Cinque Terre & Tuscany Walking & Hiking Tour
6 days
5 nights
Activity Levels 2-4
Casual Hotels
Cinque Terre & Tuscany Walking & Hiking Tour
6 days
5 nights
Activity Levels 2-4
Casual Hotels
2026: May, Jul, Sep-Oct
Coastal Italy's Seaside Charm & Tuscan Villages
Hike dramatic coastal trails and climb through vineyard-covered hills. Trace ancient footpaths between stone villages and seaside hamlets. Hear church bells echo through quiet piazzas and waves crash below cliffside towns. Let the spirit of Italy move at your pace.
Highlights
- Hike the iconic trails of Cinque Terre, passing pastel villages and sweeping coastal views
- Dine seaside on fresh seafood, then savor hearty Tuscan dishes paired with bold local wines
- Roam through quiet hill towns, olive groves and winding vineyard paths in the heart of Chianti
- Raise a glass at family-run wineries, tasting everything from crisp whites to robust reds
- Unwind at elegant seaside and countryside hotels, from the Ligurian coast to Tuscan hills
StartPisa
EndFlorence
* Start/End locations may vary. Do not book flights until your trip details are confirmed.
Itinerary
Days 1-3
Walk coastal trails lined with olive groves and terraced vineyards • Discover Cinque Terre’s World Heritage coastline by foot and by train, from colorful Riomaggiore to the beaches of Monterosso • Choose highland hikes for panoramic views or linger in cliffside towns like Manarola and Vernazza • Follow scenic paths past painted villas into chic Portofino • Explore the vibrant harborfront of Santa Margherita Ligure and the Golfo del Tigullio • Swim, sunbathe and unwind at our welcoming Ligurian hideaway • Savor Ligurian cuisine with sea views and fresh Mediterranean flavors.
Nights 1-3
Just steps from the bay of Santa Margherita, this art nouveau-style hotel is set atop a promontory, surrounded by oak, pine and palm trees. Take a dip in the sea from the hotel's private beach.
Days 4-6
Trade sea views for Tuscan vineyards as we head inland to Chianti’s timeless landscapes • Hike through Greve, Montefioralle and Panzano, pausing for farm-fresh lunches and rich reds • Wander the medieval streets of Radda, the heart of Chianti Classico • Enjoy a signature Backroads picnic at Castelvecchi’s 1,000-year-old cellars • Walk the strada bianca through olive groves and cypress-studded hills • Wind down each night at a peaceful hilltop retreat • Extend your journey with a visit to Florence, Italy’s Renaissance jewel.
Nights 4-5
Owned by the same family since the 1500s, this former manor house offers vistas of the countryside, olive groves and vineyards of Chianti Classico. (pool)
What's Included
See moreStraight Talk
We want to make sure you're on the trip that's right for you. Every Backroads trip is unique and this one is no exception.
Cinque Terre is a popular tourist destination with busy peak seasons including summer months and on national holidays. During these periods, crowds are common. To access the best hiking areas in the Cinque Terre, we will sometimes be riding on state-operated regional trains alongside locals and other tourists. The trains can be subject to delays and crowded during peak seasons. Because the national park is still recovering from trail damage from previous years, closures may occur. In the event of a trail closure, your Backroads Trip Leaders will have alternate hikes and activities available. For more information on the park and trail closures, please visit www.parconazionale5terre.it.
Our routes through this captivating terrain are a combination of loop hikes and out-and-back trails that begin and end in the same location. In some cases our shuttles will get us to and from the trailheads, but due to the nature of these trails, we usually won’t see our vehicles along the route. Ample trail support in the form of water, snacks and encouragement is provided by your Backroads leaders and local guides.
Hotels
Adventure-Ready Hotels
Ideally located with ready access to trip activities, our Casual hotels are also known for their character and charm.
Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.
Nights 1-3
Casual Hotel
Just steps from the bay of Santa Margherita, this art nouveau-style hotel is set atop a promontory, surrounded by oak, pine and palm trees. Take a dip in the sea from the hotel's private beach.
Nights 4-5
Casual Hotel
Owned by the same family since the 1500s, this former manor house offers vistas of the countryside, olive groves and vineyards of Chianti Classico. (pool)
Gallery
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Dates & Prices
Dates & Prices
Click on dates for pricing, itinerary variations (if any) and to book your trip. Price is per person, double occupancy in USD.
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