Andy is a currently a corporate pilot serving as a Gulfstream G450 Captain (manufactured in Savannah, GA).  Andy has almost 20 years in the aviation industry, where he’s previously served as a Boeing 747 Captain.

In this series Andy is going to show us how to get to experience the very finest luxury locations (Diamond Destination) without being a millionaire, and collect points along the way.  I hope you’re looking forward to learning a few tips from a frugal guy up at the very front of the plane, in the left seat.  Our first destination is Aspen, Colorado.

A beautiful destination nestled in the Rockies, the very mention of Aspen evokes thoughts of big money and America’s platinum plated elite set. The truth is, at certain times of the year, you can visit this gorgeous town without being a billionaire, and the locals are a surprisingly down to earth bunch and will welcome you even if you left your Lamborghini and black Amex at home.

The town itself is very small and easily fully explored on foot. From the end of April and into June it is decidedly off season in Aspen and the bargains come out of hibernation. The weather is normally very pleasant with temperatures in the 70′s. Here are my tips for a fabulous long weekend.

Flights into Aspen or Eagle close airport close by almost always involve a stop in Denver and are pricey. For example a round trip from Chicago or New York is $500+ at this time of year. Jump off at Denver and the fare is around $200. An enjoyable 200 mile rental car journey gets you the rest of the way and you then have a car to explore the area around Aspen.

Right now, Enterprise is offering weekly rentals out of Denver International for less than $10 a day! Taxes and fees bring it up to $109 for a compact week rental. If you have a credit card that offers full insurance all the better.

Once we’re there, where do we stay?  Seeing as we are avid point collectors we don’t want to pass up the chance of increasing our frequent flyer/ guest balances now do we?

The Grand Hyatt until the end of May and into the first week of June is showing a rate of $160 for a studio accommodation; a bargain for such a beautiful property offering the very best in service and amenities. As a comparison it’s difficult to quote high season rates such as November and December as it is fully booked already, but typical rates in mid-season are normally $475 for an equivalent room.

A potential Hyatt Gold Passport play for a couple would be alternate bookings in order to get 2 stays per person on a 4 night stay to take advantage of the current 4X/5X miles promo but only kicks in after the second stay. Participating airlines include United, Delta, and British airways.

This would net 5,000 miles between a couple assuming no prior Hyatt stays, and 8,000 if already on stays 2+. This does however mean you need to check out and back in under the other name every day and risk having to move.  That said, I have never had any issues doing so in various locations.

Also if you pay with a Hyatt Credit Card, you get 3 Hyatt points per dollar spent. On the subject of cards, remember the American Express(R) Premier Rewards Gold Card is one of the best cards to use for airfare as you get triple points (3x points) across any airline.

A must visit good value pitstop is Jimmy’s.  This Aspen Restaurant serves “Fierce American Food”. The bar features an award wining selection of tequilas and mezcals. Live Tango/Salsa music on Saturdays and live blues music on select Friday nights.  Rocky Mountain trout, ahi tuna, rotisserie chicken, meatloaf, and Chesapeake Bay Blue Crab Cakes can be found at this popular Aspen Steak House. The bar scene / people watching on a good night is world class.

Another favorite of mine is BB’s kitchen also with a great patio and Sunday-fundays with “adult brunch”: $15 bottomless mimosas, bloodies, and Shiner, or Trumer Pilsner complete with DJ.

Outside of chilling out and just soaking up the atmosphere of such a great town, the surrounding area is a treasure trove of hiking trails and natural beauty, a must visit is Maroon bells shown below.

Whether you chose to stay at the Grand Hyatt or not, the best deal on mountain bike rental seems to be Aspen sports http://www.aspensports.com/rentals/ with a location right at the hotel. Another tip would be book online for a 20% discount. This is an awesome way to fill your lungs with the fresh air, get some gentle exercise and cruise around some of the best natural beauty on the planet, maybe even catch a glimpse of the all American bald eagle.

Here’s to a wonderful mountain break!

Andy, thanks for some great tips and tricks!

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