Come together as strangers, return home as friends.

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Custom, luxury, hosted small group travel for women.

We select premium accommodations, top culinary experiences, authentic local flavor, and offer private guides and transportation in some of the most exciting places in the world. 

Explore Outlander filming locations in Scotland, enjoy cooking & wine tasting in Italy, book a girls' trip to Spain, or go shopping in Venice!


Go off the beaten path, reconnect with yourself & make new friends!

Why travel with us? A video is worth a thousand words!

P.S.: Join our women-only, private Facebook group!
Connect with like-minded women who love to travel as much as you do!

2024 Scotland: In the Footsteps of Outlander

May 4 - 11, 2024 - SOLD OUT!

and

September 1 - 8, 2024 - bring a friend & save $250 each!

An authentic Outlander-inspired Scottish experience that's steeped in tradition, history, and folklore. Trace the footsteps of your favorite characters in some of the most picture-worthy locations to feel the history, relive the moments of the Outlander series, and take a photo to make your own memories! 

This journey takes you to the iconic Outlander locations that were filmed in Scotland.

The stones are calling, the cobblestone streets, castles and villages are awaiting your arrival, and the whiskey is ready to be poured!  Bring a friend to share a room and share some laughs, or make some new friends who also love all things Outlander. 

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7-day adventure with an English-speaking, professional guide, accommodations, meals, and activities

Follow in the footsteps of Jamie and Claire in iconic locations across Scotland

Explore Scotland, sightseeing, whiskey tasting, a special sheepdog experience, and more!

2024 Foodie Adventure in Southern Italy, Puglia

Our best-selling trip! Two departure dates:

May 31 - June 7, 2024 - SOLD OUT!

and October 12 - 19, 2024

Picture yourself in Italy at the private masseria (villa/hotel) gardens with a glass of wine at sunset with your best girlfriend! This trip will take you off the beaten path of busy bustling metropolises and into charming, authentic Southern Italian towns. We'll explore Alberobello, Matera, Ostuni, Lecce, Bari and Polignano a Mare.

We'll visit dramatic sea caves by boat, meet with a cheesemaker for a burrata and mozzarella making presentations, take a walking tour of Puglia's prosperous seaside capital Bari, make fresh pasta and focaccia, tour an olive oil estate, and so much more!

Our small group will enjoy private, premium masseria accommodations. Bring a friend to share a room or make some new friends along the way. 

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!

2024 Secret Spain: Discover Andalusia

October 19 - 26, 2024 - only 2 rooms left!

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 winerywatch 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. 

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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!

Book any 2 trips and get $500 off!

Bring a friend - save $250 each!

2024 Made in Italy: Venice Christmas Edition

December 8 -15, 2024 - bring a friend & save $250 each!


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!

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!

2025 Foodie Adventure in Southern Italy, Puglia

Two departure dates:

May 3 - 10, 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.

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!

Plan ahead for our 2025 Group Trips!

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Meet Anna.

I’m the travel advisor you've been looking for. Let's make your vacation dreams come true.

If you’re on this page, you’re about to travel in a way you’ve never traveled before, and I’m so excited for you!


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 29 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 like you!