Flavors of Tuscany Gay Travel Bicycling Tour in Italy

HE Travel: Don’t miss out on this amazing adventure! Pack your bags, grab your friends, and join HE Travel to experience Flavors of Tuscany Gay Travel Bicycling Tour in Italy.

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” guilt free after all our hard work!


  • 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 cappuchino 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 breads, and ruby Chianti wines.

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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 afterwards, 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 night life, 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 breads, 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 seem 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 slabstone 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 pastas, 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, have 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!

Farther along 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.

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