Hampshire 5 Star Hotel 4/5 Day Wine & Adventure Self Drive Car Tour | Rent Luxury Villas & Chateaux With Pool

Hampshire 5 Star Hotel 4/5 Day Wine & Adventure Self Drive Car Tour


Luxury Experience

Drive though some of the finest scenery along winding country roads in the south of England and stay at quintessentially English five star hotels rich in history.

Experience the historic Chewton Glen hotel & Spa, relax or indulge in some country pursuits. Enjoy an indulgent evening dining under the care of head chef Luke Mathews, before heading off to the Langham Estate Vineyard with its wonderful wine cellar for a private tour and tasting.

Dine at Michelin starred Al Molo, famous for its seafood, caught yards from the restaurant itself, overlooking the sea.

Then jet-ski around the mythical Lulworth cove in Dorset with its arched pillars that stretch into the sea.

Follow up with a shopping tour of Weymouth harbour with its quaint shops and fishing boats.

Indulge again with dining and stay at Penn Castle, a Gothic Revival mansion on the Isle of Portland, Dorset, overlooking Church Ope Cove.

Next a scenic drive to English Oak Vineyard for a light picnic lunch, finishing up at the legendary Four Season Hampshire, for dinner and stay, with option to extend the tour and partake in some exciting traditional British country pursuits.

Day 1

Depart: 09:00


Arrive: 12:00

Chewton Glen Hotel & Spa

Overnight stay and meals at Chewton Glen Hotel & Spa

Day 2

Depart: 10:00

Chewton Glen Hotel & Spa

Arrive: 11:00

Langham Estate Vineyard private tour

Depart 12:30

Langham Estate Vineyard

Arrive: 13:00

Al Molo Restaurant

Lunch at Michelin Star restaurant Al Molo overlooking Weymouth Harbour

Depart: 15:00

Jet Ski Tour around Weymouth

Depart: 16:30

Weymouth Harbour

Arrive: 17:00

Penn Castle, Isle of Portland

Overnight stay and meals at The Pennsylvania Castle

Day 3

Depart: 10:00

Penn Castle, Isle of Portland

Arrive: 11:15

English Oak Vineyard

Vineyard tour & picnic lunch

Depart: 15:00

English Oak Vineyard

Arrive: 17:00

Four Seasons Hampshire

Overnight stay and meals at The Four Seasons Hampshire

Day 4

Depart: 11:00

Four Seasons Hampshire

Arrive: 15:00


Or stay an extra day and visit Highclere Castle, A spectacular Victorian estate in its own right, Highclere has come to fame as the principal filming location, inside and out, of the TV series and movie “Downton Abbey.”

Try your hand at horseback riding, clay pigeon shooting, canal boating or falconry, or take a shot at archery and experience the best of traditional British country fare.

Or if you feel like a bigger thrill, experience their Highwire Adventure, featuring a 235-metre zip wire and 13-metre free-fall drop.

For those who like to relax, unwind with a wide selection of relaxing nature-inspired spa treatments. (extra cost).


• All hotels and events are subject to availability on dates chosen

• Drive routes between points to be planned for optimum experiences

Celebrity Drivers/Celebrities

We also offer celebrity drivers and renowned adventurers to join us for lunch at an extra cost.  Please enquire specifying the celebrity you are interested in. We have direct access to all drivers and celebrities.

Celebrities include:

Ollie Ollerton, star of SAS Who Dares Wins.

Jason Fox, star of SAS Who Dares Wins.

Tiff Needell, Former F1 driver and TV presenter.

Ben Collins, Top Gear’s “The Stig” and Hollywood stunt driver Bear Grylls, adventurer, writer and hugely popular TV presenter

Luxury Tour Concierge

All tours are accompanied by a tour manager concierge in a support car who will select the best routes, keep up to date with traffic alerts and warnings and advise on route changes if necessary to keep the tour flowing.

They will also register at hotels, restaurants and venues in advance to ensure a smooth and efficient reception.

A second support supercar will also be there to take video and photographs of the participants and the events. These will be provided after the event to all those that request it.

Your luxury tour concierge will be able to answer any questions you may have on the tour about the locations and history of the towns and exclusive places we visit.

All tours are exclusive and one on one, meaning that you will always be shown around privately and in most cases by either the owner of the venue or the curator.

You will never queue or be left standing around. Our tours are luxury VIP experiences that normally money cannot buy.

We use our exclusive network built up over 35 years in the luxury travel, supercar, hotels, yacht, whisky, fashion, adventure sports and watch industry to put together exciting experiences you simply cannot get anywhere else.

Please do let us know any other requests such as dietary requirements and indeed anything else you may need at the time of your booking.

Price does not include the car, bring your own supercar or we can supply any supercar you wish at a lower price than any other reliable rental company. Though you are free to rent your car elsewhere too. Please enquire stating which car model you would like and we will get back with a quote for the duration of the tour, including delivery to your home or starting point.

All individual tours stops can be exchanged for many other different pursuits to suit your taste.

Nothing is set in stone, everything can be tailored to suit your preferences. These are bespoke luxury tours, tailored for you.

Let us know what you prefer in terms of gastronomy, driving, history, locations, sport, adventure, shopping, spa, rally, social, networking, celebrity, events, locations, country pursuits, water-sports etc and we will make sure it's the ultimate driving tour that you will remember and talk about forever.


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Brief Villa T&C's

No hidden charges or fees.
Some properties will take credit card details used as guarantee, or a deposit will be required, returned after departure and a check of the property.
Arrival time is given once the property has been booked.
Departure time is given once the property has been booked.
Energy costs vary by property, most include it, others will levy a charge to be paid directly to them either on arrival or departure. Please enquire for details.
Linen & towels are mostly included, others will levy a charge to be paid directly to them either on arrival or departure. Please enquire for details.
Pets welcome are welcome at some properties and not others, so please check when enquiring.
Most properties do not allow smoking inside.
Most properties have a minimum stay of 7 nights, but not all.
It is recommended that all guests take out insurance to cover against potential cancellation and any accidental damage caused during your stay at the property.
Most properties do have Wi-Fi, but do check with us if it is of vital importance.
End of stay cleaning is include by most, others will levy a charge to be paid directly to them either on arrival or departure. Please enquire for details.
Cots & high chairs can often be provided, again some properties will supply these free of charge, others may charge.
Many of the properties charge in Euros, so the GBP price quoted may fluctuate up or down, as you will be charged in GBP at the Euro exchange rate on the day of payment.