skip to main menu | skip to sub menu | skip to content

Main menu

Isle of WightFreshwater Bay

The Needles sea stacks off the Isle of Wight

Ancient cannons on the waterfront on the Isle of Wight

Walkers descending from Tennyson Down to Freshwater Bay

Guided Walking

From £349 - 3 to 7 nights

Guided Walking at Freshwater Bay

Holiday reference: FWBOB

Print guided walking itinerary information

Walk grade logo one Easier Walks Medium Walks Walk grade logo two Harder Walks

Easier Walks have gently undulating gradients. Medium Walks have occasional steeper sections. Harder Walks have a few steeper sections.

Our experienced guides offer the choice of up to three different walks each day
Choose the option which best suits your interests and fitness; take an Easier Walk one day and switch to a Harder Walk the next
We offer a social activity each evening

2012 - Itinerary One

7 night holidays
Days 1-7: Mon 12 March; Fri 13 April; Sat 12, 26 May; Sat 9, 23 June; Sat 7 July; Sat 18 Aug;
Sat 1, 15, 29 Sept; Sat 13 Oct

4 night holidays
Days 1-4: Mon 12 March
Days 4-7: Tues 15, 29 May; Tues 12, 26 June; Tues 4, 18 Sept; Tues 2, 16 Oct

3 night holidays
Days 1-3: Sat 12, 26 May; Sat 9, 23 June; Sat 7 July; Sat 1, 15, 29 Sept; Sat 13 Oct
Days 5-7: Fri 16 March
Days 2 & 7: Fri 27 April

See below for Itinerary Two

Day 1: Arrival day

Meet your leaders who will tell you more about the walks.

Day 2: Tennyson Down and Alum Bay

Easier Walk: A fabulous figure of eight walk over Tennyson Down, the grand chalk cliffs directly behind Freshwater Bay House. We'll continue to the view of the Needles at the very tip of the island and visit Alum Bay, famous for its coloured sands. 6½ miles with 775 feet of ascent.

Medium Walk: Head to the coast at Totland Bay then soak up the glorious sea view as we round the Needles headland and return over Tennyson Down. 8¾ miles with 1,025 feet of ascent.

Harder Walk: A circuit of the western tip of the island. We'll follow the Yar Valley to Yarmouth, then follow the coastal path to Alum Bay, before a glorious finale over the chalk cliffs of Tennyson Down back to Freshwater Bay. 11¾ miles with 1,200 feet of ascent.

Day 3: Eastern Wight

Easier Walk: Starting from the historic town of Brading we'll head first to the 18th century Bembridge Windmill. We'll then walk to the chalk cliffs of Culver Down, near the eastern tip of the island, and follow the coastal path to Sandown. 6½ miles with 575 feet of ascent.

Medium Walk: Soak up the sea air and views of the Solent as we follow the coastal path from Ryde to St Helens, before heading inland past the Bembridge Windmill to Brading. 9¼ miles with 375 feet of ascent.

Harder Walk: From Arreton craft village, we walk along the valley under the downs before ascending Brading Down and walking along the chalk ridge, enjoying the views across the Solent to the mainland. We'll continue over Culver Down and along the coastal path to Sandown. 11¼ miles with 800 feet of ascent.

Day 4:

For 4 night holidays arriving today, this is your chance to meet your leaders.

If you have booked a 7 night holiday today is a free day with no guided walks organised. This is a great opportunity to explore the Isle of Wight independently - see the Local Area tab for places that you may enjoy visiting.

Day 5: Shorwell and Carisbrooke Castle

Easier Walk: We start in the pretty village of Shorwell with its thatched cottages and historic church and follow the Shepherd's Trail to the impressive castle at Carisbrooke with its well-preseved walls and famous donkey well (English Heritage - admission payable). 6 miles with 825 feet of ascent.

Medium Walk: Walk from the south coast to Carisbrooke Castle via Shorwell village. 8¾ miles with 1,125 feet of ascent.

Harder Walk: A great walk along the spine of the island from Carisbrooke Castle to Freshwater Bay. We'll cross the hills to Shorwell then pick up the Tennyson Trail which runs atop the chalk downs, with extensive views throughout. 12¾ miles with 1,550 feet of ascent.

Day 6: Over the Downs to Ventnor Botanic Gardens

Easier Walk: Starting near St Catherine's Point at the southern tip of the island we'll follow the coast along the Undercliff to Ventnor's Botanic Gardens, detouring to visit the village of Whitwell. 6 miles with 400 feet of ascent.

Medium Walk: Cross the downs from Godshill to Ventnor, passing the grand ruins of Appuldurcombe House and its surrounding parkland laid out by 'Capability' Brown. 9 miles with 1,175 feet of ascent.

Harder Walk: Look out for red squirels as we walk through the woods near Sandown, then admire the widespread views on the second part of the walk which takes us over the downs to Ventnor. 10¼ miles with 1,050 feet of ascent.

Day 7: Calbourne to Freshwater Bay

Easier Walk: Visit the much-photographed thatched cottages on Calbourne's Winkle Street before crossing the downs and descending to Freshwater Bay. 6½ miles with 725 feet of ascent.

Medium Walk: From Calbourne we'll ascend over the downs to the south coast. We'll then follow the coastal path over the chalk cliffs of Compton Down back to Freshwater Bay. 8½ miles with 975 feet of ascent.

Harder Walk: Cross over the downs to Brighstone then follow the coast path along the island's southwest coast to Freshwater Bay. Tides permitting there's an opportunity to see the fossilised forest and dinosaur footprints at Hanover Point. 10¾ miles with 975 feet of ascent.

2012 - Itinerary Two

7 night holidays
Days 1-7: Mon 26 March; Sat 5, 19 May; Sat 16, 30 June; Sat 14 July; Sat 11, 25 Aug;
Sat 8, 22 Sept; Sat 6, 20 Oct

4 night holidays
Days 1-4: Mon 26 March
Days 4-7: Tues 8, 22 May; Tues 19 June; Tues 3, 17 July; Tues 14, 28 Aug; Tues 11, 25 Sept; Tues 9, 22 Oct
Days 2, 6 & 7: Mon 2 April

3 night holidays
Days 1-3: Sat 5, 19 May; Sat 16, 30 June; Sat 14 July; Sat 11, 25 Aug; Sat 8, 22 Sept;
Sat 6, 20 Oct
Days 5-7: Fri 30 March

Day 1: Arrival day

Meet your leaders who will tell you more about the walks.

Day 2: Tennyson Down and Alum Bay

Medium Walk: Head to the coast at Totland Bay then soak up the glorious sea view as we round the Needles headland and return over Tennyson Down. 8¾ miles with 1,025 feet of ascent.

Day 3: Godshill and Appuldurcombe House

Easier Walk: Explore the rolling downs south of Godshill village, the highlight of which is the impressive ruins of Appuldurcombe House with its grand Palladian facade and parkland laid out by 'Capability' Brown. 5 miles with 750 feet of ascent.

Medium Walk: This longer circuit passes Appuldurcombe House on its way onto Stenbury Down. We'll return via the village of Wroxall to Godshill where you can visit the 14th century church and see the 'chocolate box' thatched cottages. 8½ miles with 1,175 feet of ascent.

Harder Walk: The harder option follows the same route as the Medium Walk but with an additional loop to take in St Boniface Down, the highest point on the island. 10¼ miles with 1,250 feet of ascent.

Day 4:

For 4 night holidays arriving today, this is your chance to meet your leaders.

Day 5: Cowes and Solent Views

Easier Walk: Enjoy views of the Solent as we follow the coastal path from Porchfield to the famous yachting town of Cowes. 6 miles and 400 feet of ascent.

Medium Walk: Explore Cowes and the surrounding area on this circular walk. We start beside the tidal River Medina then, after an inland section, return to our starting point along the coastal path from Thorness Bay. 8¼ miles with 600 feet of ascent.

Harder Walk: Starting from Cowes we'll follow the northwest coast of the island, then head inland to the village of Calbourne with its much photographed thatched cottages in Winkle Street. 11 miles with 675 feet of ascent.

Day 6: The Undercliff

Easier Walk: Walk through the Victorian resort of Ventnor then on through the Undercliff to Shanklin, an area of widespread landslips and lush vegetation. 5½ miles with 650 feet of ascent.

Medium Walk: A walk around the southeastern corner of the island from Niton to Shanklin, with great sea views from the inland cliffs and then on through the lush Undercliff beyond Ventnor. 8¼ miles with 825 feet of ascent.

Harder Walk: Starting from Whale Chine follow the coastal path around St Catherine's Point and then through the Undercliff to Ventnor and Shanklin. 11½ miles with 1,250 feet of ascent.

Day 7: Yar Valley or the Tennyson Trail

Easier Walk: Walk beside the tidal River Yar to the historic town of Yarmouth with its bustling harbour and tudor castle. We'll return on the opposite side of the river back to Freshwater Bay. 6¾ miles with 250 feet of ascent.

Medium Walk: Starting further down the coast at Chilton Chine we'll first head inland to Brighstone village. Shortly after we join the Tennyson Trail which follows the top of the chalk downs back to Freshwater Bay with widespread sea views throughout. 8¾ miles with 1,025 feet of ascent.

Harder Walk: Follow the Tennyson Trail over the downs to the Neolithic Longstone. Having descended to the coast we'll follow the coastal path back to Freshwater Bay - tide permitting it may be possible to view the fossilised forest and dinosaur footprints at Hanover Point. 11¼ miles with 975 feet of ascent.

Local transport

On some days the walks start and finish at our Country House, Freshwater Bay House. On other days you’ll be transported to other parts of the Isle of Wight. The cost of all transport to and from the walks is included in the price of your holiday.

Our guests

The atmosphere is relaxed and friendly. There is normally a good mix of ages, of new guests and 'regulars' from Britain and overseas, and of people travelling alone, with a partner or with friends.

In the evenings

Your leaders will inform you about the choice of walks for the next day and answer any questions you may have. After a sociable evening meal you could join in an organised activity such as a quiz or a talk about the local area, relax in the bar or use the Country House facilities.