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(Almost) Free Weekends For the Taking

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There are hundreds of websites touting free travel tips, most of which revolve around credit card tricks (sign up bonuses, manufactured spending, or the like) or redeeming points/miles for trips.  But if you already travel for business, there are often many opportunities out there for free weekends.

My favorite way to get free weekends is to tack them onto trips I already have to take.  Traveling for business over 50% of the time gives me a lot of opportunities to travel without adding additional cost for myself (or for my employer/clients).  Here are a few tricks I’ve used in the last two years:

1.  Arrive early/stay late.  This weekend, I’m in Portland OR.  I was going to have to be here on Monday for business anyway (which would have meant a Sunday pm flight into the city) but there was no additional cost to fly in on Saturday morning instead.  I redeemed 7,000 points for a hotel room but otherwise my travel was free.  This trick works wonderfully when your arrival city is near where you’d already like to be.

2. Achieve cost savings.  If my airline ticket had been less expensive for weekend travel, I might have been able to get my hotel picked up as a business expense for saving money overall.  Early in my career, I worked for a firm that would pay for hotel costs if we saved money buying a “Saturday night stay” fare (which many years ago could shave hundreds off an airline ticket).  That policy meant that I gladly took a free paid weekend anytime I had to fly into a cool airport – either staying past a trip (and flying home Saturday night) or flying out on Saturday night for the following week.  I always netted a free day in the arrival city and ended up getting to explore dozens of US cities this way.

3.  Think about driving.  If you are traveling somewhere near enough to take your own car, driving can give you the freedom to head out early or leave late and tack on a weekend that way.  I sometimes find that the mileage reimbursement for driving to Austin is better than flying and I can add the extra time on with no problem.

4.  Use vouchers.  When I’m flying home, I’m sometimes flexible with my travel plans and can volunteer for an airline subsidized “bump” (payment to take a later flight, usually in the form of an airline “voucher” good for dollars off future trips or free flights).  This weekend, one of my friends came up to Portland to meet me.  She used a voucher to fly one way from San Diego from a conference and her firm picked up her flights to/from the west coast.

5.  Try multicity combinations.  If you have two close-together trips with time for a break in between, try using the multicity option to search for fares with a stop in between.  Last year I had to be in Ohio two weeks in a row – and it just happened that the weekend in between was my birthday.  I really wanted a long Paris weekend, so I priced the various city combinations until I found one that made two trips to Columbus with Paris in between cost only $75 more than two separate round trips to Columbus.  I paid the $75 out of pocket and the other trips were covered by work.  (My final routing was DFW-CMH-ORD-CDG-ORD-CMH-DFW.)  I’ve made similar trips many times over the years to Asia and Europe from anywhere to $0 to $400 out of pocket depending on the fare difference and have found that as long as I can document it well (cost of tickets otherwise versus the actual fare) that I can take the trip.  I’ve also traveled to Florida/New York (business) by way of Los Angeles at no additional cost with some creative fare searching.

6.  Consider an alternate city.  This tactic combines the arrive early/stay late concept with driving.  Sometimes the city where I want to spend my weekend is within a half-days drive of where I need to be for work.  When that’s the case, I’ll often buy a ticket to that city and drive to/from my work location to that airport.  Or I’ll purchase my one-way ticket to get to or from the work city or consider a one-way car rental.

7.  Work the layovers.  If you don’t have a ton of time but want to enjoy a few hours of leisure, consider a deliberately long layover.  I’ve used this tactic on many Fridays in my career – changing planes in Las Vegas with a Friday morning arrival and Friday night redeye departure, for example, used to be a staple of my late 20s (in 12-15 hours, you can cram in pool/spa time, some gambling, and either a fantastic dinner or a show before heading home).  In recent times, I’ve used it to hit an outlet mall near Chicago O’Hare, for dinner with friends in San Francisco, and to grab a cheesesteak and an art exhibition in Philadelphia.

There are lots of easy ways to get free leisure travel with business travel without dipping into the points and miles stash.  They just require a bit of creative thought and some patience to search for options.  With these easy tricks, however, your next weekend escape may be closer than you realize.


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