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An invigorating bike vacation in historic Tuscany

An illustrated itinerary of one of our many travel adventures for gay men, lesbians, and friends.

This information supplements our
shorter Overview of The Flavors of Tuscany.

Italy was made for biking -- as long as you can handle the hills! The friendly Italian people, varied landscapes, world-famous cuisine, and villages frozen since antiquity make each day of cycling a new adventure.

Although primarily a biking vacation, this trip will also appeal to those looking for a wider mix of activities. On three days, you'll bike from one Tuscan location to another. During layover days in Radda and San Gimignano, you can choose between biking, hiking, or simply relaxing in a beautiful setting. At the end of the trip, we have a guided tour of Siena, after which you can roam the streets, plazas, and historic buildings of Siena, one of Italy's most beautiful towns.

Our starting point, Florence, is home to many of the most celebrated works of the Renaissance, including Michelangelo's famous statue of David. You'll need at least two or three days to see even the highlights amongst the Florentine museums and plazas. We suggest either arriving early, or staying in Italy afterwards, if your schedule allows it.

This day-by-day itinerary relates a typical week. Accommodations occasionally vary, and you always have a choice of following our suggested routes, or selecting your own biking routes.

1: Florence: Gem of the Renaissance

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 a walking tour of the city.

Time permitting, our walk takes us to Piazza della Signoria, where an outdoor sculpture gallery features 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. And you'll have your first opportunity of the week, but hardly the last, to savor one of Italy's real delights: the rich, full-flavored gelatos.

After an orientation session at our hotel, we'll go out for dinner. Tuscan cuisine is famous for its creative use of fresh, flavorful ingredients. Throughout the week we'll find new ways to savour Tuscany's traditional specialties.

For tonight, we know a restaurant that makes great ravioli speckled with black truffles. Follow it up with a glass of vin santo, the famous dessert wine, and cantucci biscuits. After, those who wish can explore Florence's gay night life, while others get a head start on their sleep.

2: Into Chianti Classico Country

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.

From the wine town of Greve-in-Chianti we have a choice: A more direct route into Radda, or a longer westward loop that brings a couple extra hills, but also good scenery. As will happen throughout the week, some take the left fork, others go right.

Nobody's disappointed with their choice. Those taking the longer route will quickly be challenged by a long hill with a reward at the top: The forgotten village of Montefioralle, so small it doesn't even appear on the map. This sun-drenched cluster of narrow lanes, ancient stone homes, and gnarled oak trees feels as if nothing has changed for 500 years. We wander amongst the shuttered homes of this quiet town, cool off under a fountain, then continue onward.

Both routes rejoin in Panzano, a town as pretty as Montefioralle, yet far livelier. We stop in the church, where five elderly parishioners wait as the priest dons his robe. Colorful laundry hangs from one window, and three kids watch from their own bikes, as we search for a spot on these narrow streets where we can park ours. Then, it's on to Radda-in-Chianti.

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.

3: The Castles

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.

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 that can be harsh, but becomes mellow with proper aging.

Now we continue biking, past vineyards of Sangiovese grapes destined to become Chianti wines, to Badia Coltibuono, an abbey founded in the 11th century, set in a picturesque woods.

We pass close to two other castles today, both on lonely hilltops, in varying degrees of decay. In many parts of the world, these sites would be surrounded by parking lots and visitors. Here in Italy, with the better-maintained castles of Brolio and Meleto nearby, you can have these ruins to yourself. But only if your legs will get you up the hills.

Radda was the capital of the Chianti League, 600 years ago, and remains a center of wine production. In fact, we usually stay outside the actual town, at Castelvecchi, one of the region's many small wineries, and will have an opportunity to tour their cellars. Wherever we stay, the Chianti Classico wines will add to our enjoyment of Tuscany!

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, to the center of Radda, where several restaurants serve lunch. From there, return northeast to Volpaia, a tiny fortress-village rooted in medieval times, just across the valley from Castelvecchi. A walk through the wooded valley then brings you back home.

Northern Italy is known not only for wine, but also for its white truffles, which -- at prices of up to $100 an ounce -- rank as one of the world's most expensive foods. The shrinking of forests in Italy, Spain, France - around the Mediterranean areas most suited to truffle growth -- have resulted in a dramatic shrinking of the world's truffle supply, to only 1% of what it was a century ago, thus adding to the scarcity, price, and cult status.

Wild boar, too, live in these woods, but you won't often see these shy creatures, who have learned to be wary of local hunters.

4: The Turrets of San Gimignano

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

Just eight miles away lies Castellina in Chianti. From the crenellated castle here, we enjoy sweeping views of the countryside. 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. The distinctive skyline is visible long before we reach this enchanting town.

Some cyclists will probably want to bike directly into town to explore the narrow streets, shops, and rampart walls. Others, if there's still energy in those legs, can bike to Sant Appiano and Linari, small, quiet, and charming Italian villages, each crowning a separate hill, that seem perfectly-preserved reminders of a simpler era. Or if you prefer to explore the area on foot, you can leave your bike at our comfortable hotel, just outside of town, and walk back.

San Gimignano positively bustles. The busloads of visitors that descend each day have disappeared, but the city still has energy far greater than its population of 7,000 would suggest.

Dinner tonight is an extravagant Tuscan delight. 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.

5: Volterra

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. Stone walls 2500 years old still stand on the outskirts of Volterra. So do the columns of a Roman theater, built in the first century BC.

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. A converted 12th-century convent houses a museum of alabaster sculptures.

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. One tempting destination is Castelvecchio (no relation to the Castelvecchi near Radda), once a sprawling castle and home to at least a hundred people, now evocative ruins on a lonely spar of rock south of the town.

Whether you spend your time hiking or biking, you'll build up an appetite. Carnivores can go nuts tonight: 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.

And as long as we're tossing those diets out the window: 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.

6: Two Hilltops

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.

Further 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. 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.

7: Siena, frozen in time

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.

Built on seven hills (or three, or four -- like the towers of San Gimignano, it all depends on your definitions), crunched within the old city walls, Siena is a city of narrow, shadowed streets and towering ochre buildings that gave their name to the color burnt Sienna. 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. An alert visitor today can trace the architectural styles of that era, as the rounded Romanesque arches at the bottom give way to Gothic at the top.

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.

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 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.

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.

8: Departure Day

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

If you've got extra vacation time, we suggest you save it for after the trip, rather than before: Chances are, others from this week's adventure would like company as they extend their time in Italy.

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