What I learned cancelling 26 days of vacation: Travel Planning Amid a Pandemic

I’ve gotten lots of questions about planning new trips for this fall and I have to be honest, I have no idea what you should do. However, I can share what I’m doing and why, and I hope that’s helpful to you.

All airlines are treating this situation differently. Delta is not selling middle seats. Frontier is taking the temperatures of all passengers. Most are sanitizing the planes between each flight more than ever before. Some are offering low-risk or no-cancellation-fee flights to encourage folks to start moving around the world again.

But I’ve also heard stories of friends arriving at a busy airport, not many people wearing masks, full flights, and few terminal dining options open forcing folks even closer.

For me, it’s still too risky. Or at least in the way I have traditionally traveled.

Rewinding a bit…

Being responsible adults that we are, we thought after taking a three-week trip to Spain and Portugal in the fall of 2017 and then a three-week trip to Ireland and the United Kingdom in the summer of 2018, we should take a break for meaty international extravaganzas. So we spent 2019 exploring our own country (with a few trips to Canada sprinkled in as well).

Instead of a three-week trip, we ended up taking 15 long weekend trips. I convinced friends from two other cities to join me in New Orleans for my birthday; we explored both Portland, Oregon and Portland, Maine, Seattle, Prince Edward Island, Vancouver, Colorado Springs, Boston, Newport, Rhode Island, New York many times, and much more. It was the perfect “down time” for me while I planned Japan, Iceland, Italy and maybe Hawaii for 2020.

But of course that didn’t happen with the pandemic that hit us earlier this year.

So far, I’ve cancelled a three-and-a-half-week trip to Japan, a road trip to Dayton, a horseback riding expedition around Iceland, a trip to Montreal, and attendance at two weddings. And while I didn’t book flights to Italy, my opportunity for free lodging is lost now. Needless to say, it has taken a lot of retail therapy to get my credit card back to zero after all of these credits. (Any by retail therapy, I mean buying a house and outfitting it with new furniture and decor. Oops!)

While I’ve seen many friends and coworkers take their trips as planned or a few months delayed, I still feel it’s too risky to do the kind of traveling I planned and normally do. As I hear from my friends in San Francisco, Chicago and New York, the urban cityscapes just aren’t as appealing as they were 12 months ago. And international travel isn’t exactly a reliable choice either.

Why I’m not booking flights yet

Travel is such an emotional thing for me. It makes me feel alive; and experiencing other cultures and the scariness of the unknown is an adrenaline rush I don’t get in my everyday life. So many hours go into planning these trips to make them affordable and unique that cancelling them leaves me utterly heartbroken.

The trips I mentioned above were cancelled because the airlines and tour companies cancelled them. It wasn’t my choice. I’m grateful that choice was made for me, otherwise I might have gone anyway… I’m also grateful I got full refunds on everything I had booked. But I know that rebooking those trips right now might not end in the same result if I need to cancel again later.

Many are asking me when they can rebook. And my answer isn’t what they want to hear. While I’m tentatively planning 2021 as a complete redo of my 2020, same place, same time, same travel partners, I’m not actually booking anything. Standard travel insurance doesn’t cover these circumstances and if I rebook and things are technically open, but I don’t feel safe, I can’t cancel and get my credits back.

The risk of losing my money, the energy spent planning and booking, and the emotional drag of cancelling a second time isn’t worth it for me right now.

Traveling and travel planning should be so fun. Right now, with everything uncertain, it’s just not and I don’t want to force it.

What I’m doing instead

I get it; we’re all going a little stir crazy. Humans aren’t meant to live like this. But it’s important we are doing everything we can to not only prevent the spread to protect ourselves, but to protect our friends, family, neighbors, and coworkers.

My company isn’t allowing us to roll over vacation days or paying us out for any unused time come December. So what I would normally consider a healthy number of PTO days for a year, I now have to use in the last 6 months of 2020. Plus, for working so hard during the stay home orders, my employer was kind enough to gift us an #ExtraDayOff. With the self-imposed restrictions or no international and no flights, I’m trying to brainstorm what’s next for me.

• I’ve investigated the month-long road trip but I just don’t love driving that much, especially what I imagine is long, flat, nothing of the middle of our country in the heat of the summer.

• I’ve investigated AmTrak, but the timing of the stops are usually middle of the night so I’d want to purchase a sleeper ticket and a hotel room for the nights that we’d be in transit which doubles my costs.

• I’ve investigated just checking into an all-inclusive resort and hiding there until I drain my bank account but that might only get me a measly seven nights.

So while I thought 2019 was an interesting challenge in traveling only domestically, the second half of 2020 is taking it up a notch. Where to visit within driving distance of Columbus, Ohio where I feel comfortable wearing a mask, socially distanced from others, but still interesting enough to make taking PTO without coverage worth the effort?

So far, I’m thinking the Upper Peninsula of Michigan, the Poconos, Red River Gorge, Asheville, NC, and a white water rafting trip along the New or Gauley Rivers.

Any other favorites within a 500-mile radius of Ohio I should add to the list? I’ll share more as I finalize plans and begin to get excited about leaving my home again.

For now, you can find me still researching travel from my front porch. #StayHome still...

If you want help navigating this tricky situation, I’m happy to chat about your particular circumstances. It’s #FirstWorldProblems, I recognize, but it’s still sad and exhausting. I’m here with you.

10 Secrets to Finding Cheap Flights

Besides lodging, transportation can be one of the most expensive parts of your vacation. And while Google Flights is great, it’s not comprehensive. It doesn’t display all airlines (Southwest is notorious for not allowing API integrations with flight aggregators), and it usually only displays single airline or airline network tickets.

I won’t sugarcoat it; my way is time consuming and takes a lot of work. But it’s how I’ve gotten to travel around the world so affordably.

1. Subscribe to airline emails. At this point, I’m subscribed to most of the major airlines, but when I decide where I’m going next, I always subscribe to the local airlines. They most often share sales and new route info with email subscribers. That’s how all those cool travel websites get all their info. So consider all the wasted time between them seeing that email, writing an article about it, emailing you and then you seeing it. You’ll be able to move much more quickly on a deal (scoring better seat options) if you see it first. 

2. Subscribe to airline deal aggregators. Scott’s Cheap Flights, Fare Compare and Airfare Watchdog are great for scoping out averages for cheap airline costs, but I haven’t had much luck actually booking using those tools. Based on what I said earlier, you usually have only about 24 hours to purchase a flight if you see it through those alerts.

3. Ask around. Do you have a friend of a friend who just visited your destination? Ask if they’d be willing to share how much they spent in airfare and make it a goal to beat their cost.

4. Do the Google Flights search. It’s a great place to start and I use it throughout my research. I just don’t use it as my only option. You can use the cheapest fare listed here as another benchmark for the goal fare you’re looking to best.

5. Search in an incognito browser. I’ve heard rumors that airlines are sophisticated enough to track your cookies and increase fares on the second or third time you search for the same route, but I haven’t seen this happen. Better to be safe than sorry though, so I usually do all my travel research in an incognito browser window.

6. Start research early, but don’t buy yet. As soon as I decide where I’m going and when, I do a quick search. I almost never buy at this time though unless I’m booking fairly last minute travel. Some people will try to make a recommendation of how far out you should book based on the average data, but these recommendations are exactly that: averages. You aren’t going to find the super cheap fares this way.

7. Don’t wait until the last minute. Occasionally, I’ve found a great last minute deal, but that is usually a wholly spontaneous trip where we have a free weekend and I’m looking for somewhere to go. My friend Rachel and I flew to NYC for the weekend after finding $160 round trip flights on a Thursday (set to leave the following day). Consider who flies last minute: business travelers. Business travelers are less cost sensitive since usually their company is footing the bill. If they have to be in Vegas for a client meeting, they will usually pick the fastest direct flight and airlines know that so they don’t usually drop fares for last minute until the day or two before. This kind of adventure can certainly be fun, it’s just not how I usually operate for a planned trip.

8. Weigh time versus cost. Sometimes the cheapest flight will be a huge pain. Three layovers and 24 hours of travel that would take you 5 as a direct non-stop, fork over the cash to save the headache. 

9. Calculate fees. On that note, consider that the cheapest ticket might not be the cheapest based on all the extra fees. Some of the budget airlines charge for carry-on baggage, non-alcoholic drinks and snacks while in the air and sitting with your travel partners. Once you add in all your necessities, is it still the cheapest?

10. Start with your destination. Here’s the real secret. I almost always start with my destination. Is your destination flexible? If you’re doing Paris, London and Rome, is it cheaper to fly into Paris than London or Rome? Start there. If your destination isn’t flexible, does that city have multiple airports? Investigate which might have more options. Then I research (using Google Flights) which airlines fly in and out of those airports, even if they don’t fly to my home airport. Here’s an example. I was researching flights to Barcelona a few years ago. I found that TAP Portugal flew into Barcelona pretty affordably from many cities in the United States, but not my home city. So I matched up a TAP flight from Boston, Newark and Miami with the corresponding Delta flight from my hometown to those cities. Then I compared those totals with my other established baselines and found that if I used two different airlines and separated my round trip ticket into one way tickets, I would save a few hundred dollars. This is what takes time. This is what takes scratch paper to keep track of it all. But this is how I saved a coworker $3,000 last summer. 

If this kind of shopping around sounds fun to you, I’d love to chat about other strategies with you. If it doesn’t, let me do the hard work and save you the money and headache. Shoot me a note with where you’re heading and when and I’ll get started for you.

15 Ways To Stay Safe While Traveling

Sirens blared, the crowd roared and a stampede of rioters raced toward the market we were planning to visit for lunch in Boston yesterday.

Luckily the Lyft driver we chatted with that morning told us there was a protest (and counter protest) happening in Boston while we were there so it was on my mind as we wandered through the Back Bay and Downtown Crossing neighborhoods.

As the riot escalated, my husband and I immediately turned around and ran the opposite direction. Knowing what signs to watch for and what to do in a dangerous situation can make your vacation safer and more pleasant. And hey, we visited the market today instead.

Here are a few things to remember to give you peace of mind.

1. Talk to locals. Sure, they can share great restaurants and things to do, but they can also alert you to other things going on in the city like major events.

2. Be cautious in crowds. While crowds aren’t always a bad sign, large gathering places like shopping centers, stadiums and festivals are easy targets for criminals whether that’s pick pocketing, groping or an active shooter situation.

3. Respond, don’t react. When you hear or see something that doesn’t feel quite right, stop and think before acting. Taking a moment to analyze the situation and thinking through your options will help you make the best decision on what to do next.

4. If you do get stuck in something awful, call the authorities to get help. In the United States, 911 is drilled into our brains since toddlerhood, but be sure to check the emergency phone number in the country you’re visiting and even write it down in your itinerary for urgent access.

5. Take photos of your driver’s license and passport. Plus leave copies of your itinerary in your checked bags and with someone at home.

6. Stay connected with someone back home. If something happens in the city you’re in, you can certainly mark yourself safe on Facebook, but staying in touch with friends and family back home can help them worry less when they first see the news.

7. Sign up for STEP. If you’re traveling internationally, know where the embassies are, plus the U.S. has a great program called the Safe Traveler Enrollment Program where you can let the government know where you are traveling in case something does happen. They also send you security information and travel advisories before and during your trip. We found it incredibly helpful when we visited Barcelona during the Catalonian independence crisis.

8. Talk like a local. In my itinerary docs, I always learn a few important words in the local language in case they aren’t comfortable or don’t know English. Hello, goodbye, please, thank you, yes, no, do you speak English, where can I find, how much does this cost, where is the toilet, I would like, I’m sorry, pardon me, and cheers are a good place to start. I also like this picture book for when you really get stuck.

9. It’s okay to bail. As an experienced traveller and urban dweller, I feel comfortable in most situations. But there is no shame in revising your plans to avoid a potentially dangerous situation. Vacation is supposed to be relaxing and if you’re constantly looking over your shoulder, that will be hard. Trip insurance may help your recoup some of your sunk costs, but the airline change fees and hotel or Airbnb cancelation fees will be worth a smoother trip.

10. Wash fruits and vegetables. Visiting markets is one of my favorite ways to try local food, but don’t forget the general safety precautions you take at home.

11. Stay hydrated. You are most likely walking more than you normally do so be sure to drink lots of water. Before you leave on your trip, research if Americans can drink tap water safely in your destination. Additionally, your lodging may provide some information about water safety while you’re there. There are so many other things to consider if the water is unsafe: brushing your teeth, ice in your cocktail, and washing your fruit. No one wants to get an upset stomach on vacation.

12. Wear sunscreen. Mineral sunscreen is better for the oceans and some destinations prohibit chemical sunscreen. Also consider bug and animal safety as well as ocean and water safety.

13. Zip it up. I’m a big fan of packing a zippered crossbody bag over a backpack, but I also keep my hand over the closed zipper when I’m out and about as one more level of security. And with a crossbody bag, keep it on you at all times, no need to take it off like a backpack.

14. Protect your credit cards. RFID wallets can help protect your debit and credit cards from criminals swiping your information on the go.

15. If you can, look at your map and figure out your directions before you leave and don’t just stare at your phone as you navigate. You’ll look less like a tourist target for criminals, but you’ll also get to see more of your destination.

I can help you plan a unique and safe vacation or even just validate your choices as you plan your own. Reach out if you wanna talk about how to stay safe, or how to convince your mom that you will stay safe on your trip. Been there, done that.

5 ways to double your vacation days

We all wish we could quit our jobs and travel the world, don’t we? But for most of us, that’s not the best choice with our financial and familial responsibilities. So how do we make the most of our paid time off when we do take it.

1. Plan trips around company holidays. Travel can be more expensive around the high summer holidays of Memorial Day, Independence Day and Labor Day, but other times of the year like Martin Luther King, Jr. Day can offer an extra day of vacation without the premium flight/hotel bookings. Plus, does your company usually offer early release the day before holidays? Consider taking advantage of that discreetly too.

2. Can you perform your job remotely? Perhaps there is work you can do while you’re sitting at the airport or even on the plane. Aircraft wifi may be worth the cost if you can get a few hours of work done while you travel. Then you won’t need to take that day as PTO. Of course you should always run all of this by your manager to make sure you are meeting expectations about your work while you are away from your desk. They’ll be able to guide you through what is appropriate at your particular office and what isn’t.

3. Plan to leave immediately after work. This works well for travel times less than four or five hours. Pack your bags the evening before and throw the morning toiletries in before you leave for the office. If you can get the flight or long drive out of the way between 5 p.m. and 10 p.m., you’ll get to wake up in your destination and start exploring immediately instead of wasting the morning traveling and then the evening recouping from your travel.

4. Nap in the middle of the day (yes, like toddlers). Be a narcoleptic weirdo like me. Get up early and hit the sights by 7 or 8 a.m. Do your thing and then when you’re tired, come back to your Airbnb and take a nap. Then freshen up and head out for the evening. You’ll find that allowing yourself to take a break in the middle of the day helps you get up earlier and stay out later, giving you significantly more hours than if you started your day about 10 a.m. and ended it right after dinner. Now, I know not everyone is so lucky to be able to fall asleep in the middle of broad daylight within five minutes like me, but that downtime in the afternoon can still give you a refresh to keep dancing long into the night so you don’t have to leave the local concert before the encore. Plus you may even beat the heat of the day if you’re traveling somewhere warm.

5. Sleep before and after your trip. Try not to stay up late packing or cleaning your home before you leave. Make sure you leave for your trip well rested. It’ll improve your mood and make the whole thing a more positive experience. I think it’s okay to lose a little sleep to add in a few extra activities while you’re away. You can catch up when you return home and there aren’t as many new and exciting sights to see.

Everyone’s idea of what travel is supposed to be is a little bit different so take all this with a grain of salt when tackling your own trip plans.

Vacation: How to Decide Where to Go

Deciding how to spend your PTO next year can be an overwhelming feat. Perhaps you’ve always dreamed of the great American road trip with your spouse, taking your daughter to Bordeaux, or treating the family to a resort vacation in Jamaica. But if you don’t have something in mind, here are a few ideas to get you started.

1. Find a globe, spin it and stop it with your hand. Visit wherever your index finger lands. Just kidding! Although wouldn’t that be kind of fun to try just once? Odds are you’ll end up in the ocean, but hey, just choose the nearest island.

2. I keep a list of destinations on my Trello board so I can add things when I find myself considering the locale so I can recall it when I begin my next planning session.

3. Ask friends you trust where they have visited and loved. But also ask them where they didn’t enjoy as much so you can keep that in mind when someone else recommends it. My favorite way to take advantage of their recommendations is to mark them as Google Maps flags. You can mark places as gold stars, want-to-go, or favorites. I started my Google tagging before want-to-go and favorites were options so most of mine are just stars. It works the same way. I use this for planning later too.

4. Pay attention to daily conversations. People will recommend different things if you outright ask, but make notes when they mention things in casual conversations. If someone mentions they loved the restaurant they patroned this weekend, I’ll mark it. Random mermaid themed bar in the middle of Montana? I’m not headed there soon, but someday I’ll be glad I saved that quirky little spot. 

5. Decide what kind of trip you want this to be: relaxing or adventurous? Who will join you: your spouse and children or just your sisters? These answers can help narrow down what might be exciting for the group.

6. Check review sites, but don’t take them too seriously. They can be great for the basics, but how do you know if you have the same tastes as those weirdos from the internet? Usually the recommendations from friends float to the top of the Trip Advisor lists, but not always so it’s great to have that validation. Also I’m pretty averse to crowds and often get stressed out when I’m forced into one. So while the top restaurants on Yelp are probably delicious, they are also probably packed and you won’t be able to get a quiet table anyway. Don’t get me wrong, I’ve waited in line for three hours waiting for New Orleans’ best fried chicken at Willie Mae’s Scotch House, but I knew what I was getting into before I planned to eat there. Sometimes it’s totally worth it. But Junior’s in Times Square? Not so much. Sure, it’s convenient and everyone will recommend it, but it’s not worth the crowds and wait. There are hundreds of other options that will serve you better food, better service and fewer sweaty tourists.

If how you spend your paid time off from work is important to you, consider vacation planning an ongoing part of your week. If it’s not and you’d rather just get excited and board the plane, I’m happy to help.