Setting up a yearly travel routine: A guide for remote workers

Whether you’re a freelancer or have a job that allows you to work remotely, depending on certain circumstances in your life (finances, family, health, etc.), you may be able to travel much more than your friends who work more “traditional” jobs.

I began working remotely in 2015, first for a company and then as a full-time freelancer. Though I am still constantly learning from my travels, I have found that I enjoy being based in a city and booking ~monthly travel, rather than being a full-time digital nomad. Having a base helps me establish better personal and business relationships and it allows me to focus more on my physical and mental health.

Regardless of if you’re a remote worker like me who prefers having a travel base or if you’re a digital nomad constantly on the run, you may benefit by establishing a yearly travel routine.

What is a yearly travel routine for remote workers?

Both to keep my finances in check and for business/health purposes, I try to limit my travel to around one trip each month (and yes, I know I am ridiculously lucky to have this ability). Assuming I’m able to accomplish this goal each year, this means I’m generally taking at least 12 trips each year.

Of those roughly dozen yearly trips, there are certain destinations that I will (almost for sure) visit. For me, they are:

  • Puerto Vallarta, Mexico
  • Medellín, Colombia
  • Scottsdale, Arizona
  • Los Angeles, California
  • Hawaii
  • New York City

I consider these destinations to be part of my “yearly travel routine,” which is basically a set of locations that I try to visit once each year.

Puerto Vallarta1
Puerto Vallarta, Mexico: one of my yearly travel destinations.

Why have a yearly travel routine?

Having a yearly travel routine is not right for everyone. If your singular goal is to see as much of the world as you can while you can, having a yearly travel routine could stifle your ambition.

But for many remote workers, setting up a yearly travel routine has a lot of benefits. Advantages to having a yearly travel routine include:

  • Having a base of friends/clients in the places you’re traveling to. As a remote worker who’s traveling, your days may often be spent on your computer, on calls, and away from society. After you get done working, you may be itching for human interaction, but may not want to put forth the effort to meet someone new. By traveling to the same locations each year, you’ll slowly get to know people, and can have built-in post-work and weekend plans.
  • Assurance that you’ll have working infrastructure. Before each trip I book, I do everything I can to make sure I’ll have the necessary tools (mostly, reliable WiFi) to work. But I’ve been unpleasantly surprised before, arriving at a location where the internet was subpar (or lacking completely). Two qualities my yearly travel destinations all have in common are great infrastructure and settings which are conducive to my remote practice.
  • Knowing how to navigate these locations. Something I love about travel is having new experiences. That said, there is something great about arriving in a city and already knowing where to find the things you need and like, like grocery stores and restaurants, and having a feel for the city’s public transportation system. This can reduce time spent trying to learn a city, can lower overall costs (like knowing where the cheapest place for a great, quick lunch is), and can reduce travel anxiety.
  • Knowing where to stay. One of my favorite parts of my yearly travel routine is that for each of these locations, I already have either set neighborhoods or locations that I like to stay in. Almost uniformly, I pick these places because I’ve stayed before, have had good experiences, they are conducive to remote work, and they reasonably priced. Trying to find lodging, especially for a remote work trip, can be stressful, so having set places to stay makes planning travel a lot easier.

How to choose your yearly travel routine destinations

Choosing your yearly travel routine destinations can be difficult. Below is a brief description of how I chose my destinations:

  • Puerto Vallarta, Mexico – Since I live in San Francisco, Puerto Vallarta is an easy (and often fairly inexpensive) flight away. My friends like to go once a year, and I’ve added myself onto their annual trip, usually around March/April. The weather is perfect around that time of the year and I can save costs by splitting my room/remote office with a friend who also works remotely.
  • Medellín, Colombia – Thanks to Copa’s direct-flight service from SFO to Panama City, South and Central America have become much easier to access from San Francisco. Medellín is a surprisingly easy flight, and it’s relatively inexpensive (for around ~$50/night, you can rent an apartment in one of the best parts of the city with an amazing view in a luxury building, and for ~$20-$30/night, you can still find some amazing deals). It’s also stunningly beautiful with a great freelance community.
  • Scottsdale, Arizona – Having gone to college in Arizona, I like heading back to Arizona at least once a year to see friends, and also to enjoy the weather and lying by the pool.
  • Los Angeles, California – Since I have many friends and clients located in the Los Angeles area, I usually need to go at least once a year for business or social purposes. But even if I didn’t need to go, I still would, as I love the weather, the hikes, and (for the most part) the people.
  • Hawaii – I don’t know if I’ll live in San Francisco or California my entire life, so I want to take as much advantage of being a 4-5 hour flight from Hawaii as I can. Also, having lived on Guam, I have a lot of friends that relocated to the islands, so I can often see them whenever visiting.
  • New York City – Growing up in New Jersey and having gone to law school in Philly, I have a lot of friends in New York City. In fact, my sister lives there and I also have clients in the region. While I am not generally a fan of the northeast, the people here make it worth a yearly visit.

As you can see, one of the main factors behind the locations I’ve selected is people. In making your list, you may want to base your yearly travel routine on seeing friends, clients, and family (especially those located in amazing places).

Sunset from Scottsdale, Arizona

Another factor is reliable WiFi – every location listed above has an infrastructure that fully supports remote work. Similarly, each location above is located in a time zone that is conducive to my schedule. While I often take a few trips each year to time zones that are “difficult” to work from for me (such as Asia and Europe), my yearly travel routine is focused on destinations that I can work seamlessly from.

Something that’s also important in establishing your yearly travel routine is easy flights. Whenever possible, I like to fly direct, and with the exception of Medellín, I can get to each of these destinations directly from San Francisco.

Final tips for establishing your yearly travel routine

If you are a remote worker who is interested in establishing a yearly travel routine, I would recommend leaving room so that about half of your trips are to new (or rarely traveled to) destinations. Part of the fun of being a remote worker who can travel the world is seeing and experiencing new places. By visiting new destinations each year, you’ll be sure to expand your mind, you’ll likely have more interesting stories to tell, and you may even find new places to add to your yearly travel routine.

Are there places you try to visit every year? Let me know in the comments!

5 budget-friendly tropical islands for freelancers

If there’s anything I’m an expert on, it’s tropical islands. From a young age, I’ve been obsessed with them and even had a tropical island-themed Bar Mitzvah.  I love tropical islands so much that after law school, I spent 2 years living on Guam, an idyllic paradise near the Mariana Trench.

As a location-independent freelance attorney, my practice takes me all over the world. At least a few times a year, I try to travel to a tropical island and look for destinations that are budget-friendly with reliable WiFi/infrastructure.

Below are 5 of my favorite budget-friendly tropical islands for freelancers (and really, anyone else).

Bali, Indonesia

It’s almost a cliché to talk about how great Bali is for freelancers. Bali has practically everything a freelancer is looking for: a strong freelance community, co-working spaces, beautiful beaches and nature, and reliable WiFi.


Bali has a diverse landscape which includes rice paddies, beaches, and volcanoes. My favorite places on the island are Ubud, Seminyak, and Nusa Dua. While these places are more laid back, if you’re looking for clubs and bars, you should stay near Kuta, which is an essential stop for many backpackers and Europeans/Australians who are enjoying their gap year.

One reason Bali is so popular with freelancers is the reasonable prices of food and accommodation on the island. As an example, for $20/night, I was able to get my own 2-story bungalow at a yoga retreat on a rice paddy in Ubud, complete with an outdoor shower and bathtub. You can also find luxurious lodging for way less than what you would pay almost anywhere else in the world — for less than $100/night, I was able to get a 2-bedroom villa with my own private pool just a short walk from the beach in Seminyak.

If you use Secret Flying or The Flight Deal, you can sometimes find flights for $500-$600 round-trip to Bali from the United States.

Tenerife, Canary Islands

Europe isn’t generally known for its tropical islands; but if you keep flying south, you’ll eventually reach the Canary Islands. Located off the southern coast of Morocco, these islands are technically a part of Spain and the European Union.


Tenerife is a volcanic island with stunning beaches, great infrastructure, and affordable hotels. It’s also the largest and most populated of the seven Canary Islands (and is the most populated island of Spain).

On the north coast, you’ll find Puerto de la Cruz, which serves as the perfect base for freelancers wanting to thaw out during the winter. A rental car is helpful, but you can walk around the city’s dark, volcanic-sand beaches, explore local cuisine, and see stunning cliff-side views that are only short walk away.

While Tenerife isn’t as warm as the other islands listed here, I visited in November and it was still hot enough for me to spend my non-working hours tanning on the beach and swimming in the ocean.

The icing on the cake: with Ryanair, you can find direct, round-trip flights from Madrid to Tenerife for as low as $38.

Caye Caulker, Belize

Caye Caulker, located only a short (and cheap) boat ride from Belize City, is the only island in North America to make this list. As a rule of thumb, the Caribbean is generally not budget-friendly for freelancers or tourists, especially in the winter where tourists flock to the warm weather and pristine beaches. That said, Caye Caulker bucks this trend, with reasonable accommodations, decently priced food, and an amazing climate with crystal-clear blue water surrounding the island.


Earlier this year, I had the chance to visit Caye Caulker. I wrote a more expansive write-up of why this island is amazing for freelancers, and you can check out my blog post here: Caye Caulker, Belize: a remote worker’s dream.

Koh Phi Phi, Thailand

Thailand is one of my favorite countries in the world. And, within Thailand, my favorite spot is Koh Phi Phi, an island off the coast of Phuket.

Koh Phi Phi.jpg
Even if you’ve never visited the island, Koh Phi Phi may look familiar to you — it’s where they shot the movie The Beach starring Leonardo DiCaprio.

Koh Phi Phi is truly stunning in terms of natural beauty, it has reliable cell coverage and WiFi, and you can find more than reasonable accommodations all over the island (I shelled out less than $30/night for a room that was steps away from the ocean, with an infinity pool overlooking the Andaman Sea). The island is also easily accessible from Phuket’s international airport, being a short, inexpensive, and beautiful boat ride away.

If you have time, be sure to check out nearby Krabi, home of some of the most beautiful tropical beaches in the world.

Palawan, The Philippines

Asia is truly spoiled when it comes to budget-friendly tropical islands and Palawan, which was named the Best Island in the World for 2 straight years by Travel + Leisure, is arguably the crown jewel of them all.

I took this picture in November 2016 at Marimegmeg Beach in El Nido, Palawan.

With crystal-clear blue water, breathtaking mountains and rocks rising out of the ocean in every direction, and landscapes that look too stunning to be real, Palawan can quickly overwhelm you with its beauty. Beyond its natural beauty, Palawan is a great option for freelances because of its affordable food, transportation, and accommodations.

While WiFi is not can be spotty on the island, particularly in less-developed El Nido, you can easily find comfortable cafes with reliable connections.

If you have a favorite budget-friendly tropical island that you like to visit, let me know in the comments!

A year into my quest to improve my travel, fitness, and freelance business

Last July, I set an ambitious goal for myself – to get into the best shape of my life while running a successful business and traveling the world.

None of those things are “supposed” to go together. Traveling the world is amazing (hence, this blog!), but it’s harder to eat right and exercise while on the road, which is something I’ve discussed in previous posts. Also, running a successful business is tough enough on its own, but when coupled with working out and visiting amazing countries regularly, it can seem impossible.

But, a year later, I am happy to share that I’ve achieved my goal! My law practice has never been better, my travel in the last year has taken me all over the world (including Chile, Turks & Caicos, Colombia, the Philippines, Belize, Greece, Turkey, London, Hong Kong, and Portugal), and, below, you can see my fitness progress.

First, here’s a picture from almost exactly a year apart:

Fitness comparison.jpg
August 2016                                                                          July 2017

Though I was opposed to “progress pictures” when I started working out (hence none from July, when I first began), I’ve found these to be great motivators. There are times when I think my diet and exercise aren’t paying off, but when I look side-by-side, I can see that it really is making a difference.

Next, the numbers:

Fitness Chart

While I try not to let the numbers go to my head, taking measurements ~monthly helps me stay accountable. Some of these numbers might not be dead on (fairly certain my waist was closer to a 32 when I started, for example), but it’s accurate enough for my purposes.

The changes I’m happiest about from these numbers are:

  • Body fat down from 16.4% to 10.6%
  • Arms up from 11.9 inches to 14 inches
  • Weight is up from 150.6lbs to 160lbs

I’ve also had positive changes to my mood and self-confidence, have saved money on food by cooking most meals at home, and have only gotten sick once in the last year (and a short cold at that).

It’s challenging, though. Before starting this quest, I loved to eat cheeseburgers and cheese fries with a side of cheese pizza, and I still love that. I’m also addicted to Diet Pepsi/Diet Coke (I’m agnostic to brand, which is another one of my many flaws). I also love my bed more than life itself and consider myself to be pretty lazy.

But the results have been so good that I am going to make the same goal for myself this year, and hope I’ll be writing in July 2018 with an even cooler update.

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!