Flavors of Tuscany Gay Travel Bicycling Tour in Italy

beautiful red door peers from the corner of a historic village street in montefioralle

 2019  September 15 to 22 – One Spot in a Male Room Share

A Gay Travel Italy Biking Tour Through Tuscany

Physical Challenge:

Italy was made for biking! Join this gay Italy bike tour and enjoy the friendly Italian people, varied landscapes, world-famous cuisine, castles and splendid palaces, Etruscan tombs, museums, and medieval villages that make each day of cycling a new adventure!


  • Stroll along Florence’s picturesque Ponte Vecchio, crammed with leather shops, admire Michelangelo’s David, then check out Tuscany’s nascent gay scene.
  • Enjoy lunch in a medieval town in the heart of “Chianti Classico”, sampling the red wine that made the region famous.
  • Watch for the wild boar, pheasants, and occasional wolves that still inhabit the forests of scrub oak and pine.
  • Sip a cappuccino in Siena’s breathtaking Piazza del Campo, one of the most beautiful public plazas in the world.
  • Delight in the scents and flavors of Tuscany: Fresh-picked wild mushrooms, robust cheeses, crusty Italian bread, and ruby Chianti wines.

A Rousing Ride Through Chianti Wine Country!

Our gay Italy bike trip begins in Tuscany, in the fabled Renaissance city of Florence, and home of Michelangelo’s “David.”

Florence is just the tip of the proverbial iceberg, as recognizable names from History like Siena, San Gimignana and Radda become more than just points on a map, they become living, breathing time warps which we will cycle through and into!

After the first night in Florence, we spend two nights at each hotel, allowing time to get to know each region in more depth. Tuscany has hills, and part of the fun of this trip is riding over the hills, and enjoying the vistas as you descend the other side. This trip has the perfect combination of riding and relaxations, with plenty of art, touring, and gelato thrown in! We’ll also explore and savor all the “Flavors of Tuscany” guiltfree after all our hard work!

Our starting point, Florence, is home to many of the most celebrated works of the Renaissance, including Michelangelo’s famous statue of David. You may have seen pictures of “it” in all it’s glory, as it is without a doubt the most viewed sculpted genitalia in history!

You’ll need at least two or three days to see even the highlights among the Florentine museums and plazas. We suggest either arriving early or staying in Italy afterward; if your schedule allows it.



Day 1: Magnificent Florence

stunning sunset view of a boat beside the ponte vecchio bridge in florence

Our trip officially starts at 6:00 pm, giving everyone a chance to arrive in Florence if coming from other destinations. Early arrivals and those who have already been here a few days are invited to join us at 3:00 to try out their bikes, and at 4:00 for an optional walking tour of the city.

Time permitting, our walk takes us to Piazza della Signoria, where an outdoor sculpture gallery features a replica of David himself, along with the works of Cellini, Donatello, and other Renaissance artists. We’ll walk across Ponte Vecchio (Old Bridge), built in 1345 and encrusted with jewelry shops, and stop at the massive Duomo, the ornate 14th-century cathedral that still dominates the city. Don’t worry, we have a gelato stop scheduled as well…

delicious gelato served on a street in florence

After an orientation session at our hotel, we’ll get together for our welcome dinner. Tuscan cuisine is famous for its creative use of fresh, flavorful ingredients, and the Italian waiters will make you want to get fresh too!

Afterward, those who wish can explore Florence’s gay nightlife, while others get a head start on their sleep.


Day 2: Cycling Through Colorful Tuscany

close up of chianti wine grapes hanging on a vine


It takes us only twenty minutes to bike across the river and on to Porta Romana, where we leave most of Florence’s traffic well behind us. Soon we’re biking along rural roads, winding past vineyards and orchards.

A picnic lunch in the tiny village of Greti gives everyone a goal for the morning: Crusty bread, thin slices of prosciutto, several types of cheese, fresh salads, and an assortment of pastries. A wedge of pecorino cheese on a slice of ripe pear seems like the perfect dessert — until the pastries appear.

It’s nice to have choices, and you will have them as we ride on…Whether you take the long route or the short one, we will all end up together in the lively town of Panzana, a colorful slice of Italian life in the countryside, and then on to Radda.

beautiful red door peers from the corner of a historic village street in montefioralle

We’ll spend two nights on the outskirts of Radda, at a site known as Castelvecchi. These old stone villas sit on a hillside amidst forest and fields. Castelvecchi’s hillside location presents the only negative thing that anyone can say about this charming spot: It’s halfway up a hill, and we’re not.

Two stops en route make the climb more bearable: A lake where we can cool off after a hot day; and tiny Santa Maria Novella, a Romanesque church built in the 12th century.


Day 3: Castles and More Castles!

a shot of costello di brollo beyond a verdent vinyard

Two castles and an 11th-century abbey lie on today’s suggested biking loop, but the roads themselves provide an enjoyable day of cycling, their roadsides adorned with the pastel polka-dots of blue chicory flowers and shaded by oak and cypress trees.

Castello di Brolio, owned by the same family for nearly a thousand years and still inhabited, is a sprawling estate of gardens and vineyards, with the castle rising in their midst. From the terrace, we have sweeping panoramas of the Arbia valley.

intricate detail of a statue in radda tuscany

After lunch at an outdoor cafe, we continue to the elegant Castello di Meleto, dating from the 12th century. After walking the grounds, we can sip their estate-made grappa, a strong grape-based liquor common in the region.

Biking is optional today since we’ll have two nights at the same location. If you’d prefer a day of hiking, you can make an enjoyable loop by walking south, through vineyards and forest. Keep an eye out for wild boar!


Day 4: Hills and Towers

vineyard outside san gimignano on the HE Travel gay biking tour in Tuscany Italy

We enjoy a welcome and well-deserved descent as we roll out of Castelvecchi.

Eight miles away lies Castellina in Chianti. Just outside the town lies Monte Calvario, a large mound or tumulus that covers four Etruscan tombs dating from the 4th century BC. Although tomb robbers have long since cleared out the contents, each chamber remains open. Heads slightly bowed, we can explore the long slab stone corridors.

Then comes another delightful descent, through a forest preserve. Today’s picnic is at a Romanesque chapel located in the midst of this preserve on — where else? — a hilltop. We’re headed to San Gimignano, known as “the city of beautiful towers” for its 14 towers, preserved from medieval times. Some cyclists will probably want to bike directly into town to explore the narrow streets, shops, and rampart walls. For those who just can’t get enough, we can bike to Sant Appiano and Linari, small, quiet, and charming Italian villages, each crowning a separate hill.

close up view of a tower in san gimignano

San Gimignano positively bustles with life and has been a popular spot with visitors for centuries.

Tonight’s Flavor: Maybe rabbit flavored with saffron, or sausage made of a wild boar that forgot to be shy. Vegetarians need not worry: Tuscany is equally famous for its flavorful cheeses, savory pasta, fresh produce, and aromatic herbs. For dessert, try one of the pastries, or a regional specialty: almond biscuits called cantucci, dipped into the local dessert wine known as vin santo.


Day 5: Volterra History and Handicrafts

grazing white cow ion the hills of voleterra

The ancient city of Volterra, high on a windswept plateau, was an Etruscan stronghold for five centuries, but ultimately fell to the Romans in 295 BC. It houses the Guarnacci Museum, with one of Italy’s finest collections of Etruscan artifacts.

For those who would prefer to shop: Since Etruscan times, Volterra has been famous for its alabaster carvings, using rock quarried from a nearby hillside. Local artisans still work the translucent stone into sculptures, vases, and dishes, and Volterra’s narrow streets offer plenty of shopping opportunities. The ride to Volterra is an all-day affair, about three hours in each direction, leaving us a few hours in the city itself.

Anyone who prefers to hike today can follow quiet roads and mule tracks from San Gimignano, through olive orchards and vineyards.

stopping for a rest on the HE Travel gay biking tour in Tuscany Italy

Tonight’s Flavor: One Tuscan specialty is bistecca alla fiorentina (Florentine steak). This tender T-bone steak, grilled and served with lemon and fresh herbs, is usually split between two people — which means they still get roughly a pound apiece.

All of our biking is paying off, since San Gimignano and Volterra, like most towns in Italy, has superb gelato shops. According to legend, the Romans invented ice cream, by mixing snow with berry juices. Modern-day Italians have perfected the technique. Today, savor the rich chocolate and hazelnut flavors. Tomorrow, try the robust fruit flavors: pungent lemon, rich strawberry, and a more subtle pear.


Day 6: Two Hilltops

cyclists on the road on the HE Travel gay biking tour in Tuscany Italy

A graceful, solitary umbrella pine adorns the skyline as we begin our descent from San Gimignano for our last full day of biking. Further along, the horizon is broken by a row of tall cypress trees. Today’s biking route takes us along the Elsa river valley, with stops at two old villages, both perched on hilltops, yet utterly different.

High in the village of Colle di Val d’Elsa, surrounded by 16th-century walls and iron gates, lie the medieval mansions, arches, towers, and cathedral of the old town, known as Colle Alta. Today the graceful stone buildings host modern glassworkers, who create sparkling crystal goblets and brilliant glass flowers. A dozen workshops and display rooms line the streets, each with their own specialties. More shopping? You betcha!

Further on our route comes the fortified hilltop town of Monteriggioni. Encircled by a thick well-preserved stone wall and 14 towers, Monteriggioni was built by Siena in 1203 as one of their defenses — ultimately unsuccessful — against rival Florence. Today, it presents a dramatic silhouette against the blue Tuscan sky. Two restaurants provide an excuse to linger within these walls. Today’s Flavor: We propose bruschetta, thin-sliced Italian bread topped with fresh chopped tomatoes, then pasta with truffle sauce, melon and prosciutto, and a fresh salad.

Now just another hour of biking takes us to Siena, Florence’s long-time rival, and indisputably one of Italy’s most beautiful cities. Our hotel for the next two nights is near the heart of the city.


Day 7: Siena


Five centuries ago, Siena and Florence were deadly enemies. When Florence finally defeated its rival, the Florentines banned new buildings in Siena. That defeat, in certain ways, became a victory. Today Florence is larger; it’s wealthier, and it has more famous works of art. But many visitors find that Siena, frozen in time, has a mystery and a soul unmatched in Italy. This morning, we offer a guided walking tour of Siena, then the afternoon is free for you to explore this magical city on your own.

Any visitor soon becomes aware of Siena’s three most famous features: A cathedral, a plaza, and a horse race. Work began on the Duomo, the elegant marble cathedral, in 1136, but was not completed until another nine generations had passed. The fan-shaped Piazza del Campo, considered by many to be the most beautiful public space in the world, is Siena’s heart. Open only to pedestrians, the plaza pulses with human activity: Restaurants and vendors, tourists and businessmen, friends and lovers, all pass through as they circulate around the city. After a week of biking, it should be a simple matter to climb the 505 steps to the top of the Torre del Mangia, high above the plaza, and look at the striped black-and-white marble columns of the nearby Duomo.

a stunning view of a cathedral in siena

Twice a year, in July and August, this plaza hosts the celebrated Palio: A horse race where the city’s close-knit neighborhoods compete in a no-holds-barred competition, as highly skilled athletic Italian bareback riders, circle the plaza three times. The first horse to cross the finish line — with or without the jockey — is crowned the winner, and for weeks before and after the Palio, Siena’s streets come alive with flag-waving pageantry, festive parades, and costumed celebrations of the winning neighborhood. There are more men in colorful outfits here than a party at a 70’s themed disco party.

Tonight’s dinner is a festive affair during which we get one last chance to enjoy some of our new favorite Tuscan dishes, and also try some new delicacies. How about pasta with a sauce of walnuts and garlic? Or a delicate chicken dish with shavings of white truffles.

Then, we toast a week that seems to have gone by too fast, and new friendships, before a final celebration of the flavors of Tuscany.


Day 8: Ciao, Tuscany!

plate of cheese and glasses of wine gleaming in a tuscan sunset

The hardest thing about our trips is saying goodbye to new friends, and to a charming region of Italy.

Come early and join our Cycling Spain’s Camino de Santiago

stopping to admire a rainbow of flowers on the HE Travel gay Spain Camino Cycling tour

A Pilgrimage of miracles made by millions over the centuries, that is the Santiago de Compostela! One of the most amazing experiences one can have in a lifetime, and we will do our gay Spain tour without the walk, but riding from place to place with our new best friends.

Stay longer and join our Italy Unveiled Tour


An exquisite gay cultural tour of Italy with a congenial gay group exploring the Amalfi Coast, Capri and the enchanting regions of Basilicata and Puglia. We’ll delve into the history of Pompeii, and delight in the natural splendor of the region, admiring the tenacity with which ancient residents settled the cliffs and islands of the Mediterranean.


Price includes: Comfortable hotels each night; Services of two HE Travel tour guides; Use of 21-speed hybrid bike; All breakfasts, 2 lunches, and 5 dinners, with wine included; Five biking days, and a sightseeing day in Siena; Transportation to get luggage (and tired riders!) to destinations; A wine-tasting; Map of Tuscany and detailed routes. HE Travel provides complimentary Medical & Evacuation Insurance for every US Resident on our group tours who does not have other coverage.

Not included: Travel to Florence and from Siena; 4 lunches; 2 dinners; Souvenirs, snacks, admissions; Gratuities for guides.

Optional Tour Choices:

$1000 Single Supplement (for solo travelers who wish to enjoy a private bedroom and bathroom)

$120 Dining and Walking Tour of Florence on Day 1.

“Excellent Trip–great guides and wonderful historic sites. Plenty of wine, tasty Italian food, beautiful countryside, and camaraderie.” -Ron R., Oak Park, IL

“This trip combines outdoor exercise and culinary excellence.  It is well planned and executed with perfectly selected accommodations and guides and hosts in every city/town who make you feel welcomed and comfortable. Although my legs smiled when we said goodbye to the bikes, my heart was saddened…I truly did not want it to end!” — Brian P., Trinidad and Tobago

“Along with the wine and the beautiful Tuscan scenery, the new friends I met made for the best adventure.” — C. Burks, Sarasota, FL

“I had high expectations going into the trip and [HE Travel] exceeded every one of them. This trip has spoiled me for all future vacations, because the bar has been raised so high.”— Jeff Welshans, Harrisburg, PA

“Flavors of Tuscany featured all the things I’ve come to love about [HE Travel]: great sights, intimate views, action-filled days, and great people. The trips are a good value for the money.”— Dane d’Alessandro, San Francisco, CA

Physical Challenge Level 4

Tuscany has hills! This is a trip of moderate difficulty, for cyclists who can comfortably bike 35 to 40 miles a day over rolling terrain, and who have basic map-reading skills.


We typically supply 21- or 27-speed hybrid bikes. We find them ideally suited for cycling trips of this sort. They have upright (rather than dropped) handlebars, and a low “granny” gear for hills. The brand and model can change from one location or season to another, and we cannot promise a brand name in advance.


We also supply a lock, spare tube and patch kit, and a handlebar bag or back rack for carrying a few small items.


The seats on most bikes we use are a standard size, neither the narrow racing seat nor the wide touring seat. Therefore we recommend medium-sized gel seat covers if you wish to bring one along.

This tour starts in Florence and ends in Siena, Italy. Each bike trip officially starts at 6:00 p.m. on the starting date given on our schedule and trip overview. We’ll have a reception and briefing, followed by dinner. For those who arrive early, we offer an optional walking tour of town (along with a chance to meet other early arrivals). Finally, when our guides’ schedule allows, you can give your bike a test ride at 3:00. On arrival at the hotel, please look for our sign in the lobby giving details.


Each trip ends after breakfast. There are no group activities on that day, so if you have tight travel connections, you can get up and leave as early as you wish. When your schedule allows it, you’ll probably want to spend some time sightseeing in town, with others from the trip, before departing.


Our “7-day” trip thus consists of 6 full days and two partial days. Some companies promote a trip of this length as being 8 days since it includes pieces of 8 different days. We feel it’s more accurate to refer to this as 7 days.

Florence has an international airport with flights to London, Paris, and Frankfurt. If you can get a good fare to one of these cities, then connect to Florence, that may be your cheapest and most convenient choice.

Pisa Airport (PSA), which is about 60 miles west of Florence, is treated as the same “city” in airline computers, and you can take a bus from Pisa Airport directly to the Florence train station. They depart about every 90 minutes and cost 10-15 euros. You could also visit the Leaning Tower and then take a train to Florence.

Or, there’s good train service into Florence from Milan, Rome, Geneva, and many major European cities. Note: Milan has 2 airports. Both have bus transfers into town, but the smaller Linate airport offers much easier access to the city and train station; from the international airport, Malpensa (MXP), it will take longer.

From Siena, where we end, you can make train connections to your final destination. Or you can take a bus back to Florence.

You can get up-to-date railroad schedules, as well as information about the many different railpasses available for Europe, from the RailEurope website. For smaller rail lines, you may also need to check the website for Italy (Trenitalia).

Because this trip ends in Siena, which does not have an airport, and is not on the high-speed rail line, it is difficult to get to an airport early enough to fly home on the last day of the trip. Therefore, we strongly recommend departing after breakfast on the last day, then taking a leisurely trip to the city you are departing from, and maybe even staying a couple of days to explore your destination, such as Florence, Rome, or Milan.

If you want to travel from Siena to Florence at the end of our tour, the bus runs more frequently than the train and is faster. It also has the advantage that the bus station is near the center of Siena, while the train station is 2 km away from the city center.

The bus operator is called SITA, and buses run between Siena and Florence every 30 minutes during the day. Select a bus that says “Firenze Rapida” (Florence is Firenze in Italian). The Rapida buses take about 1 hour, 10 minutes to reach Florence, while the FIRENZE DIRETTA buses make more stops and take one and a half hours or longer. The cost is Euro 6.50.

If you go by bus, you can buy your ticket in any tobacco store, newspaper stand or any shop that has on display the sticker Tra.in

The terminal for the bus from Siena is at Florence’s main Santa Maria Novella train station (Firenze SMN). To get to the airport, change to a VolaInBus run by the Florence bus company ATAF to get from downtown Florence to the airport. It’s about a 20 minute ride, and there is frequent service.

If you prefer to take the train, you can take Siena city bus #17 from Piazza del Sale to Siena train station, about 2 km from the city center. The hourly trains depart Siena at 18 minutes after the hour most of the day (except 10:18 am).

And if in doubt, ask our bike guides what they recommend. They can certainly tell you how to get to the bus or train station for your onward travel.

Most of our trips draw more single travelers than couples. When couples do join us, it’s usually because they’re looking forward to interacting with a gay group; if they wanted a holiday by themselves, they wouldn’t have signed up to travel with us. Furthermore, the activities included with our trips serve as natural ice-breakers. Within a day, you’ll be traveling with friends.You don’t need to pay the single supplement if you’re traveling alone. We’ll be happy to match you with a roommate. Pay the single supplement only if you want a bedroom to yourself.

For selected trips, including cruises, we will charge half the single supplement if you request a roommate but we can’t match you with someone.

The support van and driver fill several functions: Carrying your luggage to the next hotel; shopping and setting up a picnic lunch on selected days; and helping cyclists who have encountered unexpected problems, be it fatigue, a mechanical failure, or one too many pastries at lunch.

The specific van schedule varies day to day, based on a number of factors: the route, whether there’s a picnic that day, and whether riders are all likely to be on the same road, or off on different options. Typically, the driver stays with or behind most of the group until about lunchtime (or earlier, if there’s a picnic to set up), then drives ahead to deliver luggage into your rooms.

If most of the group is likely to be on the same road, the driver may then circle back to see if anyone needs the van. However, we suggest various optional routes each day, and many people on our trips like to explore independently. That means cyclists may be spread out over many miles, and over several routes. In most cases, we find that a cyclist who needs help will get it fastest by calling the driver at the hotel or calling their cell phone, rather than waiting for the van to patrol all the spots where cyclists could be riding.

We’ll go over the details in more depth at the briefing when the trip starts. On paper (or on a computer screen) the system can seem uncertain because so many variables are involved. In practice, it works out well. There are many weeks when no one ever needs the van. If you do need assistance, generally you’re able to get to a cafe or other comfortable spot while you wait for help.

No. Tuscany’s hills will be discouraging for anyone without good cycling experience.

A perfect trip for couples with different levels of cycling experience is The Provencal. It includes two layover stops (when biking is optional, as we don’t change hotels), during which your partner can shop, hike, or go sightseeing, while you loop through the hilltop towns of the Luberons. On the other days of this trip, our “official” route from one hotel to the next is fairly short, but (as with all our bike trips) we’ve planned enjoyable longer options for those who want more biking.

Our two Loire Valley trips are also ideal for less experienced cyclists, yet offer longer route options and other activities for those keeping a faster pace: See Big Loire Little Loir and Valley of the Chateaux for details.

Tuscany is known for its generally mild, Mediterranean climate. Many people will find July and August to be too hot for active vacations such as biking and hiking, but in May, June, and September, you can expect weather that’s comfortably warm, without being too hot. (But don’t be surprised if the temperatures hit the high 70’s once or twice.)

While you should always be prepared for rain, and it’s not uncommon to have a light rain for half a day during the course of a week, it’s unlikely that heavy rain will greatly interfere with outdoor activities between late April and late September. Precipitation increases in October, and reaches its peak in November and December.

Somewhere around the 10th to 8th centuries BC, the people known as Etruscans settled in what is now northern Italy. Some historians believe they sailed over from Asia Minor; others that they descended from a tribe in northern Italy.

For half a millennium, the Etruscans developed their own art, culture, weapons, and political systems. Then they lost out to the growing power of Rome. The Etruscans vanished as a civilization, but many of their religious customs and architectural styles were adopted by the Romans.

Most Etruscan buildings apparently were made of wood, and did not survive. But some of their cities, such as Volterra, Cortona, and Chiusi, live on. The Etruscans developed elaborate burial rituals, with massive stone tombs and burial chambers. Although robbers have long ago looted these tombs, we can still walk inside them. And, of course, the Etruscans survive in the present-day name for the region where they lived: Tuscany.

For answers to your additional questions, please email info@hetravel.com or call 305-294-8174

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