Hunt down the gems of spectacular southeast Sicily
Sicily is a treasure trove for outdoor explorers — and its southeast region is a big, precious, shiny diamond. Bursting with historic riches, natural wonders and gastronomic gold (looking at you, cannoli...), we’ll help you unearth its many gems over six incredible days. From tranquil vineyards to majestic mountain cities and staggeringly gorgeous coastlines, join us as we pedal and plunge deeper into its landscapes and local life.
EARLY RIDER PRIZE: Be in the first 4 to book a departure and get 5% OFF the tour price*
*Not applicable with guaranteed, private, or self-guided tours, other discounts, trip credit, or special offers.
Wheels
WaterOverview
On this multi-active adventure around Sicily’s southeast corner, we’ll pedal the gently rolling hills of the serene countryside — peppered with rustic farms, ancient orchards and lush vineyards. We’ll explore mountain cities that are real-life masterpieces, packed with fabulously theatrical baroque architecture and ancient Greek ruins. And we’ll cycle along its stunner of a coastline, diving into the Ionian Sea to spot its glitzy sea life or bask in the Mediterranean sun.
Adventuring is hungry work, so feasting is necessary. We’ll dine Sicilian style — hearty pasta dishes, fresh seafood, crispy arancini and creamy cannoli are all on the menu — with local snacks along the way to keep our energy levels high. Oh, and don’t forget to practice your wine-tasting face as we’re schooled on the region’s delicious reds and whites.
At the end of the day, there’s always a relaxing spot to lay your head, and often a pool to float in or lounge by. And with our pro Tour Leader by our side, we won’t just be skimming the surface of southeast Sicily: we’ll be cycling, splashing, sipping and snacking our way into the very heart of it. Get in gear... it’s time to go!
What’s the riding like?
This tour is Riding Level 2, which means you can expect to cycle an average of 25 mi (40 km) per day — and usually no more than around 35 mi (56 km) — with regular snack stops and photo breaks along the way. Roads are mostly flat, with occasional short climbs.
In Sicily, we’re in for a smooth ride as almost all the roads are paved. We’ll mostly cycle along smaller roads and quiet country routes, covering roughly 134 mi (215 km) in total.
Need a boost?
E-bikes are available to boost your pedal power — there’s an additional fee for $125, so just give our Customer Service team a call to book one for this tour.
And if your backside needs a break — or you just fancy a breather — our Rest & Ride Vehicle is always on standby.
Highlights
- Soak up southeast Sicily’s sun-drenched landscapes — from olive groves to mountains and beaches
- Explore the magical hilltop cities of Ragusa and Modica, chock-full of baroque gems
- Swirl and sip on tasty regional wines at a local vineyard
- Ride along Sicily’s dreamy south coast, diving in for a swim or two along the way
- Snorkel in the shimmering Ionian Sea to discover a technicolor watery world
What's Included
- 5 nights in comfortable hotels, mostly with outdoor pools
- 5 breakfasts, 4 lunches and 2 dinners
- Quality bikes and our Rest & Ride Vehicle
- Passionate Tour Leader and support crew
- Healthy/local snacks and water
- All activities, transfers and site entry fees
What our Guests Say
Day to Day
*Waves* hey, it’s us... welcome to Sicily! We’ll whisk you away from Catania to the quaint town of Palazzolo Acreide, where you'll meet the small bunch of Grasshoppers you’ll be sharing the journey with. After you’ve immediately forgotten everyone’s names, we’ll get you set up on your bike to make sure you’re safe, comfy and confident on the road.
To get the wheels whirring, we’ll start with a warm-up loop ride around the town and the peaceful country lanes that surround it. Like much of southeastern Sicily, Palazzolo Acreide was wiped out by a huge earthquake in 1693. When it was rebuilt, baroque was bang in fashion — so prepare for some high-drama architecture. Our expert Tour Leader’s got lunch covered today, and they know just the spot to start sampling some of the island’s pasta-packed, cheese-crammed goodness.
Tonight, an included dinner at our elegant countryside hotel gives us the chance to get to know the group better. Let's get those names committed to memory! The adventure starts tomorrow, so for now simply kick off your trainers and surrender to slumber.
Slurp up your coffee and andiamo! It’s time to jump on our bikes and pedal through the rise-and-fall valley roads of the Hyblaean Mountains, as ancient olive groves, hazy wheat fields and perhaps the odd friendly cow greets us along the way. After a short climb into the highlands, Ragusa is our date for lunch — a lovely hilltop city dripping in history — where we'll refuel with a picnic spread of local treats. Mmm... Then let the carbs settle with a stroll around Ragusa’s winding alleys, secret courtyards and uber-grand baroque churches.
Next, it’s onto the city of Modica — another baroque beauty that clings to the sides of a steep gorge. There’s free time to taste-test its *gorge*ous (we couldn't resist) chocolate, still made using a 16th-century Aztec recipe, before we jump in the minivan and head back to our hotel for the evening. On the agenda tonight? Chilling by the pool, enjoying some alone time with a velvety glass of red, or maybe playing Rummy a little too competitively (you know who you are).
This morning = ancient history. Today we’re kicking things off with a cycle south towards Castelluccio, where 200 tombs were carved into the rock face during the Bronze Age. Impressive stuff!
Then it’s all downhill from here (literally) as we roll our way into a land of sun-soaked vineyards, meaning just one thing... wine time! Prepare for lots of nodding and saying things like ‘zesty’ as we delve into the southeast's deliciously fruity offerings, with an included lunch to top it off. Olive oil enthusiasts will be pleased to hear there’s also the option to sample some extra-virgin goodness.
When we’re back in the saddle (or hopped aboard our trusty minivan) we’ll continue on to our rural hotel near the seaside town of San Lorenzo. Dining under the stars is your mission for the evening — which garlicky, cheesy, seafood-strewn or tomato-topped pasta extravaganza will it be tonight?
Cherry tomatoes and flamingoes. Nope, it’s not a new hipster IPA (yet), but two things we might spot on our showstopping loop ride around the southeast today. Pedal your way past rustic farms, golden vineyards and fancy-bird-inhabited marshes, before we pop back out along the coast of Sicily’s southernmost tip.
Fancy a dip? We’ll park up at a beach bar in Portopalo di Capo Passero for some bobbing (or athletic front crawling) in the balmy Ionian Sea. Then we’ll cycle along the coast to the super-charming fishing village of Marzamemi, famous for its historic Arab tonno (tuna) fishery. Our Tour Leader will be digging into their pocket for lunch; maybe they’ll pick out some fresh-off-the-boat seafood or drool-inducing arancini for us to sample — gooey, rice-filled pockets of joy the same size as golf balls (but not a good substitute for them). Warning: you won’t feel like sharing.
After a leisurely ride back to the hotel, it’s time to recharge by the pool with a frosty lager or a still-but-sharp Sicilian lemonade. Bliss.
Go nuts this morning as we pedal our way through the almond groves that line the gently climbing route up to famous Noto – the Claudia Schiffer of baroque cities. Jammed with jaw-droppingly gorgeous, honey-colored architecture with all the bells and whistles, we can rely on our fact-filled Tour Leader to help us discover the best bits.
Next, we’ll zip up the coast to the rocky shores and white-sand coves of Ognina. Here we'll strap on our snorkels and dive into an underwater disco of jazzy parrotfish, flashy rainbow wrasse and the loner of the party — but still everyone’s favorite — the classic starfish. After drying off on the beach, there’s free time for lunch before we give those calves a well-earned rest and jump in the minivan up to cinematic Syracuse — the setting for our final dinner together. We may be newfound friends, but we’re still not sharing our arancini...
How did we end up in Greece?! Is what you might be saying this morning if you hadn’t thoroughly read (and enjoyed) this itinerary. Syracuse was founded by the ancient Greeks in 734 BC, and became one of the richest and most powerful cities of the civilization. Basically, it’s a big deal. We’ll explore it properly with a walking tour around Ortigia island — Syracuse’s historic hotspot — where a local guide will fill us in on all the juicy classical details.
Before our transfer back to Catania, there’s free time to hunt down a deep-fried, creamy-cheese-stuffed cannolo (or three) — it’s the law (probably). Then *sob* say ciao to your terrific Tour Leader and top-notch cycling crew. Or maybe it’s arrivederci — until we meet again.
Dates & Price
EARLY RIDER PRIZE: Be in the first 4 to book a departure and get 5% OFF the tour price*
*Not applicable with guaranteed, private, or self-guided tours, other discounts, trip credit, or special offers
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WHAT MAKES US STAND OUT
GRASSHOPPER STYLE
Buckle up, Europe — Grasshopper Adventures is rolling in with expertly crafted tours, packed with 20+ years of cycling know-how! Pedal through postcard-perfect landscapes, explore mediaeval villages, and meet the people keeping these traditions alive, all while indulging in the most delectable local delights — from sipping fine wines to feasting on scrumptious treats, your taste buds are in for an unforgettable ride!
Your Tour Leaders have been specially trained to give that signature Grasshopper touch and will be your gurus, navigators, and safety nets throughout your journey. You can count on quality, well-maintained gear for every adventure, plus comfy accommodations that let you relax, s-t-r-e-a-t-c-h, and unwind after an incredible day in the saddle!
Experience Europe Grasshopper-style, and you’ll leave with a profound passion for the delicious cuisine, rich culture, fascinating history, and breathtaking landscapes that this incredible continent has to offer!
