June 7- 14, 2027
Summer 2027:
Hidden Scotland
Explore Scotland’s Hidden Treasures
A soul-stirring journey through wild beauty, ancient history, and the magic of the Highlands
Some places don't just capture your attention — they capture your heart. Scotland is one of them. Dramatic landscapes that seem to exist outside of time. Castle ruins that whisper centuries of stories. A culture so deeply rooted in tradition and folklore that you feel it long after you've returned home.
This intentional, immersive journey takes you beyond the obvious and into hidden glens, storied estates, and breathtaking Highland scenery that Outlander fans will recognize as pure magic. But you don't need to be a fan to fall completely in love with Scotland.
Make Your Dream Come True
ONLY $500 deposit to secure your spot
Early Bird pricing - through March 1, 2026!
$10,995 USD
($15,295 CAD)
Per Person
Single Occupancy
Book more than one trip and save $500!
Bring a friend and save $250!
March 1, 2026 - $3,995 payment is due
September 1, 2026 - the final balance is due
Here’s what it’s like to travel with us:
The Trip at a Glance
Day 1 (June 7 )
Welcome!
• Morning arrival to Scotland (Edinburgh or Glasgow)
• 2:30pm - Welcome meeting
• Private Walking Tour of the Royal Mile with a guide, followed by a 2-hr Outlander walking tour and historical Old Town orientation
• Evening at leisure
Day 2
Exploring Edinburgh Castle & the historic Forth Valley
• Scottish breakfast at hotel
• 8:15am - departure
• Private Tour at Edinburgh Castle (pre-opening tour) - 1-hr private tour at Edinburgh Castle followed by free time
• Day tour of Forth Valley - visits to Midhope Castle, Blackness Castle, guided walking tour of Culross
• Two course private lunch
• 6pm - Scottish welcome group dinner
• Return to the hotel
Day 3
Exploring Falkland & Highland Perthshire
• Depart with private coach
• Morning walking tour of Falkland
• Private lunch and wine tasting
• Optional guided walk at The Hermitage near Dunkeld (beautiful walk in this historic woodland and gorge) or time to browse local independent shops
• Scottish Chocolate Tasting Experience
• Return to the hotel
• 7:30 pm - 3-course group dinner
Day 4
Exploring the Highlands and Inverness
• Scottish breakfast at hotel
• Journey north through Highland Perthshire and the Cairngorms
• Private whisky distillery tour & tasting
• Gourmet picnic style lunch
• Visit to Clava Cairns
• Working sheepdog experience
• 7:30pm - a group dinner and evening at leisure
Day 5
Exploring Strathspey and Culloden
• 9:00am - after breakfast the group will board a train for a morning journey on the historic Strathspey Railway with tea/coffee/shortbread served
• Visit to the historic Culloden Battlefield
• Enjoy a champagne afternoon tea
• Rest of evening at leisure to enjoy Inverness or relax at hotel and spa facilities
Day 6
Exploring Loch Ness and Glencoe
• Breakfast at the hotel
• Visit to Urquhart Castle and Loch Ness
• Two course private lunch
• Visit Glencoe (Visitor Centre & free time)
• Onward journey through the Highlands and the Loch Lomond and Trossachs National Park to reach Edinburgh
• Enjoy an evening at leisure
Day 7
Exploring Perthshire
• Breakfast at the hotel
• Visit to Doune Castle
• Visit to Drummond Castle Gardens
• Enjoy buffet lunch
• Visit to Tibbermore Church
• Private guided tour of the historic Royal Yacht Britannia with a glass of champagne and farewell group meal
• Return to the hotel
Day 8 (June 14)
Departure day - any time
Optional extension options may be available - please reach out directly
An In-Depth Look at Your Trip
Exploring Edinburgh & the historic Forth Valley
Arrive in Edinburgh and settle into your hotel in one of Europe’s most captivating cities, where ancient history meets vibrant, modern energy
Explore the iconic Royal Mile, historic Old Town, and experience the city’s cinematic charm on an exclusive 2-hour Outlander walking tour
Private tour of Edinburgh Castle for an intimate glimpse into Scotland’s royal heritage, followed by unhurried time to explore at your own pace
Discover the real-life Outlander landscapes of the Forth Valley — Midhope Castle, Blackness Castle, and a guided walking tour through the beautifully preserved village of Culross
Savor a traditional Scottish dinner and experience the warm, genuine hospitality this country is known for
Exploring Falkland & Highland Perthshire
Wander through the enchanting village of Falkland on a guided walking tour — a perfectly preserved time capsule that evokes the world of 1940s Inverness
Linger over a beautifully crafted lunch with wine tasting, where Scottish flavors meet global sophistication at the table
Choose your afternoon: a tranquil guided walk through The Hermitage near Dunkeld, or unhurried time exploring the charming local independent shops
Indulge in a private chocolate tasting experience with a Master Chocolatier - a decadent journey into the artistry and craft behind Scotland’s finest confections
Exploring the Highlands and Inverness
Step inside the world of Scotland’s most iconic spirit on a private distillery tour and whisky tasting, a sensory experience rooted in centuries of tradition
Enjoy a beautifully curated gourmet picnic lunch amid the sweeping scenery of the Highlands - because the best tables sometimes have no roof
Visit the mystical Clava Cairns — an ancient site believed to have inspired the legendary stones of Craigh na Dun
Experience the remarkable bond between a shepherd and their dog on a private working sheepdog demonstration at a local farm, quietly one of the most memorable moments of the journey
Exploring Strathspey and Culloden
Board the historic Strathspey Railway for a scenic journey through the breathtaking Spey Valley, a ride that feels like stepping gently back in time
Walk the moor at Culloden Battlefield, a deeply moving and powerful site that marks one of the most pivotal moments in Scottish history
Pause for a Champagne Afternoon Tea, a moment of pure elegance after a day of profound discovery
Spend your evening at leisure: explore the charming city of Inverness or unwind at the hotel spa — the choice is entirely yours!
Exploring Loch Ness and Glencoe
Visit the majestic Urquhart Castle, perched dramatically above the legendary Loch Ness, to soak in the sweeping views
Stand in awe at Glencoe, a glen of staggering beauty and profound history, with time to explore the Visitor Centre and have some free time to explore
Journey through the Highlands and the Loch Lomond & Trossachs National Park on a final, breathtaking sweep of Scotland’s wild, untamed landscape
Exploring Perthshire
Explore Doune Castle, a magnificent medieval fortress overlooking the River Teith, known to Outlander fans as Castle Leoch and to others as Winterfell
Stroll through the extraordinary Drummond Castle Gardens, a Renaissance masterpiece widely considered one of the finest formal gardens in Europe
Step into Tibbermore Church, a historic location that appears on screen in the Outlander series
Raise a glass aboard the Royal Yacht Britannia on a private guided tour, an intimate glimpse into the private lives of the Royal Family, followed by a truly royal farewell dinner for your group
What’s Included in Your Experience of a Lifetime
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Accommodations
7 nights in 4+ star hotels
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Tours & Activities
Private guide, driver and tour leader for the duration of the trip
Entry fees for all activities listed per Itinerary
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Food & Beverages
6 breakfasts, 6 lunches, and 4 dinners
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Transportation
Private group motorcoach/bus transportation to/from all activities unless stated otherwise
What Guests Said About Past Trips…
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“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 trip unique & wonderful.
The group of women brought together by Anna made the trip fantastic! Thank you for a memorable trip!"
- MJ
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“I can't say enough about Anna and Olegana Travel
Boutique!!! What an awesome trip first off, and the ladies I met OMG!!!She helped me plan an AMAZING and PERFECT itinerary.
This will not be my last trip with this Boutique.”
- Lucia
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“I went on the incredible Spain trip in the fall of 2023 and I was very impressed with the high quality of the tours, the guides and the accommodations.
Anna did a great job, and I wouldn’t hesitate to book another tour with her company."
- Lin
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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All activities, food and beverages not listed under the itinerary
All items of a personal nature and anything not expressly stated as included
Airfare to/from your arrival city and departure city
Airport transfers in your departure city
Airport arrival and departure transfers - can be arranged at extra cost
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Insurance is strongly recommended. We can offer travel insurance for American travelers. Please let us know if you would like a quote for your travel insurance policy.
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Yes, a decent level of fitness is highly recommended. We’ll be walking a lot—think 10,000+ steps a day—often on uneven cobblestone streets, hilly paths, stairs with no railings, and all the charming, ancient terrain. You don’t need to be a triathlete, but comfortable walking for extended periods is key.
If that sounds like too much, you’re welcome to enjoy a relaxing day at the hotel instead. We want you to have a beautiful, comfortable experience at your own pace.
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The group will meet at the hotel in Scotland on June 7, 2027. Everyone will be responsible for purchasing their own plane tickets to get to Scotland. We are happy to help find the best airfare options and plan a trip extension before or after the group trip. The traveler will be responsible for any extra costs associated with that.
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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 out on exploring the gorgeous castles and gardens? That’s just tragic.
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Guide and driver pre-paid gratuities of $300 per person will be collected approximately a week before the trip starts.
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Every bite tells a story—and we want you to savor all of it. Meals on this trip are carefully chosen in advance to highlight the best of the local culinary traditions.
We partner with local chefs and trusted restaurants to create a delicious experience that reflects the region’s vibrant food culture.
We ask guests to come with an open mind—and an adventurous appetite. Dining in the UK doesn’t always include the staples you might expect back home (you may not see a salad or breadbasket at every table), but what you will find is thoughtful, balanced food made with care, history, and flavor in every bite.
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We will provide a packing list closer to travel dates with suggested attire and useful gadgets. The trip is very casual, so as long as you are comfortable, you will 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.
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 amazing would you feel on the return flight home, knowing that you seized the chance to have a once-in-a-lifetime, authentic European experience and met some new friends along the way?
P.S. This date doesn’t work for you? Check out our other women-only trips here.
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 31 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!