

Tonight enjoy an included dinner at one of our favorite local hangouts.

Accommodation: Leon Bianco or Similar


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. 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 in Monteriggioni and a walking tour of Siena.

Siena boasts narrow, picturesque streets which 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 archticture 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.

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


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.

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 exhilerating. Truly a beautiful trek.

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.

We then journey on to Poggio Antico Winery for a tasting of the Brunello paired with dinner. Absolutely outstanding!

Return to Montalcino for a free evening.

Accommodation: Hotel Vecchia Oliviera or Similar


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.

Tonight is a special time as you join the Tour Captain for an included Farewell to Tuscany Dinner with your new friends!

Story Land & Sea ®  Exclusive: 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


Opt for our departure transfer to Florence Airport or extend your stay in Bella Italy!

### END ###


Our Selected Hotel for Gaiole in Chianti - 2 Nights

Castello di Meleto or Similar, 2 Nights

San Gimignano Hotel - 1 Night

Siena Hotel - 2 Nights

Fiesole  Hotel - 1 Night


  • 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® Walking Guide throughout your journey.
  • Two complimentary lightweight, telescoping Trekking Poles.
  • Complimentary waterproof travel backpack and transformable multifunctional 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® Walking Guide gratuities optional.
  • Story®'s Unique Perspective Experiences

"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 Walking Guide! Grazie Danino!" 



— 2017 Tuscany Walking Tour Prices —

Small-Group® Walking Tour Departures — Select 'true small group' departures, with No More than a maximum of 16 guests. Prices are per person, based on double occupancy. Single Supplement: $890

True Small-Group®  means a
Maximum of 16 Guests

Walking Tour
Published Date

True Small-Group®
Pricing Guarantee

Max 16 Guests May 15 $4,479
Max 16 Guests May 29 $4,479
Max 16 Guests June 12 $4,479
Max 16 Guests Sep 4 $4,479
Max 16 Guests Sep 18 $4,479
Max 16 Guests Oct 2 $4,479


— 2018 Tuscany Walking Tour Prices —

Small-Group® Walking Tour Departures — Select 'true small group' departures, with No More than a maximum of 16 guests. Prices are per person, based on double occupancy. Single Supplement: $890

True Small-Group®  means a
Maximum of 16 Guests

Walking Tour
Published Date

True Small-Group®
Pricing Guarantee

Max 16 Guests May 14 $4,479
Max 16 Guests May 28 $4,479
Max 16 Guests June 11 $4,479
Max 16 Guests Sep 3 $4,479
Max 16 Guests Sep 17 $4,479
Max 16 Guests Oct 1 $4,479

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

Or, call us now on 1 (877) 865-6711


Guest Reviews

"...making our "trip of a lifetime" come true!! "
Italy's Great Cities Tour - September 2014

Hi Elaine,

I am assuming you are enjoying Spain and Portugal. Wish I was there with you. Hopefully some day.

I just wanted to take the time to let you know what a fabulous job you did. I was so impressed with your knowledge and your leadership on the tour. I certainly got lucky when I found Queenslander. Your local guides were outstanding too. I can't say enough about the tour - the history, the food, the wine, the hotels. Everything was outstanding. I don't think I will find any better wine................ And tuscany - that just blew me away. I can't pick a favorite spot - they were all fantastic.

Also, on a personal note thank you so much for the lovely shawl and the "Italia" shirt for Tony. He has done nothing but rave about this trip!!!!!!!!!!!!!! That's because of you!! (and Queenslander)

Again, thank you for everything and making our "trip of a lifetime" come true!! You are the best Elaine!!! tata !!

~ Tish & Tony Fiamingo

"It was amazing - we can't stop talking about our experience!"
Italy's Great Cities Tour - September 2014

A week ago Dana and I got back from our Italy's Great Cities small group tour. It was amazing - we can't stop talking about our experience! There were only six travelers in our group plus Patrick Nixon our tour captain. Our group quickly gelled and the friendships that developed made the trip even more enjoyable.

Every time we walked past the other large tour groups it reminded me of a cattle drive. People being herded from one site to the next. Some groups were "branded", wearing stickers, scarves or whatever else to identify who they belonged to. I knew right then we made the right decision to go with the small group tour. I felt like we received personal attention from everyone we came in contact with, not only from the tour captain, but the hotel staff, specialized tour guides, chefs and restaurant staff. It was obvious to me that Queenslander has a very good reputation with the people we came in contact with.

Our tour captain, Patrick, was wonderful. From his first communication with us to when we finally met him, he was very approachable and easy-going. He put us at ease right off the bat, and was more than helpful throughout the trip taking care of our questions and any special needs. It is a testament to his abilities and personality that our whole group chose to dine with him on our "off nights". He would always have a new experience, new food, or new wine for us to try. We couldn't wait to see what was next.

Our group ended in Rome, but we kept on going taking the three day extension tour of the Amalfi Coast. What a terrific way to end the Great Cities Tour! We saw the beautiful coast, the Isle of Capri, and Pompeii - but, we also had plenty of time to relax and enjoy ourselves. One thing I really like about your schedule is most of the touring is in the morning when the sites are less crowded. Most afternoons were reserved for exploring on your own. I took full advantage of that and felt we got to discover some real gems on the trip ourselves.

I don't know when we will be able to plan our next trip, but rest assured - we will certainly keep Queenslander at the top of our travel list. Thanks again for helping make our trip special, and memories that we will always cherish.


~ Mark Mishoe

"Enjoyed My Recent Tour With Your Company"
Italy's Great Cities Tour - September 2014

Just wanted to tell you how much I enjoyed my recent tour with your company. I traveled with my son and 3 friends on the Great Cities of Italy tour. Never having even been aware of your company we all were a bit skeptical of what to except. Please know it met all of our expectations in food, accommodations, excursions, free time and more. What most impressed me was the location of every hotel. All were within easy walking distance of both sights and good restaurants. The wine tasting lunch and rooftop farewell dinner were both exceptional.

Our tour captain, Elaine Rodriquez, was outstanding. Her communication skills are exceptional, as well as her listening skills. Her warmth, enthusiasm and sense of humor were a hit with everyone. We felt pampered, were surprised. learned a lot and felt like we had truly made a friend. Leading a group of strangers is an art, one that she has mastered.

I will recommend your company and hope to be a repeat customer. Thanks for providing such wonderful memories!

~ Ann Nimmo

"Highly recommended!!!"
Great Cities Tour - April 2013

We just returned from a 10 day trip to Italy and used Queenslander Tours as our guide. We had a safe...comfortable and wonderful time seeing Venice, Florence, Tuscany and Rome. We stayed in hotels that were just a block to to three blocks from the historical centers of each city. In the Tuscan countryside we stayed in Cortona at...One of the most picturesque hotels I have ever seen.

The tour included 8 nights in 4-5 star properties and 5 deluxe dinners with wine. All hotels had deluxe breakfast buffets.

We had terrific tour guides in each city and a tour captain that stayed with us all the time. That's what I meant about safe!! Our captain could handle anything and had many friends in each city to call on if necessary. Highly recommended!!!

~ Sylvia

"It takes a professional..."
Great Cities Tour - April 2013

I recently returned from your Italy's Great Cities Tour...The trip exceeded my expectations...I didn't realize until I got home just how much planning and work (was) put into this order to make the entire trip exceptional, carefree and memorable...The hotels, local tour guides and restaurants could not have been better. We had the right balance between guided activity and personal time. It takes a professional to provide a city's highlights paired with activities that are less strenuous...It is difficult to pick a favorite Italian city and memory. The wine tasting and lunch in the Tuscan countryside was wonderful. The vintage sports car race through the streets of Cortona was special...our tour guide in Florence was exceptional, as was our guide in Rome. I have recommended Queenslander to my friends and family.

~ Irene

"...truly was the trip of a lifetime..."
Great Cities Tour - April 2013

Shirley and I want to thank you for a fantastic 2 weeks in Italy. You did a wonderful job arranging our personalized tour. We will highly recommend Queenslander Tours to anybody we know...Thank you, Queenslander Tours!

~ Sandra

" have done an amazing job..."
Northern Italy - April 2013

...You and your team did a fabulous job of providing us with wonderful accommodations and a great schedule of tours and events to taste that part of the world...
If we book any more trips, it will be with you. Really you have done an amazing job of finding some wonderful hotels with marvelous views and the villa was such a beautiful place of rest for me and probably the very best staff possible anywhere. The tours were wonderful-just a great job of planning our days and so nice to have that free time...
La Poesia was a real blessing. It is quaint- the room we were in was beautiful with a very spacious bath. And weather permitting the terrace for breakfast and just sitting is gorgeous. The owner is a very warm and lovely...We would definitely want to stay there again. Just all in all Steve and I were so pleased at what a great experience this was-you have been first rate from the very first e-mail.Your small group concept makes all the difference and then it is obvious you have a staff that has made these trips...
Our guide in Siena did a great job-felt more like a friend showing us around. And the basically private tour at Monte Chiaro with Alessandro...
was amazing-to sit with him to talk about the vineyards and olive trees and to have a meal there with him was just so warm and lovely. He as so many others was so very approachable and warm-so often on this tour I felt like these were all friends-very relaxed,intimate settings... provided the avenue for Steve and I to have a trip of a life time!

~ Cathy

..."had a most wonderful time..."
Great Cities Tour - October 2012

Robert and I had a most wonderful time on our recent tour. We are pleased with the way our trip was planned, the information given to us before the start of our trip, and our Tour Leader. The local guides were wonderful, and the hotels were lovely.

...much thanks to all of you at Queenslander.

~ Shirley

"We would definitely travel with Queenslander again..."
Great Cities Tour - September 2012

...Our trip was very well organized. We were impressed by the hotel locations which allowed us to walk to nearby attractions such as Piazza Navona and the Trevi Fountain in Rome as well as the Duomo and several Piazzas in Florence. We were also pleased that we had taken the five meal option. Those meals were very enjoyable and some offered us the chance to get to know the other eight people in our group...

All of our transportation was timely and the drivers, especially on the Amalfi Coast route, were cordial and clearly experts in the areas.

Our tour captain was upbeat, positive and took everything in stride. She was knowledgeable, kept us organized and on time, attentive to our needs, and got us everywhere we were supposed to be. She always had a smile, shared her insights on the city or region we were in, and went out of her way to be helpful...

We would definitely travel with Queenslander again (and) would recommend the company to our friends...

~ Winnifred & Jacqueline

"a superb experience"
Great Cities Tour - September 2012

Our tour was a superb experience for Karen and I and ALL aspects of the trip exceeded our expectations. The itinerary, accommodations, venues, tour and city guides, transportation, meals and beverages were just outstanding. We LOVED Italy-its beautiful countryside, magnificent cities, terrific hill top villages, the history and the treasures, and the wonderful people themselves. A huge contributor to our most memorable holiday was our fabulous tour guide...

What an asset to our group and obviously to Queenslander-tireless, organized beyond belief, knowledgeable, professional, and so much fun to be with-we all just loved her. We were also so fortunate to be accompanied by 7 other awesome couples who quickly became friends, and we were sad to say goodbye to everyone. Thanks so much for all your efforts in building such a high quality tour company-there was not one hitch, just perfect execution in all areas.

Best Regards,

~ Karen and Doug

"I couldn't have imagined a more incredible trip!"
Great Cities Tour - September 2012

Hi Mark! I need to send you a HUGE heartfelt "THANK YOU!" for a "DREAM" trip to Italy!...There was nothing easy or lazy about what you organized for us...I couldn't have imagined a more incredible trip! Both Dave and I will live this trip, over and over in our memories! We will definitely plan another vacation with you in the future! I have many friends who are enjoying our photos and stories of Italy, that will probably plan something with you as well...I just pray you don't get too busy, that you get booked up!???

I must say, we loved our fellow travelers! I know that is the unpredictable element of group vacations...this group of people were so much FUN!

Thank you again for EVERYTHING!!

~ Catherine and Dave

"Had the most amazing time..."
Great Cities Tour - September 2012

Had the most amazing time on this tour. Elaine was the perfect guide...her Italian flair just added so much to the experience.

I will recommend this tour company to anyone I know that would be choosing to go on a trip. Once again, thank you.

~ Pamela

"the most satisfying experience!"
Great Cities Tour - September 2012

Thank you very much for providing one of the most satisfying travel experiences of our lives. Check that, it was the most satisfying experience! While all the sights we saw were terrific, I think it was the personal relationships that made our group what it was. We had so, so much fun.

Hoping to travel with you again sometime in the future,

~ Charlie and Mary Lou