DAY 1 - Monday 16 June 2025

Welcome to Tuscany

Let’s start by running through our accommodation for the first 4 nights. Palagina is an award-winning Chianti vineyard and olive farm set in 100 hectares of vines. It’s only 40km from Florence Airport, which gives us the perfect blend of being close enough to one of the world’s most beautiful cities, yet far enough into the Tuscan hills to feel like we are truly the only people on earth enjoying this pure Italian luxury.

There are only 18 rooms in the converted farmhouse, and we’ve booked them all. You’ll have plenty of time to relax at one of the swimming pools and we’ll spend a lot of time at the 8-star restaurant which only features local produce.

Palagina is designed as a guest friendly farm. You can either opt in for the harvest, farm activities or simply enjoy the final product as it arrives at the cellar. (We won’t judge you if you go with this option.)

OK, the plan for today. We’ll have a set pick-up time from Florence Airport. In an ideal world it would be midday to 1pm to avoid traffic. If you arrive earlier, then we suggest staying at one of the airport hotels. In fact, we can book the Novotel at the airport for you and then pick you up from there.

Late this afternoon, let’s assemble the bikes and pop out for a short ride. It’s here we get to experience the local vintage for the first time.

Let’s raise a glass to you. Here’s to a magnificent 2 weeks together.

Salute,  

/ Accommodation: Palagina Estate    
/ Meals included: Welcome Dinner  

PS, 98% of this journey will be on sealed roads. Road bikes are certainly the preferred bike. But we do suggest that you have sturdy tread on your tyres. You will see (ride) white roads while we are in Tuscany as that’s what this region is famous for. That includes the driveway to our accommodation which is almost 500m long. 

DAY 2 - Tuesday 17 June 2025

Classic Chianti

Today is a great day to challenge yourself as tomorrow’s ride is shorter. We try and do this on our longer trips. Hard day, easy day, hard day, etc. until we reach the mountains. Then’s there’s no hiding – it’s more like a hard day, hard day, hard day. Great, now that we’ve set the platform.

The shortest ride is 70km and the longest ride is 120km (that includes 2400VM). Chianti as you know is a wine and this region is named after that. More precisely it is called Monti del Chianti which takes into consideration the hills and mountains. Add to that the word Bianchi.

Let’s put all of this together. White roads, hills, wine. Yes, that’s the plan. We combine those 3 beautiful elements as well as visiting (via bike) some of the most beautiful villages in the region like Creve, Castellina and most importantly – Panzano. Why is that important? It’s home to the world’s best butcher (#1) and that should be in your planning for lunch.

It’s also important that you visit Castello di Brolie which is where Chianti Classico was born. The Estate is the oldest winery in Italy with the added bonus of a beautiful white road being the only access.

Team Mac – your day looks fairly similar to the cyclists. Wineries, beautiful towns, markets. Your point of difference being that we won’t make you ride from A to B. On a daily basis, we’ll sort out a good walk though. That’s not compulsory but recommended. 

We are also aware that our accommodation has 2 magnificent pools. It would be a shame to waste them. Let’s make sure we’re back at the hotel at a reasonable hour. It is after all a holiday. 

/ Accommodation: Palagina Estate
/Meals included: Breakfast and Dinner (Lunch is own arrangements)

DAY 3 - Wednesday 18 June 2025

Looking for David!!

We’re approaching today as a less is more type scenario. After an early breakfast, we take cycle paths and quiet roads into Florence. It’s only 35km. If we leave early, then we think we can even ride across Ponte Vecchio Bridge. We’ll see!!

Our guides will be waiting for you in central Florence. They’ll have set up a home base and will look after your bikes while you head off with our walking guide. It’s a short 2-hour guide through the city highlights.

Florence literally is the Michelangelo of all the European cities. It’s stunning. After the guided tour, some of you will want to spend more time visiting the cathedrals, galleries and museums. Others will be happy to park up in a café, drink espresso and watch the world walk by. We’ll have a flexible plan for those who want more time and those who want to head back to the pool.

You can choose to ride the 35km back to Palagina or take one of the vans. It’s totally up to you. It’s probably a good idea to keep in mind that mid-June in Italy can start to get warm. Hmmm, on that point – didn’t the Italians also invent Gelato? 

Tonight, we’ve asked the Palagina to put on a cooking demonstration. You can opt in or out. But please keep in mind - this is your dinner. What a great day.

/ Accommodation: Palagina Estate
/ Meals included: Breakfast and Dinner (Lunch is own arrangements)

DAY 4 - Thursday 19 June 2025

Vallombrosa Forest

Shall we start with the important people first? Team Mac – we suggest you head off to San Gimignano. It’s only an hour away. Encircled by 13th-century walls, its old town centres on Piazza della Cisterna, a triangular square lined with medieval houses. This particular square is taken over by a farmers market every Thursday so well worth the visit.

Cyclists – let’s carry on from our easy day, hard day, easy day routine. Ahhh, that makes today a hard day. We’ve got 2 rides planned. 74km or 100km (1700VM and 2000VM respectively).

Back in the 11^th century, Monks settled and cared for the Vallombrosa Forest. It now has Italy’s tallest trees. You could be forgiven for thinking that you were indeed in Canada. The guides will again set up a spot for you to leave your bikes so you can head off for a walk.

And now for highlight # 2. Remember how later on in the trip you are climbing the odd Slovenian mountain. Well, we thought today would be a good chance to practice. The climb from Pomino to Boreselli is 12km long at an average of 4%. That’s reasonably gentle. Espresso riders also tackle Passo della Consuma which sits at 1058m above sea level.

Tonight, we all jump in the vans and visit Cappuccini. A small town only 5km down the road. There are plenty of restaurants to choose from. How’s your Italian?   

/ Accommodation: Palagina Estate
/ Meals included: Breakfast (Lunch & Dinner are own arrangements)

DAY 5 - Friday 20 June 2025

Lucca

It’s time to say goodbye to our vineyard paradise. After 4 nights you’ll be ready for a change of scenery. Our home for the next chapter of this holiday (Ride) is none other than Lucca. We were always going to spend a couple of nights here as it’s a highlight on any good Italian itinerary.

Lucca is known as an Italian "Città d'arte" (City of Art) from its intact Renaissance era city walls and its very well-preserved historic centre, where, among other buildings and monuments, is located the Piazza dell'Anfiteatro, which has its origins in the second half of the 1st century A.D.

For us, it is also well known for its amazing network of bike (and walking) paths which sit on top of Lucca’s city walls. It would be unusual to find a local who doesn’t own a bike.

Our hotel sits just outside the old town, you’re literally only a couple of minutes’ walk away from the inner-city restaurants and cafés.

OK, the plan for today… There are a lot of options.

Cappuccino – Ride 50km to Poggibonsi. Put the bike away. Drink coffee. Eat Italian donuts and get a lift to Lucca in the van.

Latte – Ride with the cappos but carry on through to San Gimignano for lunch (almost a hundy k) and then get a lift in the toot toot to our hotel.

Espresso – Life is too short for the van. We ride 140km. Hotel to hotel.

Team Mac – we’ve entered you in the Lucca Half Marathon today. You start running at 8am so it will be a very early start. Good luck.

Just kidding… We suggest you join the riders for a coffee in Poggi before heading off to one of Tuscany’s best treasures. The gardens at Villa Reale di Marlia. We’ll catch up with you later on in Lucca as we’ve also got a good walk planned.

/ Accommodation: Albergo Celide, Lucca  
/ Meals included: Breakfast & Dinner (Lunch is own arrangements)

DAY 6 - Saturday 21 June 2025

Leaning towards Pisa…

We’ll be joined by a couple of local Lucca cycle guides today as there is a lot to point out. We’ll roll out early to beat the heat. It’s a short 60km loop ride. This is one of Tuscany’s best rides according to the local guides. Short but sweet. And slightly lumpy with 1100VM.

Retail? There are no less than a dozen bike shops in Lucca. Our local guides will take us to a couple. Italy lays claim to some of the worlds premium bike brands. Pinarello, Bianchi, Colnago, De Rosa, Willier, Basso and of course Campagnolo. Now that really would be a souvenir to remember. “I’ll take a Dogma please.”

This afternoon, totally up to you. The leaning tower of Pisa is only 20km away. We will run a van there. Personally, once you’ve seen the tower it’s better that you come back to Lucca as it’s a much nicer town. (Personally, I found Pisa to be a bit of a one hit wonder… It’s really only a 45min destination and very, very touristy.) 

For those not interested in seeing a wonky building, our hotel also doubles as a health spa. It’s a good chance to book a massage. Time to give back to those weary legs.

Team Mac – we see your day as fairly similar to the cyclists. Lucca sightseeing, option of Pisa, Spa treatment followed by a nice dinner in Lucca.

/ Accommodation: Albergo Celide, Lucca  
/ Meals included: Breakfast (Lunch and Dinner are own arrangements)

DAY 7 - Sunday 22 June 2025

Moving day… Rest Day.

The Tuscany portion of our trip comes to an end. We really don’t see the need to rush today. Sleep in. By now you’ll have a favourite Lucca espresso bar so pop in there for a coffee after breakfast. Let’s leave just before 11am.  

It’s a bike free day. Some of you will have already cycled over 500km. There’s still plenty to come. Your bottoms need a rest. Even guides get sore bottoms.

It’s about a 4-hour drive. Our longest of the whole trip. Sit back and relax. (PS, European vehicles don’t have Wi-Fi so come prepared with data.) 

Our destination is Bassano del Grappa. A city in northern Italy’s Veneto region. Known for its wooden, 13th-century Ponte Vecchio bridge spanning the River Brenta. It’s also part of the Dolomites which you will no doubt have heard of. (More on that later)

Actually, let’s cover that off now. Legendary climbs like Stelvio, Gavia, Giau all sit within the Dolomites Mountain Range. As does Monte Grappa. “Hmmm, I can see where you’re going with this.”

Another (important) reason to chill today is that we ride Monte Grappa in the morning. At 27km it’s Hors category and your longest climb of the trip. Stuth… Taxi!!

/ Accommodation: Hotel Glamour, Grappa  
/ Meals Included: Breakfast and Dinner (Lunch is own arrangements) 
  

DAY 8 - Monday 23 June 2025

Monte Grappa

Let’s get back to this category thingy... Originally climb categories were based on the gear an old car (Citroen 2CV) could drive up a French hill in. Category 1 for first gear and so on. HC means Hors which simply translates to – beyond category and no, the car can’t get up there. Things have become a bit more scientific since the early days. Nowadays climbs are categorised by length, gradient and how many cafés there are along the way.

Monte Grappa – Hors Category. Gulp!!

Some stats... (look away now if you are afraid of heights) The climb is 26.4km long and rises 1567 vertical meters at an average gradient of 5.9%.  Interestingly, the actual VM stats are very similar to a certain Mont Ventoux which is offers 1594VM. Hmmm.

There’s a very famous and sombre memorial at the top which sits at 1726 meters above sea level. It is Italy’s largest WW1 ossuary (Tomb). 22000 soldiers are buried here. It is estimated that on Monte Grappa there are over 140 war cemeteries holding over 40000 people.

Lest we forget

OK, how’s today going to work? Right’o... Early breakfast, followed by early bike ride. In an ideal world you will be up and down Grappa by midday. Quick shower, lunch and then we leave for Slovenia which is 2.5 hours away.  We expect some (all) of you to fall asleep, we’ll wake you up when we get there.

/ Accommodation: Hotel Soca, Bovec
/ Meals included: Breakfast, Lunch and Dinner
  

Day 9 - Tuesday 24 June 2025

Soca River Cycling Trail

Let’s return to the Holiday part of Ride Holidays.

From our hotel there’s 38km of pure paved cycling path. That’s 38km in each direction so 76km return. Yesterday was a fairly big day and tomorrow is also quite challenging. Let’s keep today simple.

Have breakfast when you want.

Leave when you want.

Turn around when you want.

Basically – today – Do as you want!!

Team Mac – the bike path is relatively gentle. It’s not technical. Tolmin has plenty of bike hire shops. How about we hire you an e-bike for the day. It really would be the best way of seeing the Soca Valley.

For those wanting a complete rest day off the bike, we’ll run you down to Solkan which is at the far end of the bike path. This town offers stunning views over Mt Sveta Gora and is also well known for its stone galleries.

Tonight is a free night. Keep an eye on the RH App as we’ll put the plan on there for tomorrow. Hope your legs are rested.

Nite, nite. 

/ Accommodation: Hotel Soca, Bovec   
/ Meals included: Breakfast (Lunch and Dinner are own arrangements) 

DAY 10 - Wednesday 25 June 2025

Kanin Gondola for Team Mac

Mangart Saddle for the cyclists

Both are very high.

Team Mac – your day is slightly easier as you simply hop on a gondola to reach 2300VM. In winter it’s a massive ski field. In summer it attracts walkers from all over the world. It’s also known for its wildlife – specifically big birds like eagles and vultures.

The plan for the non-riders is to go for a walk and then have lunch. We’ve booked Restaurant Prestreljenik. That’s also the highest restaurant in Slovenia ticked off.

Cyclists – OK, this is where sh*t gets real. In fact, we worked the whole itinerary around today and tomorrow. You are now in Pogacar land. In fact, today’s climb is in his top 5. 

It is non-other than the Mangart Saddle which boarders Slovenia and Italy. Slovenia’s highest paved road. From our hotel to the top is 60km. You start climbing gradually from Bovec which is 25km from the summit, however the official climb is only 10km long. Ahh, with 1000VM. Hmm, let’s do some math - 10km divide by 1000VM = Hmmm. I’ll leave that with you. Let’s just say it’s undulating.

Let’s have lunch at the top and then roll back down to Bovec. We’ll then hop in the vans for a quick ride to our next hotel. It’s less than an hour.

/ Accommodation: Ramada Resort, Kranjska Gora
/ Meals Included: Breakfast, Lunch and Dinner

DAY 11 - Thursday 26 June 2025

DAY 12 - Friday 27 June 2025

Lake Bled

Instantly recognizable. This lake doesn’t need an introduction. It’s home for our last 2 nights together.

We are mindful that in the past 48 hours you have climbed both Mangart Saddle and Vrsic Pass.  Even Tadej would be up for a quiet day. We see most of you taking up the shortest ride. Hotel to hotel is only 40km. Let’s call it a café ride.

For those who still have energy…  (what are you on? can I have some?) There is the option of an additional 40 making your day 80km…. But really, personally – I’d recommend the cappuccino ride and then a walk around the lake.   

Lake Bled is a glacial lake which gives the water its beautiful blue colour. A relatively small lake (and shallow at only 29m max) but it is surrounded by picturesque mountains and forests. Making it the Jewel in Slovenia’s tourist crown. There’s a path around the outside of the lake which we suggest Team Mac walks this afternoon. It’s 6km long so just over an hour.

One last thing for today – a compulsory swim. Even though it’s glacial, the water is surprisingly warm. Bring your togs. Or go natural – it’s the Slovenian way!!

Our hotel for the next couple of nights couldn’t be any more central. It’s literally meters from the lake. We see quite a few of you spending more time here at the end of the trip. Why wouldn’t you?

/ Accommodation: Bled Rose Hotel, Lake Bled
/ Meals included: Breakfast (Lunch and Dinner are own arrangements)
 

DAY 13 - Saturday 28 June 2025

Ride Holidays Queen Stage

It’s important we finish on a high. Suddenly, it’s our last day together. It only seems like yesterday that we were sipping wine at a vineyard just outside of Florence. What an amazing trip.

The plan is to encourage as many of you as possible to ride the full 100km. We feel it’s important to finish with a century. Let’s not disappoint our strava followers back home.

Let’s start first with Team Mac – we really want to cover a few touristy things without wanting to make you feel like a tourist. If you know what I mean. You have to visit the castle, you have to take photos of the Pilgrimage Church, you have to go on one of those little boaty things and you have to go bungy jumping. (Just joking!!)

So, it will be a combination of Lake Bled’s highlights before jumping in the van to catch up with the cyclists. They’ll be out at Lake Bohinj (Slovenia’s largest Lake) and are also visiting Savica Waterfall. Bring your walking shoes.

Cyclists – as mentioned, our queen stage is just on the hundy and includes lakes, waterfalls, tiny wee little mountains (You’ll be fine!!) and a micro-brewery. Now we’re talking.

Tonight, our farewell dinner is right on the waterfront. No doubt a few stories will be told. I’m told that Slovenia is also quite proud of its sparkling white wine – Istenic. Let’s grab a few bottles of that and raise a toast. Here’s to you. Thank you for joining us. 

Na zdravje  

/ Accommodation: Bled Rose Hotel, Lake Bled
/ Meals included: Breakfast and Dinner (Lunch is own arrangements)
 

DAY 14 - Sunday 29 June 2025

The End

We expect quite a few of you to book extra nights. We will do this for you.

Otherwise, after breakfast we’ll start running shuttles to Ljubljana Airport which is only 30mins away.

The 3^rd option would be a couple of days in Slovenia's capital and largest city. It's known for its university population and green spaces, including expansive Tivoli Park. The curving Ljubljanica River, lined in outdoor cafes, divides the city's old town from its commercial hub. Ljubljana has many museums, including the National Museum of Slovenia, displaying historic exhibitions, and the Museum of Modern Art, home to 20th-century Slovene paintings and sculptures.

Whatever you decide. Safe travels. Until we see you again.

Thanks again for joining us,

The team at RH

/ Meals included: Breakfast