Florence isn’t just about Renaissance art and bustling piazzas. The city’s location makes it an excellent base for outdoor adventures—especially hiking and trekking through some of Italy’s most beautiful landscapes. Whether you’re after a leisurely walk with wine tasting, a challenging trek through vineyards, or a day exploring the stunning villages of Cinque Terre, this list has something for every type of hiker. I personally love tours that combine authentic experiences with spectacular scenery, like the Hiking Tuscany & Chianti Wine – 3 Organic Wineries with lunch, which offers a full day of vineyard trails, tastings, and Tuscan specialties.
If you’re looking for a more relaxed introduction to the region’s natural beauty, the Hiking Florence Tuscany hills with lunch & wine provides gentle trails with stunning views and a delicious farm-to-table meal. For those craving the dramatic coastlines of Italy, day trips to Cinque Terre—either guided or private—offer scenic hikes along rugged trails with unforgettable seaside vistas. Let’s explore each of these tours to help you choose the perfect fit for your adventure in Florence’s surroundings.
1. Hiking Tuscany & Chianti Wine – 3 Organic Wineries with lunch
Starting with one of the most popular ways to learn about Tuscany’s landscape, this tour combines hiking through vineyards and olive groves with exclusive visits to three organic wineries. This full-day experience is perfect for travelers who want to avoid crowds and enjoy a more personal encounter with the Chianti countryside. Rambling for about 4 miles (7 kilometers), you’ll traverse trails that reveal the rolling hills and lush scenery that make this region famous.
What sets this tour apart is its focus on authentic Tuscan wine and cuisine. You’ll sample up to 10 wines, including organic varieties, and enjoy a hearty two-course lunch with Tuscan specialties. The tour includes visits to three wineries, guided tastings, and an olive-oil tasting—meaning you get a well-rounded tasting experience. The small-group setup (rated 5/5 with 26 reviews) ensures personalized attention, and round-trip transport from Florence makes logistics simple. The guides’ local expertise shines, with reviewers praising their knowledge and warmth.
Bottom line: This tour offers a full immersion into Chianti’s scenery, wine, and food, making it ideal for wine lovers and outdoor enthusiasts alike willing to hike a moderate trail. Price reflects the quality and inclusiveness, at about $231.79 per person.
2. Hiking Florence Tuscany hills with lunch & wine
For a more relaxed but equally scenic experience, the Hiking Florence Tuscany hills with lunch & wine offers a gentle 8 km walk through some of the most picturesque areas surrounding Florence. This small-group tour (max 7 participants) combines history, stunning views, and local flavors in a 4.5-hour adventure.
The hike begins with panoramic views of Florence from Fiesole and Monte Ceceri—the spot where Leonardo da Vinci supposedly tested his flying machine. You’ll walk along trails built by locals, winding through olive groves and vineyards, with plenty of opportunities to soak in the natural beauty. The highlight is a farm lunch with wine at Fattoria di Maiano, where you’ll enjoy organic food and local wines in a rustic setting. The tour’s reviews highlight guides like Marco and Stefano for their knowledge and positive energy, making the experience both educational and fun.
This tour is best suited for those looking for an easy, scenic walk with a cultural twist. The price (~$174.16) includes transportation, lunch, and wine, offering excellent value for a semi-private experience.
Bottom line: If you prefer a leisurely walk with breathtaking views and a farm-to-table meal, this tour balances light trekking with the pleasures of Tuscan cuisine.
3. Hike & Wine Tour
This Hike & Wine Tour is a shorter, more accessible option for those who want to combine outdoor activity with wine tasting without dedicating a full day. Covering about 8 km, it takes place in the Mugello area outside Florence, where you’ll visit a family-run organic farm.
The experience is led by a licensed guide who shares insights into local agriculture and winemaking. The highlight is sampling locally produced wines and extra-virgin olive oil, often paired with local charcuterie and cheeses. Guests praise Simone’s professionalism and the quality of the food and wine—an important note if you’re looking for authentic tastes. The tour’s small size ensures a more intimate experience, and at roughly $137, it’s a good value for a half-day adventure.
This tour is perfect if you’re short on time but still want to experience Tuscany’s rural charm and culinary delights. The hike is described as strenuous but rewarding, with guests like those in reviews raving about the food and the scenic vineyard views.
Bottom line: A great option for wine enthusiasts who want a shorter trek combined with tastings and a personal guide.
4. Cinque Terre Day Trip from Florence with Optional Hiking
No visit to Florence is complete without a trip to Cinque Terre, and this full-day excursion makes it manageable. Thanks to private transportation, you avoid hours of train delays and get more time exploring these colorful seaside villages. The tour includes stops in five villages with options for walking, sightseeing, and even a boat ride in season.
The itinerary features gentle walks that include the famous trail from Corniglia to Vernazza, where you’ll enjoy a locally sourced lunch. Many reviews mention the well-organized nature of this trip, with guides helping you navigate the towns and avoid common crowds. Plus, the boat ride option adds a memorable perspective on Italy’s rugged coast.
Ideal for travelers who want to see multiple villages in one day without the hassle of public transport, this tour offers a great mix of walking, sightseeing, and relaxing by the sea. It costs about $92.89, which is reasonable considering the full day of visits and transport included.
Bottom line: Perfect for travelers who want an efficient, guided overview of Cinque Terre’s highlights with some optional hiking.
5. Private Guided Hiking Cinque Terre Day From Florence
For those seeking exclusivity, the Private Guided Hiking Cinque Terre Day offers a tailored experience for your party with luxury transport from Florence. This full-day adventure focuses on the most scenic trails in Cinque Terre, with hikes planned along rugged, breathtaking coastlines.
The itinerary includes a 1.5-hour hike (about 4 km), starting from Manarola and passing through Corniglia, with a focus on avoiding crowds and enjoying authentic scenery. You’ll explore four villages, with free time for lunch (not included) at Vernazza. The tour is designed for those wanting a more private and curated experience, with a maximum of 7 guests, ensuring personalized attention.
Guests rave about the guide’s local knowledge and the chance to experience Cinque Terre’s most scenic spots without the hassle of large group tours. The price ($576.20) reflects the exclusivity and private transport, making it suitable for discerning travelers or those celebrating a special occasion.
Bottom line: An ideal choice if you value privacy, personalized service, and scenic coastal hikes in Cinque Terre.
6. Day trip to Cinque Terre by Deluxe minivan & Hiking
This luxury minivan day trip is designed for travelers who want to avoid train transfers and maximize time in Cinque Terre. The tour covers three villages, with a combination of guided walks and free exploration.
Starting early, your driver-guide takes you along Tuscany’s scenic western coast, providing commentary along the way. Once in Cinque Terre, you’ll visit Corniglia, enjoy a hike to Vernazza including a scenic lunch, and then explore Monterosso—the largest and flattest of the villages. The hike involves about 4 km on rugged terrain, with stunning views on the coast.
Reviews highlight the convenience of avoiding train delays and the comfort of the vehicle, paired with the flexibility to explore at your own pace. The $1,060.20 cost is steep but includes door-to-door service and a full day of sightseeing.
Bottom line: For comfort and convenience, this tour is perfect if you’re willing to spend more for a stress-free, scenic day along Italy’s iconic coast.
7. Sunset Hike in Fiesole with Aperitivo
For a memorable evening, the Sunset Hike in Fiesole with Aperitivo offers a relaxed walk through the hills above Florence. The 3-hour hike takes you past Vincigliata Castle, with stunning views over the city and the sunset as your backdrop. This is less about strenuous trekking and more about enjoying the scenery, good company, and local drinks.
Guests praise the guide’s ability to share stories and local insights, creating a warm and engaging atmosphere. The aperitivo at sunset makes this a fantastic choice for a romantic evening or a gentle way to end a day of sightseeing. The tour is suitable for all fitness levels, with a price of about $149.81 per person.
Bottom line: Ideal for those who want a scenic, relaxed experience combined with a beautiful sunset and a taste of local Italy.
8. Wine Hiking Sip & Trek
This Wine Hiking Sip & Trek offers a 7-hour exploration of the Chianti region, focusing on the combination of hiking and wine tasting. Starting from Montespertoli, your private guide leads you through vineyards, forests, and olive groves, with a mid-way stop at a historic castle where you can taste local wines.
The hike covers rugged terrains, but the emphasis is on enjoying the rural landscape and the wines. Guests mention Guiseppe as an excellent guide, providing insights into the area’s history and winemaking traditions. The tour’s small group size ensures a personal experience, and at $137 per person, it offers good value.
It’s suited for travelers who want to be active but also enjoy the culinary side of Tuscany. The stroll ends with a relaxed wine tasting, making it perfect for wine lovers who want a bit of exercise along the way.
Bottom line: A well-balanced tour for those who want to combine outdoor activity with authentic wine tasting in Tuscany.
9. Semi-Private Guided Hiking Cinque Terre Tour from Florence
Wrapping up our list, this Semi-Private Guided Hiking Cinque Terre Tour offers an exclusive day exploring four villages with a maximum of 7 people. The tour covers about 4 km of hiking along rugged, scenic paths and includes stops in Manarola, Corniglia, Vernazza, and Monterosso.
Guests praise the personalized attention and the guide’s expertise, particularly in avoiding crowds and uncovering the best viewpoints. The hike from Corniglia to Vernazza is a highlight, with 382 steps leading to breathtaking views. This tour is best suited for travelers who want to experience Cinque Terre without the large-group atmosphere and are comfortable with some rugged terrain.
Pricing at $293.11 reflects its private and intimate nature, along with luxury transportation. This is perfect for those celebrating a special occasion or simply wanting an exclusive experience.
Bottom line: If privacy, tailored routes, and scenic coastal hikes appeal, this is an excellent choice for a memorable day in Cinque Terre.
$293.11 per person
How to Choose Your Perfect Hiking and Trekking Tour in Florence
Picking the right tour depends on your budget, fitness level, and interests. If you love wine and good food, the Hiking Tuscany & Chianti Wine is hard to beat for its full immersion. For a gentle introduction with spectacular views, the Florence Hills hike with lunch & wine is a perfect choice.
Travelers seeking coastal scenery and village exploration should consider the guided or private Cinque Terre options, especially the Private Guided Hiking Cinque Terre for maximum exclusivity, or the full-day group tour for a more budget-friendly experience.
For a romantic sunset, the Fiesole sunset hike offers a peaceful ending to your day. And if you’re a dedicated hiker wanting a private, scenic coastal adventure, the Semi-Private Cinque Terre trip guarantees a personalized touch.
Remember to check the season—most of these tours operate from spring through fall—and book early to secure your spot, especially for the popular Cinque Terre day trips.
Florence’s surrounding countryside and coast offer endless opportunities for outdoor exploration, from vineyard hikes to seaside villages. Whether you prefer a wine-soaked trek through Chianti or a scenic coastal walk, these tours provide a variety of ways to see Italy’s beautiful landscapes. For a memorable outdoor experience, any of these options will enrich your Florence visit—just pick the one that best matches your pace, interests, and sense of adventure.