This hill sucks. It sucks more than the last one, but less than the ones that will come after: the fifty shades of punishment that only the Tuscan countryside can deliver. I'm slumped in the saddle of my nimble little Pinarello race bike, shoving my feet against the pedals one at a time. At the opportune moment, Andy – blessed, curly-haired, Scot-accented Andy – leans over and whispers, “We're beating the Canadians!” To which I reply by standing up and cranking on the rest of this hill.

The hills and valleys of Tuscany frame a view of the Castle of Brolio

We're not racing. This is a vacation, with ultralight bikes, crazy fast roads, and five shots of espresso per day (followed by five glasses of wine per day). But Andy has raced – mostly in the mountain biking circuit – and I feel honored that he's joined on to Team Beat the Canadians. He's my coach, my navigator, and my jet pack, putting a hand on my back when I start to gas out and pushing me up the steep slopes. The tour company hosting us want you to feel like a pro racer even if, like me, you're an amateur just trying to keep up. There's a sticker on the top tube of my sleek little bike with my name and country flag on it. And on this hill, I'm trying to do the red-white-and-blue proud.

The Canadians are two spunky and tireless folks from Vancouver. Matt is a strong rider (he added a seven kilometer climb to our ride one day “for fun”) and Bobby pedals in his draft all day, the two of them darting around like dragonflies. Also in our little peloton are Steve and Lori from London, though Lori grew up in the States and also lived in Australia for a time; her dialect is a crazy chimera mix of all the places she's been. Steve is unassuming, quiet on the bike but grinding up every hill like another day at the office (an office with fresh air, vineyards and olive groves, and stone castles from medieval times perched on every hilltop). Lori is training for an Ironman. None of these strongmen wants help up anything, which leaves the support for me. Andy rides next to me when I've slid behind and gives me a strategic push to fling me in front of the Canadians.

Cyclists enjoy the open roads and fast descents of the Chianti countryside

We're here to play, and eat amazing food at hyper-local restaurants in tiny towns that you wouldn't think to stop at, and drink wine from the vineyards we pass on the road, and soar down the fastest slopes I've ever met. We take punishing rides to coffee shops, have espresso, and ride back. Our leader João Correia, who founded our tour company inGamba, knows everyone we meet from the days when he lived in this area training as a pro cyclist. For the first time, I understand the importance and the added joy of connecting with people on my travels. It was always fun to meet people on vacation before, but here in Italy as João told me, your connections give you access to experiences you can't buy with money. In context, he was referring to some of the really unique things he does, like setting up dinner in the million-dollar wine cellar in the basement of a restaurant in Siena, or showing us around the grounds of Castello di Ama, a castle turned winery and art installation with works from prominent artists from across the world.

The open central piazza of Siena hosts a neighborhood horse race twice a year

But this connection lends itself to simple pleasures too, like watching our B&B proprietress, Anna, describe the frenzied Palio horserace over breakfast in a mix of wild hand gestures and halting English. Or take Raul, the trip's Portuguese soigner who speaks the language of our sore leg muscles better than the common language of the group, who makes divine little polenta cakes and sweet pasta squares for our rides, and who dresses up in spiffy clothes on the nights that he Skypes with his beautiful wife and daughter back home. Or Luis, the Portuguese mechanic who asks, when presented with a saddle adjustment or a bottle of Limoncello, “one little more?”

It's these moments that have made this trip amazing. Moments when you feel heroic, moments when you feel crushed, moments when you laugh so hard you can't breathe. Or pedal so hard you can't breathe. Or go down a hill so fast it takes your breath away.

On the last day, I draft behind my boyfriend Logan; it's a little chilly and I'm hiding in the warm windless pocket behind him, conserving my energy because I need practice at it. To each side the hills just lay out, the quiet rows of gnarled grapevines budding with new leaves. Maybe there's only so much to say about the landscape, the subtleties between forest, grapevines, olive groves, stone towns; they just get repeated over and over. But I will say this: you can't touch the magic of this landscape in a car. A car pitches around, jittery, cage-like. On a bike the roads smooth out into sinuous curves, and the landscape unfolds one turn at a time. We ride just hard enough to feel it, how effortlessly the bikes do our bidding, how willfully our hearts follow along. I can feel mine pounding in my chest, saying its own goodbyes to Italy.

___

Emily will be hosting the free presentation "Travelling Off-The-Cuff" at Summit Hut (Speedway location) on Saturday, May 25th at 11am. She will be discussing ways to pack lighter and will share some tips for stress-free trip planning. She will highlight some key accessories to add light packing principles to any trip and explore how to select the right luggage for your trip. You’ll also learn ways to make your trip planning more flexible so that each day is its own adventure!

When you're trying to recount the newest most amazing trip you've taken in your life, it can be hard to start at the beginning. Details of things loved and mishaps overcome come rushing in all at once. So instead, I'm starting in the middle of Italy, with the day Logan and I saddled up in Florence and started riding our bicycles into the heart of Tuscany.

It felt so wonderful to be back on the bikes. We had spent months riding and planning and packing, all to arrive in Rome - crazy, beautiful, hectic, ancient, nutso Rome - and realize that Italy is quite a big place. We had imagined we would ride our bikes across this whole country and see everything; but it became quite clear that it would take all day just to get outside Rome, and in the process we very well might die in a compound collision with a scooter, a car and a bus all at the same time. So we took the train. And it was so accessible, so fast, that we ended up taking trains a lot, and lugging our bicycles in and out of bike cars all across Italy. But the landscape of Tuscany was far too legendary and beautiful to pass up.

Cycling out of Florence we got lost right away, thanks to a mysterious cue sheet in our terrible Cycling Italy guidebook. (Sorry Lonely Planet; I love you, but you led us astray on this one.) We had already encountered the interesting way that Italians give directions, having gotten lost at the train station when we were looking for our hotel. I walked into a newspaper stand to ask for help, and the man behind the counter was smoking a cigarette indoors, because you can still do that in Italy if you own the place. I was looking for a street called Via Fregene, and the man walked outside with me, pointed to a side street leading out between two buildings, and said in broken English, "turn here, 500 meters, Via Fregene." I thanked him in my severely broken Italian, bought a map, and we headed up the street. Via Fregene was not there. We finally found it on the map. In a similar fashion, just as we were nearing the edge of Florence our mysterious cue sheet told us to veer right "to Scanducci," so we veered right, climbed a steep hill and were rewarded with a beautiful sweeping downhill across green vineyards heavy with grapes. Several happy kilometers later, we arrived in Scanducci where the vineyards promptly faded away into out-of-place mega malls and industrial-looking buildings. We had missed a turn somehow, though we hadn't seen a turn to miss, and we were several uphill kilometers off route.

I threw the Cycling Italy book back in my pannier and we asked for directions at a gas station/pannini shop. I explained to the woman behind the counter that we were trying to get back toward a little town called Impruneta, and at the name she nodded and said, "Impruneta, yes! Take this street in front, go left, it takes you to Impruneta." I was surprised; the street in front of us ran north-south and we were trying to head east. I asked if we would need to turn off anywhere, and she said "no, take the street in front, go left, Impruneta." So we went left. We never got to Impruneta.

Luckily, Logan is a masterful navigator and through the poorly or completely unmarked snaky roads he forged a path that slithered sidewinder fashion into Chianti, bountiful land of wine and hills. It was a clear day with just enough cloud cover to keep us from getting hot. The hills were so steep that I felt compelled to strip them of their designation as "hills"; they may not be the jagged peaks of the Alps, but I would no sooner call them hills than I would give the same name to the Appalachians. They were tough and tall, but fully balanced by my love for the beautiful views that kept changing with each turn, each dip into a valley, each pull to the top.

The landscape of Tuscany is the kind that will never capture well in a photograph. A photograph can describe the perfect, neat and tangled rows of grapevines, and the silvery sage leaves of low olive groves, set in large blocks like a patchwork quilt draped over the hills all the way out to the horizon. It can show you how the small houses, either made of stone or touched with bright colors, dot the hillsides, some of them centuries old. But a photograph can never capture how familiar it feels here, how comforting, to see a landscape like this that has been so manicured, so well worked by generations, and yet it's a landscape that still retains a sense of freedom and space. Maybe it's from growing up in the Midwest, where my backyard expeditions involved tramping through the woods and the cow fields, constantly ducking under barbed wire fences. How do I describe why I felt at home here in Tuscany? Even though there was nothing wild about this landscape, I still felt the thrill of adventure. It wasn't out there, where you could see it in a photograph; it was inside my bones.

A few kilometers outside Greve, our destination, we climbed a big hill to go screaming down a bigger one, grapevines flying past and my mouth opening to a happy scream of its own accord. This kind of cycling, up and down all day, is positively delicious. The climbs would be snail-slow, but then on the sweet blessed descents, anything I'd felt up to that point - any exhaustion or titchyness, any doubts about traveling halfway around the world to climb another damn vineyard-covered hill just like the last for god's sake - all of that was immediately blown away by the speed and the view. To ride a bicycle down a Tuscan hill is to commune with God.

At the bottom of the hill we were met by a winery and stopped for a tasting, where I had the first rosé I have ever enjoyed. It was a bright crisp red, made from Cabernet Sauvignon grapes, as if you could distill a Cabernet to a crystalline tincture. It was incredibly refreshing after 40 kilometers of up and down cycling. This was followed by two Chianti reserves, the last one smelling like my father's garden in April. I loved that wine. Logan's last glass had a finish that was light and woody, like the way soft maple wood could taste if you tried it.

Greve was cute, but it didn't sing to either of us; it's the curse of traveling in Italy that you get to become a snob about how some little town doesn't have enough history or architecture or charm, even if said town has all three in spades compared to any cute little American town. In any case, we went onward to Radda, a medieval walled city that was 7 kilometers directly up a hill. It was a steady incline only tempered by a shot of espresso I'd had in Greve and more beautiful vineyards, farther and farther below with each turn. Then a joyful riotous downhill for a few kilometers, then bliss. We stopped in a small stretch of woods and ate pecorino cheese and sausage we'd bought at a market, plus crackers and two little jam pies we'd saved from breakfast, and a packaged pastry similar to a glorified Italian twinkie.

Soon enough we came to a small sign: Radda was up a hill, just 0.2km. So close. And yet, it was the steepest piece of hill we'd ever seen, too steep to crank through. We dismounted and walked, our heads hung, all the way up to Radda. It was charming and old and full of pretty stone buildings; just the way we liked it. Wild boar stew for dinner, with wine from a vineyard just down the hill.

As a "dry run" for our cycle tour through Italian wine country, we decided to take a tour through Arizona wine country, and on our two day trip we found more beauty and challenge than we had bargained for.

We started in Sonoita, with Logan's parents graciously playing the role of our shuttle drivers. They dropped us off in front of the Sonoita Mercantile Country Store, snapped a picture, and waved goodbye as we saddled up and started down highway 83. It was beautiful; the clouds made a thick veil, keeping the sun off and the breeze cool, a godsend in September. Fields of wild grass stretched out, scattered with lone low mesquite trees and the occasional ranch house and fence. Sunflowers closed in on the road. The purple outlines of mountains traced the horizon. It was quiet, no cars, just one smooth pedal stroke after another. Until the wind came.

Turning onto Lower Elgin Road, we encountered the first of what were to be several, then dozens, then millions of hills. On the first few, I buckled down and tried to learn the technique: keep your back straight and your grip light; stand up on the pedals sometimes to use different muscles; on really steep sections, switchback up the road to lessen the grade. I tried to keep an academic interest in how to make this difficult process more tenable. But when the breeze turned on to full wind pushing us back toward the bottom of every hill, I tried a different tactic: swearing like a filthy sailor. I thought it would be funny and that I could get both of us to laugh a little, but since my outburst also contained no small amount of real aggression, Logan was just scared for me. We had a long, long way to go.

It did get better sometimes. We came up to a ranch with beautiful horses in a white fence, four dark chestnuts with brushed black manes. We propped our bikes against the fence and I walked up to the railing, immediately greeted by the most curious of the bunch who nosed my hands and then my nose and my forehead. I've never had a horse smell my face before, but this one was very interested and I couldn't help but laugh like a schoolgirl as he smudged my sunglasses with his soft muzzle.

Elgin was a sprinkling of houses presided by a big old cottonwood tree, and we stopped under it to listen to the sound of the wind in its leaves. This is the beauty of bike packing, that we would never notice that sound, never see the same level of detail from a car. On a bike, everything is so quiet. And when the road is good and the wind is halfway favorable, you can lock into a rhythm in your legs and feel the air and space all around, be part of the landscape, track the distant peaks as they come near.

But then there was the wind and the steep. As we neared Canelo we passed into the foothills, catching the eastern edge of the Canelo Hills and passing right on into the northern fringe of the Huachucas. It was so, so beautiful and so, so hard. I had a list of complaints: my back hurt, I needed more water, I needed more fuel, my breathing was so ragged, my legs were burning, I couldn't physically pedal any harder to push myself uphill. Each one of them seemed like legitimate concerns until they kept piling up, and I realized it was my brain trying to get me out of work but I couldn't separate how much I wanted to do this from how hard it was, it was this big emotionally tangled mess in my gut and meanwhile Logan was at my side, quiet, not even breathing hard while I hurled complaint after complaint at him like I was hoping he would crack and we'd sit down on the side of the road and give up together. This is what we do to our partners, unfortunately; sometimes they're the punching bag. But this is also what our partners do for us: they keep us going anyway. Sometimes they're the trainer. If it had been me alone, I would have stuck my thumb out ten miles back, waiting for one of the three cars that would pass by all day. I would have missed the whole show.

We turned down Cimarron Road, and the hills got steadily bigger and more beautiful. We crawled to the west gate of Fort Huachuca, where one of the best jobs is held by the guy who mans the security checkpoint, sitting out in the cool breeze looking at that view all day. Inside the fort the uphills got steeper and the downhills got shorter; we finally started walking good portions of the hills. The whole section within the fort was gorgeous; the Huachucas are so pretty; but there wasn't much to say about it except that it sucked. The wind was relentless and we were done. When we finally limped into Sierra Vista for a late lunch at the Landmark Cafe, I declared my fries and pastrami Reuben and Lipton iced tea the best meal I'd ever eaten. On this first half of the day we had averaged six miles per hour. I wanted to kill the wind, if only I could figure out how to get my hands around its wispy little neck.

From Sierra Vista down to the San Pedro River on Highway 90 it's supposed to be a steady downhill. At the bike shop one of the roadies told us that he got up to fifty miles an hour on that stretch of road. When we got on it, we had to pedal hard. The wind was pushing so much that we couldn't even coast. At least it was flatter, and the scenery was still beautiful even if the highway and the detritus that comes with it was a little less appealing. Twenty more miles of keeping our heads down and pedaling and we made it to the Highway 80 Junction, where the road into Bisbee makes a five mile, endlessly steep climb up to Mule Pass. We made it a little ways in before pulling over to the shoulder and sticking our thumbs out. The second truck we saw stopped for us, we tossed the bikes in the bed and then we were flying so fast up the pass that we could hear nothing but wind. I gave the title of Second Best Meal I've Ever Eaten to a Mountain Lime Lager, a brat and a bag of Lay's potato chips at the Old Bisbee Brewing Company. After 55 hard won miles, we went to sleep wondering if we would be able to walk in the morning.

The next day we felt pretty good, and over coffee and pastries we picked out a route back to Sierra Vista. Logan had found this slim little book at Bookman's, Bike Tours of Southern Arizona by Ed Stiles and Mort Solot. It was printed by a local publisher in 1980, and you can tell by the photos, from the facial hair and the bikes being loaded from Volkswagon vans. In the "Tour of the 19th Century," a route that takes riders through big sections of Old West ghost towns on the way to Bisbee, they noted their favorite route, taking 92 out of Bisbee and turning up Hereford Road, which leads north to the tiny town of the same name. They called it "one of the most enchanting rides through southern Arizona."

They were totally right. The route is really pretty, but more exciting than that was a slight tailwind and a road that actually headed downhill. We were cruising, averaging 18 miles an hour, and we decided we loved bikes. Every couple of miles in the first stretch I sat up and howled, so elated to be moving fast in the desert, watching navy clouds gather over the peaks. Hereford Road was narrow but rarely traveled, and we could ride side by side past the ranches, watching the San Pedro veer closer and closer. The old Hereford is nothing now; in the book they describe it as "nothing more than a collection of three or four buildings, most of which are abandoned and in various stages of returning to the earth." They have returned by now. We saw only a couple of concrete slabs laid on the ground, the old foundations. The authors also warn of vicious dogs at a farm after this, but it's safe to say the dogs are long dead. The trees are older. In the photo of the Hereford bridge in the book, the bridge is sunny and the trees are sparse. Now, the San Pedro has closed in around it, shading the path with wide leaves.

From there, a turn up Monson Road began taking us incrementally uphill toward Sierra Vista. We were still going fast, and there's no other way to describe the feeling than freedom. The wind from the day before was like a vice grip, and now that pressure was gone. Arriving back in Sierra Vista after riding 90 miles over the weekend, I realized that throughout our upcoming Italy tour my mood is going to fluctuate with so many things: the terrain, my hunger, the weather. But when the fix is in on a good day, my love is deep; deep enough to save me through really hard work. Or at least keep me limping along until the next Best Meal of my Life.

It all started when a customer walked in the store for something simple--I think it was sport beans or vitalyte for a cycling event--and told me about L'Eroica. His eyes got that faraway dreamy stare as he told me of this long ride through Tuscany on historic white gravel roads called the "strade bianchi." Three routes ranging from 45 miles to 127 wind through vineyards and orchards, the aid stations are stocked with traditional stew and salami and Chianti wine, and the bikes have to be steel frames with suicide shifters on the down tube, made before 1987. It sounded like the perfect blend of fun and hardship, a tribute to the pedal giants of Italy who became world-class racers training on these roads. This customer, whose name I don't even know, spun this beautiful story for me and then left. I haven't seen him since. And sir, if you're reading this, I just want to say thanks for that day. The story sparked a passion for both me and my boyfriend Logan, and for three weeks in September to October we're going on a bike packing tour of Italy, from Rome to the coast to Florence to the Alps, and in the middle we're stopping in the tiny town of Gaiole in Chianti to ride the longest distance (hopefully) of L'Eroica.

 
My 1968 Raleigh Super Course, along the dirt roads at Cochise Stronghold.

Part One: In Purgatory, Counting Ounces and Cents

I used to think ultralight backpackers were a little crazy. Is it really necessary to cut off the handle of your toothbrush? Or spend $70 on a titanium cook pot when you could get one for $20 in stainless steel? But desert backpackers are hedging against the weight of their water, and a 1 liter stainless steel M.S.R. Stowaway pot weighs nearly a pound; the Evernew Ti Non-Stick Pot is only 6 ounces. 10 more ounces of water for the pack.

I knew all this in theory, but it finally hit home after we found and restored two beautiful vintage bikes, a 1968 green-bronze Raleigh Super Course for me, and an early 1980s Raleigh Competition G.S. for Logan, which he repainted in silver (one of its original colors) with blue accents. Steel frames, especially my older mid-range model, are much heavier than modern bikes, and after adding a rear rack and panniers, I was chugging to work like the Little Engine That Could with just my lunch and a change of clothes. The idea of throwing in camping gear, nice around-town clothes and camera equipment and setting me to work on the giant hills of Tuscany made me think I'd wind up on the side of the road crying on the first day. Which might still happen. But we started analyzing more seriously what to pack for a trip like this: three weeks in mild weather, with rain likely, hosteling and camping, with a great need to keep weight and space and expenses to a bare minimum. This is what we came up with.

  
Our bike-packing gear, all spread out.

Shelter setup: Terra Nova Adventure Tarp (1 lb 3 oz, $50) with an All Weather Blanket (12 oz, $17.75) for our ground tarp. Logan came up with this duo in a stroke of genius. The tarp is big enough that we can get our bikes underneath and still have good coverage for fairly heavy rain, or just set it up for a lounging sun shade. The blanket is large enough for the two of us and will reflect some heat so we can carry lighter sleep gear. It's a setup that's durable, inexpensive, and lightweight; a rare and magical trio.

Sleep system: Lafuma Warm N Light 600 down sleeping bags (1 lb 6 oz, $119.95) with Sea to Summit Thermolite Reactor Liners (9 oz, $54.95); underneath we'll have Exped Airmat Basic UL sleeping pads (13 oz, $89). With the all weather blanket underneath, we can skimp weight by bringing uninsulated pads for the mild weather. The sleeping bags are only rated to 40 degrees, but the liners warm them up considerably, and can be used separately when we're hosteling. This was the hardest area to try to cut down the cost. There are less expensive pads out there, but they're bulkier and heavier, and this being a vacation we decided it was worth it to invest in sleeping well.

Clothing: Here's where it's easy to pack way too much. We decided to bring one nice outfit each for going out on the town, and stuck to solid muted colors and classic cuts that are comfortable enough to wear every day, so we each have light dress pants that can be worn with our nice shirts or with the long sleeve sun shirts we'll be cycling in (For him: Mountain Hardwear Justo Trek Long Sleeve T; for me: Icebreaker Bodyfit 150 Long Sleeve. Both are rated UPF 50 for a high level of sun protection, and since mine is merino wool it won't stink). We'll carry one extra pair of bike shorts, underwear, and socks. For warmth I'm layering a Patagonia Synchilla Fleece Vest (8 oz, $79) and my rain jacket, the super light Marmot Crystalline (6 oz, currently on sale for $129.99) will double as a wind layer. If it gets colder we'll go into town, or wrap ourselves in our sleeping bags. Last accessory: a Wool Buff (2 oz, $27), which functions as a neck scarf, dust cover, balaclava, and thin beanie that fits under my helmet. When I'm not wearing it I keep it wrapped around my camera.

Personal hygiene: In addition to the run of the mill toiletries, there are some secret solutions I'm bringing along. The lightest weight laundry soap ever might be the Sea to Summit Pocket Laundry Wash (1/2 oz, $3.95), which is biodegradable, rinses clean super easily, and will wash a full sink of clothes with one dry leaf. It can also be used as a body wash, and they make a Pocket Shampoo with conditioner. The Fresh Foot Stone (2 oz, $3.99) is just a smaller version of the Thai Crystal deodorant stone, which I've used for years; it's essentially just a block of mineral salts that inhibits bacteria growth that create stink. It's odorless and doesn't leave residues on clothes, and as the name implies, you can use it on your feet too. The last and most important thing: Chamois Glide (1/2 oz, $5.99). Saddle sores absolutely happen on this kind of endeavor, and this little stick gives an awesomely thin and not-messy layer of protection. You can also use it on feet, inner thighs, or any other place that chafes.

Security: As in any major city across the world, theft is high in Rome and Florence, and thieves are always getting smarter. Now there's a way to steal your information from credit cards and your passport without actually taking them, by scanning with an RFID reader. Inside our money belts we'll have everything tucked in PacSafe RFIDsafe 50 sleeves (1 oz, $19.99) that block scanning.

After cameras, first aid kit, and bike tools, my rough estimate is that we've got 10-12 pounds of gear on each bike. Which, when I did the math, sounds pretty impressive and hits right on the mark for a respectable, recommended bike packing weight. It still felt heavy crawling up Mount Lemmon.


Bikes packed and ready to ride!

 More on that ride soon. Stick around!