Luxury small group trips to Europe & the Caribbean for women
Created by women, for women, our thoughtfully designed journeys blend beautiful destinations, exceptional stays, memorable food, authentic local experiences, and private guides and transportation.
Perfectly designed for solo travel for women over 50, our small groups make it easy to explore the world’s most exciting destinations with confidence, comfort, and great company. Come solo, leave with new friends, and become part of a community where connection and relationships matter just as much as the destination.
Our trips at a glance:
PUGLIA,
ITALY
2026 & 2027 DATES
VENICE,
ITALY
APRIL 2027
UK CASTLES &
GARDENS
MAY 2027
Save the date! Details coming soon:
Dolomites & Lake Garda, Italy | Fall 2027 & Fall 2028
Christmas in Rome and Umbria | Dec 11 - 18, 2027 AND Dec 11-18, 2028
Caribbean: Barbados & Canouan | March 2028
Secret Venice | April 19-27, 2028
Sicily, Italy | May 2028
Puglia, Italy | May 3-10, 2028
AND Oct 2-9, 2028Japan | November 2028
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.
Looking for 2027 trips? Join our exclusive email list!
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.
“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
“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!
“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
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Connect with like-minded women who love to travel as much as you do!
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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 33 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!