Tour Details

We leave the city behind and head south from London Waterloo, crossing the Solent to the timeless shores of the Isle of Wight — a place where sea air, slow travel and sweeping landscapes set the tone for a truly restorative walking escape.

For three nights you’ll stay at The Wellington Hotel in Ventnor, one of the UK’s sunniest seaside towns, celebrated for its champagne air, gentle microclimate and long-standing reputation as a centre for health and wellbeing. It’s the perfect base from which to explore this unique island — now recognised as a UNESCO Biosphere Reserve.

Departure & Return Location 

London Waterloo Area

Accommodation

The Wellington Hotel, Ventnor

Perched above the English Channel, The Wellington Hotel combines classic Victorian charm
with relaxed coastal comfort. Set in Ventnor’s unique microclimate, the hotel enjoys some of
the island’s mildest weather and sweeping sea views.

Guests stay in comfortable en-suite rooms, many with panoramic views across the Channel.
After a day exploring the island, unwind in the welcoming bar and restaurant or relax by the
log fire with a drink in hand. Private steps lead directly to the beach below, where red
shingle, golden sand, and vintage beach huts create a timeless seaside atmosphere.

Shared and private rooms available.

Price Includes

• Return London–Isle of Wight travel in our Road Trip Co minibus
• 3 Nights Hotel Accomodation
• Ferry crossings to and from the Isle of Wight
• Small group camaraderie (max 14 guests)
• All transportation in destination location

Price Excludes

• Drinks unless stated
• Personal expenses / souvenirs

What to Expect

This journey is about more than miles walked it’s about time well spent.

From historic coastal trails and rolling chalk downs to sunshine, sea air and slow evenings in Ventnor, the Isle of Wight reveals itself as one of the UK’s finest destinations for outdoor escape, rest and renewal.

This isn’t just a trip. It’s a road trip the way it should be —thoughtfully planned, gently paced, and rich with moments to stop, look out to sea, and truly breathe it all in.

Itinerary

Day 1Day One — Arrival

After arriving on the island, we settle into The Wellington and begin our holiday. Refreshed and ready, we step straight into history on the Armada 1588 Coastal Trail, a beautiful 4-mile
heritage walk tracing the dramatic events of the summer of 1588. This atmospheric route follows the clifftop locations where warning beacons were lit to signal the sighting of the Spanish
Armada sailing up the English Channel. As we walk, the views open out across the sea, offering the first taste of the island’s extraordinary coastal beauty and storytelling landscapes.

We return to The Wellington in the late afternoon for a light supper, before
enjoying a relaxed evening in the hotel bar — the perfect place to unwind
after our first day on the island.

Day 2Day Two — The Tennyson Trail

Today brings one of the Isle of Wight’s most iconic walks: The Tennyson Trail. We travel to West Wight and begin a challenging yet rewarding 14-mile walk across Tennyson Downs and on towards Alum Bay. The route climbs steadily onto the chalk ridge and follows the high crest through ancient woodland, past prehistoric burial mounds and the striking Tennyson
Monument, with uninterrupted views across land and sea. The path continues towards the
island’s most famous natural landmark The Needles and the multi-coloured sands of Alum Bay.

Along the way, we stop to enjoy a pre-packed picnic lunch, surrounded by some of the finest scenery the island has to offer.

We return to Ventnor in the afternoon, with time to rest before a free evening exploring the town. Just a short walk from the hotel, Ventnor offers welcoming pubs, independent restaurants and a gently curving beach or you may choose to stay in and enjoy the hotel bar once more.

Day 3Day Three — Bembridge to St Helens

Our final walk explores the island’s gentler eastern coastline on the Bembridge to St Helens Walk.
This scenic coastal path offers panoramic views across the Solent, with wide skies and ever-changing light. As we stroll between St Helens and Bembridge, keep an eye out for the historic sea forts rising from the water, reminders of the island’s strategic past.

We pass through the beautiful StHelens Duver, a National Trust- managed nature reserve known for its rolling sand dunes and rich wildlife. A picnic lunch allows time to pause, relax and take in the calm rhythms of the coast.

The afternoon is yours once we return to Ventnor, wander, rest or simply sit and enjoy the sea air before our final evening on the island.

Day 4Day Four — Return to London

After breakfast, we check out of The Wellington and make our way back across the Solent to the mainland. By afternoon, we arrive back at London Waterloo — refreshed, rebalanced and
inspired by days spent walking, breathing deeply and moving at island pace.