Isles of Scilly Guided Island Hopping Holiday

Guided Island Hopping


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Activity types:

  • Coastal


  • 2
More information

Choosing the level of your walks

Our easy grading system shows whether a region offer gentle strolls or more challenging routes to help you choose the right holiday for you. Difficulty is measured on many factors such as distance, ascent/descent, terrain, weather and more. There's no magic formula, but from our experience we grade our walks 1 to 5 (where 1 is easy and 5 hard). Our challenger holidays require a high level of fitness and stamina.

More about difficulty levels

From £895.00 - 6 nights


Prices are per person

Room 1:
Room 2:
Room 3:

Holiday overview

Download the Isles of Scilly Trip Notes 2019

The unique character and beauty of this archipelago is undeniable. Stunning silvery white beaches, translucent turquoise seas, rugged coastline bounded by golden gorse. Tiny pocket-sized bulb fields filled with scented narcissi - this charming landscape, warmed by the breezes of the Gulf Stream, is the ideal escape for leisurely walking, peace and relaxation. Hop from island to island discovering the individual identities. Explore tropical Tresco and visit the famous Abbey gardens. See the stunning array of Bronze Age archaeological sites on St Agnes and Gugh. 

Price includes:

  • 6 nights Half Board en-suite accommodation
  • The services of an experienced local leader.
  • Ferry tickets on walking days
  • A traditional cooked breakfast, and evening meal each day 

In pictures...


 Bell Rock Hotel exterior

Bell Rock Hotel, St Mary's - 6nts

You will be staying at the Bell Rock Hotel on St Mary’s, the largest of the islands stretching to two-and-a-half miles by one-and-three-quarters. Mid-way between the two beaches of Porthcressa and Town Beach, it is situated on a quiet street, minutes from the shops, and a short stroll from the harbour. The hotel has a small heated indoor swimming pool and good WiFi. Rooms have a hairdryer, tea and coffee making facilities and a boot tray.

The holiday is Half Board with the opportunity to eat in pubs and cafes at lunchtime, experiencing the local produce, rather than buying a packed lunch.

On occasion we may need to change the accommodation listed above. If this happens, your replacement accommodation will be of the equivalent standard or higher. In the rare instance this is not possible, we will contact you in advance.


Download the Isles of Scilly Trip Notes 2019

The daily itinerary has to be very flexible as our itinerary, like life on Scilly, is determined by weather and tide. We have provided you an outline of the selection of walks on each of the islands which could be included in the itinerary. There are lots of things to see on each island, so some of the walks are not as lengthy as others. The holiday runs at a relaxing pace so that you get a real flavour of island life.

Explores the Isles of Scilly with HF Holidays

Day 1: Arrival at the Bell Rock Hotel on St Mary's

Check into the Bell Rock hotel, were you will meet your trail leader

Day 2: Tresco

Day 6 isles of scillyThis is the second largest of the islands. Tresco and its garden are world-renowned and attract many visitors each year. We will see white sand beaches and a panorama of islands from the coastal path and explore the north of the island with its wild heathland, rocky coastlines and 16th and 17th century castles. There will be the chance to visit the Abbey Garden (admission £15.00 or £13.50 for concessions in 2016; payable locally) and to explore this collection of sub-tropical plants, and also to see the Valhalla museum – housing figureheads salvaged from shipwrecks from around the islands’ shores. 6 miles (9.6km)

Day 3: St Agnes and Gugh

Day 2 Isles of ScillySurrounded by rocks and reefs, St Agnes is the most south-westerly community in the UK, where the whitewashed lighthouse and traditional stone cottages tumble down to tiny bulb fields, and pocket sized farms. Our circular walk will take us past the old lifeboat station, Troytown Maze, a labyrinth laid out in beach pebbles, and the granite outcrop of the Nag’s Head. From the coastal path we will have impressive views of the treacherous Western Rocks and the famous Bishop Rock lighthouse. A visit to Gugh (pronounced like the name Hugh, but with a G) is determined by the tide. This small island is home to a bounty of archaeological sites. 5 miles (8km)

Day 4: St Martin’s  

Day 3 Isles of ScillyThough the third largest of the islands, St Martin’s is a narrow island only 2 miles long. Easily recognisable from its fine shimmering white sandy beaches, the shores of St Martin’s have the longest stretches of sand in Scilly. Following the coastal path takes us past kelp pits, through scented gorse heathlands, to stone and rope labyrinths. We follow the sandy shore of Little Bay and Great Bay, before turning inland to the flower fields and glasshouses of Higher Town. We also head over the golden gorse heathland of Chapel Down to St Martin’s Head with its chapel, Daymark and ruined Signal Station. 6 ½ miles (10.5km)

Day 5: St Mary’s circular

Day 4 isles of scillyOur walk circumnavigates the Islands’ hub of St Mary’s, starting out from our base in Hugh Town. We explore the coastline, passing by the archaeological sites of Bant’s Carn and Innisidgen, the granite tors of Porth Hellick and Peninnis Head, and the one and only set of traffic lights on the islands, at the airport! Before returning to Hugh Town, the coastal path brings us to Old Town– a favourite haunt and now the resting place of the former Prime Minister Harold Wilson. 10 miles (16km)

Day 6: Bryher

Day 5 Isles of scillyBryher is wild, windswept and unkempt, and has a very individual feel to it. Fewer than 100 people live here. There is only one road, and the locals quote the definition of a traffic jam as being “when two tractors meet”! The island has a magnificent variety of scenery, from the wild and rugged Hell Bay in the north, to the peaceful bays and secluded beaches of the south. Our walk will take us across heather moorland, past prehistoric cairns and boulder walls and along sandy coastal paths to see these different sides of Bryher. 5 miles (8km)

The itinerary may be subject to change at the discretion of the leader. Weather or sea conditions may cause changes to the published programme.



By ferry:

The Scillonian III ferry departs from Penzance at 9.15am for the 2hrs 40min crossing to the Isles of Scilly. Some departures can be affected by the tides – please make sure to confirm the exact sailing time when making your booking. See for timetables and bookings.

Make sure to be at the check-in for the ferry 1 hour before departure in Penzance and 45 minutes before departure on St Mary’s. The return ferry leaves St Mary’s at 16.30hrs arriving in Penzance at about 19.10 hrs.

 Ferry heading to the Isles of Scilly

 Travel by plane

By air:

Flights to the The Isles of Scilly are from Land's End, Newquay, and Exeter. They are operated by Skybus, and administered by the Isles of Scilly Travel. For details of prices and the timetable of scheduled flights:  Tel: 0845 710 5555

The Skybus fleet consists of 8 and 19-seater aircraft, each with a luggage allowance of 15kg/person. Photo ID is required at check-in and can be in one of the following forms: passport, driving licence with photo or council issued bus pass.

A shuttle bus will meet you as arrive on St Mary's (payable locally), to transfer you and your luggage to the hotel.

 Plane to the Isles of Scilly

Driving to us

By car:

Car parking is available at each of the airports, or at Penzance. See the following websites for further details:



Land’s End:

Penzance: or



Katharine Sawyer

Katharine first visited the Isles of Scilly in 1993 and, having become captivated by them, moved there in 1999. She has a degree in Archaeology and Anthropology and, since living in Scilly, has obtained a PhD for her research on the Bronze Age burial chambers of the islands. She has worked as a guide since 2000 but, in common with many residents of small islands, has a range of other jobs which include archaeological monitoring and recording, adult education teaching and human resources consultancy. She has been leading our Isles of Scilly holidays since 2011 and really enjoys showing the islands to visitors. Her interests include bird and wildlife watching, gardening and travel.


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Dates & Prices

Date Description Nights Brochure price Book
20 Sep 2019 XSLDW - Guided Island Hopping on the Isles of Scilly 6 £965.00 Book Now
4 Oct 2019 XSLDW - Guided Island Hopping on the Isles of Scilly 6 £895.00 Book Now

Prices are per person


  • Single room: £108 (complete holiday)

If at eight weeks prior to the start of the holiday a sharing partner is unavailable, a single room or room for single occupancy with associated supplement will be allocated to you instead. 

  • Non-member associate fee: £10 per person

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