Florence is not just about Renaissance art and architecture; it’s also a fantastic base for Hiking and Trekking Tours that reveal Italy’s stunning landscapes just outside the city. Whether you’re after a leisurely walk through Chianti’s vineyards or a challenging trek along the Ligurian coast, Florence offers a variety of experiences. We particularly love the full-day Chianti wine hike, which combines scenic trails with visits to organic wineries—an authentic taste of Tuscany’s countryside. Another favorite is the Sunset Hike in Fiesole, perfect for those wanting a shorter, scenic escape with a sunset view and local aperitivo. These tours are ideal for travelers who want a deeper connection with Italy’s natural beauty and culinary delights, all while staying active.
The list below features diverse hiking options: from immersive day trips through vineyards and olive groves, to scenic coastal walks in Cinque Terre, and even urban trekking with panoramic city views. Each tour has its own personality—some focus on wine tasting and local food, others showcase Italy’s coastal cliffs or Tuscan hills. Whether you’re a serious hiker or just looking for a gentle stroll, there’s something here for every fitness level and interest. Ready to lace up? Let’s explore the best of Florence’s walking adventures.
1. Hiking Tuscany & Chianti Wine – 3 Organic Wineries with lunch
At number one, this full-day small-group tour offers an immersive experience through the heart of Chianti’s rolling vineyards and olive groves. You’ll trek around 4 miles (7 km) along well-maintained trails, soaking up views of the iconic Tuscan countryside. The highlight is visiting three organic wineries, where you can sample up to 10 wines and enjoy a hearty Tuscan two-course lunch. This experience is perfect if you want to combine hiking with wine tasting without the hassle of organizing logistics yourself. The guide ensures you don’t need to worry about navigation, making the day stress-free. Reviewers mention how genuine and personal this tour feels, with one calling it “incredible” and praising the local guide Lorenzo for his expertise. The small-group size makes it intimate and tailored, ideal for couples or small families. It’s a bit pricier but offers a full sensory experience with organic wines and Tuscan specialties. Bottom line: a highly recommended, authentic way to explore Chianti’s landscape and wine culture.
2. Hiking Florence Tuscany hills with lunch & wine
Rated a perfect 5/5, this half-day hike offers a gentler, more manageable adventure near Florence. You’ll follow in Leonardo Da Vinci’s footsteps at Monte Ceceri and its historic square, then walk 8 km through trails with spectacular views of Florence and the Tuscan hills. The tour includes a delicious farm-to-table lunch with local wine at Fattoria di Maiano, a family-run farm that emphasizes sustainable practices. The guide, Lorenzo, is known for sharing deep insights into the landscape, history, and local life, making it a truly educational experience. The route is ideal for those who want a balanced mix of nature, culture, and cuisine—perfect for a morning or afternoon escape. Reviewers love the personalized experience, praising the “tremendous knowledge” of the guide and the organic lunch. Bottom line: an accessible, scenic hike with excellent food and wine, suited for those seeking relaxation and natural beauty close to Florence.
3. Florence: Hiking Tuscany & Chianti wine 3 wineries and lunch
This eight-hour tour takes you into the Chianti Classico region, where you’ll explore vineyards, olive groves, and scenic hills by foot. Visiting three biodynamic and organic wineries, the focus is on sustainable wine production and authentic local flavors. The itinerary includes a stop in the charming town of Panzano for lunch, guided wine tastings, and a chance to meet local producers. The intimate group size (max 7) ensures a personalized experience. Reviewers appreciate how this tour combines wine, food, and nature, with the guide sharing detailed insights about Tuscany’s agriculture and wine culture. It’s especially suited for those who want to support local businesses and enjoy a rich, sensory day in Tuscany. The tour emphasizes eco-conscious tourism, making it a meaningful choice for responsible travelers. Bottom line: a well-rounded, sustainable day exploring the Chianti countryside with plenty of tastings and cultural touches.
4. Hike & Wine Tour
Offering a shorter, 3-hour escape, this guided hike outside Florence takes you through vineyards and olive groves in the Mugello area. You’ll visit a family-run organic farm, sample their wines and oils, and enjoy a light Tuscan lunch. What makes this tour stand out is its focus on authentic local flavors and the scenic trails just outside the city—perfect if you’re pressed for time but craving a taste of Tuscany’s countryside. Reviewers mention that Simone, the guide, “grew up in Vicchio” and shares engaging stories, and that the wine and olive oil tastings are top-notch. It’s an ideal choice if you prefer a shorter, more relaxed experience but still want to learn about local agriculture. Bottom line: a concise yet rich experience of Tuscany’s rural charm, with excellent tastings and a friendly guide.
5. Cinque Terre Day Trip from Florence with Optional Hiking
This full-day adventure is perfect for those wanting to see Italy’s famous Cinque Terre without the hassle of multiple train rides. It includes round-trip transportation by private vehicle, visits to all five villages, and an optional cliffside hike. The tour is very popular, with thousands of reviews praising the well-organized logistics and breathtaking coastal views. The hike from Corniglia to Vernazza or between villages offers rugged terrain but rewards hikers with spectacular vistas. The boat ride option (March to October) adds a charming perspective of the coast. Reviewers love the balance of guided tours and free time to explore shops and cafes. It’s best suited for travelers with a full day to spare who want to indulge in some light activity and sightseeing. Bottom line: a comprehensive, scenic day that covers all five villages with flexible hiking options.
6. Private Guided Hiking Cinque Terre Day From Florence
If privacy and tailored experiences are your priority, this luxury private tour offers a full day of hiking along the most scenic routes of Cinque Terre. Using private transportation, your guide will lead you through four hikes totaling about 7 hours, including visiting Manarola, Corniglia, Vernazza, and Monterosso. The hikes involve rugged terrains with steep stairways, but they promise spectacular views of the Italian coast. The tour is designed to avoid crowds and offers an exclusive way to experience Cinque Terre’s stunning landscape. Reviewers highlight the professionalism of the guide and the quality of the hikes, noting that it’s ideal for serious walkers wanting a more personalized, less touristy experience. The high price makes it best suited for travelers who value exclusivity and comfort. Bottom line: a premium, scenic, and private way to explore Cinque Terre’s most beautiful trails.
7. Sunset Hike in Fiesole with Aperitivo
For a shorter but memorable escape, this 3-hour sunset hike offers stunning panoramic views over Florence from the hills of Fiesole. Starting in Vincigliata Castle, the trail passes through lush greenery, culminating in a perfect spot to watch the sunset. Afterward, enjoy a classic aperitivo with local drinks and snacks, making it a relaxed yet unforgettable experience. Reviewers rave about the breathtaking views and the friendly, knowledgeable guide Stefano. This tour suits travelers seeking a photogenic, culturally rich experience without a long commitment. It’s especially good for those with limited time but wanting a taste of Tuscany’s natural beauty. Bottom line: ideal for sunset lovers and those wanting a scenic, easy trek with a local touch.
8. Wine Hiking Sip & Trek
This 7-hour guided tour takes you through vineyards, forests, and olive groves in the Chianti region, with a focus on local wines and scenic paths. Starting from Montespertoli, a private ride gets you into the countryside, where a moderate trek includes a pitstop at a historic castle for wine tasting. The guide shares insights into local wine history and production, making it educational as well as scenic. The tour is perfect for anyone wanting a relaxed, wine-focused adventure with manageable hiking. Reviewers highlight the personalized experience and the quality of the wine and food. It’s well suited for wine lovers who want to combine activity with authentic tastings in beautiful surroundings. Bottom line: a well-balanced mix of walking, wine, and local stories, ideal for a laid-back yet enriching day.
9. Semi-Private Guided Hiking Cinque Terre Tour from Florence
This semi-private tour offers a very intimate experience of Cinque Terre, with a maximum of 7 travelers. It includes about 4 km of hiking over rugged terrain, with stops in Manarola, Corniglia, Vernazza, and Monterosso. Specially designed for those who want to explore the most scenic trails with a small group, this tour provides a more personalized and less crowded atmosphere. The walk from Corniglia to Vernazza, with its steep stairs, is a highlight, offering breathtaking views. The guided aspect means you get detailed insights without the rush of larger groups. Reviewers remark on how well-organized and knowledgeable the guides are, making it a top pick for hikers wanting exclusivity. The high price tags reflect the private, curated experience. Bottom line: a premium, scenic coastal trek for those seeking exclusivity and top-quality guiding.
10. Private Cinque Terre Day Trip from Florence with Optional Hiking
Designed for travelers who want an exclusive, customizable experience, this private day trip covers the main villages with optional hikes. Traveling in a private vehicle, your group can explore Manarola, Corniglia, Vernazza, and Monterosso at your own pace. The hikes include rugged paths with about 4 km of scenic trails, plus time to relax or explore each town. This tour is perfect for those who prioritize privacy and flexibility—whether you want to focus on hiking, sightseeing, or both. Reviewers highlight the comfort of the private transport and the flexibility to tailor the day. It’s ideal for groups or families who want a luxury experience with personalized attention. Bottom line: an exclusive, hassle-free way to see Cinque Terre with the option to walk some of Italy’s most picturesque coastal trails.
11. Florence: Cinque Terre Day Trip with Optional Hiking or Pisa
This long, all-in-one day trip is perfect if you want to combine the colorful villages of Cinque Terre with a visit to Pisa. It includes guided visits to three of the five villages, with optional hikes along rugged trails. The tour also features a visit to Pisa’s famous Leaning Tower if you choose to add it. With a duration of 12-13 hours, it’s a full-day commitment but offers a comprehensive experience. Reviewers praise how well-organized it is, especially for those with limited time. It’s suited for travelers eager to see both the coast and iconic landmarks without multiple trips. The optional hikes add a bit of adventure, perfect for active visitors who don’t mind a long day. Bottom line: a comprehensive, sightseeing-packed day for those who want maximum variety.
12. Florence: urban trekking between the historic center and the Tuscan countryside
This short, 2-hour urban trek offers a unique way to see Florence from a different perspective. Led by a local environmental guide, you’ll walk through lesser-known streets, panoramic viewpoints, and lush gardens like the Rose Garden. The tour highlights Florence’s natural elements, connecting the city’s art and architecture with its green spaces. It’s an easy, accessible option perfect for those who want a taste of both urban and natural Florence without a full-day commitment. Reviewers mention how this walk reveals hidden viewpoints and historical connections, making it a delightful addition to any trip. It’s especially suitable for travelers with limited time or those interested in a more relaxed, cultural experience. Bottom line: a quick, insightful walk that combines Florence’s city charm with its natural beauty.
How to Choose Your Ideal Hiking or Trekking Tour in Florence
Selecting the right tour depends on your fitness level, interests, and schedule. If you’re passionate about wine and want a full-day immersion, the Hiking Tuscany & Chianti Wine offers a deep dive into Tuscany’s landscapes and flavors. For a shorter, scenic escape, the Sunset Hike in Fiesole provides stunning views with a relaxed vibe. Travel budget also matters—while private options like the Private Cinque Terre Day Trip are more costly, they deliver exclusive comfort and flexibility, suiting those seeking personalized experiences. For active travelers who want to combine coast, culture, and vigorous trails, the Semi-Private Guided Hiking Cinque Terre or the full-day Cinque Terre are excellent options.
Consider the time you have available: shorter hikes like Florence: Urban Trekking suit quick city breaks, while full-day adventures are better for dedicated outdoor days. Always check the physical demands and your own comfort level before booking. And, if in doubt, book early—popular tours fill quickly, especially during peak season.
Florence’s hiking and trekking options are as diverse as its art. From vineyard walks and coastal hikes to city panoramas, there’s a trail for every adventurer. For those craving a deep connection with Tuscany’s landscape, the Hiking Tuscany & Chianti is a top pick. Meanwhile, the Sunset Hike in Fiesole offers a shorter but equally rewarding experience. You can also combine a love of Italy’s coast with scenic walks in Cinque Terre, whether in a group or privately. No matter your choice, these tours promise a memorable way to see Florence’s surroundings on foot—so lace up and enjoy the journey.
