Deeper Dive into Travel Rewards

After I published an introduction into travel rewards credit cards last month, I’ve heard from friends and family who are curious to learn more. Haven’t read my earlier post? Go back to the basics here with “Dipping a Toe into Travel Rewards.”

So today, I’m sharing my strategy as a resource for folks in my life who want to join me on my free (!) travels or for anyone who hasn’t yet discovered the educational resources I find most valuable. As a reminder, travel rewards credit cards are for folks without credit card debt and who are paying off their credit cards in full each month.

Here’s my personal travel rewards journey to date:

• I had the same travel rewards credit card for ages. I thought it was great because I had no foreign transaction fees, and because there was a travel portal where I could get up to 3% cash back for booking. That travel portal was hacked and my data was likely stolen. I realized around that time that my card wasn’t that great and I was missing out on a lot of travel rewards opportunities.
  • In summary, Bank of America isn’t great, but you already knew that.

• I didn’t know much about travel rewards, but I applied for the Capital One Venture Card and received a $500 sign-up bonus (as of writing, this card waives its first year’s annual fee) after putting $3,000 of expenses on it in three months.
  • How I used the bonus: I went with the option that is basically cash back on the card. I spent it on regular monthly expenses.
  • How I avoided fees: I paid my card on time. As I approached one year with the card, I called Capital One to downgrade to the Venture One Card, which has no annual fee.

• I applied for the Chase Sapphire Preferred Card and received a 50,000 Chase Ultimate Rewards point sign-up bonus after putting $4,000 of expenses on it in three months (at the time, this card used to waive the first year’s annual fee).
  • How I will use the bonus: This is enough points to fly to Iceland or Italy. I haven’t decided where I’m going yet! I’ll likely log into the Chase portal to book, but I can also transfer the points to an airline partner like JetBlue, United, or British Airways.
  • How I will avoid fees: I paid my card on time and no longer use this card. As I approach one year with the card, I will call Chase to downgrade to the Chase Freedom Card, which has no annual fee.

• I applied for the Chase United Explorer Card and received a 40,000 United MileagePlus points sign-up bonus after putting $2,000 of expenses on it in three months (as of writing, this card waives its first year’s annual fee).
  • How I will use the bonus: This is enough points to fly to pretty much anywhere in Mexico. I’d love to visit Oaxaca and Mexico City.
  • How I will avoid fees: I will make one phone call to Chase to downgrade to another United card which has no annual fee.

• I’m next working toward Southwest Airlines’ Companion Pass and the 125,000 Rapid Rewards points it requires. I’ll achieve this by opening two Chase Southwest cards, one business and one personal, which each have a 60,000 point sign-up bonus and putting $5,000 total on the cards within three months in early 2020.
  • How I will use the bonuses and Companion Pass: Once I get the Companion Pass, I can travel using my points and someone else can travel with me nearly for free for the remainder of the year I get the pass and the entire following year! My hope is to visit Hawaii within the next two years. Let’s see if I can convince my family to come along with me (hey, I know you’re reading this)! I’d also love to visit some of the National Parks out west⁠—I especially love desert landscapes.
  • How I justify the fees: These two cards both have annual fees ($99 and $69 for the business and personal cards I selected) which are not waived for the first year. But if I fly even one time using points and the Companion Pass, I feel I will have covered these upfront costs.

So that’s that. To make this happen I did lot of research (not all of which is required, but I’ve been an overplanner all my life), filled out a few online applications, made a handful of phone calls, put a new credit card in my wallet every few months, and referenced back now and again to a spreadsheet I use to organize everything. As a result, I might have six or more free roundtrip flights on my horizon.

Was this helpful? If so, let me know and I can follow up with simplest strategies for you to get started yourself, with links to more resources and a copy of the spreadsheet I use so you can track your travel rewards credit cards.

Are you ready to get started with travel rewards? I highly recommend the Chase United Explorer Card, since it has no annual fee for the first year and a lower requirement to spend $2,000 within three months in order to receive the sign-up bonus. And because the rewards are airline points, it helps ensure you get more world wandering in your life! If you wish to apply for it you can consider doing so with my referral link here (full disclosure: I will receive some bonus points, a travel win-win! I think it’s a great opportunity for any responsible credit card user, but please first read up on the terms and conditions for yourself).

The Mistakes I Made in Morocco and Spain—Ranked

When I picked out Morocco and Spain as the next big trip, I got straight into planning. I knew I needed to get tickets to Alhambra in advance, I knew I wanted to book some of the small riads, or guest houses, in Marrakesh that fill up quickly, and I knew I’d need to plan some internal travel to get between countries.

Despite my intentions, not everything went as expected. It was a great trip, but I learned some lessons along the way—which you can perhaps learn from!

In an attempt to organize the disorganization of my trip, I rated my personal travel fails on a scale of 1 to 10. Here 1 is a mistake that’s worth it or has such a silver lining I’d do it again, and 10 is an extreme travel mishap that’s hard to bounce back from. Check out my list of travel fails and lessons learned:

• Following someone who says they’ll help you find your hotel (3/10). This is a costly mistake, but a relatively benign one. We knew that we didn’t want this random man to show us to our riad in Marrakesh. Even though we had a map, he managed to stay one step ahead of us because our taxi driver told him where we were going and he didn’t have luggage to carry. He demanded payment, and we had to give him cash to get him off our backs. It was a mistake to not get rid of him sooner and one we’d been warned about, but I admire the hustle so I’d rate it a mid-level mistake. Lesson learned: Don’t tell your taxi driver your exact destination and/or just walk the other direction to get rid of someone.
• Losing a passport (9/10). As a rule, this is a very bad thing to do. Governments don’t like it. Police departments don’t like it. Luckily, I lost mine in Spain, a relatively small country where the government recognizes emergency passports (Some countries are big! Some countries don’t recognize emergency passports! Try extra hard not to lose your passport far away from the capital city or in a place like France where they don’t recognize emergency passports). Unluckily, we had to make a pricey day trip to Madrid where the U.S. issues emergency passports, but it’s a nice place to visit. It doesn’t take that long to fill out the paperwork and they don’t charge much to get a same day emergency passport, but you can be scrutinized extra hard when coming back into the U.S. It was a hassle, but I had an understanding travel partner for which I’m grateful and honestly, it could have been worse. Lesson learned: I don’t think I learned my lesson. Frankly, there weren’t enough consequences to compel me to start wearing a travel fanny pack.
• Not finding the most famous attraction (4/10). Somehow we booked advance admission to Granada’s famous Alhambra fortress and palace complex, printed our tickets, got in line at our time slot to visit the most famous and beautiful palace, and didn’t visit the palace? It turns out we went to the wrong ruin and after hours getting lost in the huge grounds, we left. Lesson learned: Read the signs. But also, you can always tell yourself you’ll go back to visit.

Looking for Nasrid Palace

Not the famous Nasrid Palace

• Getting the train timetable wrong (5/10). Generally speaking, if there are enough trains running, this shouldn’t be an issue. For us, it caused us to miss our flight back home. Lesson learned: Don’t trust online timetables.
• Missing a flight home (8/10). This is pretty darn bad, mostly because it can be expensive. I’d never missed a flight in my life so it was an experience for me! We were lucky and only had a $100 change fee per person, but we had to book an extra hotel night. Lesson learned: Plan to get to the airport early. Even if you arrive before your flight leaves, there are rules for some airlines that prevent you from checking in. I also learned I’m capable of putting on a show for the airline staff in French! They weren’t particularly moved by my tears.
• Booking a bad hotel (2/10). Our last-minute hotel after missing our flight was fancy (thanks, Hotel Tonight), but happened to have a terrible sewage issue. It’s hard to sleep if you’re not sure if you’re sniffing sulfur… or something else. Lesson learned: Read the most recent one-star reviews. Temporary factors like construction, traffic, health hazards, or yes, sewage smell seeping into your walls might not affect the average ratings right away, but might be the very reason that a place has availability or a discount.
• Finding out the flight you missed ended up delayed (9/10). Now this caused me agony. It was bad enough that we knew the plane hadn’t left yet and they wouldn’t let us through security. I never wanted to know this and the anger I feel about this will probably never go away. Lesson learned: Don’t ever let yourself or your loved ones look into flight status after you miss your flight. Let what’s in the past stay there.
• Eating food that makes you sick for days (1/10). I’d do it again. The food in Morocco tastes great and it would be more of a mistake to not eat adventurously. Lesson learned: Gatorade packets and mini mouthwash are great travel companions.

I definitely hope to visit both Morocco and Spain again, but maybe I’ll review this as advice to myself first.

Have you made some major travel mistakes? I’m sure I have more ahead of me, so share your lessons learned in the comments.

A view of a traditional village in the Atlas Mountains of Morocco.

Dipping a Toe into Travel Rewards

Over the past year, I’ve begun researching and diving more into travel rewards. For the longest time, I understood that the purpose of frequent flyer mile programs was to reward people who fly all the time, always with the same airline. That’s true, but for people like me who typically fly just a handful of times per year and take whichever airline is cheapest, there’s more opportunity when responsibly (key word here!) playing the travel rewards credit card game to rack up miles and points.

Like most people of my demographic in the U.S., I pay for the majority of my expenses with a credit card. I thought I was doing it right by paying off my bill in full each month and using a card that gave me 1.5% or 2% cash back on all purchases. But when it comes to the cash back, there’s a lot more to explore. For example, if I were to open a new credit card like Capital One’s Venture Card, once I spent $3,000 I’d get a bonus of $500. That’s closer to 16% cash back! I’m not endorsing this credit card in particular, I just find its value very straightforward. Imagine the opportunity if you got a bonus like that multiple times per year.

There are dozens of blogs out there explaining the ins and outs of each credit card offer and how to get the most out of each opportunity. I’d estimate I spent upwards of 40 hours learning about the rules and finding the strategy that is right for me. I don’t recommend this for everyone, because you can check in with someone you trust who knows this stuff and ask them to help you.

If you’ve handled credit cards responsibly in the past, you might be interested to learn more and test the waters. Here are some high-level things to keep in mind:

1. Pay off your card in full. I can’t stress this enough. If you’re failing to make your payments on time, the benefits of credit card points will be canceled out by the interest you owe and your credit score will prevent you from taking advantage of rewards in the future.
2. Keep an eye on your credit score. For many people, opening a new credit card actually boosts their credit score. That’s because your utilization rate (or the amount of credit you use each month relative to your total credit available) will go down. But for a short period right after opening a new card, your credit score may fall by 5 or 7 points, which is not ideal if you’re about to take out a loan or a mortgage.
3. Consider non-airline and non-hotel cards. The cards I find most flexible are actually not linked to a particular airline or hotel brand. As someone who flies different airlines and avoids pricey chain hotels, the best deals for me are travel cards from brands like Capital One (Venture Card) and Chase (Sapphire Preferred).
4. Check out cards that waive their first year’s annual fee. As of this moment, the Capital One Venture Card and United Explorer Card waive their first year’s annual fee. After your first year, you can request a change to a different, no annual free credit card from that brand, without impacting your credit score.
5. Plan your spending. If you’re going to be making a big purchase soon, you might consider opening a new card.
6. Track your timing. Make a simple spreadsheet for yourself tracking the date you applied for a card, the date you were approved for the card, and the date by which you’ll need to reach the minimum spend for the card’s bonus.
7. Sign up for as many airline and hotel reward programs as you can. That way you won’t leave any opportunity on the table. You can use AwardWallet to monitor your many reward balances for free. When you sign up for rewards programs, you’ll learn of lot of extra points opportunities from their email lists. For example, my credit card is now linked to an airline’s cash-back dining program operated by Rewards Network. I ignore the promotional emails that prompt me to dine at particular restaurants in the Rewards Network, but once in a while I’ll see I earned an extra chunk of change back for paying with that linked credit card at a restaurant that was participating without my even realizing!
8. Refer friends. Besides opening new cards yourself, the best way to earn points is often to refer friends. I find that this isn’t super straightforward.

In the past year, credit card points have proven to be a much better investment of my time than pet sitting, couponing, or any other frugal tactic. The best part to me is that this value is set aside for the activity I love most, travel. I’m working toward a possible trip to Hawaii and I expect to be able to get myself and someone else there for free. I already have enough points across three programs to fly to Bolivia, Mexico, and Iceland. I hope that this will enable me to go on longer trips to more far-flung destinations, and to splurge on activities since I don’t have to worry as much about the cost of getting there.

Stay tuned to see if I get to these places and hold me accountable to spending all these hard-earned points!

Adventure Without An Agenda in Costa Rica

When I boarded the plane to San Jose, Costa Rica, I did so knowing I didn’t have much in the way of a plan for when I landed. I made my way to the very back row of the plane, looking for my assigned middle seat, knowing I’d have something of an unpleasant journey ahead of me. I heard my future seatmates, a man and a woman, conversing in Spanish, so I told them in Spanish a basic “Hola, estoy aqui” with a more useful hand gesture and plopped down between them when the man shifted for me to slide past.

He asked me about my trip, and I told him I was traveling to Costa Rica for vacation for the first time.

“You’re in luck!” he said. He had learned our other seatmate worked in Costa Rica’s tourism industry.

The plane ride proceeded with almost four hours of recommendations for the preferred hot springs, debate about the best beaches, discussion as to whether there was any food a vegetarian should try in Costa Rica (the obvious answer: gallo pinto), and suggestions of how to best celebrate Independence Day. I took their advice to heart, and I knew it would be a trip full of surprises—not least after one seatmate decided he needed to drive me to a safer bus stop and the other invited me to go out with her friends. I said yes to these offers and some of the other unexpected opportunities along the way.

After I landed, I was welcomed on my first full day in Costa Rica with Independence Day parades and street sellers hawking red, white, and blue bandanas or pañuelos. The museums I thought I might visit were mostly closed for the holiday, and I took that as a sign to ditch my Lonely Planet ebook.

Many of the museums were closed for Independence Day, but we witnessed plenty of culture in the capital city anyway. (San Jose)

After meeting up with my friend who was traveling with me a day later, we soon escaped the city, following the itinerary of so many other tourists that scatter from the capital to the rainforest, volcanoes, and beaches. We found all the Costa Rican adventures we sought, but with absolutely no planning more than 24-48 hours in advance.

This is a drastic change from any other trip I’ve taken myself on. For various reasons (maybe the challenge of planning a trip as friends in two different cities or the thought that we’d figure out which areas were having better weather during rainy season if we waited it out) we simply showed up with a hotel booked for the first night only, and weren’t sure where we’d go next or how we’d get there.

The guidebooks would tell you it was rainy season, but we never got caught in the rain. Instead, we had weather like this. (Monteverde Inn)

Here’s what I learned from the experience of traveling without an agenda:

• It helps to travel during the off-season. A lot more is possible at the same price when you visit during the off-season. But equally important, you can get around with more options and less planning if things aren’t booked up.
• Say “yes” to things that aren’t in the guidebook. Some of the most interesting experiences I had in Costa Rica were going out to drinks with the gal I met on the plane, sitting in the hot springs river (free) across the street from the deluxe hot spring spa ($100+), and letting a taxi driver stop to show us poisonous snakes and baby sloths in trees. None of these things made any loose itinerary I had in my head, but they are some of the most memorable moments.
• Say “no” to hitting more destinations. Packing new places in, especially places that require more long bus rides or journeys through airport security, doesn’t guarantee you do more.
• Give yourself the opportunity to visit again in the future. Feel comfortable promising yourself this doesn’t have to be your only trip to this continent/country/region/city. In this way, you can give yourself permission to do a less than perfect job of checking off every bucket list item.
• Traveling solo is fun, but traveling with someone might put you more at ease. I have traveled solo in the U.S., Montreal, and pretty extensively through Western Europe. But as a woman, I felt more comfortable traveling in a new region and a place where I didn’t speak the language fluently alongside a close friend, and I was grateful for how it allowed me to be more open to new people and new ideas without being as worried about my safety.

There’s a chance that I’m at least partially changed from my old ways—daily schedules driven by TripAdvisor and Google Maps—to something of a more free-spirited traveler. I’ve not yet planned what destination my next no-itinerary trip might take me to, but maybe that’s the point.

The next adventure awaits. (Selvatura Park)

5 Last Minute Gifts That Give Back

With so many meaningful gifts out there, you may not have time to sort through them all. I sourced this list of gifts from 4-star Charity Navigator-certified charities and top ranked B Corp certified businesses to make giving easy (even with just two weeks ’til Christmas!).

1. Give the gift of giving: GlobalGiving, which features thousands of nonprofit projects in 160+ countries, offers eCards and print-at-home options for gift giving in a pinch. (Full disclosure: I work for this organization, which also means I can vouch wholeheartedly for the incredible nonprofit projects your gift recipient can choose from!)
2. Plant a tree in tribute:  Lots of organizations claim to plant a tree for a donation of starting at just $1. But the National Forest Foundation is one of the few with a 4-star rating from Charity Navigator.
3. Share something sweet: Greyston Bakery makes the delicious brownies used in Ben & Jerry’s ice cream and operates an open hiring policy that provides job opportunities. Find them at Whole Foods or order online (they offer UPS ground shipping only so grab ’em fast)!
4. Support sustainability: Eco-friendly outdoor brands are easier to find than ever.  But Patagonia packs a purpose a notch above the rest, leading the industry as a company with B Corps certification, 1% for the Planet membership, and a history of eco-friendly product development. Gift something cozy for a warmer winter or enable adventure with a gear purchase for an outdoor hobby.
5. Lend a hand to literacy causes: With Better World Books, you can sustainably shop secondhand books and other media. For every book you buy, they will give a book to someone in need (they’ve donated 26 million to date). They’ll ship your order free in 5 to 9 business days. Gift a cookbook, artsy coffee table book, or a New York Times bestsellers – they carry them all!

Have a suggestion from a purpose-driven brand or top notch charity? Leave a comment!

Photo background by Leone Venter on Unsplash

How to Staycation Like It’s Your Job

I recently found myself with handful of days in which I had no obligations – no work, no travels, no obligations. I knew that sitting at home would get dull pretty quickly, so I made a list of all the things I’d heard or thought about doing in my new city (Washington, D.C.), but always assumed I couldn’t find time for:

• Visiting free tiny museums with limited hours
• Taking an off-the-beaten path guided tour
• Waiting in a long line for a popular restaurant
• Completing a (free) screening for TSA Pre-Check
• Eating through all the free food coupons that come my way

I can now breeze through airport security, I’m way more knowledgeable about Deaf education in the United States (thanks Gallaudet University Museum), and I have greater certainty that I’ll never be a real foodie (a restaurant may be famous, but I’m still a picky vegetarian).

I realized I don’t actually have to miss out on all these weekday wonders; I can take advantage of my own city with a staycation.

These are five things to consider to make the best of scheduled time off spent in your own town:

1. Ask around for advice.

Collecting ideas from friends or family about what to do and where to go is always a good idea, but it’s even more helpful when you can leverage your network that lives within that own city. Find out what places are beloved by own your neighbors.

2. Plan as much as is needed, and no more.

On the one hand, staycations should involve minimal scheduling and stress. That said, some activities require that you book months in advance, so it can pay to be organized.

3. Don’t do the things that you can easily save for the weekend.

Treat your staycation time as a special chance to do things you wouldn’t normally do. Otherwise, your “home spa treatment” day could morph into something inane like scrubbing the bathtub or clipping your fingernails.

4. Pretend you’re off the grid.

If you’re going to truly refresh, you won’t want to get sucked into work. Turn off notifications from your work email and apps, avoid the route you usually take to work, and plan your staycation dates around any must-attend after hours work activities.

5. Act like a tourist. Or don’t.

Where I live, there are plenty of tourist sites to be seen, and I feel it would be a shame not to take advantage of them. I also didn’t have any plans to stay somewhere other than my home. But your interests, budget, and location might dictate another plan. You can stay at home, book a stay in a hotel like an out-of-towner, or live out an alternate life in an Airbnb on the other side of town. You might want to spend a day at a coffee shop working on a passion project rather than doing something active. Either way, make the most of your free time!

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Have you staycationed where you live? Was it worth staying in your own town to get a new perspective? Or do you prefer to see somewhere new every chance you get? Share your thoughts!

What To Do When You Really Want More Paid Time Off

Most Americans don’t live life to the fullest. This is a bold statement, but I can back it up with data: the majority (52%) of U.S. workers don’t use up all their annual paid time off (PTO).

If you’re among the few who are already making the most of your PTO by using every one of your vacation days, these tips are for you. This is your guide to finding more time in your life for the fun things you’d like to be doing.

1. Get a new career.

Most jobs have 10 or so days of PTO. There are plenty of notable exceptions for career paths that will help you advance your vacation and travel goals.

• Work at a school: Take summers off, forever, by becoming a teacher or school administrator at an educational institution where summers are still sacred. The trade-off: low pay and burnout.
• Work for yourself: Set your own hours and decide when the can’t-miss meetings will take place by starting your own business. Ideally, your business won’t be brick-and-mortar, so wherever you travel can become your office (see: digital nomad). The trade-off: Never having a day off from being the responsible one.
• Work seasonally: Vacation destinations and farms often have jobs where it’s perfectly acceptable to stay for just the summer (or fall, or winter, or spring). By stringing along enough seasonal gigs, you can afford to take time off in between. The tradeoff: You may lack stability and you’re unlikely to make a fortune.
• Work in a travel profession: Traveling nurse, flight attendant, event planner, flight attendant, study abroad coordinator, au pair, English teacher. These entry-level careers can get you someplace new. The trade-off: You may be underpaid and you won’t necessarily be able to travel on your own terms.

2. Find a workplace culture that isn’t vacation-shaming.

Office life can be competitive in any number of ways. Who can brew the best pot of coffee? Who has the funniest meme in their presentation? It’s problematic when sizing up “Who is most dedicated to their work?” This takes the form of working long hours, being on email at all hours, or perhaps most tragically, rarely taking a vacation.

If you’re job searching but not ready to fully switch careers, look for a place of employment where you’ll feel comfortable actually using the vacation time that is part of your benefits package. This means avoiding workplaces where you receive “unlimited vacation,” which is often code for “vacation at your own risk.” A good way to judge is to ask a current employee or the hiring manager, “How much vacation do you typically take, and what are your expectations around vacation?”

3. Negotiate more time off.

Perhaps your company has long-standing policies around vacation, corporate holidays, personal days, and sick days. Maybe a PTO balance is something you earn with seniority. But people are creative (if there’s anything people excel at, it’s finding ways to not do their work) and you can take a lesson from the brilliant minds who have come before you.

• Delayed start date: The easiest and hardest time to take a vacation is before starting a new job. Your life may be in flux, but on the plus side, you have free time. Negotiate a few extra days, weeks, or months before you begin working.
• Comp time: If your work has a busy season, or you travel for extensive periods, push for “comp time” or compensatory time — days off to balance out the value of your overtime.
• Floating federal holidays: Most workers receive a handful of days off, scattered throughout the year. Some of these may have more meaning to you than others – Labor Day, Veteran’s Day, and Presidents’ Day are a few that, for me, hold no special meaning. Negotiate to take off the equivalent of some of these solo days together to form a full vacation week.
• Vacation seniority: Push for more vacation days in recognition of your years of dedication to your current employer.

4. Buy yourself time, literally.

Some employers will let you pay them (or deduct money from your paycheck) in order to get extra vacation time. Known as a “vacation buy” or “PTO purchase,” this is a trade-off between making money and having free time (you might guess my bias!).

There may also be the option to take unpaid time off, just check with your company policies first. Ask yourself how much you value your free time and how much money you need to meet your financial goals, then make a judgment call.

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I’m continuing to share out about topics at the intersection of travel and self-care, with a forthcoming post all about “staycations.”

Do you have advice or ideas for folks who want more paid time off? Share them in the comments.