September 10 - 18, 2027
Fall 2027: Dolomites & Lake Garda, Italy
A women's group trip to the Dolomites, Lake Garda & Italy's wine country
Picture a glass of Franciacorta in a castle courtyard, the vines running right down to the road. A boat sliding across Lake Garda toward an island garden. And a few days later, the moment the pale rock of the Dolomites turns pink in the evening light, and nobody on the terrace says a word.
This is our first women's group trip to the Dolomites, and it's a slow one. Nine days from Bergamo's walled old town to the shores of Lake Garda and up into the mountains of South Tyrol, through wine country, lemon houses and Alpine villages, with three nights at a wellness hotel in the Dolomites to finish. By the time we reach the peaks, the women around you won't feel like strangers anymore.
Meet your hosts: Anna and Kerry
Hi, I'm Anna Fishman, the founder of Olegana Travel Boutique.
I'm hosting this trip together with Kerry, which means two of us will be with you for all nine days, from the welcome dinner in Bergamo to the farewell dinner in the Dolomites.
With 34 countries under my belt, I've combined my own travels with the expertise of trusted local partners to craft journeys where you can reconnect with yourself, discover somewhere new, and make friends along the way.
Kerry
Kerry's European adventure began over forty years ago, taking her from Virginia to the southeast of England, to the heart of Paris and the forests of Fontainebleau, and finally to Italy, where she made her home with her former Italian husband and their two grown children, Eleonora and Lorenzo.
She grew up in a family of eleven where every meal was home-cooked, and she learned early what food and time around a table do for people. That grew through years of living in Turin, Verona and Friuli, so northern Italy isn't just a destination for Kerry. It's where she made her life. Her involvement with the Slow Food movement, her Master's in Italian Cuisine and Oenology from ICIF, and her sommelier training with AIS all come from the same place. She also founded the English-Speaking Happy Hour in Verona, which grew into an international community that still nurtures friendships across the world.
As a host, she brings food and wine expertise, both American and Italian cultural depth, and a genuinely attentive personal touch.
Whether it's Franciacorta in a castle cellar, a glass of Vino Santo by Lake Toblino, or a morning in Bolzano's market, Keri leads with affection and attention, helping women step outside their comfort zone, find the joy in it, and make new friends.
Kerry now divides her time between Italy and the United States, and she keeps doing what she has always done: creating experiences and connections that last.
We can't wait to meet you.
What’s included in your experience of a lifetime
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Accommodations
8 nights / 9 days in handpicked 4-star and 4-star superior hotels, including three nights at an adults-only wellness hotel in the Dolomites
Your own room every night, with no single supplement
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Tours & Activities
Your hosts, Anna and Kerry, with you every day, plus local English-speaking guides and a private driver throughout
A hands-on cooking class, three wine tastings, and coffee and chocolate tastings in Rovereto
Entry fees for every activity listed in the itinerary
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Food & Beverages
8 breakfasts, 5 lunches, and 8 dinners
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Transportation
Private coach and driver throughout, including all transfers between regions and to and from every activity
Not sure if this trip is for you?
I hear it all the time - "I would love to come with you BUT..."
BUT I've never traveled alone!
This is a perfect option if you’re a solo traveler on a journey of self-discovery: you can be part of a larger group of women (usually 50+) that share your interests and have likely been in your shoes before, while going through a new stage of life like retirement, divorce or loss of a partner. Everyone is as excited to be on this trip as you are so you're not alone.
BUT I've never been to Europe!
That's ok - that's the beauty of travel and exploring new places! With our group, you don't have to worry about the logistics in an unfamiliar, new place. You're part of a small group that travels together with a professional, English-speaking guide and you get to know one another.
How would it feel on the flight home, knowing you finally took the trip you have been putting off, and made a few friends along the way?
P.S. This date doesn’t work for you? Check out our other women-only trips here.
Fall 2027
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Fall 2027 ⋆
15 of 16 spots remain
What your trip costs
ONLY $500 to secure your spot
Your trip investment covers nearly everything: eight nights in handpicked hotels, twenty-three meals, three nights at a wellness hotel in the Dolomites, a cooking class, three wine tastings, two cable cars, two boats, a private coach, and every entry fee on the itinerary.
Your own room is included, not an extra. Most group trips charge a single supplement of two thousand dollars or more. Here you have your own space every night, and it's already in the price.
EARLY PRICING - BOOK BEFORE OCTOBER 31, 2026
$12,995 USD
($18,595 CAD)
Per Person
Single Occupancy
AFTER NOVEMBER 1, 2026
$13,995 USD
($20,085 CAD)
Per Person
Single Occupancy
Book more than one trip and save $500!
Bring a friend and save $250!
February 1, 2027 - first payment of $3,995 is due
May 1, 2027 - the final balance is due
Here’s what it’s like to travel with us:
"She truly made this the trip of my lifetime. Private tours, beautiful views & the hotels were unbelievable."
— Steve C., past Olegana Italy client
Day 1 (Sep 10 )
We begin in Bergamo
Our first home is a converted monastery in the heart of Bergamo, founded by Celestine monks in 1309, and it's exactly the kind of quiet, thick-walled place you want after an overnight flight. The afternoon is gentle. We take the funicular up to Città Alta, the old town inside its sixteenth-century Venetian walls, now a UNESCO World Heritage Site, and look out across the Lombard plain.
In the evening, our welcome dinner, and the moment you meet the women you're about to spend nine days with.
The trip at a glance
Nine days of lakes, vineyards and mountains, from Bergamo to the Dolomites.
Day 2
Franciacorta, a castle cellar, and an island without cars
Franciacorta is Italy's answer to Champagne, made the same way and taken just as seriously. We spend the morning at Castello di Bornato, walking through its Renaissance rooms, underground passages, Italian garden and private chapel, then down into the old cellar for a tasting. Lunch is in the castle's former stables, with vineyards on every side.
In the afternoon, a short ferry across Lake Iseo to Monte Isola, the largest lake island in southern Europe, where fishing families still hang their nets to dry and hardly anyone drives. Dinner back in Bergamo.
Day 3
Sirmione, an island garden, and the road north
We reach Lake Garda at Sirmione, an old town built on a narrow finger of land and guarded by a moated castle, with the ruins of a Roman villa at its tip. Lunch in Sirmione, then a boat along the western shore to Isola del Garda, where a Venetian-style villa and its gardens sit right on the water, still home to the family who own it.
Late in the afternoon, we drive to Riva del Garda at the lake's northern tip, where the cliffs drop straight into the water and it looks more like a Norwegian fjord than Italy. We stay here three nights.
Day 5
Dumplings, dessert wine, and an afternoon by the water
Canederli are the bread dumplings of the Alps, and this morning, in the wine village of Isera, you'll learn to make them properly, then eat them for lunch with the people who taught you.
Then the road to Lake Toblino, where a small castle sits on the water, for a tasting of Vino Santo Trentino, an amber dessert wine made from grapes left to dry for months before they're pressed. Very few families still make it, and it's protected as a Slow Food Presidium.
Back to Riva with the late afternoon free by the lake.
Day 4
Lemon houses, olive oil, and a cable car that turns
For centuries, lemons were grown on Lake Garda further north than almost anywhere else in Europe, in tall stone lemon houses built into the hillside at Limone. We walk through one, then sit down to lunch with a tasting of Garda olive oil from some of the most northerly olive groves in the world.
In the afternoon, Malcesine and its castle on the rocks, and the cable car up Monte Baldo, whose cabins slowly rotate as they climb so everyone gets the view. Botanists call Monte Baldo the garden of Europe. Most of us just call it the best view of the lake. Dinner at the hotel.
Day 6
Coffee, chocolate, & into South Tyrol
We leave the lake behind and stop first in Rovereto, where two of the town's historic cafés and chocolate makers are waiting for us. Then north into South Tyrol, where the road signs switch to German and Italian, for a wine tasting and light lunch in Caldaro. Gewürztraminer takes its name from Tramin, the next village down the road, and you'll taste it alongside Pinot Nero and Lagrein, the red grape South Tyrol keeps mostly for itself.
We reach our wellness hotel in the Dolomites in the afternoon, with time for the spa before dinner. Three nights here, and no more packing.
Day 7
Among the peaks
A cable car lifts us up onto the Alpe di Siusi, the largest high-altitude meadow in Europe, beneath the jagged wall of the Sciliar, in the heart of a UNESCO World Heritage landscape. We stop at a traditional mountain hut for a South Tyrolean snack of speck, cheese and bread, and whatever else they're proud of that week.
Back down, a gentle walk through the village and an afternoon at the spa. If you're on the terrace around sunset, watch the rock. The locals call it Enrosadira, the moment the Dolomites turn pink.
Day 8
Bolzano, and our last dinner together
Bolzano is where Italian warmth meets Alpine order, and you feel it within five minutes. A guide walks us through the arcaded streets of the old town and the daily market in Piazza delle Erbe, and then you're free to find lunch wherever the smell of it leads you.
The afternoon is yours, back at the hotel.
In the evening, our farewell dinner.
Day 9 (Sep 18)
Time to say goodbye
You fly home whenever suits you, from Verona, Innsbruck or Munich, or stay on for a few days of real rest in Merano, an hour away.
An In-Depth Look at Your Trip
Explore Bergamo, Franciacorta & Lake Iseo
An afternoon in Città Alta, Bergamo's walled upper town, reached by funicular and ringed by Venetian walls that are now a UNESCO World Heritage Site
A private visit to Castello di Bornato, with its Renaissance rooms, underground passages, Italian garden and historic wine cellar
A tasting of Franciacorta, Italy's traditional-method sparkling wine, followed by lunch in the castle's old stables among the vines
A ferry to Monte Isola, the largest lake island in southern Europe, still home to fishing families
Explore Lake Garda
Sirmione, its moated Scaliger Castle, and the Roman ruins of the Grotte di Catullo
A boat along the western shore to Isola del Garda, its Venetian-style villa and lakeside gardens
The historic lemon houses of Limone, and a tasting of Garda DOP olive oil
Malcesine and the rotating cable car up Monte Baldo, the "garden of Europe"
Explore Trentino
A hands-on canederli cooking class and lunch in the wine village of Isera
Vino Santo Trentino at Lake Toblino, a rare amber dessert wine and Slow Food Presidium
Coffee and chocolate tastings in historic Rovereto
Explore South Tyrol & the Dolomites
A wine tasting and light lunch in Caldaro: Gewürztraminer, Pinot Nero and Lagrein
Three nights at a wellness hotel in the Dolomites, with gourmet dinners and time in the spa
A cable car to the Alpe di Siusi and a South Tyrolean snack in a mountain hut
A guided walk through Bolzano's old town and market, and a farewell dinner
Need testimonial here from Anna
— Zaira C., past Olegana guest
You Might Be Wondering…
Read through our frequently asked questions.
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Yes, only women (she/her) are welcome to join.
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Airfare to and from Italy
Airport arrival and departure transfers, which can be arranged at extra cost
Meals and drinks beyond those listed in the itinerary
All items of a personal nature and anything not expressly stated as included
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Insurance is strongly recommended. We can offer travel insurance for American travelers. Please let us know if you'd like a quote.
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A reasonable level of fitness. Bergamo's upper town and Sirmione are cobbled and hilly, Monte Isola is explored on foot, and older buildings have stairs without railings. Expect 8,000 to 10,000 steps on most touring days.
In the Dolomites we go up by cable car to around 1,800 meters (about 6,000 feet), where the air is thinner and cooler. We don't hike. If you have a heart or breathing condition, it's worth checking with your doctor before you book.
If any day sounds like too much, you're welcome to stay at the hotel instead. The itinerary balances guided days with free time on purpose.
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The group meets at our hotel in Bergamo on September 10, 2027. Most travelers fly into Milan Malpensa, about 70 minutes away, or Milan Linate. I'm glad to help you find the best flights.
The trip ends in the Dolomites on September 18. The nearest airports are Verona, Innsbruck and Munich, and we can arrange your transfer.
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Each day is designed to flow smoothly. If you’d rather skip an activity and relax at the hotel, no problem—just let your tour host know well ahead of time.
To keep things on track and respect our local hosts, please be punctual. We’ll give friendly nudges, but the group won’t wait forever. And missing the lemon houses or the Dolomites at sunset? That's just tragic.
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Guide and driver pre-paid gratuities of $500 per person will be collected approximately a week before the trip starts.
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Every bite tells a story. Northern Italy eats differently from the south, and that's half the fun: lake fish on Garda, canederli and polenta in Trentino, speck, strudel and Alpine cheeses in South Tyrol, and pasta when you least expect it.
Meals are chosen in advance with local chefs and our hotels to show off the best of each region. We ask you to come with an open mind and an adventurous appetite.
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September is one of the loveliest months here. Expect warm days on the lakes, often in the 70s Fahrenheit, and cooler air in the mountains, where mornings and evenings can drop into the 40s. Pack layers, a light waterproof jacket, comfortable walking shoes with good grip, and a swimsuit for the spa. We'll send a full packing list closer to the date. The trip is casual, so as long as you're comfortable, you'll be fine.
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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.
Arriving early or staying on?
Most travelers fly overnight into Milan, and a night in Bergamo before we begin is the easiest way to arrive rested. You wake up in the old town, have a slow breakfast, and meet the group without an airport in between.
At the other end, the most natural next step is Merano, about an hour from where we finish. It's an old spa town of palm trees and promenades with the mountains all around, and I can arrange three, five or seven nights at a celebrated wellness hotel there, with a personalized treatment program for anyone who wants to go further. Others head to Verona or Venice before flying home. If you love this part of Italy, our spring trip to Venice, Asolo & the Prosecco Hills is its natural companion, and our Puglia week is the south at its most generous.
I build every extension privately, shaped around what you actually want to see. Mention it on our call and we'll plan it together.
Meet Anna
Anna Fishman is the founder of Olegana Travel Boutique, a luxury travel company specializing in bespoke European itineraries and women-only small group journeys.
With 34 countries explored and years spent building relationships with the finest local guides, chefs, and hoteliers across Europe, Anna designs travel experiences that feel personal, seamless, and impossible to replicate on your own. Her Puglia journeys have become a signature, with multiple departures selling out each year.
She lives in New Jersey, with her family and she cannot wait to welcome you on your next journey.