May 13 - 22, 2027
Spring 2027: Castles & Gardens, UK
Castles and gardens await…
Close your eyes and picture the soft mist rising over ancient stone castles, their towers silhouetted against the dawn. You're wandering through manicured gardens, the scent of blooming roses in the air, with history whispering from every ivy-covered wall.
This journey is more than just scenic beauty—it's a step back in time, guiding you away from crowded cities and into the heart of the UK's storied past, its history and timeless elegance.
Spring 2027
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Spring 2027 ⋆
9 of 12 spots remain
Make Your Dream Come True
ONLY $500 deposit to secure your spot
$11,995 USD
($16,895 CAD)
Per Person
Single Occupancy
Book more than one trip and save $500!
Bring a friend and save $250!
July 21, 2026 - $3,995 payment is due
October 1, 2026 - the final balance is due
Here’s what it’s like to travel with us:
"Just finished my second trip with Olegana, it was even more amazing than the first! Two weeks of luxurious accommodations, fabulous local food, great conversations, and a wide variety of sites and activities each day! If you want a stress-free trip (or two...) of a lifetime, I cannot recommend Anna and her team highly enough!"
— Cindy B., past Olegana Scotland and UK guest
The Trip at a Glance
Day 1 (May 13 )
Welcome!
• Morning arrival to Scotland (Edinburgh or Glasgow)
• 2pm - Welcome meeting
• Floors Castle and Gardens - the largest inhabited house in Scotland
• 7pm - Scottish cocktails at the hotel
Day 2
Exploring the historic Scottish Borders
• Scottish breakfast at hotel
• 9:30am - departure
• Abbotsford House & Gardens – home of Sir Walter Scott
• Scottish Textiles Mill Experience
• Return to your hotel for the rest of the day. Optional walking in the grounds or relax at the pool and spa
• 7pm - Drinks & group dinner
Day 3
Castles of the Northumberland Coast
• 9:30am - Depart with private coach and guide to travel across the border into England
• Bamburgh Castle and walled garden
• Light lunch in a local farm shop or café/restaurant
• 3pm - Craster and salmon smokehouse tasting experience
• 5:30pm - early evening meal at a local waterside inn
• Return to the hotel for an evening at leisure
Day 4
Alnwick Castle & Gardens
• Scottish breakfast at hotel
• Enjoy a morning visit to the unique Alnwick Garden with a private tour
• Special lunch in The Treehouse Restaurant
• 3pm - Enjoy a private History and Hollywood guided tour of Alnwick Castle
• 7:30pm - return to the hotel for dinner at leisure (not included)
Day 5
Northumberland to the Cotswolds
• 9:30am - after breakfast the group will board a train to Cheltenham Spa (first class rail tickets included)
• Visit Bourton-On-The-Water Model Village located in the real village of Burton-On-The-Water in the Cotswolds
• Enjoy a scenic drive through these beautiful heritage villages
• 7pm - a special group private dining experience at the hotel
Day 6
The Cotswolds and Shakespeare’s Globe Theatre
• Breakfast at the hotel
• 9:45am - Possible morning visit to local lavender and wildflower fields (subject to annual opening times)
• 11am - 1:00pm - A guided walking tour of Stratford upon Avon
• Enjoy an afternoon performance at the world famous Royal Shakespeare Theatre
• An early evening meal at leisure in Stratford Upon Avon (not included)
Day 7
The villages of the Cotswolds and Blenheim Palace
• Breakfast at the hotel
• 10:30am - 2:30pm - Private guided tour of the spectacular Blenheim Palace and Gardens, birthplace of Sir Winston Churchill
• Enjoy lunch at leisure (not included) in one of the café / restaurant options at Blenheim
• 3:30pm - 5:30pm Cotswolds Gin Distillery Experience
• 7pm - group dinner at the hotel
Day 8
Exploring Highclere and on to London
• 9am - departure
• Highclere Castle - one of the finest Victorian mansions in the United Kingdom, also the fictional seat of Lord Grantham of Downtown Abbey
• Transfer to London by private transport
• 7pm - Optional drinks followed by a meal at the hotel restaurant, or guests may wish to head out at leisure to enjoy a local restaurant (not included).
• Evening at leisure
Day 9
The Chelsea Flower Show Experience
• 9:00am - depart after breakfast
• Enjoy a full day at leisure exploring the world famous Chelsea Flower Show.
• 4pm - private group transfer back to hotel
• 5:30pm - 9:00pm - cocktails and farewell group dinner
• Return to the hotel
Day 10 (May 22)
Departure day - any time
An In-Depth Look at Your Trip
Explore the historic Scottish Borders & the Northumberland Coast
Private guided tour of Floors Castle and its spectacular gardens, the largest inhabited house in Scotland, and every bit as grand as that sounds
Step inside Abbotsford House, the private home of 19th-century novelist Sir Walter Scott, and wander its extraordinary Baronial architecture and beautifully composed Regency gardens
A private mill tour revealing the heritage, artistry, and enduring global prestige of Scottish tartans and tweeds, a craft that has never gone out of style
Explore the dramatic Bamburgh Castle and its enchanting Walled Garden, perched above a breathtaking coastline
Wander the charming harborside village of Craster, famous for its centuries-old tradition of oak-smoking kippers & salmon
Explore Alnwick Castle and Gardens
A private morning tour of the extraordinary Alnwick Garden, including the infamous Poison Garden, the Serpent Garden, the Rose Garden, a bamboo labyrinth, and the magnificent Grand Cascade
Lunch in The Treehouse Restaurant at Alnwick Garden — a dining experience as unique and memorable as the setting itself
A private History & Hollywood guided tour of Alnwick Castle — the inspiration and filming location for Hogwarts in the Harry Potter series, and also featured in Downton Abbey and Robin Hood: Prince of Thieves
Explore the Cotswolds
Visit the delightful Bourton-on-the-Water Model Village, nestled within the real village it so charmingly replicates
A scenic drive through some of England’s most treasured heritage villages, the kind of countryside that makes you want to slow down and stay
A possible visit to local lavender & wildflower fields (subject to seasonal opening), a quietly magical moment that stays with you
A private behind-the-scenes tour of Blenheim Palace and Gardens, birthplace of Sir Winston Churchill, a UNESCO World Heritage Site, and the backdrop for Bridgerton, Cinderella, Harry Potter, Queen Charlotte, and James Bond
Tour and tasting at a beautiful rural gin micro-distillery
Stratford upon Avon and travel east through Oxfordshire and Berkshire to London
A guided walking tour of Stratford-upon-Avon, uncovering the architecture, history, and enduring legacy of William Shakespeare in the town where it all began
An afternoon performance at the world-renowned Royal Shakespeare Theatre (subject to schedule) - theatre as it was always meant to be experienced
Visit Highclere Castle, one of Britain’s finest Victorian mansions and home to the Carnarvon family for over 300 years and beloved worldwide as the setting for Downton Abbey
Arrive in London and enjoy free time to settle in and explore at your own pace
The Chelsea Flower Show Experience
A full day at the world-famous Chelsea Flower Show for the most fitting finale imaginable for a journey through Britain’s most spectacular castles and gardens
Wander extraordinary garden installations, breathtaking floral displays, and exceptional shopping and dining at your leisure
A celebratory farewell dinner in London — the perfect close to an unforgettable journey
"If you can imagine beginning each day exploring historical castles, strolling through luscious gardens, and tasting delicious specially prepared meals in magical towns, you'll love the Castles and Gardens trip. Thank you Anna and Jane."
— Zaira C., past Olegana Castles and Gardens UK guest
Meet your host: Jane and her trusted team
While Anna leads many Olegana trips personally, the ones she does not are entrusted to a partner she has worked with closely for years. On both of our 2027 Britain trips, that partner is Jane.
Originally from Perthshire, Jane has spent more than thirty years exploring Scotland's Highlands, islands, and west coast, and she knows where every back road leads.
She has spent the last decade hosting luxury small-group trips through Britain. The relationships she has built across the country, with the gardeners at National Trust properties, the stewards at the castles, the chefs at the country hotels and Highland inns, are why she is the right partner for these journeys.
Jane works with a small, hand-picked team of local hosts and guides who share her standards. Together they look after every detail on the ground, from the moment you arrive to the moment you leave: the timing, the dietary needs, the surprises that should stay surprises, the small things you do not want to think about.
That is the boutique difference. You are not a name on a manifest. You are a guest.
What’s included in your experience of a lifetime
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Accommodations
9 nights/10 days 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
10 breakfasts, 4 lunches, and 6 dinners
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Transportation
Private group motorcoach/bus transportation to/from all activities unless stated otherwise
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 May 12, 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 $500 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.
"What a great company! Olegana travel will make your experience a magical one, will immerse you in spectacular settings with spectacular sights and a wonderful group of ladies who will definitely become your friends for life."
— Lucia A., past Olegana Castles and Gardens UK guest
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!