WE BIKED 300 MILES ACROSS TUSCANY (world's most beautiful bike ride)

A portion of this video is sponsored by Gatorade Fit.

Tomorrow morning, we are starting a 300 mile bike ride through the beautiful hill towns of Tuscany. This is an organized event and over 3,000 people from around the world are showing up to attempt this ride down.

The east coast of Italy.

We are really hoping that this week is going to be the perfect mixture between enjoyment and challenge.

Enjoyment, because we're going to be soaking in the views of what we have been told is the most beautiful region in all of Italy, as well as consuming as much pizza, pasta, wine, and gelato as possible.

But it's also going to be a.

Challenge because we are going to be riding over 50 miles per day for the next six days.

Kara and I have not been on bikes this entire year. Actually, the last time we got on a bike was during Rack Rye, which.

If you've never heard of, is a 450 mile bike ride across Iowa.

You can pay $8 for a shower, but she is currently shaving her legs with a fire. Hyder.

While Ragbrai is technically longer, I think the Tuscany Trail is going to be much harder.

Harder.

This ride across Tuscany is going to be mostly off road and we have to climb 22,000ft in vertical elevation, which is equivalent to climbing most of the way up Mount Everest.

It's definitely going to be hard, but it should be amazing.

I cannot think of a better way.

To see Tuscany for the first time.

Do I look as ridiculous as I feel right now? We are minutes away from starting the Tuscany Trail. They've given us a bunch of free swag, so I'm wearing a spandex jersey for the first time. But before we get started, I wanted.

To quickly explain how the Tuscany Trail works.

It's technically an organized event, but the reality is only three things have been organized. They tell us where to start, where to finish, and they give us a route to follow. Everything in between is totally up to us, like, where we stop to eat, where we stop to sleep. This is eight people trying to put together one tent.

It's like a choose your own adventure book. And as usual, we have done very.

Little planning coming into this week.

So we're going to be completely making.

It up as we go. Should be fun. So this is like.

Yeah, it's like a cheering thing.

Okay, this is Julia. We'll introduce you to her later. She's currently teaching us the Italian phrase that will become our team mantra for the week.

Avente vollutta la viccresta albenso italiano.

All right, those are the first pedals of 300 miles right now. The adrenaline's pumping. I'm feeling great. Also, we've got a pretty big team with us this week. I'll introduce everybody later today, but I'm not gonna get hit by a car on the side of the road. W. Look at this.

Amazing. I can't believe you're the only one that has access to a gps. For all of our sake. I can't believe them.

This is awesome.

Look at this. We are about 15 minutes into the ride, surrounded by vineyards on one side and olive trees on the other.

I need a glass of wine.

It is also very hard to ride this bike with one hand. Absolutely stunning.

I forgot the difference.

Free water. Look at that. Is it cold? Does it have beer inside of it?

Our first water fountain. We're about three fourths of the way to the end town. Is that right?

No.

On a scale of bath water to ice water, I'd say it's like a four.

This is another massive perk of Italy. They have free public water fountains in all the towns, and the water's at least okay. It's kind of cold when you drink it. It's a lot colder when you pour it on your head.

Yo, yo.

Wow. This is incredibly beautiful. I'm so bad at changing these gears. I do it wrong every time.

This is crazy.

It just keeps getting more beautiful around each corner. It's kind of terrifying flying on pavement, but it's fun.

Darn it. Already had to walk.

Oh, this is deep.

Okay, so it's definitely not going to be all flat farmland and beautiful vineyards. I guess that Mount Everest elevation had to come in somewhere. Good work, team.

This is amazing.

If the rest of the trail is gonna be this good, I never want it to end.

I feel like I'm in a movie.

Wow. Look at this. All right, we are 22 miles into today's ride, and we just stopped for lunch in the town of Bulgari.

Bulgari.

Bulgari. I'm doing it again.

Dude.

This is he. Ciao. The reason we're all here, my brother Dusty. Sarah. Have you recovered from the island?

Yeah, 100%.

And of course, no long bike ride would be complete without Rick and Beck. Yeah, buddy. Everyone's gonna want to know where the girls are.

They're at home with grandma, possibly for life, I think. We're not leaving here.

Lady. Chin chin.

Yes.

Today has been nothing but enjoyable so far, except for that one H. But even that was kind of fun. I'm still riding on this, like, day one. High I know I'm gonna crash at some point, but right now, I'm so glad we're here.

These are just the appetizers. A gigantic meat plate, olives and carrots. That's kind of weird.

This is one of the many reasons I love Italians. First of all, our waiter talked us into ordering all of the appetizers, and he's come out twice now asking us to eat more before he takes it away.

And we still have a main course coming, and he just keeps coming, and.

He'S like, keep eating. We have so much food.

Wow. You ready? Oh.

That was it.

We finally got our mains, and I ordered truffle pasta. Oh, my gosh. Forgive the Tuscany trail. I'm gonna work at this restaurant and eat this every day. You want me to explain how good this lettuce is to you?

Oh, the ravioli was good, but the truffle pasta was definitely the way to go. There's this combination of a full belly, a little wine, and some lingering jet flag, and I really need a nap.

But we still have 25 miles to go.

A meal in Italy is not complete without gelato.

I deserve this. Even though we just started, basically.

This is incredible. And it's nice and shady.

Best bike ride of my life.

Getting better.

We're just in this long, flat, straight, shaded forest. All the Italians are walking by.

Speaking Italian it was already worth flying all the way to Italy just for the first half day of this bike ride. We have gotten to ride through more beautiful terrain than I could ever imagine. We started off with vineyards and olive groves, then into the medieval hill towns, and I was like, how does it get better than this? A beautiful forest with pine needles lining the ground. So good.

My expectations for this was that it was going to be really hard, and I was very underprepared. I still think I'm under prepared, but so far, it's been easier than I thought it was going to be.

Okay, I think we have one more big climb until we get to the town where we're hopefully sleeping tonight. I say hopefully because we're not exactly sure what the camping situation is. This is the first really hard thing we've done today.

Oh, we made it. Now to find somewhere to camp. Job.

Yeah, buddy. Okay. We decided not to sleep in town, and we are pushing onto a lake, which is an additional seven or so miles. We're gonna be really glad tomorrow when we squeeze in an additional seven miles tonight in this beautiful weather.

The sunset is so beautiful, and my legs aren't so bad.

There was a Sweet spot there. But apparently there's a sort of not so nice farmer. There's a space just up here, like I guess a barn that's much safer.

So we're close.

We're very close.

Just a couple minutes up the road.

Oh well. It turned out to be a bit harder than we thought to find a camping spot, but at 9pm we finally found one. We hit the road this morning around 11. We've been going for about 10 hours, but to be fair, we did have like a two or three hour lunch and now we've ended up under some farmers barn. We have pizzas, beers. Good thing we added some water to the mix and more beers. Also, if you're wondering how we got the pizzas and beers here, there's two more teammates that I need to introduce you to. Welcome Chris and.

Hello.

Hello.

So this is Chris and Julia. They just finished building out their van in April. They've been living in it full time for two months now and they are the support van for the trip. So they're moving our tents from place to place each night. They picked up the pizzas and brought them to us all around. We're gonna have a much more comfortable journey because of these two.

We wanted to chill in the beach, you know, we wanted to like look around, take pictures of the van with a nice view. So yeah, we were supposed to to sort all your bags. We didn't.

Things have escalated quickly. I think a thunderstorm is rolling in and the wind just picked up like crazy. So we are attempting to use the van as a barrier so we can set up our tents and sleep in peace.

If we all sleep right here at.

A ball tonight, then we can get.

Out of the wind, sleep inside a hay belt.

I kind of love this night.

This is just like eight people trying to put together one tent.

How does it look? Oh, wow. This is gonna be a very restful night. How's that going for you, Rick?

So far not so good.

They go on a tectonic plate. Is it possible if four people are in a tent, can it still take off? Yeah. Tell us how it feels.

I mean, it's definitely loud from the wind, but I don't feel like I'm.

Gonna blow away that tent. Took us an hour to set up. This one on the package said it takes two seconds. Ready?

Good night. He hope you don't fly away. I know. And this is home sweet home.

So cozy.

It's better than the shelter on the island and hopefully there's no cramps. Night, everybody. What a day. Wake up and do it all again tomorrow.

My body hurts.

Well, that was an interesting night. How'd you sleep?

It was really bad. I started raining in the middle of the night, and so I was getting a little wet, and I was like, you know, I'll just go into the little open air barn because, you know, it's not windy anymore. So I, like, just picked up my tent, brought it inside, and then it started getting really windy, and the tent was just, like, slapping my face.

So this wasn't waterproof?

No, it was. I just. It was the middle of the night, and I was tired. I couldn't figure out how to make it not waterproof.

But there's the flap.

So instead of doing that, you moved your whole tent over there.

I mean, I just picked it up.

I think we were all fighting our own battles last night.

Thank you, sir. That's service.

Everybody. Giggles Rolled over from last night to this morning.

Thank you.

Ready for this?

Oh, that's worse than I thought. Oh, I don't think I can do it.

Oh, gosh. Ah.

Oh, it's bad. After I pedal for a couple minutes, I'll forget about it, but right now it really hurts.

Wow. Of course. It's beautiful. Look at this.

Team.

Team Chain. Chain.

We've already knocked out the first hour of our ride, and we stopped for a quick espresso. I think yesterday was way easier than any of us expected.

But looking at the elevation profile, I.

Think today is going to be quite a challenge. Yesterday we made it to here. Today we have to do all three of these massive mountains.

Okay, guys, we'll see you on the beach.

See you soon.

Riders on.

Here we go. We're about to start a climb.

I know these climbs don't look like much in the camera, but trust me, they were way steeper in real life. But the great thing about hills is that what goes up must come down.

Wow. All right, Heath, you got it?

Feels so good.

Oh, this is gonna be beautiful. Oh.

We're grinding out our first big climb. The good conversations are pushing us through. Oh, the downhill is beautiful. A little scary. Loose gravel and small tires.

Oh, the rocks are back. Good. Work.

Hard. Morning.

I definitely hit a wall just now. Unfortunately, all of the towns are up on hills, and we went up this really steep hill. I thought we were gonna get to a town, and then we went straight back down and back up, so we made it.

The towns being on hills make them extra beautiful, but also extra terrible when you're on a bike.

It was kind of bittersweet. It's like, oh, we're going to lunch. And then it's like, oh, we gotta go all the way up there.

I hope the event organizers have told these towns that this is going on, because the bikers have completely taken over. So beautiful. Just like every other town we pass through. Well, today's lunch isn't quite as romantic as yesterday. This was literally all the guy had left in his shop. It's meat and tomatoes and very dry bread.

I just asked these gentlemen if I use the olive oil at their table, and no, it's a little better.

It's probably good that we couldn't sit down for a big one today, because I think this is going to be the hardest day of the entire trail. So we'll scarf these down and keep moving.

MVP of the day here.

You're my favorite person of my whole entire life. Still, out of number two of the trip, I'm honestly a little disappointed in us that we haven't had more, but, man, this is hitting the spot.

All right, we are back on the road. It took us five hours to do our first big climb, and we have about five hours of daylight left. Problem is, we have two more big climbs left. We'll see how this afternoon plays out.

I feel like each time we get to a town and I get off my bike, I'm like. I feel really good, but, like, while I'm on this bumpy gravel road and everything kind of hurts. I'm like, man, this is hard. I think overall, I feel better than I thought I would, but my neck is in a lot of pain, and my hands. What in the world?

I can't remember if I've said this before, but neither one of us have ever ridden a bike that has these type of handlebars. We both showed up expecting to be more miserable than we currently are. So because we set our expectations low, it's been much easier. And just look at this.

The views have vastly exceeded my expectations. It's incredible. Look at where we are.

Wow.

That was fast. Here the climb starts.

Details are brittle, but these yellow flowers here are beautiful.

Whoo.

Okay, the little buildings on the top of the hill up here, that's the end of the second climb. Doesn't look like it, but we're almost there. We're almost there.

Whoa. Look at these doors. This is amazing.

Oh, wow. We made it to Volterra, but the climb was brutal. Hard day. Well, come on.

You're doing great.

You just have 100 miles left today.

I'm not doing 100 more miles. I hope I do about 100 more feet. Also, look at this. Did you see all those little black spots on my arm? Apparently I killed a thousand gnats on the way down a hill, and they all just stuck to my arms. This is disgusting.

For tonight's campsite, this adorable Italian couple agreed to let us pitch our tents in the olive robe behind their bed and breakfast, free of charge. Much better than the bar.

Good work, Julia. You're the best. Home sweet home. Yeah, home sweet home. Two second tent.

Two second T. Take two.

Oh, closer than last night.

That was pretty close.

I think that was probably like four seconds, but tomorrow it'll be two.

We should have just bought all of these and not a big one. Hopefully this goes together faster than it did last night. 3 seconds tent. This tent is the worst. Yeah, just a little faster than yesterday.

Just adding one more thing to the list of a million reasons why we love Chris and Julia. They just let me use their shower, and I kid you not, the water was brown. I can't tell you how much bite chain grease and dirt and sunscreen was just caked on my skin. I feel so much better. We are just living in luxury. Also, I didn't have to shave my legs in a fire hydrant this year.

Look at these streets.

Can you tell? I can barely walk right now. Like, trying to walk normal. Everything hurts.

We've made our way back up into town. Yesterday's bike ride was way easier. But this evening is shaping up to be much nicer than last night. The days are just pretty much the complete opposite. Wow. This keeps going.

We're eating in a cave.

Kind of. It kind of smells like a cave.

A wine cellar is a better way to describe it.

This is amazing. A private cave for dinner. Good find. Thanks.

Much. Crazy. She hasn't even started drinking yet.

Cheers to doing hard things.

Right.

And here I am down here by myself. Thank you.

Wow.

My life is about to be described as pre carbonara with truffle, and post carbonara is probably my favorite Italian dish. It hasn't been on any menu since we've been in Italy. And not only do they have it at this restaurant, they have it with truffle. I'm so excited.

I know people are going to stop believing me, but it's the best pasta I've ever had in my entire life.

It's. It's everything I want.

I don't want to explain anything because otherwise me is on video. And then if they die, it's me killing two people, and they're kind of famous as well. Sometimes. So basically, here, these are really fresh items. You're supposed to make a hole at the top, a hole at the bottom.

Then suck it all out.

Is this a traditional Italian thing?

A pilot?

Have you ever heard of it? Good morning. It's day three of the bike trip. Apparently, I'm about to eat a raw egg because that's what the host of this place has told us we need to do this morning. It's gotta be for power.

Oh, gosh.

This is a joke to tell you.

White block.

I haven't even got my yolk yet.

Should I go for the rest of her?

Half as good. We think the yolk's still in there.

They're gonna be so insulted.

All right, let's go ride bikes.

It actually does not hurt as bad as it did yesterday.

Wow. This is a beautiful way to start the day.

Remember those three big climbs that we were supposed to knock out yesterday? We ended up cutting yesterday's ride a bit short, so we're starting on the first big one this morning. Everything looks much flatter in the GoPro.

We were also looking at our map, and we realized we have not been averaging enough mileage. First two days, we averaged 40 miles per day, and we need to be averaging at least 50 in order to get to the in town in time to return these bikes that we rented. So today's goal is to do at least 50, if not more, miles from Volterra to Siena. Look at these flowers. This is beautiful.

Here we go.

Go, Kara. Go, Kara.

After 17 miles and three hours of biking, we finally made it to our first town. The downhill to get here was probably my favorite moment on a bike in my entire life. We were just flying down this road with the most beautiful views. This town was in the distance, and then there were farms and vineyards and olive trees. It was magical. I'm still very tired, and everything hurts.

We have a lot of miles to make up today. We can't take as many breaks. We're going through this beautiful town, and everyone decided a coffee was a good idea. So we're attempting what we're calling an espresso pit stop, which is how quickly can we get seven espressos and get out of town?

So far, not so good. What are we at?

15 seconds.

One of seven.

I ordered a piece of sourdough bread, and she just gave me the rest of the loaf.

I'm so happy right now. And espresso and bread ready to go. I'm gonna stick it in my back pocket.

You're so aerodynamic. This is so Beautiful.

Here we go. Here's that flat gravel stretch. Going with the flow.

Yes, we can.

Yes, you can.

I don't know if I can do it. Yes, I can.

Yes, you can.

Oh, but my legs are so tired.

Embrace this feeling of misery and celebrate that you got yourself here.

Oh, I like that. Yeah, I love this burn. I ask Cara to give me your best motivational speech. I need to record you for later.

We made it to lunch.

I'll be here all week.

Julia, what are you making for lunch?

Riso, pretto, melona, compression beers, coke with everything.

Julia's Italian and she's cooking lunch for us today. They couldn't find any good restaurants in town, so they went to the grocery store and we're getting a home cooked meal.

Look at this. Olive bread, rice, olives, a little bit.

Of cheese, and you have it cold. Where are we, Sarah Kim Big.

So we did this this morning, and I think right now we're somewhere in here. Thanks for lunch, guys. All right, see you on the other side.

Off we go.

As I've been pedaling up this hill, I've just been thinking about how much Cara has been absolutely crushing it over the past couple of days. She's never done anything like this before. We did the big bike ride across Iowa last year, but she was on the back of the tandem, so she was just pedaling. She's never had to control her bike down sketchy gravel hills, and she's never even done a big climb like the one we're doing today. It's just all so impressive. No matter what I throw at her, she just continues to thrive. Whether it's climbing the vertical elevation of Mount Everest with no sleep, she's dancing. Or if it's surviving on a deserted island, she's the one making coconut curry for the team. She beat me swimming from Alcatraz, and now she's thriving on this bike ride. So I guess I just want the Internet to know how grateful I am for my wife. Kara, when you're watching this back, way to go. I love you, and I'm gonna wreck if I don't find my break soon.

Ah, we just stopped in the beautiful town of Monte Monteriggioni. Never been so happy to see a town. Being able to get up here wasn't insane, but they have gelato. The sun and the breeze are out. I got a medium because treat yourself with chocolate and nachola, which is hazelnut, I think. It's not dark chocolate, but at this point, I would eat any flavor. All right, it's melting.

This is terrifying.

Crashing it.

I lost all strength in my hand. That was awful.

Oh, my gosh.

How do y' all do that?

Here goes nothing.

Yes. I lived. Pedal through it. Don't get speed, please. Go well, lean back.

Keep going, keep going.

Keep.

Getting speed.

Good effort.

Good effort.

Rick made it look easy.

51 miles and 5,000ft of vertical elevation later, we've made it to Sienna. It smells like pizza and pasta. This has by far been the hardest day.

Good morning. I have a confession to make. Last night, after exhausting all of the convenient camping options, we.

We booked a hotel in the middle of the city. It was a nice change from the tents.

Just a heads up, Part two of this series turned into an emotional roller coaster. So sorry.