April 1 - 9, 2027
Spring 2027:
Venice, Asolo & the Prosecco Hills
Venice & Beyond: Luxury Women's Group Tour
Venice does not give herself away quickly. Five nights in the Serenissima are what it takes for the city to soften, for the rhythms of the water to settle into your own. This is a small group of women who chose Italy in spring, and chose to do it slowly, and well.
Five nights in a refined boutique hotel in the heart of the city, a private cooking class in the home of one of Venice's most respected chefs, exclusive entry to artisan workshops most travelers never see.
Then three more nights in the green hills of the Veneto: Asolo's medieval rooftops, Verona's Roman bones, the rolling vineyards of Prosecco country, and a celebratory farewell dinner on a villa terrace overlooking it all.
This is not a Venice tour. This is a Venetian spring.
This is where most Venice itineraries get it wrong. Two days in the city, the same crowded basilica every group is photographing, a 30-minute gondola ride down a canal lined with other 30-minute gondola rides. This journey is built on the opposite premise - that Venice is a city to live in, not to tick off.
What makes this trip different
A typical Venice tour
Two or three nights in the city, then onward
The same crowded San Marco everyone photographs
A 30-minute gondola ride along a canal full of other gondolas
Lunch in restaurants where the menus are translated into six languages
A glass factory pitch ending at the showroom
Coach drop-offs at the next city, never the countryside
This journey
Five unhurried nights in the heart of Venice
Private morning at the Rialto Market with a renowned Venetian chef, then his home kitchen
An exclusive private opening of one of Europe's last great mosaic workshops
An afternoon in the studios of a 17th-century costume atelier and your portrait taken in Venetian silks
Three nights in a celebrated villa hotel in the medieval hilltop town of Asolo
Lunch with the family at a Valpolicella estate; tasting Prosecco in the UNESCO hills
Make your dream come true
ONLY $500 deposit to secure your spot
$11,995 USD
($16,895 CAD)
Per Person
Single Occupancy
What happens after you apply?
Apply and book a call. Fill out a short application and schedule a time on Anna’s calendar. No commitment. No pressure.
A personal call with Anna. This is your chance to ask questions, share what you’re looking for, and make sure this journey is the right fit. We’re selective about our groups — that’s what keeps the experience exceptional.
Secure your place. Once we’ve confirmed the fit, you’ll receive an invoice for your $500 deposit. From there, you’ll get a welcome guide, packing list, and a direct line to Anna for anything you need before departure.
June 1, 2026 - $3,995 payment is due
October 1, 2026 - the final balance is due
When you & a girlfriend book together, you each save $250
Book more than one Olegana trip & save $500
The trip at a glance
Day 1 (Apr 1)
Welcome to Italy!
• Arrive in Venice, private water taxi transfer to a refined boutique hotel in the heart of the city.
• A welcome dinner with the women alongside whom you'll spend the next eight days falling in love with Italy.
Day 2
Venice on Foot
• A morning of palaces, basilicas, and the slow theater of the Serenissima - Doge's Palace, St. Mark's, and a gondola through the quieter canals.
• The afternoon and evening are yours, to wander, nap, or to find your own corner of Venice.
Day 3
The Rialto, a Chef's Table & Venetian Silks
• Visit at the Rialto Market with a Chef and a private cooking class in his home.
• A historic costume atelier - try on a Venetian costume (selected from photos sent to you in advance), aperitivo in the atelier, and a one-hour photo walk through the city with a professional photographer.
Day 4
Murano & Burano
• The fire of the glassblower's furnace, a long lunch on the lace-makers' island of impossible colors, and an unhurried afternoon among artisans whose families have shaped these crafts for centuries.
Day 5
Venetian Artisans
• An exclusive private opening of one of Venice's most extraordinary artisan treasures, a 19th-century mosaic workshop
• A walk through the world's first Jewish quarter, with a guide who brings 5 centuries of history into the present.
Day 6
Historic Venice & Asolo
• A morning with one of Venice's most legendary textile houses, lunch in Cannaregio, then a private coach into the green hills of the Veneto.
• A celebrated villa hotel in the medieval hilltop town of Asolo, one of the most romantic small towns in all of Italy.
Day 7
Verona & Valpolicella
• A guided morning in Verona - Juliet's balcony, the Roman arena, a panoramic ascent above the rooftops and the Adige.
• A centuries-old wine estate in the Valpolicella hills, the home of Amarone, for a long lunch and a slow tasting.
Day 8
Bassano, the Prosecco Hills & Farewell
• A morning in the elegant town of Bassano del Grappa
• An afternoon among the UNESCO-listed Prosecco vineyards
• A farewell dinner on the terraces of the villa as the sun sets over the Veneto.
Day 9 (April 9)
Departure day - any time
A final breakfast in the villa gardens, then private transfers back to Venice - and home, slowly.
Optional extension options may be available - please reach out directly
This is luxury small group travel, thoughtfully designed
No large groups. No generic, overcrowded activities. Not a coach with forty strangers and a microphone. Not a packaged tour with the same itinerary as everyone else's.
A small group of women (not more than 12) who chose to do this together, with private guides, exclusive access, and the kind of meals that take three hours because no one is in a rush. The hotels are refined and personal. The pace is human. And the company that by the end of the trip, feels like the part you didn't know you needed.
An In-Depth Look at Your Trip
Venice | 5 nights
A city suspended between water and dream. Five evenings here means time enough to fall in love with her layers: her artisan quarters, her quiet morning canals, the meals that happen behind doors most travellers never open.
Your home for these 5 nights is a 16th-century palazzo in the Cannaregio district, the authentic, lived-in heart of Venice, away from the crowds of San Marco. Individually-designed rooms, a walled private garden (rare in this city), and the kind of quiet you didn't know Venice still held.
A morning at the Rialto Market with a Chef. Walking the stalls with someone who has shopped here for thirty years changes what you see. The cooking class that follows happens in his home kitchen that’s built for teaching, with the kind of light and warmth a professional restaurant rarely has. A hands-on class, then a long lunch at the table he eats at every day.
Exclusive private access to one of Europe's last great mosaic workshops. Open for our group before the doors open to anyone else. A 19th-century furnace, the same techniques that have shaped Venetian mosaic for over a century.
An afternoon at a historic costume atelier. Before the trip, you'll receive photos of 4-5 Venetian costumes hand-selected to your measurements to choose from. On the day, you're welcomed into the atelier with the history of Venetian masks and Carnival, fitted into your costume, given an aperitivo, and then taken on a one-hour photo walk through the city with a professional photographer. You leave with images you couldn't take anywhere else.
Murano, Burano, and the Jewish Ghetto with a synagogue's own guide. The glassblower's furnace, the lace-maker's needle, and a walk through the world's first Jewish quarter - a city within a city, layered with five hundred years of trade, faith, and survival.
The Veneto countryside | 3 nights
Where UNESCO-listed vineyards roll across green hills and the medieval town of Asolo holds court above them. The final 3 nights are the slower half of the journey: long lunches, panoramic terraces, and the kind of countryside that explains why Venetians have been retreating to it for six centuries.
Three nights in a celebrated villa hotel in Asolo. A Palladian-era villa transformed into a hotel by Giuseppe Cipriani himself - the founder of Harry's Bar in Venice, the man who invented the Bellini. An English garden recognised as one of the most magnificent in the world by Historic Hotels Worldwide, an infinity pool overlooking the valley, and a kitchen that anchors the second half of your trip.
Lunch and a tasting at a centuries-old Valpolicella wine estate. The home of Amarone - a single afternoon at one of the most distinguished wineries in the region, with the family pouring.
A morning in Verona: Roman arena, Juliet's balcony, the panoramic ascent. Shakespeare's city, with a guide who can tell the literary myth from the Roman fact. A funicular ride above the rooftops for the view that quietly explains why the city has been painted for a thousand years.
An afternoon among the UNESCO Prosecco Hills, and a farewell dinner on the villa terrace. A tasting at one of the leading Prosecco producers, then back to the villa for a long, celebratory dinner.
“Our hotel was beautiful & since it was a small boutique hotel, we had the hotel for ourselves."
– Peggy A
What’s included
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Where you stay
Five nights in a refined boutique hotel in the heart of Venice
Three nights in a celebrated villa hotel in the medieval hilltop town of Asolo
Daily breakfast at both properties
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How you travel
Private water taxi transfers throughout Venice
Private coach for all transfers between Venice, Verona, Valpolicella, Asolo, and the Prosecco Hills
Local guides in every city: none of them shared with another group
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How you eat
A welcome dinner in Venice and a farewell dinner on the villa terrace
A private cooking class and lunch in the home of a renowned Venetian chef
Lunches at hand-selected island restaurants, a Valpolicella wine estate, and a leading Prosecco producer - wine paired throughout
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What you experience
Private opening of a Venetian mosaic workshop, an afternoon at a historic costume atelier with a professional photo walk through the city
Guided walks through the Jewish Ghetto, Cannaregio, Murano, Burano, Verona, and Bassano del Grappa
Doge's Palace, a gondola ride, and an afternoon at a Valpolicella estate
Here’s what it’s like to travel with us:
What past Olegana guests have said…
“I travel a lot and I am not usually a group travel person, but this being a small group travel, it was intimate and we were able to experience things you cannot experience in a large group."
– Peggy A
“We came together not knowing each other and left as family."
– Carol F
“The small group allowed us to have a more intimate experience and some flexibility that you would never get in a larger group tour - it felt like traveling with a group of close friends!"
– Allison M
You might be wondering if this Venice trip is right for you…
This journey is designed for women who…
Have travelled before and are ready for travel that's slower, more curated, and more personal
Value time over checklists, depth over coverage, and a long lunch over a packed schedule
Want the comfort of a small group while keeping the freedom of solo travel
Are comfortable on cobblestones and stairs - Venice is bridges, and Asolo is hills
Love food, art, history, and the kind of conversation that happens over a third glass of wine
This trip may not be the right fit if you…
Prefer all-inclusive resorts or cruise-style itineraries
Are looking for a budget tour or a fast 'see Italy in a week' overview
Need significant mobility accommodations (Venice has steps and bridges throughout, and several days involve substantial walking)
Are looking for nightlife, late nights, or a party atmosphere
Read through our frequently asked questions.
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Well-travelled women, mostly 50 and beyond, mostly travelling solo. The group is small — no more than 12 — and the rhythm of the trip is built around women who know what they like and want to be in good company while they enjoy it.
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Most of the women on this trip are travelling solo. The whole experience is designed for it - shared meals, easy ways to meet, plenty of free time when you want your own afternoon. By the end of the welcome dinner you'll know everyone's name.
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Moderate. Venice is bridges and cobblestones and there is no avoiding stairs in this city.
Walking days range from 2 to 4 miles, and the morning in Bassano and Verona involve some hill climbs.
Most days have a real afternoon break. If you have specific mobility considerations, please raise them on our get-to-know-you call so we can talk through what's reasonable.
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Insurance is strongly recommended. We can offer travel insurance for American travelers. Please let us know if you would like a quote for your travel insurance policy.
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In Venice, a refined boutique hotel in the heart of the city — five nights in canal-facing or canal-near rooms with daily breakfast, Italian elegance, and a personal level of service.
In Asolo, a celebrated villa hotel with garden terraces, a renowned restaurant, and panoramic views of the Veneto. Both properties are hand-selected for this group.
Every guest has her own room throughout — no sharing, even if you've come with a friend.
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The group will meet at the hotel in Italy on April 1, 2027. Everyone will be responsible for purchasing their own plane tickets to get to Italy. We are happy to help find the best airfare options and plan a trip extension before or after the group trip. The traveler will be responsible for any extra costs associated with that.
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Vegetarian, gluten-free, kosher, and most other dietary needs are accommodated easily — please share details when you apply. Italy in general, and these chefs in particular, are deeply attentive to this.
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International airfare, arrival and departure airport transfers (quoted separately based on your flights), travel insurance (required), gratuities, and meals or activities marked 'at leisure.'
City taxes are paid at the hotel — about €4.50 per person per night.
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They're quoted separately because arrival and departure times vary.
We'll arrange a private water taxi for you in Venice and a private transfer back to the airport from Asolo on the final day.
Details are confirmed once your flights are booked.
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Verona and Valpolicella.
About 90 minutes by private coach to Verona in the morning, a guided walking tour, then a long, generous lunch and tasting at a Valpolicella wine estate, before returning to Asolo for a free evening.
The drive each way is the price of admission for what's at the other end of it.
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Guide and driver pre-paid gratuities of $300 per person will be collected approximately a week before the trip starts.
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Yes. The Venice hotel offers extra nights at the same negotiated rate, and the Asolo property has limited extension availability as well. Many guests come a few days early to acclimate to Venice slowly.
Ask Anna on the introductory call.
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No, this is an adults only group, for people 18 years old and older. If you’re under 50, don’t shy away - everyone is welcome! If you are interested in a family friendly adventure through Italy or any other country in Europe, we would be happy to create a custom trip for you. Please book a time on Anna's calendar here to discuss further.
Spring 2027. Venice and the Veneto. A small group of women, all of whom said yes.
Looking for a different style of journey?
Explore our Puglia, Italy; Hidden Scotland or UK Castles & Gardens trips.
Meet Anna
Hi - I’m Anna Fishman, the proud mastermind behind Olegana Travel Boutique, your go-to hub for unforgettable journeys.
I live for family adventures with my travel-loving husband and our little jetsetters in training. With 31 countries under my belt, I’ve combined my personal globetrotting escapades with the expertise of local destination gurus. Together, we craft personalized itineraries that are perfect for you to reconnect with your inner self, to discover the world, and to make new friends.
I can’t wait to meet you on our next group trip for incredible women!