The Classicist: Win a Private Tour of Ralph Lauren's Car Collection & More

From now through Oct. 21, Ralph Lauren is auctioning off a number of extraordinary items and experiences to mark the 10th anniversary of Pink Pony, the designer's global initiative to raise awareness and funds in support of the fight against cancer. The online auction, the first of its kind for the Pink Pony cause, is being produced in partnership with luxury charity auction site charitybuzz. Highlights of the incredible event include several once-in-a-lifetime forays into the private world of the famed fashion designer and his luxury empire, including classic cars, polo, chauffeured Bentleys, sexy models and shopping sprees. You check out full details and register to place bids at www.charitybuzz.com/RalphLauren; meanwhile, here are The Classicist's top picks:

1. A private tour of Lauren's incredible car collection, estimated at $150,000: You and a friend will be shown the cars, including the ultra-rare 1936 Bugatti Type 57SC Atlantic (above), worth an estimated $40 million, a $28 million Ferrari 250 GTO, Mercedes-Benz 300SL Gullwing, McLaren F1LM and more, by Lauren himself at his lavish estate in Bedford, New York. You'll also get a ride in one of these world-class driving machines and take home a signed copy of Speed, Style, and Beauty: Cars from the Ralph Lauren Collection. 

2. A weekend at Lauren's private Round Hill Villa in Jamaica, estimated at $150,000: A priceless opportunity to spend four days and three nights for you and up to three guests at the designer's personal Jamaican paradise. The fully staffed villa, which sits on a magnificent, picturesque cliff over the crystal blue Caribbean Sea, has been featured on the covers of House & Garden and Architectural Digest. Enjoy a swim in the villa's infinity pool and private beach access, as well as complimentary tennis lessons and a yoga session. 

3. Play polo with Nacho Figueras and stay at The Breakers in Palm Beach, estimated at $15,000: Take a lesson from Nacho Figueras, world class polo player and Ralph Lauren model. You and a guest will refuel afterward during lunch with Nacho, and you'll also spend three nights at the exclusive Breakers hotel in Palm Beach, including a spa treatment for two at the Breakers Spa; a round of golf for two; a $1,000 private shopping experience at the Ralph Lauren store at the Breakers; and VIP access to the U.S. Open at the International Polo Club.

4. Front row seats to the Ralph Lauren fashion show and an outfit from the runway, estimated at $25,000: Bring along a friend when you meet the designer and sit in the elite front row at his Fall 2011 Fashion Show in New York. Then, select your favorite look from the runway to add to your own personal collection. Enjoy two nights at a penthouse suite at The Setai Fifth Avenue hotel, including breakfast for two and one signature spa treatments.

5. Legendary Wimbledon Experience, estimated at $15,000: You and a guest will meet tennis star Boris Becker and receive a signed racquet when you experience the pageantry and competition of London's famed Wimbledon 2011 Championships. A chauffeured Bentley will drive you to and from the All-England Club, and you'll enjoy lunch at the exclusive RL Marquee where you'll return after the matches for traditional English cream tea. You'll spend one night in style at the The Savoy in London, with breakfast and full butler service included. 

6. Bespoke tailoring experience, estimated at $9,000: Go behind the scenes with the Ralph Lauren menswear senior design team as you preview the Fall 2011 collection. Take a private tour of the men's showroom, and spend the afternoon at the flagship Rhinelander Mansion in New York City where veteran tailors will handcraft a custom suit just for you. The perfect dress shirt, necktie and bench made shoes will be personally chosen to complete your splendid sartorial look.

7. Ralph Lauren Weekend in Paris, estimated at $7,000: You and a guest will spend two nights at the luxurious Bristol Hotel in Paris, enjoy a $3,000 shopping spree in the breathtaking new Ralph Lauren store on Boulevard St. Germain and a receive a $600 gift certificate to Ralph's, Lauren's exclusive new restaurant everyone in Paris is talking about. 

8. RL and Carlyle Hotel Madison Avenue experience, estimated at $5,500: Enjoy a 2-night stay at the famous Carlyle Hotel in New York City in a deluxe room for two people, along with a $3,000 Ralph Lauren Madison Avenue Shopping Experience at the nearby Rhinelander Mansion, which includes a private appointment with a Ralph Lauren wardrobe consultant.

9. Go behind the scenes at a Ralph Lauren ad campaign shoot, estimated at $5,000 (each): You and a friend will meet the gorgeous models and crew and get a rare glimpse at what it takes to create one of Ralph Lauren's iconic advertisements in New York City; both men's and women's ad campaigns are available.