Luxury small group trips to Europe for couples
Embarking on a luxury couples’ tour through Europe is the ultimate adventure.
With a small group and a thoughtfully curated itinerary, every moment is designed to delight—whether it’s sipping wine under the Italian sun at sunset, or discovering hidden gems with expert local guides.
Traveling with a select group allows for meaningful experiences without the crowds, so that you can relax and truly immerse yourselves in the magic of Europe.
It’s not just a trip—it’s a shared journey of elegance, culture, discovery, connection, and unforgettable memories.
After years of creating unforgettable luxury adventures for women, we’re opening the door to something new: couples trips!
Travel with us to…
Luxury couples trips
to the world's most exciting destinations
Luxury Couples Trip: Foodie Adventure in Puglia, Italy
April 27 - May 4, 2026
Close your eyes and imagine the golden glow of an Italian sunset lighting up the sky in fiery shades of orange and pink...
You and your partner are wrapped in luxury, glasses of rich, velvety wine in hand, as laughter echoes and the magic of the moment sinks in.
Forget the usual tourist trail—this adventure takes you deep into the heart of Southern Italy, where every cobblestone street, every bite of handmade pasta, and every hidden piazza tells a story.
Wander through the fairytale trulli homes of Alberobello, explore the ancient cave city of Matera, and get lost in the beauty of Ostuni. Feel the passion of Lecce’s baroque flair, dive into the dramatic cliffside charm of Polignano a Mare, and soak up the seaside vibrancy of Bari.
This is not just a getaway—it’s an unforgettable journey of discovery, connection, and romance that stays with you long after you return home.
Trip Highlights
7-day adventure with an English-speaking, professional tour leader, accommodations, meals, and activities
Savor the sights, sounds, and flavors of Italy amidst the warm hospitality of its people
Sightseeing, wine tasting, visit an olive oil estate, hands-on focaccia and pasta cooking class, and more!
Bring another couple and save $500 each!
Luxury Couples Trip: Scotland’s Hidden Treasures
June 7 - 14, 2026
Wander ancient castles. Toast with whisky by candlelight. This is not a vacation, it’s a chapter in your love story.
Only 7 couples will join us on this once-in-a-lifetime small group journey. Every detail is curated for romance, discovery, and delight. Just you, your person, and an authentic Scottish experience that's steeped in tradition, history, and folklore.
The dramatic landscapes of the Highlands set the stage for castle tours, cozy evenings by the fire, and scenic journeys through lochs and glens.
The stones are calling, the cobblestone streets, castles and villages are awaiting your arrival, and the whisky is ready to be poured!
Trip Highlights
7-day adventure with an English-speaking, professional guide, accommodations, meals, and activities
Savor the sights, sounds, and flavors of Scotland amidst the warm hospitality of its people
Sightseeing, whisky tasting, a special sheepdog experience, Royal Yacht Britannia, and more!
Our 2026 trips
at a glance:
Bestseller! April 27- May 4 | Puglia, Italy
NEW! June 7-14 | Scotland
NEW! July 18-25 | Food Valley, Italy
NEW! October 18-25 | Andalusia, Spain
What it’s like to travel with us:
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!