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.
Meet your host: Anna
Hi - I’m Anna Fishman, the proud mastermind behind Olegana Travel Boutique, your go-to hub for unforgettable journeys.
I am hosting this trip myself, which means I will be there for all ten days, from the welcome meeting in Scotland to the farewell dinner in Windsor.
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!
What’s included in your experience of a lifetime
-
Accommodations
9 nights/10 days in 4+ star hotels
Your own room every night, with no single supplement
-
Tours & Activities
Private guide, driver and tour leader for the duration of the trip
Entry fees for all activities listed per Itinerary
-
Food & Beverages
9 breakfasts, 4 lunches, and 6 dinners
-
Transportation
Private coach and driver throughout, including all transfers between regions and to and from every activity
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 would it feel on the flight home, knowing you finally took the trip you have been putting off, and made a few friends along the way?
P.S. This date doesn’t work for you? Check out our other women-only trips here.
Spring 2027
⋆
Spring 2027 ⋆
11 of 16 spots remain
What your trip costs
ONLY $500 to secure your spot
That is roughly $1,200 a day, and it covers nearly everything: nine nights in 4-star-plus hotels, twenty-two meals, a private guide and driver for the full ten days, and every entry fee on the itinerary, including the private Poison Garden tour at Alnwick, the Treehouse lunch, Highclere, Windsor Castle and Hampton Court.
Your own room is included, not an extra. Most group trips charge a single supplement of two thousand dollars or more. Here you have your own space every night, and it is already in the price.
$11,995 USD
($16,895 CAD)
Per Person
Single Occupancy
Book more than one trip and save $500!
Bring a friend and save $250!
September 30 2026 - second payment of $3,995 is due
January 15, 2027 - 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
Ten days through the castles and gardens of Britain, from the Scottish Borders to Windsor.
Day 1 (May 13 )
We begin in the Scottish Borders
We start in a hotel with grounds you will want to walk before you have even unpacked. Over lunch you meet the women you are about to spend ten days with, which is always the moment a trip becomes real. In the afternoon, we visit a working textile mill in Selkirk, where tartan and tweed have been made for centuries and the people who make it will tell you why it still matters.
Scottish cocktails before dinner, and then an early night, because you have earned it.
Day 2
Walter Scott's house and tea in a queen's garden
Sir Walter Scott built Abbotsford for himself above the Tweed, and it is the kind of house that tells you everything about the man who lived in it. Then Floors Castle, the largest inhabited house in Scotland, where we take a traditional Scottish afternoon tea in the Queen's House in the walled garden. Queen Victoria took tea in that same room in 1867.
Afterwards the castle is ours to tour privately, and dinner is back at the hotel.
Day 3
Across the border, and the Northumberland coast
We cross into England and the coastline opens up. Bamburgh Castle sits above one of the great beaches of Britain, and its walled garden is the sort of place you linger in longer than you planned. Lunch is seafood in Craster, a village that has been oak-smoking kippers and salmon for generations, and if the weather holds there is a thirty-five minute walk along the cliffs to the ruins of Dunstanburgh. We finish in Alnwick, where we stay two nights.
Day 4
A garden that can kill you, and a castle you already know
The Alnwick Garden is one of the most ambitious gardens built in Britain in the last century, and the Poison Garden inside it holds more than a hundred plants that could do you real harm. We tour it privately, before the gates open to everyone else. Lunch is in the Treehouse, genuinely up in the trees, on furniture someone made by hand. Then Alnwick Castle, which you will recognize as Hogwarts, and which was Downton Abbey before Highclere was. The evening is yours to spend in town.
Day 5
South to the Cotswolds
We drive south through England with a stop for lunch somewhere worth stopping, and arrive in Broadway in the late afternoon with time to settle in and do nothing for a while.
Dinner is at the hotel, from a menu created by the British chef James Martin, and after a day of watching the country change through a window it is exactly what you want.
Day 6
Cotswold villages, Shakespeare, and dinner under the trees
Broadway Tower first, then Snowshill and Chipping Campden, two villages that look the way people imagine the Cotswolds and rarely find. Lunch is on the rooftop at the Royal Shakespeare Theatre over the Avon, followed by a tour behind the scenes into the costume and set workshops. Then Stratford itself on foot, with a guide who knows which of the stories are true. In the evening we drive ten minutes to an open-air deck on the Farncombe Estate and eat looking out over the forest.
Day 7
Hidcote, Highclere, and on to Windsor
Hidcote in the morning, which is a garden made of rooms, each one hidden from the last until you walk through the hedge into it. It changed how the twentieth century thought about gardens. Lunch is at a country pub in the unspoilt village of Ilmington, and then we leave the Cotswolds behind and drive to Highclere, where the Carnarvon family has lived for three hundred years and where Downton Abbey was filmed. We reach Windsor with time to settle in, and the evening is your own.
Day 8
Windsor Castle, and an afternoon to yourself
Windsor Castle in the morning, the oldest and largest occupied castle in the world and a royal residence for nearly a thousand years, taking in St George's Chapel and the State Apartments. Then the afternoon is genuinely free.
Wander the town, walk the Long Walk, or sit in the hotel and do nothing at all, which by day eight is a perfectly good choice.
We come back together for dinner.
Day 9
Hampton Court, and the last dinner
Hampton Court was Henry VIII's palace on the river, and sixty acres of it are garden. The Privy Garden, the maze that has been confusing people for three hundred years, and the Great Vine, planted in 1768 and still producing grapes. Lunch on the grounds at your own pace, then back to Windsor for cocktails and our last dinner together.
Day 10 (May 22)
You fly home whenever suits you. Heathrow is twenty minutes from Windsor
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
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 Castleand its enchanting Walled Garden, perched above a breathtaking coastline
Wander the 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
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 visit to Hidcote Manor Garden, a series of hedged garden rooms laid out in the early twentieth century and among the most copied gardens in the world. Mid-May is one of its finest weeks
Broadway Tower, Snowshill and Chipping Campden, three of the most unspoilt corners of the Cotswolds, followed by a private open-air barbecue on the Farncombe Estate
Stratford upon Avon and travel east through Oxfordshire and Berkshire to Windsor
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
Continue to Windsor and settle in, with the evening free
Windsor and Hampton Court
A morning at Windsor Castle, a royal residence for nearly a thousand years, taking in St George's Chapel and the State Apartments, followed by time to wander the town and the Long Walk at your own pace
A full day at Hampton Court Palace, Henry VIII's riverside palace, with sixty acres of gardens including the Privy Garden, the maze, and the Great Vine, planted in 1768 and still producing fruit
A farewell dinner in Windsor, a fitting close to a journey through Britain's finest castles and gardens
"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."
— Zaira C., past Olegana Castles and Gardens UK guest
You Might Be Wondering…
Read through our frequently asked questions.
-
Yes, only women (she/her) are welcome to join.
-
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
-
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.
-
A reasonable level of fitness. There are uneven streets, stairs, long touring days, standing during guided visits, and the need to keep pace with the group.
Expect 10,000 or more steps a day on cobblestones, hilly paths, stairs with no railings, and all the charming, ancient terrain.
If any day sounds like too much, you are welcome to enjoy a day at the hotel instead. The itinerary balances guided experiences with free time on purpose.
-
The group meets at the hotel in Scotland on May 13, 2027. You book your own flights into Edinburgh, and I am glad to help you find the best options.
Many travelers add a night or two in Edinburgh beforehand to arrive rested, and some stay on afterwards in London, which is forty minutes from where we finish in Windsor. I build both as private extensions, priced separately and shaped around what you want to see. Just mention it on our call.
-
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.
-
Guide and driver pre-paid gratuities of $500 per person will be collected approximately a week before the trip starts.
-
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.
-
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.
-
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
Arriving early or staying on?
Most travellers fly overnight into Edinburgh, and a night or two there before we begin is the easiest way to arrive rested rather than running on airport coffee. The Old Town, the castle, a good dinner, and a proper sleep before the group meets.
At the other end, we finish in Windsor, twenty minutes from Heathrow and forty from central London. The Chelsea Flower Show runs the same week we finish, and London itself needs no argument.
I can build either extension privately, shaped around what you actually want to see. Mention it on our call and we will plan it together.
Meet Anna
Anna Fishman is the founder of Olegana Travel Boutique, a luxury travel company specializing in bespoke European itineraries and women-only small group journeys.
With 33 countries explored and years spent building relationships with the finest local guides, chefs, and hoteliers across Europe, Anna designs travel experiences that feel personal, seamless, and impossible to replicate on your own. Her Puglia journeys have become a signature, with multiple departures selling out each year.
She lives in New Jersey, with her family and she cannot wait to welcome you on your next journey.