experience Italy, off the beaten path

Women’s Classic Tuscany with Venice & Cinque Terre by Strada Toscana

Fall in love with Tuscany, Venice and Cinque Terre, off the beaten path, on a truly unforgettable journey. Visit tucked away places that still honor tradition and authenticity and be enchanted by local Italians who treat you like long-lost family. From Venice’s quieter neighborhoods and romantic canals and Florence’s Renaissance avenues to tucked away fishing villages in le Cinque Terre and less-traveled strada of Tuscany, your carefully crafted itinerary includes hand-selected experiences, private visits and intimate, insider tours.

Designed for seasoned women travelers or first-time visitors who are looking for more than the usual sightseeing tour, our Women’s Classic Tuscany with Venice & Cinque Terre tour features the rich and ancient heritage of some of Italy’s most beloved regions through delectable culinary traditions, precious artisans, hidden hamlets, ancient civilizations, medieval marvels, exceptional wines and so much more.

TOUR details: At a Glance

  • 10 Days/9 Nights
  • October 26 – November 4, 2018
  • Trip Price: $3,998 USD per person based on double occupancy in Venice, Florence & Cinque Terre, single occupancy w/ensuite bathroom at villa accommodations
  • Single Supplement (Venice, Florence & Cinque Terre) $495 USD



DAY 1: Arrival

  • Visit to St. Mark’s Square, tour of St. Mark’s Basilica, “maze of alleyways” insider walking tour, gondola ride, welcome dinner
  • Dinner included

AFTERNOON: Our journey together begins in a tucked away neighborhood inside the historic center of Venice. After arrival via water taxi and check-in at our boutique, canal-side hotel, you’ll have time to freshen up and enjoy lunch on your own before we meet in the lobby for our official tour kick-off and orientation! From here we walk together through the winding alleyways of Venice to visit famous St. Mark’s Square and St. Mark’s Basilica. Then it’s back to our quieter neighborhood for our “maze of alleyways” walk, followed by a classic gondola ride together.

EVENING: Dinner at our friends’ classic Venetian restaurant in a former gondola boathouse

DAY 2: Venice

  • Early morning walk to Rialto Bridge and Market (optional), vaporetto to the islands of Murano and Burano, Venetian concert (optional)
  • Breakfast included

MORNING: This morning after an early breakfast we’ll walk to Venice’s beautiful Rialto Bridge for a stunning view of the Grand Canal and a stroll through the historic Rialto Market (optional). Then we’re off to catch our vaporetto for a ride through the Venice Lagoon to the islands of Murano and Burano. First top is Murano (world famous for its blown glass works!) where you can peek in countless glass shops – or even visit the Murano Glass Museum. Then it’s on to charming Burano, a centuries-old fishing village – known for its handmade lace and adorable, painted houses. Explore the colorful alleyways on your own and grab lunch at one of the island’s many charming restaurants.

LUNCH: On your own Burano

AFTERNOON: We make our way back to Venice by vaporetto where you’ll have time on your own to relax, shop or explore.

EVENING: We suggest an earlier than usual dinner, on your own, as afterwards you might choose to attend a classic Venetian concert.

DAY 3: Florence

  • Walking tour historic center of Florence, Santa Maria del Fiore (Florence Duomo), Piazza della Signoria, Mercato San Lorenzo
  • Breakfast and dinner included

MORNING: This morning you’ll travel by private Mercedes Benz van service from Venice to Florence.

LUNCH: On your own in-route to Florence

AFTERNOON: After check-in at our boutique hotel in the very heart of Florence, we’ll set out together to explore the city’s historic center where Renaissance art and architecture is virtually everywhere. Our first stop is the world famous symbol of Florence, the magnificent duomo (cathedral) Santa Maria di Fiore, followed by a walk to Mercato San Lorenzo where you’ll find a multitude of leather goods, scarves, gifts and more.

EVENING: Walk through Piazza della Signoria on our way to enjoy a Florentine style dinner at our friends’ family-run trattoria.

DAY 4: Florence & Le Cinque Terre

  • Ponte Vecchio morning walk (optional), Piazzale Michelangelo, walking tour Monterosso al Mare

MORNING: After breakfast it’s off to Ponte Vecchio for a walk across the famous bridge while things are still quiet (optional). Those who wish can revisit Mercato San Lorenzo before check-out, and before our drivers transport us to panoramic Piazzale Michelangelo for one last spectacular view of Florence – from high above – before continuing to our quaint seaside accommodations near the Cinque Terre villages.

LUNCH: On your own in route to le Cinque Terre

AFTERNOON: After check in we’re off to explore Monterosso al Mare – the northernmost of the Cinque Terre villages – with its picturesque alleyways and walking trails that meet up with the sea. You might stroll the beautiful beachside promenade (and grab a gelato), walk up to the Convento di San Francesco (where you’ll find stunning views of the sea!) or meander through Monterosso’s charming alleyways and shops.

EVENING: We dine together at our friends’ chic, seaside restaurant

DAY 5: Le Cinque Terre

  • Exploring Le Cinque Terre villages, Panoramic vineyard walk Manarola (optional), evening on your own
  • Breakfast included

MORNING: Be sure to put on your best walking shoes – and to bring your camera –  because after breakfast we’ll be traveling by train to explore the picturesque villages of Cinque Terre, including Vernazza, Manarola and Riomaggiore. At each stop you’ll have the opportunity to walk the seaside paths, shop along the quaint, meandering (and steep!) avenues or simply take in the incredible postcard views.

LUNCH: On your own in Manarola

AFTERNOON: We continue our exploration of the Cinque Terre villages.

LATE AFTERNOON: After returning by train to our “home” village of Monterosso al Mare, you can enjoy some time on your own to relax, sip a glass of Prosecco, or perhaps take a stroll alongside the Ligurian Sea.

EVENING: Dinner on your own in Monterosso al Mare

DAY 6: Fabro

  • Welcome tour Il Colombaio, herb lesson, vineyard walk, cantina tour and wine tasting
  • Breakfast and dinner included

MORNING: After breakfast in Monterosso it’s off to the village of Fabro and your characteristic farmhouse accommodations, nestled along the border of Tuscany and Umbria.

LUNCH: Lunch on your own in route to Fabro

AFTERNOON: After check-in, you’ll have an opportunity to relax and settle in before joining us with owner, Irma, for a welcome tour of the farmhouse and grounds, followed by and herb “walk” and lesson to learn Italians’ best kept secrets for using herbs in cooking and for wellness. Then it’s off for a leisurely walk tour to a nearby vineyard where you’ll enjoy a private cantina tour and wine tasting with delightful sommelier, Paola.

EVENING: Welcome dinner prepared by the talented Chef Adorno

DAY 7: Montepulciano & Montichiello

  • Private visit with hand-hammered copper artisan, private Vino Nobile tasting and lunch in our friends’ 15th century cantina, Montepulciano historic center, vineyard photo op, bruschetta-making lesson
  • Breakfast, lunch and dinner included

MORNING: After breakfast, those who wish may opt for an early morning walk in along a countryside land. Then it’s on to regal Montepulciano with its Renaissance palaces and spectacular views. We begin in the historic center of town with a fun, private visit with Cesare, a delightful copper artisan, whose hand-hammered cookware is nothing short of stunning. Then we’re off to our friends’ 15th century cantina for a private wine tasting of Vine Nobile di Montepulciano – one of Italy’s finest DOCG wines.

LUNCH: A light lunch will be served during our private wine tasting in our friends’ 15th century cantina

AFTERNOON: Enjoy time on your own for shopping (we’ll point out our favorite artisan shops), visiting churches or for wandering and grabbing a gelato. Later we’ll stop for a photo op in a picturesque vineyard followed by an afternoon passeggiata together in charming Monticchiello.

EVENING: Bruschetta-making lesson, aperitivo hour, chef-prepared dinner

DAY 8: Città della Pieve

  • Olive oil tasting, village walk, saffron lesson and tasting, Adoration of the Magi (Perugino), pasta-making lesson
  • Breakfast, lunch and dinner included

MORNING: After a lovely buffet-style breakfast, we’ll make our way to a nearby frantoio (olive press) where you’ll learn first-hand the real secrets of pressing extra virgin olive oil, followed by a delicious tasting of the local, extra virgin olive oil. Then it’s on to Città della Pieve, one of Umbria’s most beautifully preserved medieval villages with its distinct red-brick construction – famed throughout the centuries for its production of saffron, “red gold”. We begin with a guided walk along winding alleyways (including one of the narrowest streets in Italy!) and a fascinating saffron tour and tasting with our friend, Alessandro, including a peek at a spectacular fresco by Renaissance painter, Perugino (born in Città della Pieve) who was known for using vibrant yellows in his paintings – tinted with (you guessed) saffron!

LUNCH: Lunch is served up at our friend, Cristian’s, adorable cafe – complete with a “hidden” 14th century wine cantina

AFTERNOON: After lunch, you’ll have time on your own to explore or shop before we return to the farmhouse where you’ll don an apron for an oh-so-fun pasta-making lesson with Signora Antonietta!

EVENING: Aperitivo hour followed by a delectable dinner prepared by talented Chef Adorno that includes (you guessed it) your handmade pasta!

DAY 9: Pienza & Val d’Orcia 

  • Pienza “passeggiata” walk (optional), visit of an organic sheep farm, pecorino cheese tasting, tour of historic La Foce Gardens, wine pairings aperitivo
  • Breakfast, lunch and dinner included

MORNING: After breakfast we’re off to picturesque Pienza – famous for its ideal Renaissance layout and pecorino cheese. Opt to enjoy the town’s “passeggiata” with stunning views of the Val d’Orcia or browse the many artisan shops and/or tour the cathedral and Papal Palace. Next stop is our friends’ organic sheep farm where you’ll enjoy a tour and delectable pecorino cheese tasting.

LUNCH: At our friends’ organic sheep farm

AFTERNOON: In afternoon we make our way along the winding, cypress-lined roads to historic La Foce Villa for a private guided tour of the spectacular gardens overlooking the Val d’Orcia.

EVENING: Wine pairings aperitivo hour with Paola, followed by special farewell dinner prepared by Chef Adorno

DAY 10: Departure

This morning our drivers will transport you to Rome Fiumicino Airport.



Situated on romantic canal, historic, Ca d’Oro is quintessentially Venetian with its beautifully decorated rooms (featuring stunning Murano glass chandeliers) and regal, Byzantine architecture. A panoramic rooftop terrace offers a ideal setting for an evening aperitivo, and the Rialto Bridge and St. Mark’s Square are just a few minutes walk away, making Hotel Ca d’Oro our favorite accommodations in Venice.

Situated on Piazza della Repubblica, in the very heart of the historic center of Florence, Hotel Pendini boasts a rich decor, fascinating history and exemplary level of service. Rooms are decorated with elegant appointments and antique furnishing, and the hotel’s breakfast room (always a highlight) is housed in the palazzo’s famous archway – one of the city’s unique landmarks.

Hotel Palazzo Vannoni is located in the charming, historic center of the seaside village of Levanto, tucked away from the hustle and bustle of Le Cinque Terre and just a short stroll from the azure, Ligurian Sea. Built in the early seventeenth century, the hotel overlooks Piazza Cavour, the main square of the town, and boasts rooms with fresh, white linens and painted ceilings. The ideal, beautiful location for easy-access to Le Cinque Terre.

“Where the doves live” is meaning behind the name of your characteristic farmhouse accommodations, nestled along the border of Tuscany and Umbria in a panoramic position that boasts spectacular views in all directions. With cozy, individually decorated rooms, a sweeping terrace for dinners under the stars, an inviting swimming pool and a talented in-house, Tuscan chef, the setting for your culinary experience in Italy is nothing short of ideal.


  • 2 nights stay at Hotel Ca d’Oro in Venice
  • 1 night stay at Hotel Pendini in Florence
  • 2 nights stay at Palazzo Vannoni in Levanto (Cinque Terre)
  • 4 nights stay at Agriturismo Il Colombaio
  • Private Mercedes Benz van service to/from all cities, towns and sites included in the itinerary
  • Private Mercedes Benz van service to Rome Fiumicino Airport upon departure
  • All generous breakfasts with made-to-order Italian coffees
  • 3 lunches
  • 6 regionally inspired dinners at award-winning restaurants or prepared by an award-winning Tuscan chef
  • Regional wines with each included lunch or dinner, featuring local vintages and DOCG wines
  • Accommodations for special dietary requirements, including gluten free, dairy free, Paleo and Vegan
  • Tour inside St. Mark’s Basilica
  • Walking tour of St. Mark’s Square
  • Visit to Rialto Bridge and Rialto Market
  • “Insider Alleyways” walk in Canneregio
  • Vaporetto to the islands of Murano and Burano
  • Classic Venice Gondola ride
  • Visit inside the Basilica Santa Maria di Fiore
  • Walking tour of Florence
  • Shopping in Mercato di San Lorenzo
  • Picturing-taking stop at Piazzale Michelangelo
  • Train transportation Cinque Terre
  • Walking tours in Cinque Terre villages
  • Private demonstration with copper artisan
  • Private Vino Nobile wine tasting in a 15th century cantina
  • Pasta-making class
  • Bruschetta-making lesson
  • Saffron tour and tasting
  • Pecorino cheese-making tour and tasting
  • Guided tour of Villa Le Foce
  • Countryside walks (optional)
  • Entrance fees to all sites included in trip itinerary
  • Daily accompaniment with Strada Toscana guides and/or hosts
  • Gratuities for restaurant meals and tours
  • And some fun surprises!

Not included: Airfare, gratuities outside of those listed, alcoholic drinks or wines ordered “on your own”, ground or water transportation outside of that listed in the trip itinerary

The Unexpected is Part of the Journey: At Strada Toscana we weave amazing, authentic experiences into every trip, but sometimes unexpected things come up. If Mario calls to tell us they’re pressing olives at just this moment, off we go (I mean, we wouldn’t let you miss his newly pressed olive oil!), and if a site has an unscheduled closing, we improvise to include something equally as wonderful and interesting. On that note, if our usual boutique hotels or B&Bs can’t accommodate us (which rarely happens), you can rest assured you’ll stay somewhere of an equal or higher level. The quality of our tours is never at risk, as our team is committed to excellence, along with our vast, local, Italian connections.

Women’s Classic Tuscany with Venice, Florence & Cinque Terre

  • October 26 – November 4, 2018
  • 10 Days/9 Nights
  • Trip Price: $3,998 USD per person based on double occupancy in Venice, Florence & Cinque Terre, single occupancy w/ensuite bathroom at countryside accommodations
  • Single Supplement (Venice, Florence & Cinque Terre) $495 USD

A $500 deposit is required to secure your space on this tour, $100 of which is nonrefundable.



Have questions? Visit our Frequently Asked Questions Page

REVIEWS : What People Are Saying

“You might be able to find the places that Pamela visits on her Italy trips, but it would be impossible to find the connections. As a group we came together to create a wonderful experience, but without Pamela it wouldn’t have been possible. If you’re thinking about a tour to Italy with Pamela Haack, follow your heart. You won’t be sorry!” Pam Erb Melville

“The BEST time I have ever had!!! So organized, exciting, inspiring, uplifting and special trip I have ever been apart of. Pamela, I would go anywhere with you. BEST TIME from start to finish!! Can’t wait to do it again.” Yolanda Ward