Millionaire Date Doctor


Italy’s Amalfi Coast is one of the most picturesque places on earth, and it’s here that you’ll find legendary restaurants and hotels that will take your breath away. Spend 4 nights in Positano at Il San Pietro di Positano and one of those days take the ferry over to Capri for a full day of activities. While in Positano, have dinner on the village’s main drag at the famed Chez Black (I recommend the Zucchini Pasta. It’s not that expensive and exceptionally mouthwatering). For a little night life flavor check out the wine and oyster bar at Le Sirenuse (expensive so don’t eat a full meal there). If dancing is your thing, once the clock strikes midnight you’ll want to head to Music on the Rocks. It is Positano’s only night club located on a cliff edge terrace, steps from the sea. Day 3 of your trip I recommend taking the ferry over to Capri early in the morning.

When you dock on Capri head right up the hill for a 15 minute walk to JK Place (one of the most beautiful hotels on the island). Get a quick tour of the property and have a nice lunch on their patio. After a leisurely lunch, take a cab or the hotel car up to Piazza Umberto, where most will sit, people watch, and enjoy a cappuccino at one of the outdoor cafes.  After your cappuccino walk around the same boutiques that fashion legends like Jacqueline Kennedy, Grace Kelly, Sophia Loren, and Clark Gable shopped in all the way back in the 1960s. The history that lines these little cobblestone streets is unbelievable! If you are a little hot from all the walking grab a fresh gelato at Gelateria Buonocore. (Their homemade waffle cones and ice cream are famed as the best in Capri and it’s only 5 minutes or so from the Piazza). Head back to Positano on the last ferry out at 7pm. For your last day in paradise enjoy your hotels’ fine amenities; which include a complimentary boat ride everyday to swim in the med stocked with olives, sangria, and San Pellegrino. After the boat, lay out on the hotel’s world famous ocean deck in their orange lounge chairs. This trip is not cheap! A basic hotel room (in season is July & August) will run you $1,000 US per night but trust me it is worth every penny. It will truly be an experience you’ll never forget!

As the Millionaire Date Doctor I have been to many places in the world but few pull on my heart strings as much as the Amalfi Coast. Don’t believe me, celebrities love to stay in Positano by the droves so you can expect to bump into Denzel Washington, Sienna Miller, Gemma Arterton, Anne Hathaway, Eddie Redmayne or Reese Witherspoon who recently spent her second honeymoon there.  When I was in Positano in 2015 Bradley Cooper was checking out of the il San Pietro di Positano when I was checking in. Amazing who these hotels let in these days… but celebrity rif raf aside, Positano and Capri are Millionaire Date Doctor approved and should be at the top your fantasy destination list!


Toronto in Ontario, Canada is one of the most captivating destinations in the world. Especially if you’re a fan of the movies!  For ten days every September downtown Toronto becomes a celebrity-packed city with all the glitz and glamour worthy of its “Hollywood North” nickname. Because of the Toronto International Film Festival (founded in 1976) this is where several pictures premiere internationally and hundreds more are screened leading into awards season. If you love rooftop parties, great dining, and celebrity studded events this destination is certainly worth adding to your bucket list.

Millionaire Date Doctor recommends a 2 night/3 day stay for this trip at the beginning of the festival. This will keep your costs manageable and your adrenaline high!  Here is the lay of the land… Toronto is really broken up into two distinct areas for this event. One is the fashion forward Yorkville neighborhood which was once the hotbed of action for the festival. It still is a hotbed of fashion, art, restaurants, and only a ten minute cab ride to the TIFF Lightbox headquarters. If you plan on staying here it is home to two of the best hotels in Toronto, The Hazelton Hotel (that houses a fantastic restaurant for brunch or drinks called One Restaurant) and down the street is the iconic Four Seasons Toronto (that houses a fantastic bar and breakfast spot as well called dBar & Cafe Boulud respectively). For dinner in this area check out the popular Italian restaurant Sotto Sotto.  The second area where all of the movie action and most of the parties takes place is closer to downtown near King West District. Many of the premieres take place at Roy Thompson Hall so naturally the Ritz Carlton Toronto across the street is fully booked with sky high prices. Check it out for a drink or glass of champagne, but personally I don’t think its worth staying there when they are commanding north of $1,000/night for a basic room. Some of the parties are open to the public for hefty donations to great causes ahead of time. The Tiff Soiree is a great opening night party with extensive A-List turnout and the too expensive (in my opinion) Ambi Gala is hosted by James Franco and Prince Albert II of Monaco every year. After you hob nob with some the A-list and make new friends, you’ll want figure out a away to get into the Soho House for the after party which is a member’s only club. Having new A-list friends will be a huge benefit to gain entry. For dinner check out an area favorite Brassai and for more rooftop views experience the Thompson Hotel Toronto.

I know this is a lot of information to take in especially for a quick 72 hour span but if you are up for the challenge and the expense it’ll be a once in a lifetime experience I promise you. Where else can you have cocktails and talk about future movie projects with Michael Fassbender (I did this in 2016) and then walk a red carpet premiere all in a 24 hour span with the likes of Denzel Washington, Chris Pratt, Ethan Hawke… Totally bonkers for sure but definitely Millionaire Date Doctor approved and should be another stop on your fantasy travel destination list.

MONTE CARLO – Coming Soon

LONDON – Coming Soon

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