Follow us on:

Idyllic Islands of Scotland

  • Scotland

itinerary Map

Idyllic Islands of Scotland

7 Days

Unearth the hidden charms and legends of the ancient isles that surround Scotland. Discover the rugged and untouched landscapes of the Orkney Islands as well as the Outer and Inner Hebrides. Steeped in rich heritage and history, many of the landmarks on the islands are thousands of years old and remain beautifully preserved to this day in order to give visitors a chance to step through living history.

Perfect for those looking for peace and tranquillity, explore deserted beaches, and breath-taking, unspoilt scenery in this secluded corner of the world.



A Scottish Island Dream Escape programme could include any of the following unique experiences:

  • A private look behind-the-scenes of the most northerly of Scotland’s whisky distilleries. Sample the water of life and meet the people behind the casks in typically off-limits parts of the distillery.


  • Explore the Neolithic Orkney World Heritage Site that covers four remarkable and well-preserved monuments. Including a specially arranged twilight tour of Skara Brae, a site older than the Egyptian Pyramids or Stonehenge.


  • Visit the pure sand and crystal-clear waters that line the vast beaches of the Isle of Harris and experience the bracing sea air and uninterrupted views of the Atlantic Ocean.


  • Marvel at the awe-inspiring stones at Calanais, another famed prehistoric site. They date from around 3000 BC and, to this day, approximately 50 in total stand on a rise.


  • Discover the tales of a lost way of life on the Outer Hebrides at the Blackhouse Museum.


  • A tour of Lamb Holm, now uninhabited, but also home to the unique Italian Chapel constructed by prisoners of war during World War 2.


  • An island-hopping trip to St Kilda, one of only 24 global locations to be awarded ‘mixed’ World Heritage Status for both its natural and cultural significance.


  • Pick up a sample of hand-spun Harris Tweed, internationally recognised as one of the finest fabrics in the world and the perfect memento for your trip.


Our accommodation suggestions for this trip are two equally charming properties, one on Orkney and another on the Isle of Lewis.

Your first home for your trip is a luxury guest house full of period features that will allow you to immerse yourself in life on the Orkney Islands.

For the second part of your trip, stay in a stunning holiday-home with a difference. While being thoroughly modern, this building, based upon the traditional island houses, blends seamlessly into its surroundings complete with stunning ocean views through floor to ceiling windows.

Contact our Creative Planners Now








The Calanais stones, a spectacular Megalithic complex comprising around 50 stones.  At its heart stands a solitary monolith around 5m high. Dating from around 3000 BC, they are older than the pyramids of Egypt and are one of the most famous prehistoric sites in Scotland.


Visit Lamb Holm, a small island off Holm and the unique, Italian Chapel. Originally a set of huts, they were exquisitely transformed into what you see today by the same prisoners of war that built the barrier. Lovingly restored in 1960 by the artist Domenico Chiocchetti, who was responsible for the original design, it is a touching token of the triumph of the human spirit over adversity.


Take an exclusive and private tour at the most northerly of Scotland’s distilleries. Accompanied by a distillery guide, venture behind the scenes to typically off-limits parts of the distillery. Sample whisky straight from the cask, and meet the people behind the whisky. The experience concludes with a tutored tasting of four spectacular vintages – 1968, 1970, 1971 and 1976 – and a sample from an exclusive single cask bottling in front of a crackling fire.


Visit the home of the island’s most noted export, Harris Tweed. Before the Industrial Revolution, most of Scotland wove cloth from home; unlike the rest of Scotland, Harris has never lost the tradition. Harris Tweed can now be seen on the catwalks in various fashion capitals, be bought in the many of the islands shops and is recognised as the one of the world’s finest fabrics.



Spectacular Skara Brae, which lies near the dramatic white beach of the Bay of Skaill is about 5000 years old, it was inhabited before the Egyptian Pyramids and Stonehenge were built.


The Ring o’ Brodgar is part of the heart of Neolithic Orkney World Heritage Site. The stone ring was built in a perfect circle, 104 metres wide, and originally contained sixty megaliths. Today, only twenty-seven of these stones remain.



Abundantly rich in heritage, the Orkney Islands have been inhabited for over 5500 years. They are particularly known for traces of Viking legacies, remarkable Neolithic sites, haunting wartime remains, stunning listed buildings and some of the most breath-taking scenery, where the word “unspoilt” takes on a whole new meaning.


The Outer Hebrides also known as the Western Isles are an island chain off the west coast of mainland Scotland. They have been included in many publications as one of the Top 100 Places to Visit in the World.  In addition to having a captivating history with a rich sense of Gaelic tradition, they are noted for their stunning beauty; unspoilt white beaches, clear waters and a sublime coastline.  Lewis and Harris make up the largest island in Scotland.   They are joined by a small strip of land and are frequently referred to as if they were separate islands.


The Outer Hebrides also known as the Western Isles are an island chain off the west coast of mainland Scotland. They have been included in many publications as one of the Top 100 Places to Visit in the World.  In addition to having a captivating history with a rich sense of Gaelic tradition, they are noted for their stunning beauty; unspoilt white beaches, clear waters and a sublime coastline.  Lewis and Harris make up the largest island in Scotland.   They are joined by a small strip of land and are frequently referred to as if they were separate islands.


The archipelago of St Kilda is the remotest part of the British Isles and lies over 40 miles west of Benbecula, in Scotland’s Outer Hebrides. Its islands, with their exceptional cliffs and sea stacks, form the most important seabird-breeding station in north-western Europe. The earliest written records of island life date from the late Middle Ages. Since this time, the population has probably never exceeded 180. On 29 August 1930, the 36 remaining residents known as St Kildans, were evacuated at their own request from Hirta, the only inhabited island, to the Scottish mainland.

  • "Dream Escape, to no one’s surprise, is the best in the business. I cannot begin to thank you for crafting a perfect vacation for these clients. They had nothing but fabulous things to say about each and every event."

    Nancy Ebel, Virtuoso Travel Advisor

  • "Couldn’t have asked for a better 1st trip to London!......The sites we saw were the best & Sally, you went above & beyond to make it memorable"

    Shannon Marie Long - Reed and Mackay

  • "Delightful to spend time and see the incredible city of London with you all. Dream Escape for a flawless job in seeing the best bespoke sites, Sally you are amazing. Thank you again as this was amazing"

    Josh Whitaker - Owner, Rudi Steele Travel

  • "Probably the best of the best in the UK and Ireland for organising amazing trips. They know their stuff, have fantastic relationships with suppliers and always go the extra mile."

    Rob Arrow, Al Tayyar Group

  • "Lovely suite. Fabulous private tours. Everything has exceeded our expectations. "

    William A Heim, Client

  • "I had the most wonderful time with you and learned so much...What you offer is rare and much needed in the truly exclusive travel world. "

    Jean Newman-Glock, Signature Travel Network

  • "You were the heart and soul of the trip….I truly admired your sunny personality, sense of humor, organization and professionalism.  You also demonstrated  that a guide’s work is never done as you were constantly researching….. Did you ever rest??? "

    Sharon Delano, Frosch

  • "We want to thank you and the team from Dream Escape.  All six of us in our group had a wonderful time, and we all agreed we owed that in large measure to the work of Dream Escape. From the onset of working with you, you demonstrated a tremendous knowledge about all the activities we wished to pursue —from playing golf to dining at excellent restaurants to seeing historical sites and the Tattoo and Fringe Festival.  And, then you executed "

    Thomas Cohen, Client

  • "THANK YOU a zillion times over for choosing/assigning Rosie to be with this family.  She MADE the trip for them – there’s no other way to put it! "

    Jill Jergel, Frontiers International Travel

  • "Our holiday in Scotland now tops their lists of best trips…… To their growing list of amazing and memorable first-time experiences, our sons may add fishing for trout and salmon on the River Tay; steering a motor boat on Loch Ness; and taking private guided tours on Culloden Moor Of the eight full days we were in Scotland, Alex and Mattie thought each and every day was the best"

    Michael Guadarrama & Trammi Nguyen, clients of Peter Carideo. CRC Travel

  • "All six of us were deeply moved by the whole experience. Bravo Dream Escape "

    Max Levy, Direct client

  • "Thank you Karen and all of the staff and guides affiliated with Dream Escape…..the Flemings are having an awesome tour of Scotland. You all have made me look like a star! "

    Joni Gerace, The Travel Society, LLC

  • "Thanks for all your help and we can chalk this one up as a big success!   Our anniversary celebration was all we could have hoped for "

    Clients of Courtney Regan, Affiliate of Brownell Travel

  • "Rosie was MORE than outstanding – she went out of her way to help us in every regard...She was so knowledgeable – we all loved her"

    Jill A. Jergel, Frontiers International Travel

  • "I cannot thank you, Nicola and all the Dream Escape “clan” for the wonderful care & attention you have provided, and are providing for my clients"

    Cindy Evans, Travel Consultant

  • "I hope I have another opportunity to work with Dream Escape in the near future. The company is so professional, yet approachable and easy to work with. It has been a pleasure!"

    Carole McFarland, Universal Travel

  • "Dream Escape is delivering in a superb manner. Jim Johnston is a great driver and one of the best guides we've had - I wish to very much thank the Dream Escape Team for fulfilling a Dream…"

    Donald M. Davis, President, Luxury Travel, Inc.

  • "Thank you all so much it's great to have trusted friends on the ground to take care of our clients!"

    Peter Carideo, CRC Travel

  • "The trip was great.... Dream Escape is the name of the game"

    Ann Lipschitz, Worldview Travel

  • "Your level of service is just outstanding"

    Debra Fini, VWTI

  • "Dream Escape don’t just organise trips – they create adventures"

    Financial Times, How to Spend it

  • "It was, without doubt, one of the most spectacular weekends I have ever had"

    Country Life

  • "David Tobin’s an ace at getting inside private castles and estates and he’s well connected.... "

    Conde Nast Traveller Magazine

  • "The level of service they provide is outstanding. They truly care about every aspect of the trip to ensure you have a fantastic stay. Rosie is a hidden gem of a tour guide. Just fabulous."

    Yvonne Malka, Signature Travel Network, April 2018