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Last week, I discussed a job perk called alternate weekend travel. This policy allows employees to add personal travel to obligatory business trips as long as it doesn’t increase the cost paid by the company or client.

While reporting the story, I spoke to employers who offered the perk and employees who took advantage of it — but I’ve yet to meet anyone maximizing the “alt weekend” to its full potential.

In the five years I spent traveling weekly to clients when I was an IT consultant, I used alternate weekend travel to fly to a destination of my choice more often than I flew home. I racked up hefty mileage account balances and unforgettable experiences at little to no cost to me.

A free weekend in Copenhagen? I
A free weekend in Copenhagen? I’ll take that adventure and those miles.

My Experience With Alternate Weekend Travel

When I was a consultant, the policy was rarely explicit. It didn’t have an official term like “alternate weekend travel.” Many of my coworkers just called it “whatever Brian does on the weekend.”

My employers allowed the practice but sometimes deferred to the client who was less familiar with the concept. The policy usually came down to the project manager (read: the person approving my expense reports).

I took full advantage of this perk, and at times it seemed like I was the only one. Through completely approved methods, I fine-tuned the process and expanded my reach, all while maintaining a successful project role and happy bosses. It made me a happy employee, too. I actually stayed with companies longer than I otherwise would have if I didn’t have the option for these weekend trips.

Most of my alternate weekends were within the US, which wasn’t uncommon for my colleagues, either. I visited most major US cities, as well as Disney World, Las Vegas and Yosemite. I took ski trips to the Rockies and motivated an ex-girlfriend to move to Charleston, South Carolina, because I’d much rather visit her there than Charleston, Illinois.

Eventually, I began using my alternate weekends to travel beyond the continental US, visiting England (three times); France; Italy; the Netherlands; Iceland; Denmark; Ireland; the Caribbean destinations of Puerto Rico, the Cayman Islands, the Bahamas and Jamaica; Belize; Guatemala; Mexico (also three times); Canada; the Hawaiian islands of Oahu, Maui, the Big Island, Kauai and Molokai — some more than once; and Alaska.

Not only was I getting free weekends in these far-flung lands, but I was also collecting the miles from all of these travels. Unfortunately, most airlines now award miles based on spend instead of distance, but I did pull in some great weekend tallies at the time. My alternate weekend to Japan netted me over 21,000 redeemable miles and cost me nothing.

Of course, the miles on these trips still counted toward elite status. I maintained United Airlines 1K status for all five years and reached American Airlines Platinum for a handful. Alternate weekend travel was a big reason I earned United Million Miler status.

While my examples may be extreme, they were all within the bounds of my project rules and received the approval of my managers. But successfully pulling off these weekends was a bit of an art that I perfected over the years.

While I’m thrilled to see companies adopting — and even encouraging — alt weekend policies, my friends in consulting still say it’s underutilized. That’s why I’m sharing the best practices I developed to maximize (but never abuse) this very valuable job perk.

Understand the Corporate Policy

Look through your company’s travel and expense handbook for a policy on combining personal travel with business travel. If it’s not specifically addressed, ask your human resources representative for clarification. Just don’t make this the first question you ask as an employee. Remember: This is a job perk and shouldn’t be the focus of your job.

Earn Respect From Your Manager

First and foremost, when assigned to a project or working under a new manager, you need to show your priorities are in order, understand your job responsibilities and demonstrate your value. Again, if your initial focus is alternate weekend travel, you won’t create a good impression with your new bosses.

Ultimately, the ability to maximize alternate weekend travel is left up to your manager, project lead or whomever is approving your expense reports. When these bosses see your priorities are the business, you’ll often be rewarded with more freedom and privileges.

This means you may not be booking alternate weekends in the first weeks or even months into your new gig. I didn’t start booking weekends to Europe until over a year into my projects. But after telling my boss on one engagement, with whom I already had a good working relationship, of a domestic trip I booked for myself and some coworkers, he told me he thought it was a great idea. I was young and available, he agreed, so I should be making the most of these weekends. So I did.

My first stay in a hostel was during this alternate weekend in Paris. I
My first stay in a hostel was during this alternate weekend in Paris. I’ve since made hostels a way of life.

On another engagement, I checked in with my manager on a Monday morning in January after spending a weekend in Hawaii, and she noticed my tan.

“Nice weather in Chicago this weekend?” she asked with a smirk.

“How would I know?” I replied. We laughed, then continued our Monday.

Learn Your Optimal Flight Options

If you are on a long-term engagement that requires a weekly commute to a client site, and you’re anticipating frequent alternate weekend travel, your “home” airport actually shifts from your actual home to the client site. This is from where you’ll be booking your alternate weekends. Learn the best airlines and flight options from this airport. Perhaps consider doing a status match or challenge with an airline that operates a hub in this airport.

From your new hub, you may have access to destinations that are more expensive or difficult to reach from home. These destinations could be a quicker or easier commute than a flight back home would be, giving you more time to enjoy your alt weekend.

While most of my alternate weekend travel was domestic short hauls, I often opted for longer flights to more exciting locations that I was better positioned to reach from my client site. From the West Coast, flights to Hawaii were only 90 minutes longer than flights home to Chicago. From the East Coast, while flights to Europe were substantially longer, I found great deals in the winter.

I discovered this hike through Haleakala crater on an alternate weekend in Maui.
I discovered this hike through Haleakala crater on an alternate weekend in Maui.

If the nature of your work doesn’t require repeat visits to the same site, you can still stay the weekend in the city you were flown to, but you’ll be responsible for weekend lodging costs. Or, if you find a one-way flight elsewhere that costs the same or cheaper than your return flight home, you could book your flight there for the weekend. Then you’d only be responsible for the final leg.

Document Flight Prices

Whenever you book alternate weekend travel, take screen shots of what a return flight home would cost. You should be able to show the flights you’ve booked cost the same or less than your standard return flight. Even if you manager doesn’t initially require it, it’s good to have in the rare case an issue does arise or questions come from the client.

Push for Flexible Hours

If your job calls for a set number of work hours every week, inquire about a flexible work schedule. When I was working at client sites, I often didn’t mind working well into the evening when the alternative was sitting in my hotel room. I’d often put in my 40 hours by Thursday, then fly out for an alt weekend on Thursday night. I’d get a long weekend without paying for flights and without taking any PTO.

Gamble With Flights in Advance

You’ll generally be given a guideline as to how far in advance you should book travel. For me, it was two to three weeks in advance. These policies are in place so companies wouldn’t have to absorb the cost of several months of tickets if an engagement abruptly or unexpectedly terminated. Therefore, the price allowance for alternate weekend travel was usually the cost of a ticket to return home two to three weeks in advance.

However, for some of the more extreme alternate travel I did, I found fares several months in advance. I knew that if my project or role ended, I would be on the hook for the ticket cancellation fee. It was a gamble I was willing to take to be able to spend a weekend in Europe, and I only took it when I was confident my project role would continue. For the many flights I booked outside of the standard booking window, which includes most of those listed above, I never had to swallow the cost of a ticket.

OLYMPUS DIGITAL CAMERA
London was one of my first and favorite international spots for alternate weekend travel.

On most of my engagements, we were given a maximum reimbursable amount for alternate weekend travel. For flights that cost more, I’d apply certificates I’d gathered from flight delays or issues. So be sure to ask for compensation when appropriate.

On the conclusion of one engagement, we were told not to book our flights for our final weekend until we knew the exact schedule of our final presentation. Because we had put in long, exhausting hours, we were given an extra long weekend for free. My managers had already left, and I was told to book my flight home for that evening. On a whim, I decided to check last minute flights to Iceland and found comparable airfare. I decided, even if I had to pay for the flight out of pocket, the weekend in Iceland would be worth it. At the risk of sounding old, this was long before going to Iceland was cool.

After the weekend and our final presentation, I told my boss I hadn’t gone home the previous weekend, but I was willing to pay for the flight that I did book. He asked where I went, and when I told him Iceland, he laughed for about a minute. He asked the price, congratulated me on finding a good fare and told me to expense it. “I hope you had fun,” he added.

When I was staffed in one of the few cities in the US serviced by Icelandair, I gambled on an alt weekend to Iceland.

Some companies make you book travel through a corporate travel agency or with company cards, and that may complicate this process. Some may not approve flight bookings outside of the standard booking window. So this method especially requires you to have a good understanding of your project’s policy and your manager’s attitude toward alternate weekend travel.

Combine With Mileage Runs

Calculate what your elite status will be at the end of the year after all of your expected travel. If you are close to the next status level, use alternate weekend travel to get there.

I used this method when I first qualified for United 1K status. I was on pace to end the year five segments short, so rather than booking direct on my final four flights of the year, I booked three flights with a stop and one flight with two stops. It didn’t cost the client any more money, and for just a bit more of my own time, I was rewarded with 1K status and all of its perks.

Fly in a Friend

If you decide to spend the weekend in the city where you have been sent to work, often you’ll be allowed to fly a friend or family member to join you given the cost to fly them out is the same or less than your weekend flight home would be. Of course, verify this practice is allowed before doing so.

Alternately, if you don’t fly out a friend, you may be given the option to expense the additional nights in the hotel instead of a flight home, provided the hotel costs no more than the airfare would have. You could fly a friend out and remain in your hotel, but you’d only be allowed to expense either the flight or the hotel. This may be a good time to redeem your hotel points for the additional nights or your airline miles for your friend’s flight.

If you plan to spend the weekend in the city where you’re working, and you are renting a car for work, compare the daily rate to the weekly rate. I often found a weekly rental cost the same as a four or five day rental. I would then document the rental price of the work week, then book and expense the full weekly rental.

It
It’s a small world when you have free flights taking you to many parts of it on the weekend. This picture is from when I flew an ex-girlfriend to LA and spent the alternate weekend at Disneyland.

Use — Don’t Abuse

My approach to alternate weekend travel may seem like a bit … much. But I eased into it and always put work first. I had managers who didn’t mind where I went as long as I did my job well and didn’t cost the client any more money. And they got a happier employee for it.

The alternate weekends took work to put together, but the payoff was immeasurable. The stories and experiences I accumulated could fill a significant portion of a memoir. Like the time I had a Monday morning commute to work across nine time zones from Copenhagen to Los Angeles. Or the time a friendly conversation on my flight to Mexico got me an invite to a family reunion replete with mansions and yachts. Or the time I had so many flight disruptions on my alt weekend to Ireland that I was booked on 16 different flights at some point from an original four-segment itinerary.

I could have gone back to Chicago for the weekend, or I could have gone to Belize.
I could have gone home to Chicago for the weekend, or I could have gone to Belize.

And, of course, there are the many friends I made along the way — some I’m still meeting for regular reunions. So, if your company requires you to travel, don’t take a one-dimensional view of it being a work trip. See if it could be an opportunity for so much more.

The Points & Miles Backpacker is a weekly column appearing every Monday. TPG contributor Brian Biros, who has backpacked the globe for the past 15 years, discusses how to fund this adventurous, budgeted and increasingly popular form of travel with points and miles. He’ll also explore all things backpacking-related. Read his story here and his high-level approach here.

If you’re looking to back that pack up and get some guidance, send your questions to backpacker@thepointsguy.com!

Feature photo by Mantas Hesthaven on Unsplash. All other photos are by the author.

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