Scotland
Hiking the Fife Coast and Shetland Island
September 13 - 21, 2025
Embark on an unforgettable journey through Scotland with our "Hiking the Fife Coast and Shetland Island" tour. Immerse yourself in Scotland's rugged coastline's breathtaking beauty and rich history. Wander through quaint seaside villages, stroll along pristine sandy beaches, and discover the storied past hidden within charming old harbors and ancient buildings. Your adventure starts with a full day of exploring the vibrant city of Edinburgh, where medieval and modern worlds seamlessly blend. Join us for a week of stunning landscapes, cultural treasures, and exhilarating hikes.
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September 13 - Arrive Edinburgh
Upon arriving in Edinburgh, the air is filled with a mix of excitement and the rich history of the city. Meeting up with our group leaders at the Edinburgh Airport (EDI), we quickly gather our belongings and make our way to the awaiting transport. The drive through the scenic outskirts of Edinburgh offers glimpses of rolling hills and historic landmarks, setting the stage for our upcoming adventure. Our destination is the magnificent Dalhousie Castle Hotel, a grand and storied fortress just outside the city limits. For the next two nights, this 13th-century castle, steeped in history and luxury, will be our home as we explore the enchanting charm of Edinburgh.
Dalhousie Castle Hotel
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September 14 - Edinburgh
Kick off your adventure with a full day of exploring Edinburgh, Scotland's vibrant capital. Begin your journey by wandering the cobbled streets of the historic Old Town, where you'll encounter iconic landmarks such as the majestic Edinburgh Castle and the Royal Mile, brimming with centuries-old architecture and intriguing tales. Delve into the city's rich literary history at the Writers' Museum and enjoy panoramic views from Arthur's Seat, an ancient volcano. Savor traditional Scottish cuisine in one of the many charming pubs and restaurants. This captivating day sets the stage for the unforgettable hikes along the Fife Coast and Shetland Island that await.
Dalhousie Castle Hotel
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September 15 - St. Andrews & The Fife Coast
This morning, we will transfer to Anstruther for a three-night stay at The Bank Hotel. On our way to our hotel, we will stop in St. Andrews and take a guided tour of the birthplace of golf.
Each day will be filled with breathtaking walks and exploration, and each evening, we will return to the comfort of The Bank Hotel to rest and recharge for the adventures that await us.
Dinner is available at The Bank Hotel with a reservation each night, or you can explore the town and choose your own restaurant.
The Bank
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September 16 - Lower Largo to St Monans
Join us for an easy and well-marked 8-mile walk along the stunning East Neuk in Fife. Starting in Lower Largo, the birthplace of Alexander Selkirk, the inspiration for Robinson Crusoe, this walk offers a glimpse into the area's rich maritime history.
We’ll begin by traversing shingle beaches and dunes leading to scenic Largo Bay. The path then takes us to the rugged headland of Kincraig Point, offering spectacular views of the wide Forth and distant Lothian. For the adventurous, there's an optional Chain Walk, reminiscent of the Alpine via Ferrata, running along the base of the cliffs for nearly 2 miles. Our route, however, continues up to Kincraig Hill.
Descending to the shore, we'll follow a beautiful sandy bay to reach Earlsferry and its neighbor, Elie. From here, we’ll cross the neck of Elie Ness and stroll along unspoiled shorelines, passing the remains of Ardross Castle and Newark Castle. Our journey ends in the charming former fishing village of St Monans.
This walk is the perfect introduction to the natural beauty and historical charm of East Neuk in Fife, with an option to shorten the walk at Elie if needed.
Total of 8 miles.
The Bank
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September 17 - St Monans to Crail
Embark on an easy-to-follow coastal walk from St Monans to Crail, covering 7-8 miles of scenic beauty. This path features convenient bail-out points at Pittenweem and Anstruther.
Our journey begins in St Monans, leading us along grassy coastal paths that link four renowned villages, each with picturesque waterfronts and solid East Neuk architecture. Leaving the town, we soon encounter a restored windmill, which in the 18th century pumped water for the salt pans.
Continuing along the coast, we reach the charming village of Pittenweem, known for its small fishing boats and grand historic buildings. From there, we head east to Anstruther, winding through some 16th-century buildings before descending a narrow wynd to the sea and regaining the coastal path.
Our route takes us past deeply sculpted sandstone stacks and the historic Caiplie Caves, where St. Aidan met his end at the hands of Vikings in the late 800s. The final stretch leads us over a low headland and into Crail, considered one of the finest historic villages in the country.
This walk offers a delightful mix of natural beauty, historical intrigue, and charming village scenes, perfect for anyone exploring the East Neuk of Fife.
Tonight we will enjoy a group dinner in Anstruther at an award-winning fish and chips restaurant, The Wee Chippy.
Total of 7-8 miles.
The Bank
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September 18 - Crail to Kingsbarns/Boarhills & Ferry to Shetland
Leave the bustling village of Crail and its sprawling caravan park behind as we venture into the serene Kilminning Coast Wildlife Reserve. Our path winds around the peninsula of Fife Ness, jutting into the North Sea, offering stunning coastal views.
We head northwest past rocky lagoons to the legendary Constantine’s Cave, where a Scottish king is said to have been killed by Viking raiders in 870 AD. The route then takes us up and down the high sandstone cliffs of Randerston Castle, across a rocky foreshore, and over a footbridge to reach the beautiful Cambo Sands. Here, we'll follow the sandy shore until we arrive at Kingsbarns, marking the end of this picturesque walk.
Total 6 miles.
This afternoon, we will take a plane to the Shetland Islands. We will take a walk from the hotel on the south coast of Shetland.
Sumburgh Hotel.
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September 19 - Shetland Island Walk
Experience the raw beauty of Shetland Island with a walk that takes you through some of Scotland's most dramatic landscapes. Traverse rugged cliffs that drop into the turbulent North Sea offer breathtaking views and the chance to spot a variety of seabirds, including puffins and gannets. Wander through serene coastal meadows dotted with wildflowers and discover secluded beaches where your only footprints are yours. Along the way, you'll encounter remnants of ancient settlements, providing a glimpse into the island's rich history. This hike encapsulates the untamed spirit of Shetland, making it a highlight of your journey.
Sumburgh Hotel.
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September 20 - Shetland Island & Back to Edinburgh
We have an early morning departure by plane to return to Edinburgh. Returning to Edinburgh for a solo day, especially before our final night, offers a chance to savor the city’s charm at your own pace.
As the morning slips into the afternoon, you might climb Calton Hill for panoramic views of the city, the Firth of Forth, and Arthur’s Seat. With the city sprawling beneath you, the moment feels reflective, the perfect way to soak in Edinburgh’s layers of history and beauty. You could settle into a pub near Grassmarket or Victoria Street for lunch—places buzzing with locals and visitors.
Afterward, you may want to visit the Scottish National Gallery or explore one of Edinburgh’s hidden gems, such as the peaceful Dean Village, away from the hustle and bustle. If the weather is fine, walking along the Water of Leith or wandering through the Princes Street Gardens could be a serene way to pass the time.
Our final night will be at Courtyard Edinburgh West, near the airport, for early morning departures.
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September 21 - Departures from Edinburgh
Today marks the farewell to our group of travelers. Please arrange to schedule your departure flight from Edinburgh for your journey back home.
The provided itinerary and hotel arrangements are subject to change. While we strive to ensure the accuracy and availability of the listed accommodations and activities, unforeseen circumstances or events beyond our control may necessitate adjustments to the schedule. Rest assured, any modifications will be made with the utmost consideration for the comfort and enjoyment of our guests. We will do our best to communicate any changes promptly and provide suitable alternatives when needed. Flexibility is critical, and our team is dedicated to delivering an unforgettable travel experience, even in the face of unexpected changes. Your satisfaction and safety remain our top priorities throughout the journey. Thank you for being so understanding, and we look forward to creating beautiful memories together.
GOOD TO KNOW
GOOD TO KNOW
What’s Included?
Luxury hotel accommodations are in Edinburgh, Anstruther, Shetland, and near the airport. Tips for hotel staff are included.
Breakfast at the hotel is included each morning.
Guided hikes and packed lunches on trekking days
Private coach van transportation throughout the tour
Internal RT flights between Shetland/Edinburgh
Airport Transfers for guests arriving and departing on designated “arrival and departure” days
Dalhousie Castle Hotel
Just eight miles from Edinburgh but a million miles from the hustle and bustle of city life, our ancient fortress is the perfect spot to relax and unwind in blissful seclusion. Standing in eleven acres of private parkland and wooded valleys, it’s a place to make memories, to bring to life 800 years of history and to enjoy the best of Scottish hospitality.
The Bank
The Bank is situated in one of the finest locations in Anstruther, offering a stunning view where the Dreel Burn merges with the Firth of Forth. This picturesque setting provides a serene and captivating backdrop, with the tranquil waters meeting the rugged coastline, creating a perfect blend of natural beauty and peaceful ambiance. The hotel's vantage point allows guests to take in the breathtaking scenery, making it an ideal spot for relaxing and enjoying the surrounding landscape.
Sumburgh Hotel
Built in 1867, this former laird’s home offers accommodation in an ideal location in the South Mainland of Shetland. This privately owned and run hotel is perfect for business and pleasure, with the airport only 5 minutes away and abundant local attractions in the surrounding area.
Olive Group Travel partners exclusively with Team Long Run (www.teamlongrun.org), a Maine-based 501 (c)(3) nonprofit that helps kids from challenging circumstances improve their futures through literacy and active play. We provide adventure travel opportunities that range from hiking remote glaciers in Iceland to strolling through the Latin Quarter in Paris. The trips are original, fun, safe, affordable, and memorable. We keep our groups small; half the fun is making life-long friends as we see the world. We offer a variety of destinations and itineraries, so please take a look and find the one that’s just right for you! As always, every penny from our profits goes toward Team Long Run’s programming, so this truly is “Philanthropic Travel.”