With its historic attractions, beautiful beaches and a wide choice of eateries, Hampshire and the Isle of Wight is your perfect weekend destination.
Day one
Start in Winchester by fuelling up with a hearty breakfast and perhaps the best coffee in town at Cafemonde on The Square. This independent café is full of character and a great place to watch the world go by. Next, wander over to Winchester Cathedral. Take a tour with one of the expert guides to hear about Winchester during Anglo-Saxon times, what happened when the Normans invaded and the other events that have left their mark on this magnificent building.

See the majestic interior of Winchester Cathedral
Work off your breakfast by climbing the cathedral’s tower – 213 steps later and you are rewarded with breathtaking views across Winchester. For your afternoon, head east along the M27 to Portsmouth and to Gunwharf Quays at Portsmouth Harbour. Hit the shops or take a tour of the harbour before tucking into a three-course seafood treat at Loch Fyne.
If shopping isn’t your thing, then you could spend your afternoon exploring Hampshire’s quaint towns and beautiful countryside instead. The historic market town of Odiham in the north of the county sits on the banks of the Basingstoke Canal.
- Check out the Spinnaker Tower at Portsmouth Harbour
- Ruins of the 13th-century Odiham Castle in Hampshire
Its picturesque high street offers a broad mix of shops. A wander along the canal towpath takes you to the flint. In the heart of the charming Test Valley, Stockbridge is another historic town worth visiting. Fine brick buildings house independent boutiques, specialist food shops and art galleries. If time allows, this area is perfect for a leisurely country walk along part of the 44-mile Test Way before enjoying a hearty country pub meal to round off the day.
Day two
Start off your second day with a trip to Osborne. The house here was built between 1845 and 1851 for Queen Victoria and Prince Albert as a summer home and rural retreat. Inside the house you’ll get an intimate glimpse into royal life as you explore private apartments and grand reception rooms.

Osborne in East Cowes
Outside, wander among flower-filled gardens, discover the quirky museum in the Swiss Cottage and relax on the beach where the royal children learnt to swim. From here, head inland to the award-winning Monkey Haven, a primate rescue centre where you can learn all about these fascinating creatures, their personalities, and how they came to be at the haven.
Head slightly west to Newport for lunch at Thompson’s where Chef Patron Robert Thompson serves up well-presented dishes from his open kitchen. Travel south from Newport and you’ll be rewarded with rolling countryside and outstanding views across the Isle of Wight Area of Outstanding Natural Beauty (AONB).
- Monkey Haven, Isle of Wight
- Chalk Ridge, Isle of Wight
From dazzling chalk cliffs to rolling rural hills, the Isle of Wight AONB has a slice of scenery to please every hiker. There are 30 named hills here, the highest and the most prominent being St Boniface Down, which stands at 791ft. Round up your second day in style at The Royal hotel in Ventnor. Its two AA Rosette-winning restaurant offers a fine dining experience you’ll never forget. The menu reflects the abundance of quality produce harvested from the Island matched with a selection of wines.
Read more
Things to see and do in Hampshire and the Isle of Wight: our top picks
Outings for history and heritage buffs in Hampshire and the Isle of Wight