Shared Semi-private

Multiday Tour - Tuscany Highlight Journey

Discover the best that Tuscany has to offer in one complete offer!


Day 1 Highlights:

  • English speaking licensed Guide, Driver and State-of-the-Art Minivan throughout the day
  • Guided Visit of Siena
  • Local specialty tasting in Siena
  • Explore and shop: free time in San Gimignano
  • Typical Tuscan specialty dinner at Relais Villa Olmo’s restaurant
  • Spend the night at Relais Villa Olmo 

Day 2 Highlights:

  • English speaking licensed Guide, Driver and State-of-the-Art Minivan throughout the day
  • Guided Visit of Le Cinque Terre
  • Typical Lunch, and regional wines, at a Seafront Restaurant
  • Walk/hike along splendid cliffside paths and vineyards
  • Typical Tuscan specialty dinner at Relais Villa Olmo’s restaurant
  • Spend the night at Relais Villa Olmo 

Day 3 Highlights: 

• Drive along Tuscany’s most beautiful country roads aboard a roaring off-road vehicle
• Roam the vineyards led by the knowledge of a friendly guide
• Explore a farmhouse and its cellars, and savor delicious wines
• Enjoy a tasty typical Tuscan lunch 



Everyday at 2:00 PM


3 days






Gorgeous landscapes and charming centuries-old towns, breathtaking art and architecture, scrumptious local fare and superb wines. Tuscany has it all!
Discover the best that Tuscany has to offer with the privilege of traveling in a small group, aboard a comfortable minivan and a rumbling state-of-the-art Range Rover Defender, led by our expert guides. Wander through ancient cobblestone-paved streets to uncover the treasures of Siena and San Gimignano, admire Le Cinque Terre’s spellbinding coastline and sample the amazing seafood. Journey along country roads to stunning wineries, taste precious blends and fine specialties.

Relish Tuscany’s authentic colors and flavors, discover its soul!

DAY 1 – Siena, San Gimignano and Tuscan Dinner: Welcome to Tuscany!

Meet your dedicated guide and driver in Florence and set off to discover two of Tuscany’s most remarkable jewel towns (our staff will take care of your luggage, delivering it directly to your Hotel). Your first stop will be Siena. Set in a beautiful landscape, surrounded by vineyards and olive groves, it is one of the most enchanting medieval cities in Italy. Led by your specialized knowledgeable guide discover the town's most striking sights, admire Piazza del Campo - where twice a year dashing horses compete in the heart-rendering Palio race - and enjoy a flavorful surprise: a tasting of a local specialty.
Then travel on to San Gimignano, UNESCO World Heritage Site and one of the most splendid examples of an ancient walled town. Renowned as “the city of beautiful towers” it boasts an exceptional skyline, is certainly one of the and most well-preserved, towns in the whole of Italy and has, in fact, been used as a background in many movies. Stroll the maze of quaint cobblestone streets at leisure, discovering the many tall towers, once homes, which characterize the town.
Then journey on to your Hotel, to check in and relax enjoying the view of the vineyard-clad Chianti hills before savoring a scrumptious genuine Tuscan dinner. Enjoy the mouthwatering flavors of an authentic typical meal splendidly paired with different excellent wines.

Sweet dreams at Relais Villa Olmo 

DAY 2 – Breathtaking vistas, cliff villages and outstanding seafood:  Le Cinque Terre

After a delicious breakfast at the Hotel, and a brief drive, meet your dedicated guide and minivan and fellow travelers and depart for Le Cinque Terre, one of the world's most spectacular coastal areas. Enjoy the privilege of exploring this fairytale destination in a small group, led by the knowledge and personal attention of your dedicated guide.

Unveil the secrets and authentic charm of the area off-the-beaten tourist path, relish the flavors of ancient typical cuisine and aromas of sensational wines. Set amid some of the most dramatic coastal scenery on the planet le Cinque Terre, five ingeniously constructed fishing villages, are a Unesco World Heritage site since 1997, and still today look very much like a version of a seafront garden of Eden! Travel in full comfort aboard our comfortable minivan, lay back and admire the scenery: sinuous paths run across stunning cliffsides, and a 19th-century railway line cut through a series of coastal tunnels ferries the footsore from village to village. Learn all about the Cinque Terre's history and unique feature from your guide: the steeply terraced cliffs bisected by a complicated system of fields and gardens hacked, chiseled, shaped and layered over the course of nearly two millennia. So marked are these artificial contours that some scholars have compared the extensive “muretti” (low stone walls) to the Great Wall of China! And all enhanced by the charming villages - Riomaggiore, founded in the 8th century by Greek settlers fleeing persecution in Byzantium, Vernazza, Corniglia, Manarola and Monterosso - which look onto the gleaming pristine waters of the sea. Lose yourself in the gorgeous scenery, hike/walk along the famous trails and explore a few of the fascinating villages traveling by boat, train and on foot.

Crown your day with a memorable typical Ligurian seafood feast, and exquisite regional white wines, in a lovely seafront restaurant.

Learn about the area's one-of-a-kind grape harvesting techniques enjoying an exclusive leisurely hike through luxuriant seafront vineyards: nobody in sight apart from the deep blue sea, verdant vines, your group and guide. Weather and sea conditions permitting you will also admire the scenario from the water during a fabulous cruise.

At the end of the tour travel back to the Hotel and enjoy more luscious Tuscan flavor: the chef’s daily specialties!


Sweet dreams at Relais Villa Olmo 

DAY 3 – Tuscany Wineland Safari: a thrilling off-road journey to discover the most beautiful spots of the rolling Chianti hillside
After enjoying breakfast and checking out meet your professional driver guide at Relais Villa Olmo and set off with a roar aboard a sturdy off-road Land Rover Discovery. Travel along winding roads lined by swaying cypress trees to an authentic period farmhouse, explore the grounds and wander through the mysterious cellars. Journey on through the beautiful Tuscan hilltop silent roads: you will see quaint villages, golden meadows, vineyards and a magnificent ancient abbey dating back to the 13th century!

Catch hidden views, take splendid photos and stop alongside a lovely field for a picnic snack and some fabulous local wine. The fresh breeze and sweet scents of the countryside will lead you straight to the greenest heart of the Chianti Classico hills, where luxuriant vineyards sparkle and thrive, to relish the best of Tuscan local fare during a memorable 3-course typical lunch accompanied by the rich aroma of Chianti wine. Crown your day viewing a real Tuscan hillside jewel: a majestic Medieval castle, with its fascinating turrets and merlons, rising in an outstanding position.
Take in the last, unforgettable views, traveling back to Florence by minivan.





2 night stays at Relais Villa Olmo or similar
Buffet Breakfast
Free subscription to our Food & Wine Club (25-Euro value), to access special discounts online on wine and typical products
Day 1
Transportation IN/OUT Florence by comfortable Minivan
English speaking driver/tour leader
Guided walking tour of Siena with professional English speaking guide
Surprise tasting in Siena
San Gimignano visit with free time
Typical Tuscan dinner in a Tuscan boutique winery in Chianti wine region
Guided visit of the winery cellars
Wine tasting
Day 2
Professional English speaking driver/tour leader
Transportation from Relais Villa Olmo by comfortable A/C Minivan
Guided tour of Cinque Terre by English speaking professional tour escort.
Tickets for Cinque Terre National Park
Train tickets
Boat Ride along the Riviera (weather and sea conditions permitting)
Delicious Full Lunch (with seafood) and Wine, in a typical restaurant
Light hiking through seaside vineyards
Day 3
Off-road Chianti hills tour aboard a state-of-the-art Range Rover Defender
English-speaking professional driver and tour escort
Wine tour of a Chianti farmhouse and its cellar
Picnic snack with wine
Viewing of an ancient abbey
Typical 3-course Tuscan light lunch
Visit to a Medieval Castle
Transportation to Florence city centre by comfortable minivan

Meeting Point

FLORENCETOWN TOURS & NEWS STAND - Piazza della Repubblica (next to the APPLE STORE under the loggias, corner with Via Pellicceria) - Florence - SEE ON MAP


We regret to inform that this tour is not suitable for guests with wheelchairs or with impaired mobility.
The Via Dell'Amore (Cinque Terre) is temporarily closed to the public due to a mud slide that has made it inaccessible.
The actual itinerary inside the Cinque Terre National Park may slightly vary depending on weather and trail conditions. The tour quality will always be preserved.
Please note that Italy's law doesn't permit selling alcoholic beverage to teens under 18 y.o. so clients under this age will be served non-alcoholic beverages.
Please inform us of any food intolerance or allergy in advance.
Boats do not operate in bad weather conditions and when the sea is rough. On these occasions transfers between towns is by local coastal train or by minivan.
We suggest good walking shoes (no flip-flops!) as well as hat and sunscreen.

Rain Policy

This tour runs rain or shine.

book now

from 849

from EUR 849 p.p. (price based on a party of 2 pax in a double room)
EUR 999 p.p. ( for a single traveller in a double room for single use)

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