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Tuscany Luxury

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Tuscany Luxury

Quintessential Luxury of Chianti and the Val d'elsa

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Sun-drenched landscapes, the warmth of the Tuscan locals, and the region's incredible cuisine and wine are the recipe for an unforgettable and magical Tuscany bike tour.

A breathtaking blend of great cycling, awe-inspiring scenery and the finest food and sumptuous hotels await the discerning traveler. All while enjoying the "allegria" that permeates throughout the Tuscan region. Pedal along Cyprus tree-lined lanes and lush vineyards into the heart of the Chianti wine region where time appears to stand still. Vibrant local markets await leisure cyclists while the roads famous in the Strade Bianchi and L'eroica call out to more avid cyclists. Here you'll savor the revered wines and intimate hospitality of the Mascheroni Stianti family at their private Castello di Volpaia estate, feast on exquisite Michelin-starred Tuscan cuisine and perfect your pizza spin with our expert pizzaiolo, all while staying in hotels known for centuries as the height of luxury. Sun-drenched landscapes, the warmth of the Tuscan locals, and the region's incredible cuisine and wine are the recipes for an unforgettable and magical Tuscany bike tour.

Learn more about your Perfect Day in Tuscany»

Dates:


Daily Itinerary

View Day-To-Day

Day
1
Day
1

Today's Ride:

Castelnuovo Berardenga to Gaiole in Chainti
Approximately 14 miles with 1,100 feet of climbing

Description:

Your Trek Travel guides will meet you at the Hotel Montebello Splendid at 10:30 AM on the first day of the trip. After a 90-minute shuttle, you will arrive at a family run winery to taste the original heritage of Sangiovese grapes. We'll visit their vintage cellars, sip renowned Chianti Classico wines and indulge in world-class olive oils. After a delicious picnic lunch, your Trek Travel guides will spend some time familiarizing you to your Trek bicycle and ensuring you have an excellent fit. A warm up ride will take you along winding roads past the grand Castello di Brolio and into the tiny village of Gaiole in Chianti where our luxurious hotel for the next three nights, Castello di Spaltenna, awaits. This evening you'll gather for drinks on the terrace overlooking the hotel's own Sangiovese vineyards before we enjoy our first gourmet meal together.

Hotel:

Castello di Splatenna
Visit Website

Included Meals:

Lunch | Social Hour | Dinner


Day
2
Day
2

Today's Ride:

Gaiole in Chianti to Castellina in Chianti Loop
Approximately 40 miles with 3,700 feet of climbing

Short Option:

Gaiole in Chianti to Castellina in Chianti with shuttle
Approximately 20 miles with 1,600 feet of climbing

Avid Option:

Gaiole to Castellina in Chianti to La Strolla Loop
Approximately 54 miles with 5,400 feet of climbing

Description:

This morning, you'll climb high up above the vineyards, where you'll be rewarded by rich panoramic views of rolling, sun-drenched Tuscan hills. As you gently descend you'll float through tiny medieval hamlets and into the heart of idyllc Chianti. For lunch, choose to stop and wander the picturesque cobbled streets or sample some locally crafted percorino, proscuttio, olives or pizzas for lunch. This afternoon, opt to cruise back to the hotel with your Trek Travel guide and unwind in style by the pool or take the road less traveled and tackle a few more of Tuscany's stunning hills. This evening we’ll shuttle into the medieval town of Siena, home to the famous "Palio Race" and the storied Mangia Tower. Here, you'll learn the secrets of this historic città from a local guide and see the world-famous Duomo. Afterwards, peruse the glittering streets and allow all manner of Tuscan specialties to unfold before your eyes. Plus, your guides will have plenty of suggestions on where to find culinary favorites like wood-fired pizza or a bowl of Cinghiale (wild boar) pasta accompanied by a glass of Brunello.

Hotel:

Castello di Splatenna
Visit Website

Included Meals:

Breakfast


Day
3
Day
3

Today's Ride:

Gaiole in Chianti to Volpaia Loop
Approximately 38 miles with 2,700 feet of climbing

Short Option:

Gaiole in Chianti to Volpaia with shuttle
Approximately 19 miles with 2,200 feet of climbing

Avid Option:

Gaiole in Chianti to Volpaia Loop with Luccarelli
Approximately 44 miles with 5,100 feet of climbing

Description:

Today’s ride traverses the lush vineyards, forested hills, and olive groves of the Chianti region. Pedal through the village of Lecchi and enjoy an espresso with the locals before continuing up to Radda, the ancient capital of the League of Chianti. You'll have time to explore this vibrant village, filled with bustling shops and galleries—the perfect place to pick up some mementos to bring home. Your midday destination is Castello di Volpaia, where the Mascheroni Stianti family personally welcomes you for a wine-paired lunch in their villa. Afterward, we invite you to enjoy an exclusive visit of the castle’s cellars and olive oil press. From here, continue on to our hotel for an afternoon of relaxation, or hop back on your bike to take in more of the surrounding landscape. This evening, an exquisite Michelin starred dinner awaits you at Castello di Spaltenna.

Hotel:

Castello di Splatenna
Visit Website

Included Meals:

Breakfast | Lunch | Dinner


Day
4
Day
4

Today's Ride:

Gaiole to Castello di Casole with Mensano Loop
Approximately 48 miles with 4,300 feet of climbing

Short Option:

Gaiole to Castello di Casole
Approximately 41 miles with 3,600 feet of climbing

Todays Activity:

Evening masterclass, perfecting your pizza spin with our expert pizzaiolo.

Description:

The breathtaking Elsa Valley awaits you today. Its quiet roads offer rich, colorful vistas of golden hills dappled with silver olive groves, framed by dark green cypress. After a beautiful morning ride, you’ll enjoy a stop for lunch in Casole d'Elsa, an ancient Etruscan settlement. This village sits atop a ridge commanding magnificent views of the surrounding countryside. Stroll through the main square and be sure to visit La Rocca, easily Italy's most beautiful town hall. Feast at a family-run Osteria in town featuring handmade Tuscan pasta dishes and seasonal salads. This afternoon, we'll continue our ride up to the stunning five-star Castello di Casole. This incomparably resplendent hotel is simultaneously one of Tuscany's most impressive destination hotels—and formerly an estate to the 10th century elite. Tonight, take part in a private pizza-making class, where you'll learn how to spin your own pizza dough and make the pie of your choice with a trained pizzaiolo.

Hotel:

Castello di Casole
Visit Website

Included Meals:

Breakfast | Lunch | Dinner


Day
5
Day
5

Today's Ride:

Castello di Casole to San Gimignano Loop
Approximately 40 miles with 3700 feet of climbing

Short Option:

Castello di Casole to San Gimignano
Approximately 24 miles with 2,400 feet of climbing

Avid Option:

Castello di Casole to Montaione to San Gimignano Loop Option
Approximately 59 miles with 5,000 feet of climbing

Description:

It's pure extravagance to awake at Castello di Casole, and after a leisurely breakfast, we'll mount our bikes for one last amazing day. We start with a descent from Casole into the valley below, where you’ll ride across vine-covered slopes and up to the medieval town of San Gimignano where you're welcomed by the vibrant colors, sights and sounds of it's legendary open-air market. Sample fresh regional olives and “picci” pasta before taking a stroll through the stalls of the local artisans offering one-of-a-kind wares. This afternoon spin back to the hotel to enjoy some time by the infinity pool overlooking the gorgeous Elsa Valley. Or, choose one of the many activities available at the hotel, including a lesson in ceramics, a watercolor class or indulge at the destination spa. Tonight, you'll savor the trip's final gastronomic delight: a capstone meal at the hotel's renowned restaurant, La Tosca. Soak in the magical atmosphere of this elegant retreat and raise your glass to a week of wonders in Tuscany.

Hotel:

Castello di Casole
Visit Website

Included Meals:

Breakfast | Social Hour | Dinner


Day
6
Day
6

Today's Ride:

Castello di Casole to Mensano Loop
Approximately 14 miles with 1,200 feet of climbing

Today's activity

Hot Air Balloon flight

Description:

Arise early this morning to enjoy a hot air balloon flight and witness the sunrise creeping over the stunning Val d'elsa or enjoy a final spin through the Tuscan countryside that is surely now starting to feel like home. Or, if you’d rather, simply linger over a hot cappuccino and enjoy a leisurely morning soaking in the gorgeous views from the breakfast patio before you bid your farewells. * Note: Hot air balloon flights must be pre-booked 30 days in advance with Trek Travel*.

Included Meals:

Breakfast


Dates & Pricing

The earlier you book, the greater the rewards

We reward our guests with lower pricing and more dates to choose from the earlier you book. Rest assured, once you book, your price and date are guaranteed.

2018


Apr
22nd - 27th / 6 days / 5 nights
$4999 / Person, $1600 / Single Occupancy
Guaranteed *
May
20th - 25th / 6 days / 5 nights
$4999 / Person, $1600 / Single Occupancy
Guaranteed *
Jun
3rd - 8th / 6 days / 5 nights
$4999 / Person, $1600 / Single Occupancy
Guaranteed *
Jun
10th - 15th / 6 days / 5 nights
$4999 / Person, $1600 / Single Occupancy
Guaranteed *
Jul
15th - 20th / 6 days / 5 nights
$4999 / Person, $1600 / Single Occupancy
Guaranteed *
Jul
22nd - 27th / 6 days / 5 nights
$4999 / Person, $1600 / Single Occupancy
Guaranteed *
Jul
29th -
Aug
3rd
/ 6 days / 5 nights
$4999 / Person, $1600 / Single Occupancy
Guaranteed *
Limited Availability
Aug
5th - 10th / 6 days / 5 nights
$4999 / Person, $1600 / Single Occupancy
Guaranteed *
Aug
19th - 24th / 6 days / 5 nights
$4999 / Person, $1600 / Single Occupancy
Guaranteed *
Aug
26th - 31st / 6 days / 5 nights
$4999 / Person, $1600 / Single Occupancy
Guaranteed *
Sep
2nd - 7th / 6 days / 5 nights
$4999 / Person, $1600 / Single Occupancy
Guaranteed *
Sep
9th - 14th / 6 days / 5 nights
$4999 / Person, $1600 / Single Occupancy
Guaranteed *
Sep
16th - 21st / 6 days / 5 nights
$4999 / Person, $1600 / Single Occupancy
Guaranteed *
Sep
23rd - 28th / 6 days / 5 nights
$4999 / Person, $1600 / Single Occupancy
Guaranteed *

What is Single Occupancy?

Sometimes it’s more convenient and comfortable to have your own room while on vacation. We understand and that’s why we offer a Single Occupancy option. The additional price guarantees a private room all to yourself.

Hotels

Enjoy Castello di Spaltenna on our Tuscany bike trips

Castello di Spaltenna

Gaiole in Chianti, Italy

Trip Advisor Certificate of Excellence Award This medieval hamlet in the heart of Chianti, a sub-region of Tuscany, complete with castle and church, has been transformed into an elegant hotel surrounded by vineyards and woods. Weaving modern luxuries with its rich history, Castello di Spaltenna offers uniquely decorated rooms, fine dining, a full wine cellar, outdoor and indoor pools and impeccable service.
Stay at Castello di Casole on a Tuscany luxury bike tour

Castello di Casole

Casole D'elsa, italy

World's Best Awards 2017 Logo A Timbers Resort, ranked the #1 Resort in Europe by Travel + Leisure magazine, is a beautifully restored castle set on a 4,200-acre private estate. This five-star boutique hotel boasts an incredible destination spa, gourmet and relaxed dining and exquisite suite accommodations that effortlessly combine Old World Tuscan charm with modern luxuries.

What's Included

We Include More

Every moment of a Trek Travel bike trip has more than you could have ever dreamed. More romance. More scenery. More choice. It's the little additions to every Trek Travel cycling vacation that make it truly special. And that’s how we help you create more memories. See more

  • Gratuities for all scheduled special events, restaurants, hotels, local guides and transportation during your trip.
  • Private tours
  • Entrance fees to all group events/activities
  • All luggage transfers
  • All transportation during the trip, including private coaches
  • 5 nights of accommodation
  • In every region we travel, we first visit ourselves to uncover the area’s best, and most delightful accommodations. On our Tuscany trip, you'll stay in a medieval hamlet high above Gaiole and a restored 10th century Italian castle on a centuries-old country estate. Both feature 5-star meals, unique on-site activities and accommodations that weave old and new together to create the pinnacle of luxury.
  • Daily breakfast, 3 lunches, 2 social hours, 4 dinners, and all snacks and drinks for each day
  • On our Tuscany trip, the cuisine is characterized by fresh, seasonal ingredients, prepared in a simple, classic style. Lunch offers bountiful selections of local specialties. Dinners are enjoyed at local trattorias and feature hand-made pastas among other favorites. You will also dine at a Michelin starred restaurant which highlights the very best of the region and season. On other occasions, you’ll be free to choose your own restaurants to discover your own personal favorites!
  • The knowledge, support, and camaraderie of experienced guides
  • Daily route support
  • Paper route guides also available upon request
  • Comprehensive trip literature
  • The use of a Trek Domane SL 7 carbon road bike with Shimano Di2 electronic shifting, or Trek 7.6 FX Hybrid bicycle
  • Trek Electric Assist XM700+ also available in a limited quantity
  • The use of GPS cycling computer
  • The use of Bontrager bike helmets and other gear and equipment to make your ride comfortable
  • Trek Travel water bottles
  • Coupon valued up to $500 off a new Trek Bicycle. Contact us for details.
  • Trek Travel Bontrager RL jersey and cycling socks

Thank your Guides, by tipping

Gratuities for your Trek Travel guides are not included in your trip price. We recommend tipping 7.5-10% of your trip price for the guide team. Local currency is preferred and unless you want to tip separately, guides will divide tips amongst themselves. Please tip your guides at your discretion, based on their level of professionalism, guest care and service.

  • Airfare and transportation to and from the trip pick-up/drop-off locations
  • Lodging before and after the trip
  • Personal items purchased during the trip
  • Optional activities not scheduled by Trek Travel
  • On select trips some meals are not included. On these trips, Trek Travel invites you to explore the local cuisine at your leisure.
  • Gratuities for your Trek Travel Guides may be given at your discretion in response to their professionalism and leadership.Industry standard is for each individual guest to tip the guide team 7.5-10% of the trip price.

FAQs

Trip Changes

Our itineraries are an approximation of our trips. Trek Travel strives to offer each and every guest a vacation of a lifetime on every trip. At times routes, hotels, activities, etc. listed here may change at the discretion of the trip designer or guides to improve the trip experience.

  • Rider Type | 3
  • Average Daily Mileage | 30
  • Terrain | Hilly
  • Average Daily Elevation | 2,000 feet

On all of our vacations, Trek Travel strives to find quiet, paved secondary roads or bike paths to experience a region; busy roads are avoided as much as possible. Tuscany is best suited for our Type 3 Riders. Our Trek Travel guides can also easily accommodate Type 2 Riders, who seek less mileage or fewer uphills, with a boost in the van. Those who wish to ride every mile but are concerned about their physical ability may want to try our electric bike option–you still get a workout but can climb alongside even the strongest rider. Type 4 Riders will enjoy the extra mileage the avid route options offer. The terrain is consistently rolling, with quiet, narrow, and winding roads. Many towns sit atop hills and, although the ascents are not exceptionally steep, they are often upwards of 5km long. See Itinerary for specific daily ride distance and elevation options.

On most Trek Travel trips, we offer non-riding options for riders who want to take the afternoon off, or travel companions who want to spend little or no time in the saddle. Some of these options may need to be scheduled before your trip–please contact one of our Trip Consultants for more information. Expenses and/or related transportation to these activities may not be included in the trip price. See Included In The Trip Price for more information. Some non-riding options on this trip are:

  • Discover why Tuscan wines are so renowned during our private wine-tasting
  • Visit historic Siena
  • Indulge at the Spa
  • Relax by the pool
  • Take part in a private Pizza making cooking class
  • Visit to San Gimignano for market day

Spring and Fall in Tuscany is usually clear and sunny, with warm daytime temperatures (75F-90F) and evening temperatures 10-15 degrees cooler. A jacket or wrap will be useful in the evening. Summers are hotter with higher daytime temperatures (80F-95F) and evening temperatures 10 degrees cooler. Rain is always a possibility, however, so be prepared with wet-weather gear in order to best enjoy your vacation.

For an additional fee you may request to upgrade to the brand new Trek Emonda SLR with Shimano Di2 Electronic shifting or Bontrager Aeolus carbon wheels for the ultimate riding experience. Contact our trip consultants for more details.

If you’re going we’re going on almost all our trips. Trips with 1 guest booked are guaranteed to run. Select trips like Cross Country, Race and Special Edition trips require a minimum number of guests to run and are not guaranteed until that number is reached. Contact your Trip Consultant for more details.

In the event that a departure has low enrollment, we will notify guests at 60-90 days before departure to give the option to select a different date with more guests booked. Please do not reserve airfare before confirming your Trek Travel trip.

When a trip is booked, a guest confirmation letter is immediately sent out. One week prior to the trip start you will receive an email containing a trip start meeting location reminder and any last minute information that you will need to know before your trip. Once you arrive at your destination Trek Travel staff will brief you on the day-to-day plan for the trip and provide you with daily route guides and a detailed map allowing you to ride with complete confidence and independence.

Please review our packing list page for more details.

We understand things happen in life and sometimes you have to cancel or change your bike tour. We want to make it as easy as possible to do so and below you will find our timeline. If you ever have a question, just give us a call, 866 464 8735. Read our cancellation policy.

Didn't find what you were looking for? Check out our General FAQs section. You will find answers to all the most common questions that don't necessarily pertain to a specific trip.

Meeting & Departing

How to get there

We suggest that you arrive at least one day prior to the trip start, which will enable you to adjust to the time zone and minimize the risk of missing the trip start due to flight-related delays. We recommend that you fly into Florence’s Amerigo Vespucci Airport (FLR). The Florence airport is about 3 miles from the town center. You can take a taxi (~20 euros) directly to the hotel, or a bus which departs hourly.

Rome and Milan also offer flight options. From Rome’s Fiumicino Airport (FCO), you may take a direct train to Rome’s central station, Roma Termini. Follow the “Stazione/Railway Station” signs. Trains depart twice hourly. Tickets can be purchased at a Biglietteria office or from ticket machines. All tickets must be validated before getting on the train: do this by stamping your ticket at the yellow boxes near the platform. The ride takes 30 minutes. From Roma Termini, transfer to a train for Florence. The Eurostar trains depart frequently and are the quickest. The trip takes 1-1/2 hours and costs between 44-62 euros one way per person. In Florence, taxis are available to take you to your hotel. Taxi service is available from Rome Fiumicino Airport to central Rome for ~50 euros.

Hotel Montebello Splendid | Florence, Italy

Your Trek Travel guides will meet you at the Hotel Montebello Splendid (Via Giuseppe Garibaldi, 14, 50123 Florence, Italy) at 10:30 AM on the first day of the trip. Should you wish to reserve a room at this hotel pre or post trip, please contact your Trip Consultant for a discount code. You’ll then shuttle 90 minutes to your lunch spot for a taste of Tuscan cuisine. Have your first day’s cycling clothes and riding gear easily accessible, separate from your luggage. After lunch, your guides will do a bike fitting to ensure your comfort on your Trek Domane this week, before you take your first spin through the countryside.

If you will be late for the pick-up or are going to miss it altogether, please inform your guides. You will receive an email a week before the trip start with their names and contact details. If you cannot reach them, please call our first hotel, Castello di Spaltenna (+39 0577 749483) and leave a message with your expected arrival time and contact details. You may take a taxi to the first night’s hotel for approximately 200 euros. The trip takes over an hour from the center of Florence.

Hotel Montebello Splendid | Florence, Italy

You will say farewell to your guides at 10:00 AM at the Castello di Casole, Casole D'elsa. You’ll depart by private shuttle for Hotel Montebello Splendid, Florence, arriving close to 11:30 PM. The hotel is a 10 minute taxi from Santa Maria Novella train station where trains connect to many European cities. Please do not book seats before 1:00 PM. The airport in Florence (FLR) is 3 miles from the city. You can reach it by train, taxi, or shuttle bus; please do not schedule a flight prior to 4:00 PM. Visit www.TrenItalia. for train information.

Before: Florence, Italy

Florence is the majestic heart of Renaissance art and intellect. Several days can be spent wandering the streets in the shadow of Brunelleschi’s Duomo and strolling beside the Arno. Along with the Duomo and Ponte Vecchio, the Uffizi gallery, a pillar of the Renaissance and Medici eras, merits a visit. Michelangeo’s David in the Galleria dell’Arte is not to be missed. Keep in mind while exploring Florence that opening hours vary and are quite often inconsistent. Different museums are open on different days and lines can be very long. It’s worthwhile to pay a few extra euros and pre-book your tickets—this will enable you to bypass long lines of visitors at the entrances. We recommend the following accommodations for your pre-trip hotel.

Number Nine

This brand new luxury boutique is located in a noble Florentine residence. Enjoy the finest hospitality while savoring the heart of Florence.

Via de’ Conti, 9 | +39 055 5383583 | www.FirenzeNumberNine.com

Residenza del Moro

Escape the bustle of the city in this private hideaway complete with rooftop garden in the heart of Florence. Rooms in this 16th century palazzo are sumptuously furnished, and stunning centuries old frescoes juxtaposed with magnificent modern art adorn the walls and ceilings. The ambiance is private, luxurious, and serene.

via del Moro, 15 50123 Firenze | +39 055 290884 | www.ResidenzadelMoro.com

Hotel Montebello Splendid

The Hotel Montebello Splendid is an elegant 5 star, boutique hotel located just 10 minutes walk from all the main monuments and points of interest in Florence. Take advantage of their concierge services to plan your stay in Florence to the last detail A serene atmosphere including a gourmet restaurant completes the setting—perfect for those wishing to find an exclusive hideaway within walking distance of the Santa Maria Novella train station. Should you wish to reserve a room at this hotel pre or post trip, please contact your Trip Consultant for a discount code.

Via Giuseppe Garibaldi, 14, 50123| + 39 055 27471| montebellosplendid.com | ~$250

After: Rome, Italy

In every region we travel, we uncover the area’s best, and most delightful accommodations. On our Tuscany trip, you will stay in a historic palazzo in charming San Quirico, a luxurious country villa surrounded by rolling hills, and a former castle of a medieval hamlet high above Gaiole. We recommend the following accommodations for your post-trip hotel.

Hotel Barocco

This 37-room hotel is tucked away in central Piazza Barberini. It boasts a refined, simple style with all of the comforts and amenities needed for a relaxing Roman getaway.

via della Purificazione, 4 00187 Roma | +39 06 487 2001 | www.HotelBarocco.com

Hotel Capo d’Africa

Located in the heart of Imperial Rome, between the Forum and the Domus Aurea, the Hotel Capo d’Africa boasts contemporary decor within a beautiful, early 19th century building. 64 rooms.

via Capo d’Africa, 54 00184 Roma | +39 06 772801 | www.HotelCapodAfrica.com

Mecenate Palace

In front of the Basilica of Santa Maria Maggiore, this hotel is within walking distance of most of the important monuments and shopping areas found in Rome. Guests can enjoy a panoramic view of the city from the hotel’s roof garden. 62 rooms.

via C. Alberto, 3 00185 Roma | +39 06 44702024 | www.MecenatePalace.com


* Hotels listed above are local properties we love. We do not have special rates available.

Experience It

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Trek Travel Difference

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the all-new, ultra smooth Trek Domane SL 7, to the new Trek Electric-Assist XM700+ and the comfortable Trek 7.6 FX Hybrid, to our numerous upgrade options, you deserve the best ride on your vacation.

Our Guides

Our guides are trained to make your trip magical. They aren't just experts in riding; they're trained in delivering uncompromising service in ways you won't believe. We know that it's the unexpected surprises that make a trip magical. That's why our guides pride themselves on anticipating your needs before you ask.

Your Day. You Decide.

Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.