Hotel accommodations

Mr. Widzer: Allow me to first offer my compliments on the Penny Pincher’s Passport to Luxury Travel. I bought it recently and went through it in two days. Thank you for sharing your experience and wisdom with the rest of us. I would like your suggestions regarding applying the recommendations in your book to reserving hotel accommodations on a trip I plan to take this November with my wife for our anniversary. Our trip starts in Washington, DC for a business conference I am attending. Taking your contrarian advice, we then plan to go to Montreal for 1-2 days, and to Quebec City for 5-7 days around Thanksgiving. As it turns out my conference is at the Fairmont in DC and we would like to stay at the Fairmont Chateau de Frontenac in Quebec City as well. I’m inclined to approach Fairmont for accommodations throughout my trip in each city. However, I’m not sure how to maximize my itinerary and off-season schedule. Do you suggest calling the hotels in each of these respective cities separately on a Sunday evening to make reservations and request upgrades, or approach with one point of contact, like a corporate HQ sales manager, for reserving accommodations in each city? I would greatly appreciate your suggestions. Also, I work as a lawyer representing many timeshare developers and management companies. The DC conference is for a timeshare industry trade association. I thought your mention of timeshares in your book was fair and accurate. Quite unusual; I’m more used to hyperbolic vilification in the media and your reference was both candid and refreshing. I look forward to your suggestions and thank you once again.
Best regards,
Joshua Glazov Chicago, Illinois

Dear Joshua,
Thank you for your kind words. You are on the right track…I would suggest that you call each hotel separately, perhaps starting with the city where your convention will be held. Try to get a contact name from the hotel in DC, and ask if they know of anyone at the other hotels whom you can contact. Also ask if they can send an email to the hotel’s General Manager (GM) stating that you are planning on staying at the three hotels during your trip. Then call the GM’s of the other two hotels and introduce yourself mentioning the point of contact in DC. Than explain what you are planning on, and go for the upgrade and any rate special. Follow the same steps for the next hotel. Remember to stress your loyalty to the hotel during this trip. I have always found it helpful if you ask the GM or their assistant to mark your record upon arrival, if possible. That way the front desk will see this note from the GM's office and will take your request seriously, and do their best to upgrade you.
Have a fun trip; you are traveling to three great cities.