Ciclismo Classico

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Ciclismo Classico Cycling tours that turn dreams into reality in Europe and North America since 1989. Connecting you to the world, one pedal at a time. What sets us apart?
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At Ciclismo Classico, creating an active experience that sparks your passion is our sole mission. Like chefs who intuitively know, love and seek out delicious flavors to blend into a succulent dish, our Ciclismo Classico team combines an insatiable love of cycling, travel and culture with a rich imagination for creating one-of-a-kind, two-wheeled and photography tours. Guides: All accomplished cyclists, the guides of Ciclismo Classico plan each tour with a magnificent cycling experience as their first priority. Predominantly native Italians, they have intimate knowledge of amazing routes not known to many tourists. Cultural immersion: Touring with Ciclismo Classico is experiencing foreign travel from the inside-out, getting intimately close to the local culture and mindset in a way few travelers get to experience. With passion, Ciclismo Classico transforms your cycling trip into a soul-satisfying, life-altering adventure youโ€™ll never forget. Food: Just as family is the central fixture in Italian culture, so is the group dynamic on Ciclismo Classico tours. Each evening meal is an opportunity for your group to reconvene, share laughs and strengthen relationships. Youโ€™re deep inside the local culture and always with friends. Unique itineraries: On less-travelled roads, against a backdrop of spectacular scenery and fascinating historical and cultural locations, Ciclismo Classico transforms your cycling trip into a soul-satisfying, life-altering adventure youโ€™ll never forget. After inspiring thousands of guests and designing the worldโ€™s most innovative cycling itineraries, one simple principle remains at our Ciclismo Core: life should be active, fun, delicious, educational, flowing, strengthening, energizing and deeply connected with beautiful places and their people. Whether you are pedaling a bicycle or looking through a lens, you will discover, on a Ciclismo Classico tour, that life itself is a dream waiting to happen.

๐Ÿ“ฃ Today we ride!Join Ciclismo founder Lauren Hefferon for a series of FREE lunchtime rides from Arlington Center.Come ri...
10/21/2026

๐Ÿ“ฃ Today we ride!

Join Ciclismo founder Lauren Hefferon for a series of FREE lunchtime rides from Arlington Center.

Come ride. Bring a friend. Meet fellow Ciclismo travelers. And enjoy a little โ€œspinning dialogueโ€ about cycling, travel, favorite rides, dream destinations and whatever else comes up along the way.

Choose your adventure:
๐Ÿšฒ 20 miles on the flat Minuteman Bike Path
๐ŸŒณ 35 rolling miles to Concord Center and back
๐Ÿ’› Relaxed 12โ€“14 mph pace
๐Ÿ“… Wednesdays: Oct 21 & 28 remaining!
โฐ 12:30-3:30 PM
๐Ÿ“ Starbucks, Arlington Center
๐ŸŽŸ๏ธ FREE for Ciclismo alumni AND prospective travelers

Because sometimes the best way to talk about your next cycling adventure is while youโ€™re already pedaling. ๐Ÿ˜Š

Bring a friend and come ride with us! RSVP to Lauren at [email protected].

This is Portugal. ๐Ÿ‡ต๐Ÿ‡น๐Ÿšดโ€โ™€๏ธWhere the Atlantic meets adventure.Where vineyard-covered hills and historic villages invite you...
10/19/2026

This is Portugal. ๐Ÿ‡ต๐Ÿ‡น๐Ÿšดโ€โ™€๏ธ

Where the Atlantic meets adventure.

Where vineyard-covered hills and historic villages invite you to explore.

Where the food is irresistible, the hospitality is warm and the roads seem to lead to another unforgettable discovery.

From beautiful scenery to incredible w**e and the friendships formed along the way, Portugal is a destination that stays with you.

And discovering it from the saddle makes it even more special.

This is Portugal. This is Ciclismo. ๐Ÿ’›

Who's ready to pedal Portugal?

To the people who started as fellow travelers and somehow became friends:Some of the best souvenirs from a Ciclismo adve...
10/17/2026

To the people who started as fellow travelers and somehow became friends:

Some of the best souvenirs from a Ciclismo adventure aren't things you pack in your suitcase.

They're the people and memories you carry home.

So here's a little postcard from the road. ๐Ÿ’Œ

Where did you make your favorite Ciclismo memory? Tell us below, and tag someone who was there with you!

๐Ÿ‡ฎ๐Ÿ‡น๐Ÿšดโ€โ™€๏ธ THIS IS LE MARCHE! Italyโ€™s Best-Kept Secret! ( FYI. Itโ€™s East of Tuscany & Umbria, central Italy)Imagine Tuscanyโ€ฆ...
10/17/2026

๐Ÿ‡ฎ๐Ÿ‡น๐Ÿšดโ€โ™€๏ธ THIS IS LE MARCHE! Italyโ€™s Best-Kept Secret! ( FYI. Itโ€™s East of Tuscany & Umbria, central Italy)

Imagine Tuscanyโ€ฆonly wilder, quieter, more untouched. Rolling hills that look like paintings, winding country roads with hardly a car in sight, and tourists? Practically ZERO!

Welcome to Le Marche! A region of Italy that few travelers have discovered and even fewer cyclists have had the pleasure of exploring.

For me, Le Marche is especially close to my heart in so many ways. This is the land of my motherโ€™s Orazietti & Fracassini ancestors, and every time I return, I feel a deep connection to these hills, villages, and people. Le Marche is where I developed the start of one of our most beloved tours, Bike Across Italy that starts in Pesaro, travels to Urbino then Genga before traversing into Umbria, Tuscany and then to the sea

For me Le Marche offers a sense of belonging that is hard to explain. Put in a word. Soulful. Like deep down itโ€™s where I belong and I crave to share it with my cycling friends

Cycling here is pure magic! ๐Ÿšดโ€โ™€๏ธ Roads that seem made just for us meaning so few cars that you feel like the place is yours.

Tiny hilltop villages where you feel like youโ€™re the only visitor. Landscapes that unfold like paintings, one after another. Chunky, rich Soil that has been turned for centuries awaiting the next crop.

Le Marche has ALL the ingredients of Italyโ€™s more famous regionsโ€”extraordinary food, unique local specialties, wonderful w**es, centuries of fascinating history, and dialects that seem to change from one village to the next!

And the best part? It still feels like the Italy of another time. Authentic, wonderfully wild, and refreshingly undiscovered.

This is the Italy I love most. โค๏ธ The wild places I discover by bike

This is LE MARCHE!

Come discover it with us at Ciclismo Classico! We have some exciting new cycling itineraries brewing, and I canโ€™t wait to share them with you.

Stay tunedโ€ฆ the best of Italy is often found where nobody else is looking! ๐Ÿ‡ฎ๐Ÿ‡น๐Ÿšดโ€โ™€๏ธ

We got that covered

Fall in Italy comes with a delicious side of adventure. ๐Ÿ„๐Ÿท๐Ÿ‡ฎ๐Ÿ‡นEspecially in Piedmont, where autumn means golden vineyards,...
10/14/2026

Fall in Italy comes with a delicious side of adventure. ๐Ÿ„๐Ÿท๐Ÿ‡ฎ๐Ÿ‡น

Especially in Piedmont, where autumn means golden vineyards, earthy truffles, incredible w**es and meals worth lingering over.

Imagine spending the morning pedaling through beautiful countryside, then settling in for fresh pasta topped with fragrant truffles and a glass of Barolo.

Because on a Ciclismo tour, the food isn't simply fuel for the ride.

It's part of discovering the place, the people and the traditions that make every region special.

And sometimes the best memories happen around the table. ๐Ÿ’›

Your turn: Truffle pasta or a glass of Barolo? (Yes, choosing both is allowed. ๐Ÿ˜‰)

๐Ÿ‡ฎ๐Ÿ‡น๐Ÿšดโ€โ™€๏ธ๐Ÿฆ LA BELLA PUGLIA โ€” Sunshine, Smiles & LOTS of Gelato! โ˜€๏ธWhat a fabulous finale to another unforgettable Ciclismo ...
10/14/2026

๐Ÿ‡ฎ๐Ÿ‡น๐Ÿšดโ€โ™€๏ธ๐Ÿฆ LA BELLA PUGLIA โ€” Sunshine, Smiles & LOTS of Gelato! โ˜€๏ธ

What a fabulous finale to another unforgettable Ciclismo Classico adventure in Southern Italy!

Eight glorious days of spectacular weather, beautiful cycling, delicious food, fascinating culture, and a group that developed a SERIOUS obsession with GELATO! ๐Ÿฆ๐Ÿ˜‚ Apparently, no amount of pedaling was complete without scouting out the next gelateria. And who could blame them? Thatโ€™s the Ciclismo way!

From the sparkling Adriatic coastline and charming seaside villages to Lecceโ€™s Baroque beauty, ancient olive groves, the magical trulli of Alberobello, and the extraordinary cave city of Matera, this group experienced the very best of Puglia!

๐Ÿ‘ A HUGE shout-out to our superstar guides, Filippo and Massimo, whose warmth, humor, extraordinary knowledge, and passion for sharing their beloved Italy made this journey so special. Our guides are truly the heart and soul of every Ciclismo adventure!

And to our wonderful guests โ€” grazie mille for bringing such great energy, enthusiasm, and appetites for adventure (and gelato!) to every single day!

Great rides. Gorgeous weather. New friendships. Countless gelati. La Dolce Vita at its finest! โค๏ธ๐Ÿ‡ฎ๐Ÿ‡น

Come discover the magic of Puglia with us in 2027!

๐Ÿšด https://ciclismoclassico.com/tours/la-bella-puglia/

๐Ÿ“ฃ Tomorrow, upgrade your lunch plans.This October, join Ciclismo founder Lauren Hefferon for a series of FREE lunchtime ...
10/13/2026

๐Ÿ“ฃ Tomorrow, upgrade your lunch plans.

This October, join Ciclismo founder Lauren Hefferon for a series of FREE lunchtime rides from Arlington Center.

Come ride. Bring a friend. Meet fellow Ciclismo travelers. And enjoy a little โ€œspinning dialogueโ€ about cycling, travel, favorite rides, dream destinations and whatever else comes up along the way.

Choose your adventure:
๐Ÿšฒ 20 miles on the flat Minuteman Bike Path
๐ŸŒณ 35 rolling miles to Concord Center and back
๐Ÿ’› Relaxed 12โ€“14 mph pace
๐Ÿ“… Wednesdays: 14, 21 & 28
โฐ 12:30โ€“3:30 PM
๐Ÿ“ Starbucks, Arlington Center
๐ŸŽŸ๏ธ FREE for Ciclismo alumni AND prospective travelers

Come for one Wednesday or ride with us all month.

Because sometimes the best way to talk about your next cycling adventure is while youโ€™re already pedaling. ๐Ÿ˜Š

Bring a friend and come ride with us! RSVP to Lauren at [email protected].

This is Tuscany. ๐Ÿ‡ฎ๐Ÿ‡น๐Ÿท๐Ÿšดโ€โ™€๏ธWhere the roads roll through vineyards and olive groves.Where medieval villages wait at the top ...
10/12/2026

This is Tuscany. ๐Ÿ‡ฎ๐Ÿ‡น๐Ÿท๐Ÿšดโ€โ™€๏ธ

Where the roads roll through vineyards and olive groves.

Where medieval villages wait at the top of the hill.

Where lunch is an experience, not an appointment.

And where every ride seems to end with a great story and an even better glass of w**e.

Tuscany is where Ciclismo's dream began, and it's still one of our favorite places to share the joy of discovery.

Because some places are beautiful to see. Others are unforgettable to experience.

This is Tuscany. This is Ciclismo. ๐Ÿ’›

Have you ridden Tuscany with us? What's the one moment you still remember?

๐Ÿ‡ฎ๐Ÿ‡นโ˜€๏ธ Southern Italy at its most delicious, colorful, and unforgettable! ๐Ÿšดโ€โ™€๏ธ๐Ÿ‹๐ŸทOur Taste of Southern Amalfi tour is every...
10/09/2026

๐Ÿ‡ฎ๐Ÿ‡นโ˜€๏ธ Southern Italy at its most delicious, colorful, and unforgettable! ๐Ÿšดโ€โ™€๏ธ๐Ÿ‹๐Ÿท

Our Taste of Southern Amalfi tour is everything we love about cycling in Italyโ€”spectacular coastal roads, charming villages, breathtaking Mediterranean views, fabulous food, and those wonderful cultural encounters that make every day an adventure!

And what makes this trip even more special? Our SUPER guides, Dana and Frank! โค๏ธ These two never cease to amaze our guests with their extraordinary leadership, infectious sense of fun, and deep knowledge of Italian culture and the special places we explore. They bring the history, traditions, food, and people of Southern Italy to life in a way that only truly passionate guides can.

Of course, there is plenty of laughter, delicious meals, great cycling, and the camaraderie that makes our Ciclismo trips feel like traveling with family. Bravissimi, Dana and Frank! You are the heart and soul of the Ciclismo experience! ๐Ÿ‘๐Ÿ‡ฎ๐Ÿ‡น

Thank you, Dana, Frank, Jeri, Tom, Brent a d Jan for the super photos

๐Ÿšดโ€โ™€๏ธ Come discover the magic of Southern Italy with us!

https://ciclismoclassico.com/tours/taste-of-southern-amalfi/

๐Ÿฐ๐Ÿจ๐Ÿซ Life is sweet. But this deal is even sweeter! ๐Ÿ’›๐Ÿšดโ€โ™€๏ธFrom gelato stops to decadent desserts, we know our Ciclismo gues...
10/09/2026

๐Ÿฐ๐Ÿจ๐Ÿซ Life is sweet. But this deal is even sweeter! ๐Ÿ’›๐Ÿšดโ€โ™€๏ธ

From gelato stops to decadent desserts, we know our Ciclismo guests have a sweet tooth for adventure!

And here's a little something sweet just for our Ciclismo alumni. ๐Ÿ‡ฎ๐Ÿ‡น

โœจ ONE WEEK LEFT to save $500 per person on your next European adventure in 2027!

Our Alumni Savings Program is our way of saying grazie for the miles we've shared, the friendships we've made, and the memories still waiting to happen.

๐Ÿฏ Book by October 15: Save $500 per person
๐Ÿท Book by December 31: Save $350 per person
๐Ÿฐ Book by April 1: Save $200 per person

The sweetest memories are the ones we make together. And your next adventure is calling!

๐Ÿ“ฃ Don't miss this sweet deal. Start dreaming, choose your 2027 tour, and save before October 15!

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30 Marathon Street
Arlington, MA
02474

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