5 differences between working remotely and going on vacation

While it is true that I travel a lot, I almost never take a vacation.

Because of my business as an attorney, I need to, at the very least, be accessible to my clients and engage in some kind of work wherever I go.  Despite all my travel last year, the only true vacation I took was to Palawan in the Philippines, and that was forced on me by staying in a village without any reliable WiFi.

After having just returned from an amazing South America trip, which took me through Colombia and Chile, I’ve been thinking about how working remotely differs from taking a vacation (aside from the obvious factor of having to work!).  Here are the top 5 ways the trips differ:

1. Reliable WiFi is key

The number one factor that dictates where I travel to is whether there will be reliable WiFi.

As a digital nomad, I can travel and work from virtually wherever I want, so long as I have steady access to reliable WiFi.  In terms of reliability, I need a connection with fast download speeds, that’s strong enough that I can have a call through Google Voice on it if need be, and where I can access the WiFi at all times from anywhere I am staying.

It’s often hard to determine places that will have great WiFi.  I’ve stayed at 5-star hotels with bad service and I’ve stayed in Airbnb’s in remote locations with strong signals. One way to ensure that you’re traveling to a place with strong WiFi is to stay at a place with reviews on TripAdvisor, Airbnb, or the like that mention a strong internet connection.

It’s also likely that more developed countries/cities, places with a large number of digital nomads, and touristy places will have better WiFi.  This isn’t always true, though – I recently was at a hotel in Santorini that had awful WiFi, despite me having no issues anywhere else on the island.

When I book real vacations, I am much less concerned about having reliable WiFi (and sometimes would prefer going without it).

2. Need to stay in one location for longer

When I travel for pure enjoyment, I usually like to bounce around a lot. I’ll often get to a city, stay for a night or two, then wander to a new location, and keep doing this until I have to go home (except if I’m relaxing on a beach somewhere, in which case I usually don’t mind staying put).

But when I work remotely, I realize that most days spent traveling are days in which I can’t work. On my recent trip to South America, I really wanted to check out Valparaiso in Chile, and even to head down to the Lake District. But because I had just bounced between Cartagena and Bogotá, I knew that it mean I’d have to stay put for a few days straight, and I ruled out any side travel from Santiago.

When you travel and you’re working remotely, depending on your business, you want to make sure that you’re spending most weekdays in one location, and limiting to travel to times when you wouldn’t otherwise be busy working.

3. Determining activities based on time difference, length, and accessibility

When you work remotely, you still want to experience the location you’re in. Sometimes this means doing something “touristy,” like booking an excursion, or going on other adventures.

When looking for activities, you want to make sure the length is only for a few hours (instead of for the full-day), that the activity doesn’t need to occur when you need to be working, and that you’ll have access to your phone and e-mail if you need it.

For example, I was recently in Belize and wanted to experience the snorkeling around their famous barrier reef. In picking a tour (full-day v. morning v. afternoon), I decided to go with an afternoon tour because my mornings were busier than my afternoons at that time, and I couldn’t justify taking a full-day off from work, despite the amazing tour itinerary.

4. Look for different types of rooms

Some friends who travel with me call me “Princess,” but I don’t mind. I love things like comfortable beds, hot baths, and great service.

In booking travel for remote work, I still look for all of these things, but something that is noticeably different is that the type of room I look for changes. For instance, on a typical vacation, I would be fine with a room that’s basically a studio, with only a bed, TV, and a very small desk.

When working remotely, though, that type of setup would not work for me.  Generally, I like some separation between my sleeping and working area, and I like places with large enough desks for me to have my laptop and at least a notebook and some papers comfortably next to me.  Additionally, I like finding places that have kitchens, so that I can cook food for myself, as venturing out for lunch in a new city/country can take a lot of time.

The places I get when working remotely are much more like apartments than hotels.

5. Views matter more

If you’re traveling to a new location and are working remotely, you may not leave your place much during the day. One trick to still enjoying your new location is to try and grab a place with an amazing view.

During a trip to Medellín, Colombia last year, I had so much work that I was pulling 10-15 hour days every day of my trip.  Luckily, I snagged an Airbnb with this amazing view.


When I think back to that trip, even though I barely left my apartment, I think about it fondly. That view was amazing, and I can’t wait to go back and experience it – and the city – again.

The pros and cons of San Francisco as a travel base

Having lived in San Francisco for over 5 years, I wanted to evaluate what I love and what I dislike about the city as my travel base.


It’s an awesome city

San Francisco1.jpg

One thing I always try to do is to live somewhere I’d like to vacation. For me, San Francisco is absolutely that. When I’m leaving an amazing trip, I rarely think, “Oh no, I have to go back home!” Instead, something I like about having San Francisco as my travel base is that it’s a city I like (sometimes love) and a destination I’d want to visit.

This makes travel much more enjoyable.

Great travel to Mexico, Hawaii, Asia, Alaska, and Australia

While New York City certainly has many advantages over San Francisco as a travel base, it’s much easier to travel to Mexico, Hawaii, Asia, Alaska, and Australia from San Francisco than it is from almost anywhere else in the country. Some may say Mexico is easier from New York, but this is really only true with Cancun/Tulum/the Yucatan. For travel to Mexico City, Puerto Vallarta, Cabo, Mazatlan, and almost every other destination in Mexico, San Francisco is closer, faster, usually cheaper, and has direct flights.

Cabo San Lucas, Mexico

I really love having Hawaii less than 6 hours away. While it’s not an easy flight, the time difference between San Francisco and Hawaii makes it possible to take long (or even regular) weekends there. Generally, if you leave SFO Friday night, you’ll arrive in Hawaii in time for Friday dinner, and then if you leave at, say, 11pm on a Sunday, you’ll get home in time for work on Monday – something I’ve taken advantage of.

Also, while I love Europe, I am more geographically connected to Asia and Oceania, having lived on Guam prior to San Francisco. So, I really enjoying living in a hub with so many direct flights to Asia, Sydney, Melbourne, and Auckland.

It’s also really cool being around 6 hours away from Alaska, which is something I’m finally going to take advantage of this year.

United/Star Aliiance Hub

Star Alliance.jpg

Admittedly, I have a love/hate relationship with United, which tends to swing more heavily on the latter. That being said, of the 3 major U.S. airlines, United by far has the best mileage redemption program. Additionally, the Star Alliance has significantly more destinations than any of the other alliances, which I’ve found to be incredibly valuable while traveling the world.

3 airports (SFO, SJC, and OAK)

San Francisco has 3 airports which are close enough to fly out of, although San Jose can take about 1.5 hours to get to. Oakland Airport is a quick BART ride from the city (and I think it’s technically closer to San Francisco proper than SFO), and SFO is a breeze to get to.

Oakland brings with it a lot of great deals, particularly with Norwegian flying into/out of it. I haven’t flown from San Jose in a while, though I’m constantly seeing deals coming out of it, particularly with direct flights to Hawaii. Having 3 different airports to choose from is awesome.


Europe is too far away

It takes over 10 hours to fly direct from SFO to London, and that sucks. While San Francisco has direct flights to many European destination, such as Amsterdam, Paris, London, Copenhagen, Oslo, Stockholm, Zurich, and Frankfurt, it’s just harder to get to.

The time difference between Europe and Pacific Time is also more substantial, making remote work a bit more difficult.

Not enough direct flights

Me trying to catch a connecting flight

One area of travel where NYC clearly has San Francisco beat is how many direct flights originate from NYC. From NYC, you can take direct flights to places all over Central and South America (like Buenos Aires, Rio, and Guatemala), whereas there are no direct flights from San Francisco.

This is getting a bit easier with Copa’s direct service from SFO to Panama, which is usually fairly reasonable and Avianca’s direct service to San Salvador. But still, San Francisco could use a little more direct service.

Far from the Caribbean

Perhaps this is because I’m a few hours away from catching a red-eye flight to a Caribbean beach (Caye Caulker, Belize), but it’s not ideal being 5-10 hours away from the Caribbean.

Tropical Beach.jpg

The only direct flight from San Francisco to the Caribbean is to Cancun, which clocks in at just over 5 hours. While having Hawaii “close” is awesome, the beaches sometimes can’t compare to the turquoise-tropical beaches which are so easy to get to from NYC.

The above is hardly an exhaustive list and please feel free to weigh in on what you think the pros and cons are of using your city as a travel hub!








Traveling the world (in style) this winter for $900 and 90k in points

It’s only the beginning of January and I already have so much travel planned to look forward to.

As a freelancer, it’s hard for me to plan my travel too far ahead, since it’s hard for me to predict what my revenue and workload will be like. As a result, I don’t like to plan trips out more than a few months in advance, unless I find an incredible deal to a location I’ve been dying to visit.

That said, I felt comfortable enough to book my travel through April. I not only wanted to go to amazing destinations, but I wanted to be comfortable while traveling. As a result, I looked for trips where I could get good deals on business/first class, focusing mostly on either using miles or booking flights where it’s likely I will get upgraded.

My 4 trips, which include 2 confirmed international first/business class legs and 3 additional legs which are likely to be in first/business class, cost  a combined $907.90 and 90,000 United MileagePlus award miles. My 4 trips are:

Caye Caulker, Belize

I’m starting off my travel this year with a trip to Caye Caulker in Belize, which I scored for 35,000 miles and $66.91 in fees on United.


I booked this trip pretty randomly. A person I follow on Instagram was there a few weeks back, and it looks really stunning. It’s very cold and rainy in San Francisco right now, and I was dreaming of a tropical beach, so, I made Caye Caulker my first trip of 2017. I haven’t been to Belize since a cruise in 2007, so I am really excited to head back.

Flights from San Francisco were around $450 at the time I booked (they have gotten cheaper since then), so I decided to go with miles for this trip. As a United Premier Silver member, I qualify for upgrades on Complimentary Premier Upgrade (CPU) eligible flights, and all of the flights in this reservation are CPU eligible (the flight is from San Francisco to Houston to Belize City, and home the same route). Based on current capacity, I expect, at the least, to get a complimentary upgrade to Economy Plus for all of these flights and to be upgraded on at least 2 of the flights.

Approximate business/first class legs: 2

Chile and Uruguay

In winter months, I like to chase summer, and there’s no better way to do this than to visit South and Central America (particularly if you’re an American freelancer who needs to stay close to a specific time zone).

Santiago, Chile from San Cristobal Hill

My friend Julie is living in Uruguay right now, so I was looking up ways to visit her. While searching for different South American hubs to fly to, I found an amazing deal: 55,000 miles and $49.86 in fees on United to fly international business class from Santiago, Chile to San Francisco (with a layover in Toronto).

Notably, international business class on Air Canada comes with lie flat beds.

I still haven’t figured out how I’m going to get to Chile, though I am considering jumping from Mexico City to Bogotá, Colombia to Uruguay, before eventually heading to Santiago. This route would cost about $200 for a direct flight from SFO to Mexico City and 40,000 in miles to fly business from Mexico City to Montevideo, Uruguay with a long layover in Bogotá.

Full disclosure that this will, of course, add to the overall cost of my trip, but because I can book this completely with miles or with Chase points, and because I’m too excited about the travel to wait to post this, I haven’t included this cost in the total yet.

Confirmed business/first class legs: 2

Puerto Vallarta, Mexico

As a San Francisco gay, I would be remiss if I went more than a year without visiting Puerto Vallarta. Puerto Vallarta is one of my favorite destinations to visit for many reasons, including my love for Mexico and the Mexican people, its ease to get to from San Francisco (usually around $300-$400 and a 4-5 hours direct flight away), the great weather, good infrastructure for remote work, and one of my favorite hotel pools in the world.

My happy place in Puerto Vallarta

Having a friend already going in March, I tagged along to his trip. I purchased this ticket outright on United there and Alaska on the way back. I had a $125 voucher to use on Alaska from a flight to Portland that was delayed 3 hours, which brought the total for this flight to $229.27 total.

The flight I’m taking to Puerto Vallarta is still very empty and it qualifies for a Complimentary Premier Upgrade, so I am sure I will get Economy Plus and am also expecting to be upgraded to United First.

Approximate business/first class legs: 1

England and Italy/Spain/Portugal/Morocco

Maybe it’s cliché, but I love Europe. I also love flying direct on an airline I have status with. So, when I saw a $561.86 direct SFO to London ticket on United, I booked it for April. Really, I would have rather booked it for May, June, or July when the weather would be better but, as mentioned earlier, it’s hard for me to predict my life in May enough for me to book travel out that far.


So, my plan is to celebrate my friend Bob’s birthday in London and visit with some friends, and then fly south to either Portugal, Morocco, Spain, or Italy to thaw out. Full disclosure that these flights could add to the cost of this trip, but as nothing is booked and I could end up staying in England (unlikely), I haven’t included these costs.

My guess is that I’ll be able to upgrade to Economy Plus for these routes, but they aren’t CPU eligible, so I almost certainly won’t be in business or first.

Approximate business/first class legs: 0

I feel like I made out pretty well for my winter travel and am excited for the adventures ahead!

How going to a bar in the Castro earned me 7 miles per dollar spent for 2017

Having enough miles to book amazing award travel doesn’t just happen – you’ve got to work for it.

Perhaps the best and most efficient way to do this is through credit cards with great mileage-earning programs (I’ll have more on the best strategies to approach credit cards in future posts). However, there are other ways to maximize your mileage-earning potential, and one is through dining programs, such as United’s MileagePlus Dining and American’s AAdvantage Dining.

The way it works is that you register your credit/debit cards with the program, and when you use that card at a participating restaurant, you will earn either 1, 3, or 5 miles per dollar spent, depending on the type of membership you have. To get 5 miles per dollar spent, you need to dine out using a registered credit card at a participating restaurant at least 12 times per year. While other airlines have programs similar to United’s, my understanding is that you can only register your card for one of these programs (though you can have multiple cards on each program).

A few weeks ago, I got the Chase Sapphire Preferred card, which gets me 2 miles per dollar spent on travel and dining and 1 mile per dollar spent on everything else. I am a big fan of Chase’s point system and have found flights priced cheaper through their travel site than elsewhere online. The Preserve card has a $95 annual fee, though it’s waived for the first year.

I registered my Chase Sapphire Preferred card with MileagePlus dining so that I could receive 2 miles per dollar spent, which I’d get as points on Chase’s Ultimate Rewards (which can be converted to United or other miles), and 5 miles per dollar spent on United.

The only problem? As of December 30th, I had only 11 qualifying dines in 2016, and I needed one more before the end of the month to get VIP status for 2017. I already had plans that night to see the University of Arizona Wildcats crush the Cal Bears in college basketball. But afterwards, I knew I had one mission – to secure VIP status for 2017.

There are a lot of great restaurants and bars in San Francisco which are featured on United’s MileagePlus Dining, and one is Blush! Wine Bar in the Castro. Blush! was a MileagePlus Dining member a few months back, but terminated their relationship until recently. While it seems a huge percentage (maybe 90-95%) of MileagePlus Dining establishments are restaurants, what I liked about Blush! is that it’s a bar you can eat it (instead of the other way around). Blush! also has an amazing Belgian beer collection, which is a favorite of mine.

So, with many friends out of town for New Years and a plot formulated without any time to get others on board, I went to Blush! and sat alone at the bar, drinking my pain away, until the glorious moment came when I could whip out my credit card and secure my VIP status.

It already says on my United MileagePlus Dining account that I’m a VIP member for 2017, which puts a spring in my step as I enter the new year.