Escape the city and discover the winter magic of the Isle of Wight. This small-group weekend adventure blends invigorating coastal hikes, cosy fireside evenings, and the charm of peaceful island landscapes. Perfect for travellers who love crisp air, scenic winter walks, and relaxed evenings in warm, welcoming surroundings.
Travel in comfort by minibus and ferry, explore hidden villages and coastal paths, and enjoy hearty local food beside crackling fires. With just 14 guests, expect a friendly, personal, and flexible experience.
Waterloo Station, London → Isle of Wight → Waterloo Station, London
Friday 3:00pm
The Wellington Hotel, Ventnor
Perched above the English Channel, The Wellington Hotel marries the elegance of Victorian architecture with modern comfort. With its own unique microclimate, Ventnor offers a serene seaside escape — the perfect winter hideaway.
Relax with panoramic ocean views from the terrace or snuggle up by the log fire in the hotel’s intimate bar and restaurant. Just steps from the southernmost beach on the island, the hotel features 22 charming en-suite rooms, each offering picturesque sea views.
Private steps lead directly to the beach, where red shingle, golden sand, and vintage beach huts create a nostalgic coastal atmosphere.
Winter Hiking & Scenic Adventures
The Isle of Wight’s coastline and countryside are especially atmospheric in winter. Enjoy crisp walks with dramatic cliff views, forest trails, and quiet village paths. Our guides will ensure routes are safe, enjoyable, and suited to the group.
Cosy Fireside Evenings
After hiking, relax with hearty dinners and warming drinks by the fire. Share stories with fellow adventurers and soak up the seasonal charm of the island.
Small Group Comfort
With a maximum of 14 guests, expect a personal and friendly experience. Travel in a comfortable minibus, enjoy the views on the ferry, and benefit from flexible planning.
Authentic Island Experience
From coastal villages to hidden winter landscapes, we go beyond the tourist trail. Discover local pubs, scenic viewpoints, and quiet spots only locals know.
Bring Your Curiosity & Winter Gear
Sturdy boots, warm layers, and a sense of adventure are essential. Optional photography, sketching, or
journaling along the way is encouraged.
Depart London and travel by minibus to Portsmouth for the ferry. Evening arrival on the Isle of Wight and check-in at your cosy hotel/B&B. Gather for a welcome fireside dinner and orientation.
Sleep: Isle of Wight (Night 1).
Bus & Ferry: ~3 hrs.
Walking: light.
After breakfast, set out on a guided winter hike along the island’s stunning coastal cliffs and countryside paths. Stop for scenic photos, short breaks, and a winter picnic (weather permitting).
Afternoon options include visiting local villages, cafes, or short forest walks.
Evening fireside dinner with local seasonal dishes.
Sleep: Isle of Wight (Night 2).
Walking: moderate.
Morning guided hike in the island’s winter countryside, taking in forests, hills, and quiet coastal views.
Return to the hotel to check out and begin the return minibus back to London.
Arrive at Waterloo Station by 7:00pm.
Bus & Ferry: ~3 hrs. Walking: light-moderate.
