Category Archives: Travel

5 Nights in Cancun on Points

I am by no means a travel hacking professional, but I am trying to learn more and move past being an amateur. I’ve probably opened a new credit card once every six to twelve months or so for the past few years, but haven’t been that strategic about it.

I have a friend (let’s call him Mike) who I would classify as a semi-professional travel hacker / credit card churner and he’s been egging me on to get more serious about it like him. I have obliged somewhat, but when I start mentioning FIRE to him, he doesn’t return the favor.

Mike went to the brand new Hyatt Ziva Cancun all-inclusive resort right when it opened at the beginning of 2016. He was only there two nights but couldn’t stop raving about it. He told me “YOU HAVE TO GO!” I brushed him off for a while, but then started getting the vacation itch. The girlfriend and I were trying to think of what we wanted to do next for vacation. Europe was high on the list and we talked about it for a couple of months. We discussed the different destinations and possibility of visiting some friends over there. But in the end schedules didn’t work out and we decided to put this off until second half of 2017 most likely.

Then I started putting my travel hacking hat on. I started inquiring with Mike and reading some travel blogs. It seemed that Hyatt was offering a smoking deal for it’s Chase credit card. If you signed up for the card you received a $50 statement credit along with two free nights at ANY Hyatt property once you spent $1,000 in the first three months. The annual fee is waved for the first year, and then $75 per year after that. On every anniversary of receiving the card, you also receive a free stay (some restrictions) which will easily offset the $75 fee. This seemed like a no-brainer to me. I discussed with my girlfriend and she agreed, so then we both applied for the card.

Once we received the cards and both spent the $1,000 (we just did this with our normal spend), we were armed with a total of four free award nights. After doing some more research and talking to Mike, we were super pumped about booking the Hyatt Ziva in Cancun. I thought “if we’re flying down to Mexico, let’s try to stay another night.” So with a little more research I found out booking a 5th night was only 25,000 Hyatt points. I had 11,000 from work travel, my girlfriend had 5,000, so I only needed to come up with 9,000 more. Luckily Hyatt is a transfer partner for Chase Ultimate Rewards. The Chase Sapphire card is my everyday card so transferring over 9,000 for an extra night was nothing!

I was a little nervous how much of a pain booking it would be since we were using my two nights, my girlfriend’s two nights, and 25,000 in points. I called with both of our Hyatt Passport numbers and booking it was easy peasy. It took less than 10 minutes. At the end of booking the reservation the Hyatt representative said “you know… if you booked this with cash it would have cost about $3,200!” I also have Hyatt status so she said there was a good possibility we would be upgraded. As a reminder this place looks like the bee’s knees and is all-inclusive.

Flights were pretty simple as well. We’re traveling in January which is pretty far away so I wanted to book flights that wouldn’t cost me an arm and a leg to change or cancel. When you book with Southwest using points, you can change or cancel your flights with full redemption of points and fees. So we booked two round-trip tickets to Cancun on Southwest for 47,000 Southwest points (transferred from Chase Ultimate Rewards) and $157 on fees. The Points Guy values Southwest points at 1.5 cents each so our flight “cost” us 47,000 x 0.015 + 157 = $862. Since there is no repercussion for canceling these flights, I’m going to be keeping an eye on flights using cash and if we can get a good deal, I’ll save the points for another day.

As you can tell we’re extremely excited for this trip but it’s still far away. In the meantime I’ll be enjoying the summer and having a winter trip to look forward to.

Am I still a travel hacking amateur? Have you used points for a recent vacation? If so, share your story.

Note: I am not affiliated with any of these brands and the blog is not monetized. This story was just too good that I had to share.

The Move

The Move is officially complete and I’m publishing this post from the Midwest. The last month has felt like a blur. With a bachelor party, grabbing dinner and drinks with friends/coworkers in the city before I left, actual work, cleaning my apartment, throwing junk away, donating clothing, and selling furniture (I ended up selling basically all of my furniture and netted about 440 bucks which I was pumped about), I’ve been quite busy.

Figuring out how to get myself and my stuff to the Midwest was stressful to say the least. I learned that moving companies price their one-way truck rentals based on supply and demand of each location. The big name truck rental companies wanted about $1,200 for a one way truck rental. I almost spit out my coffee when that popped up on my computer screen multiple times. Apparently they need trucks in the Northeast and don’t need them in the Midwest. If I wanted to drive a truck from Atlanta to NYC, it would of only been around $200. Renting a truck quickly fell off my list of ways to move.

So then the wheels started spinning in my head of what to do. I could rent a bigger car or SUV and drive it to the Midwest with my stuff. But then I would have to sell all my furniture. I ran into the same pricing issues with driving the truck rental one way. I’m way too frugal to spend an arm and a leg on a car rental to move my not-that-valuable crap to the Midwest.

Then the best plan of them all came. My sister volunteered to drive her SUV the 2.5 hours to my apartment in Manhattan and help me load it up and bring it to my parents’ house. I thought this was great idea, because it would really force me to pair down my stuff and then I could find a cheap flight to the Midwest and call it a move. I’ve been trying to welcome more minimalist qualities so this ensured that I would have to sell my furniture, donate a ton of clothes, and throw away stuff I didn’t use. This option was a win on all accounts.

This plan worked to perfection. I paid my sister for her gas and troubles, and took her out to lunch. I then booked a $150 flight out to my girlfriends’ in the Midwest (I also got upgraded to first class and was able to check three bags for free, that has to be a good omen for the move and relationship right?). The approximately $200 in moving costs definitely trumped the driving time and potential $1,200 plus gas I would have had to spend on a truck rental or $500 plus gas I would have had to spend on a car/SUV rental.

My parents are doing me a big one by letting me store a bunch of stuff at their house. I luckily (or unluckily, depending on how you look at it) have to come back to the Northeast about a half a dozen times this year for weddings and other events, and will fill a big suitcase every time I swing by my parents. Aren’t parents great?

The stress of the process was a pain, but I’m very happy the move is finally over and that it went according to plan. Now I can concentrate on living the Midwestern life, my girlfriend, and my FIRE goals.

Other happenings

On a side note, some of you saw my tweet a week ago about how an email saved me $2,000. Without going too far into the weeds, when I moved to NYC work loaned me $2,000 with the expectation that I’d pay them back when I moved out. Well that time came and HR emailed me to start figuring out my repayment plan. I obviously would rather keep the $2,000 for myself so I replied to the email noting that I didn’t think it was necessary for me to repay the amount for XYZ personal situation reasons. I didn’t hear back for about a week and then I got an email noting that forgiveness of the loan was approved and it’ll be treated as income, but they’ll foot the tax bill as well! It never hurts to ask people

My boss, who I discussed in my last post, took a group of us out to dinner for my farewell. It was a great time. The core group of guys I work with are the reason I haven’t left my company, even though I could make more elsewhere. We enjoyed a great dinner at a nice restaurant, with a few bottles of red. I felt appreciated which was nice and these types of events funded by work are something I’ll definitely miss when I leave.

I’ve had a string of good fortunes lately which I cannot deny. I hope I don’t revert back to the mean anytime soon with a string of bad luck. I hope everyone’s Mays are off to as good of a start as mine.

Any big life changes on the horizon? Anyone moving to another state?

Attaining A Remote Work Arrangement

In my last post I shared how although my job is in NYC, I will be working remotely for six months and moving in with my girlfriend in the Midwest. It is an exciting time, of which I spend a lot of figuring out the logistics of the move (which will take place in May) and what to do with all my stuff. I am currently in the process of going through my belongings and donating, throwing away, and selling things (cha-ching!).

Let’s take a step back and talk about how I was able to convince my employer to allow me to do this. I’m going to be fully transparent when I say it took a little bit of skill and a lot of luck to make this happen. To be considered for a remote work arrangement, I think you and your job need to meet certain criteria.

Do a majority of your work from a laptop. In my line of work I spend 95% of my time staring at my laptop. We even do conference calls from out laptops now and don’t even have to pick up the phone! If you’re a plumber, carpenter, or high school teacher, it is very highly unlikely for you to get a remote work arrangement for this reason. In my line of work I travel once a month on average and this will allow me to catch up with coworkers on a regular basis to ensure they know I’m still around. If work or clients don’t sponsor trips like this, it can be harder to have real life face-time with your coworkers and bosses.

Be highly rated and respected at work. Let’s face it if you’re the average worker just punching the clock, it’s less likely your boss would approve something like this. I don’t plan on my career lasting until I’m 65, so I don’t see a point in wasting my time now coasting by. I try to show that I care about work and exceed expectations. This allows me to get away with certain things that some coworkers may not. It gets me more autonomy, more paid for lunches and dinners, and apparently a six month remote work arrangement.

Convey to your boss that your performance will remain the same. Some people have a bad perception of remote work arrangements. Maybe people think you’re just going to sit on your ass all day in your pajamas and get nothing done. I actually do great work when I’m not at the office since I don’t have many distractions. I made sure to convey that my work product would not change at all. My boss did voice concern about my ability to develop those in the ranks below, but I assured that this would not be an issue.

Have a good boss or one who seems to care somewhat about your well being. I’m quite friendly with my main boss. Me working for him wasn’t exactly random. I knew I liked the guy and working on his projects, so once I had the opportunity to work for him, I made sure to do a bang-up job so that he’d keep me around and it’s definitely paid off. He’s a family man and values his time out of the office, and therefore seems to value mine as well. If I was consistently working on projects for the people who eat, sleep, and breath for working at the office, they probably wouldn’t have been as supportive. Some people think that you don’t have any control over who you report to in your career, but I’ve found out with careful planning and some effort, this can be managed to your benefit.

Get lucky! I understand this isn’t an option for everyone and realize that luck did play a role, and for that I’m very grateful.

After the fact I did some reflecting on how I actually presented this idea to my boss. In hindsight I realize I didn’t really ask permission. I had been trying to meet with him live for over a week but he was traveling, so the first thing I did when I caught him in his office was joke that I wasn’t putting in my two weeks to lighten the mood. I laid out my plan for working remotely from my girlfriend’s (he knew I was in a long distance relationship) and assured him we could make it work, that my performance would remain high, and that this was something personal I needed to do. He voiced a couple BS concerns of which I countered, and then he voiced his support. I wonder if my outcome would have been different if I walked in and asked his permission instead…

Do you work remotely? If so, how did you negotiate that arrangement? If not, what is keeping you from asking/telling your employer this is what you would like to do?

Leveraging Friends and Family for Cheap Travel

I use my friends and family to save money on traveling and I’m not afraid to admit it. Why pay for a hotel or Airbnb when you have friends and family more than willing to have you at their homes or second homes for free? Why pay for a rental car when your family has a spare they’ll let you use while you’re in town? This kind of trip also kills two birds with one stone. You get to travel and see places that you enjoy, while spending time with the people you love and maybe don’t get to see as often as you’d like.

I just got back from one of these trips down south and it was great! And while I never classified myself as frugal, this is a great way to take a lot of the cost out of vacationing. See the breakout of my expenses for the 7 day trip below:

Flight – $256
Restaurants & take-out – $182
Transportation – $68
Groceries – $40
Entertainment – $23 (park entrance fee and greens fee)
Grand total – $569 or $81/day

Spread that over 7 days and my trip only cost me $81 per day. Not bad considering some of these costs covered part of my girlfriend’s expenses and a thank you breakfast out for our hosts.

Things we did over the course of the week: saw a minor league baseball game, walked up to the highest point in Georgia, went on a boat, golfed, ate out multiple times, walked on the Appalachian trail, grilled, did Sudoku’s, watched a movie, etc. Not bad for 81 bucks a day, if I do say so myself. Plus for a majority of the trip it was nice to “sign-off” from being connected as where we stayed most of our trip did not have wifi or much cell phone service.


Views from the lake

I definitely plan on returning the favor to my friends and family down the road (once I move out of a shared apartment in NYC). Whether that be hosting guests in my RV while I travel, at my home wherever I decide to make it, or in my month long rental in Barcelona if I decide on that. Traveling is fun and it’s even more fun if it is with friends and family, on the cheap!

Do you leverage friends and family for cheap vacations? Do you invite others to your residence while they travel?

The MIA to LGA Debacle

It has been a hectic month or so with work and a bunch of personal events and travel. Seeing family and friends and sharing experiences with them has been great, but my recent trip home from Miami was less than ideal.

The flight down to Miami was exactly how you wish every flight is – uneventful. Coming home was another story. I had arrived at the airport pretty early, about an hour and a half earlier than my departure. I hadn’t ate breakfast yet, so I went over to the food court area to grab a bite and kill time. I walked back over to my assigned gate and my flight had been delayed about two hours due air traffic control. Apparently NYC airports were experiencing high traffic and congestion and therefore we were taking off around 1pm instead of the scheduled 11am.

I was returning from a bachelor party so obviously this delay seemed about two days, not two hours. We finally board the plane and take off around 1pm headed for LGA. We were supposed to land around 330pm (originally scheduled for 130pm). I looked at my watch and 330pm came and went. I was wondering what was going on. Finally the co-pilot came on and said we were going to be hanging out in the airspace to the south of LGA while traffic cleared up. Oh great, more delays. Another 20 minutes or so passed and we get the announcement that we’ll be landing in about 10 or 15 minutes. It was very overcast that day so I couldn’t see anything out the window but clouds. Then I heard the landing gear come down and I thought “About time!”

Well I learned if the landing gear comes down, it doesn’t mean you are actually going to land. I could feel the plane pulling back up and the landing gear retract. It’s approaching 430pm at this time and the co-pilot comes on again. He said that we were low on fuel and headed to Bradley International and he’d have more information for us when we are on the ground there. For those of you not from the Northeast, Bradley International airport is in Connecticut half way between Springfield, MA and Hartford, CT.

About 20 minutes later we’re on the ground in Connecticut. Apparently people were not listening to the previous announcement because when we landed I heard a bunch of people saying things like “This isn’t LaGuardia!” or “Are we in Connecticut?” One girl in my isle that might of had one too many vodka sodas had to be told twice that we weren’t in New York. We get to our gate and the pilot comes on explaining what had happened (air traffic control basically would not let our plane land due to congestion), but had no idea what was going to happen next. I had already been traveling for about eight or nine hours at this point. I was starving as all I had was breakfast at the airport and some Delta peanuts. I was also a little pissed off since I was scheduled to land at LGA at about 130pm and it was now 530pm and I was in Connecticut.

They kept us on the plane for about a half hour and then said we could get off the plane and grab food and wait to hear more. Myself and many others had decided that this was our final destination and made other plans. Delta were unsure if and when the flight would be returning to LGA. I said “screw this! I’m taking Amtrak back to Penn Station.” I grabbed my carry on luggage and headed to the train station.

I got home around 1130pm (about 9 hours after originally planned) and was exhausted. I was just happy to be home, and wasn’t going to let a bad travel day ruin the fact that I had a blast the past few days.

The next day rolls around, and as you know I love to negotiate when I think the service or product I’ve received has not been worth what I had paid for it. I go on to Delta’s webpage and filed a complaint. I explained everything that happened which I discussed above, plus the fact that I’m a frequent Delta flyer for business and personal which is true. I asked to be compensated for the lack of information I was given throughout the whole process, my Amtrak ticket, and the delays.

So as you are probably wondering, let’s go over the numbers:

I had spent $230 on the flight which was a round trip Delta flight (LGA to MIA). I then spent $42 on an Amtrak ticket from Hartford, CT to Penn Station which I was not planning on. When the Delta representative responded to me the next day, they had said they were issuing me a $42 refund for my Amtrak ticket and 5,000 Delta points for my hassles. At first I was like well the $42 is nice and 5,000 points will get me maybe a fourth of a flight. I told my travel hacking friend what they had given me and he basically said it was terrible and that I need to respond back with another complaint, which is exactly what I did.

I basically laid out all the facts again, but in a harsher tone (not mean but I made it clear I was not happy with my service). They responded back quickly with a $50 gift and said they’d follow up with another email shortly. I thought the $50 gift would have to be used for Delta, but to my surprise (and delight) I was able to get a $50 Amazon gift card. Then I received another email saying I would get a $101 refund as well (why $101, I have no idea). So in the end, with my persistence, I received $101 refund, 5,000 Delta points, and $50 gift card. Not bad if I do say so myself, and Delta did not lose a customer in the process.

Have you been compensated for travel issues? How did you go about getting the best deal for yourself?