Luxury small group trips to Europe for women
Join a small group trip created by women, for women! Enjoy select premium accommodations, top culinary experiences, authentic local flavor, and private guides and transportation in some of the most exciting places in the world.
Go off the beaten path, reconnect with yourself & make new friends!
Travel with us to…
Come together as strangers, return home as friends.
Want to travel with other women who share your passion for travel?
Whether it’s your first trip to Europe or a return to a beloved destination, our expertly crafted small group trips to Europe ensure unforgettable experiences and lifelong memories.
100+ Five-Star Reviews
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“I just wanted to thank Anna Fishman with Olegana Travel Boutique for a wonderful trip to southern Spain.
From start to finish Anna planned a wonderful trip. The hotels, tours & transportation were top notch. The days were filled with a great balance of history and fun activities.
This was my first women's only solo trip and I look forward to my next one!”
ELLEN S.
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“This was my first solo trip after the loss of my husband and I’m so happy that I found Anna's Facebook page which opened my mind to all the possibilities to live life through travel with other like-minded women.
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.
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“I recently embarked on my first solo trip, and it exceeded all my expectations! I made lifelong friends with fellow travelers, which was a delightful surprise.
Our tour leader was exceptional —deeply involved & always responsive.
I can’t recommend this experience enough for anyone considering a solo journey. It was a transformative experience that I’ll cherish forever!”
TRACY B.
2024 Made in Italy: Venice Christmas Edition
December 8 -15, 2024 - SOLD OUT!
Join us for a women-only getaway that's a classical Venice tour with an extra twist! Picture yourself gliding along the iconic canals in Venice, Italy, surrounded by the twinkling lights of charming Christmas decorations, enjoying the sights, sounds, and flavors of this breathtaking city.
"Made in Italy: Venice Christmas edition" will focus on local artisans, the art of Venetian masks & Carnival dresses, Murano glass, Burano lace, and a special Carnival-themed dinner celebration with a surprise.
Picture yourself visiting lovely Prosecco hills with a chilled glass in hand, or sipping a lovely glass of wine with a view of the iconic St. Mark's Square. A trip to remember!
Trip Highlights
7-day adventure with accommodations, meals, and activities
A classical Venice tour with a focus on local artisans & a special twist!
Explore Venice, Venetian masks, Murano glass, Burano lace, and a special Carnival-themed dinner celebration!
New 2025 Trip Alert:
Wine, Chocolate & You, in Sicily!
Our most-requested trip is finally here! This is the women-only adventure you’ve been waiting for.
“Anna and her team in Italy did a fantastic job in making sure we had an amazing time visiting Puglia. There were so many “out of the box” experiences that made this 7-day trip very unique and wonderful.
The group of women brought together by Anna made the trip fantastic! Thank you for a memorable trip!”
– MJ
2025 Foodie Adventure in Southern Italy, Puglia
Two departure dates:
April 27 - May 4, 2025 |
October 19 - 26, 2025
Close your eyes and imagine the golden glow of the Italian sunset, painting the sky with hues of orange and pink. You and your best girlfriend are lounging in luxury, sipping on glasses of velvety wine, and soaking in the beauty of the moment.
But this trip is more than just relaxation—it's an adventure off the beaten path, whisking you away from bustling metropolises and into the heart of authentic Southern Italian charm. Prepare to be enchanted as we explore the enchanting towns of Alberobello, Matera, Ostuni, Lecce, Bari, and Polignano a Mare.
Every moment is a journey into the soul of Puglia. So, raise your glass to friendship, adventure, and the magic of Southern Italy. This journey promises to be a feast for the senses and a treasure trove of unforgettable memories.
Trip Highlights
7-day adventure with an English-speaking, professional guide, accommodations, meals, and activities
Explore off-the-beaten-path iconic towns in Southern Italy
Explore Italy, sightseeing & walking tours, olive oil, burrata & mozzarella tasting, and more!
“I am happy to let anyone know what an amazing experience this was and to not miss this incredible opportunity to experience the best that Italy has to offer.
You and your team put together a trip of a lifetime for me and the other ladies. I feel so fortunate that I invested in myself and did this trip. It truly filled my cup. ”
– Joanna
Buy two trips, get $500 off!
Bring a friend and save $250 each!
Wine, Chocolate, & You - in Sicily
October 5 - 13, 2025
Leave your day-to-day life behind and say “Ciao!” to Sicily.
Our most-requested trip is finally here! This is the women-only adventure you've been waiting for.
Close your eyes and imagine the golden glow of the Italian sunset, painting the hills with hues of orange and pink. You are lounging in luxury, sipping on a glass of velvety wine and soaking in the beauty of the moment.
We’ll visit a Roman villa, explore history in Ragusa and Taormina, “the Ionian Pearl,” shop for local artisanal crafts, take a private sail boat to Grotto Azzurra & Isola Bella, learn Sicilian cuisine during a hands-on cooking class, sample wines and chocolate, and so much more!
Trip Highlights
8-day adventure with an English-speaking, professional guide, accommodations, meals, and activities
Explore charming towns and architectural wonders of Sicily, Italy
Sightseeing, wine & chocolate tasting, a private sail boat, Sicilian cooking class & more!
“Best time ever!! So well organized and amazing places we got to see and experience along with a great group of ladies I can now call friends !
Anna, you are great! Kind and thoughtful and very good at what you do.
I highly recommend joining one of Anna’s trips!! ”
– Dana
2025 Secret Spain: Discover Andalusia
October 12 - 19, 2025 - Details & Itinerary Coming Soon!
Join us for an adventure in Southern Spain - visit the Andalusian gems of Grenada, Seville, Cordoba, Ronda, Cadiz and Jerez!
We'll visit the Alhambra, a UNESCO World Heritage monument and the most remarkable monument to Moorish art in Spain, sample local tapas, tour an olive oil estate, experience the magic and beauty of flamenco dancing, enjoy wine tasting in an old convent that's been transformed into a winery, watch a live paella cooking and a sangria-making demonstration, and so much more!
This trip will take you off the beaten path of busy bustling metropolises like Madrid and Barcelona, and into charming, authentic Southern Spanish towns.
Want more details? Join the waitlist!
Trip Highlights
7-day adventure with an English-speaking, professional guide, accommodations, meals, and activities
Explore charming towns and architectural wonders of Andalusia - Southern Spain
Sightseeing, wine & olive oil tasting, a flamenco experience, paella cooking & more!
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 30+ 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!
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