The Journey So Far: 

We bought Sonder in the US Virgin Islands in November 2018, sold everything in Colorado and moved aboard in February of 2019. We sailed from the USVI up to Massachusetts where we got married in July 2019, after a sailing “honeymoon” in Maine we headed south again. We departed from NYC for the Caribbean in November 2019 and have been working our way through the island chain since then. We’ll return back to New England in May, with plans to cross the Atlantic to Ireland in August, fingers crossed!

Since we moved aboard in Feb 2019 we have sailed 5,120 miles at an average speed of about 7mph (more if we count all the small hops back and forth we make while exploring). 

Work & Expenses: 

In Boulder, Roxy worked as a software quality assurance analyst while Phil was a musician and music teacher. We’ve since taken an old side project—a pop-up greeting card company called PopLife—and turned it into our main gig to keep afloat (financially!). We also employ an awesome full-time virtual assistant, John, who helps us with photo editing, data entry, copywriting, email campaigns, graphics, and more.

Our expenses are roughly $3,500/month, including our $1,350 boat payment. We took out a loan, similar to a mini-mortgage, to buy our sailboat. It’s the first piece of “property” like this we’ve ever owned.

Weekly, we spend ~$500 for groceries, eating out, boat maintenance, laundry, fuel, customs/immigration fees, etc. This doesn’t include our annual costs like health insurance and boat insurance premiums. However, we know cruisers who get by on as little as $1000/month!

How We Prepared to Work Remotely and Sail the World: 

We had already made the leap to working for ourselves about a year prior, but while on a short 2-week sailing trip in the Bahamas on our first boat (a much smaller boat named Impetuous), we saw a big community of full-time cruisers living on their boats while traveling and the spark was lit for us. We started scheming a month later—outsourcing the location-based parts of our jobs, looking for the “right” boat online. We also stopped buying stuff for our apartment in Boulder.

Only a month or so of dreaming went by before we started taking small steps to see if it could be done. Within six months we were starting to seriously look at boats in-person and researching financing, etc. 14 months after the original idea sparked, we were flying down to the USVI from Colorado with five suitcases of stuff to our name!

We lived on Sonder for five weeks with non-stop work to get her ready to safely sail us back to the US. We were nervous wrecks. We also discovered a lot more problems than were obvious when we first purchased the boat, but this is typical when buying an older boat! Fun fact: Sonder was originally built in Hong Kong in 1986.

Diary of a Remote Worker: 7 Days on Sonder

DAY ONE

9:45 a.m. – I wake up to a loud thump. It sounded like we got hit by something hard, but really it was just a larger-than-usual wave hitting the side of our sailboat. Phil has been up for a couple hours already, but I’m just rubbing the sleep from my eyes. I was up till 2 a.m. working yet again. The online business we run together is 100% remote so in theory I should be in control of my own hours, but most of the people I work with directly are in Asian time zones. I get up and grab a mango yogurt and iced coffee from the boat’s fridge for a quick breakfast.

11:10 a.m. – We’re reading the news on our phones, a typical slow start to our day. Phil is on to his 2nd or 3rd cup of meticulously hand ground aeropress coffee. We have ample battery power and space on our boat to keep an electric coffee grinder aboard… but that just wouldn’t be “Phil” enough, he’s got to work for it. We sit and discuss the day and decide we should go ashore and explore today because the weather will get rough later in the week. We jump in our inflatable dinghy and zip off towards shore. This little dinghy has taken the place and role that our cars had when we lived on land. It gives us the freedom to get around, explore, do errands, etc.

“‘Sonder’ means the realization that total strangers have a life just as complex as you do.”

12:00 p.m. – We dock the dinghy, and set off in the general direction of town. We’ve never been here before, and even though we have a guidebook somewhere, we’ll probably just wing it. Phil has packed our laptops and chargers in his backpack and if we find a good spot (shady tables, free wifi, and people that won’t mind us loitering for several hours) we’ll stop and work for a while. We do find a quiet cafe near the water and settle in to get some work done during the heat of the day. 

3:15 p.m. – Well, the cafe did have Wi-Fi, but apparently it hasn’t worked in a week and they’re still waiting on the island IT guy to come fix it. Since we already bought $25 worth of coffee drinks and so-so looking pastries, we just use our phone’s hotspot to get connected. We use an international phone plan that has a 22gb high-speed data limit per month, so we’re very careful and task oriented when connected to it. I reply to some customer support inquiries while Phil sets up an ad campaign for one of our company’s newly released designs. I came up with the idea for this particular design during a night watch shift on our 6-day sailing passage from NYC to Bermuda. I guess being self-employed means our “work brain” never really turns off.

6:50 p.m – We walk around for a bit and then find our way up to the crumbling old fort atop the hill above town. There are some rusty old cannons lying about and a few signs posted on the stone walls with historical info. We notice the sun is about to set and hurry back down to get to our dinghy. We forgot to bring a flashlight (again), so I use my iPhone to light our way and make sure we’re visible to other boats nearby. When we’re back, Phil cooks dinner while I settle in to reply to some colleagues in Asia by WhatsApp and email. Sounds like they’ve run into some supply issues. It’s going to be another long night.

DAY TWO

10:00 a.m. – Phil’s making bacon and eggs for breakfast. Using the oven always heats up the boat quickly and it’s already 85 degrees outside, so we go and eat out on the shady side of Sonder’s cockpit. We start to talk about work, but I get annoyed when our meals feel too “meeting-like,” so we settle on talking about what to do in the afternoon. Phil has some overdue boat projects he wants to tackle and I want to swim and clean the bottom of the boat. Yes, mostly just an excuse to swim.

11:45 a.m. – While I’m cleaning growth from the bottom of the boat with a scrub pad, I spot a sea turtle munching on grass at the sandy bottom about 25 feet below our boat. I think about calling out to Phil to come see, but we’ve already seen about 15 turtles this week, so I leave him to his project. I dive down to get a closer look, but the turtle pays me no mind. I hover above him for a bit before shooting back up for air. I can only hold my breath for 40 seconds or so, something I’m trying to work on.

“I spot a sea turtle munching on grass at the sandy bottom about 25 feet below our boat.”

2:10 p.m. – We head into town on the dinghy to find a grocery store. Caribbean grocery stores are not for the faint of heart. They simultaneously make Whole Foods look dirt-cheap and Trader Joe’s feel like a paradise. In the store I find they just got their produce in from the weekly “food” boat from the mainland… there are avocados and mixed greens! Phil finds imported Cuban white rum for $9 a bottle. This is turning out to be a damn good day. We pack up our backpacks and hurry for the dinghy. The tropical sun and heat is brutal on perishable food, we have to get everything back to our refrigerator ASAP.

4:50 p.m. – I’ve been dreaming about a hot shower all day. I go to turn the hot water heater on, but our lithium boat batteries are too low. It must have been too cloudy the last few days, and our solar panels haven’t quite been keeping up. Phil goes to turn on our diesel generator but discovers a problem. It’s always something with a boat. There are many more systems than a typical house, from making fresh water out of salt water, to making our own electricity, to storing our waste. It’s a lot to keep up with. Phil does fix the problem eventually and I take a glorious shower, careful not to use more than about 2-4 gallons of our precious water supply.

7:00 p.m. – Dinner is jerk chicken and a big leafy salad from the day’s grocery haul. We plan to finish watching the last couple episodes of the Witcher on Netflix over dinner (which we expertly downloaded with my parents’ Wi-Fi while home for Christmas), but we get to talking about business again and suddenly it’s too late.

11:15 p.m. – Phil is in bed reading a book while I’m still staring at my laptop out in the salon (the main living area of the boat). I’m having a burst of late night inspiration and have been mocking up some brand new designs, while also fielding emails from our production managers about the crisis du jour. We’re in for some rough weather tonight and I’m dreading the poor sleep we’re bound to get.

DAY THREE 

3:27 a.m. – I’m startled awake for about the 10th time by a sudden gust of wind hitting the boat and tossing us around like a toy. It’s dark, but the moon is shining directly down through the hatch above our bed, casting a perfect square of light on our bed. Our bed is actually a big triangle because it’s up in the very front of the boat (the “bow” in boat-speak). 

I listen to the grinding sound of our anchor chain as it tenses up, straining against the wind and waves. It’s moments like this that we pat ourselves on the back for having invested in the bigger anchor. 105lbs of pure galvanized steel dug into the sandy bottom 27 feet below us. “We’re okay, we’re okay, we’re okay,” I repeat silently in my head. Phil snores loudly. I miss my square bed back in Boulder. 

“I’m startled awake for about the 10th time by a sudden gust of wind hitting the boat and tossing us around like a toy.”

10:25 a.m. – I wake up to the hot sun shining on my face. The wind finally calmed around sunrise and welcome sleep had washed over me. Phil smiles amusedly as I get up, “Sleeping in again, are we?” I grimace. He’s reading the New York Times on the iPad and catching up on some marketing tasks. We get some more work done and talk about our next sail. We’ve already spent about four nights in this anchorage and a couple days exploring town. We could easily spend more time here, but there are so many places to go and things to see… and hurricane season is approaching.

2:00 p.m. – After a quick clean up and stowing session, the boat is ready to move. I stand on the bow, directing Phil with hand signals which way to turn the boat as we trace our chain and hoist up the anchor. We’re on our way. The next island we’re headed to, Sint Maarten, is only about seven miles away and we should be there in an hour or so. We hoist our sails and kill the engine, enjoying the quiet sounds of Sonder slicing through the water. We are physically moving our home with only the power of the wind to a new place we’ve never even been. The novelty of it all hasn’t ceased to amaze me. 

4:30 p.m. – We’ve arrived. Phil is applying sunscreen… liberally. It’s all white and not rubbed in inside his ears, but I’ve given up pointing it out. I just smile and thumb casually through the guidebook at all the places this new island has to offer, knowing we will probably only scratch the surface of it. It’s hard to juggle exploring a new place while also keeping our business running, doing normal chores, and boat maintenance. Add a little personal time and staying in touch with friends and family back home and the days practically fly by with hardly a moment to ever be “bored.” I think I miss being bored—just a little.

8:00 p.m. – We have an easy dinner of frozen gnocchi and pesto sauce. Phil has disappeared to set up his keyboards and mobile music studio in the spare bedroom on Sonder. He was a working musician back in Boulder, and moving onto a sailboat has been a big transition for him. He was used to practicing on his piano for several hours a day, now he’s lucky if he gets to play at all some weeks. I sit in the salon catching up on text messages with friends and family, listening to Phil play as rain starts to fall on the fiberglass roof. 

DAY FOUR

8:45 a.m. Today is laundry and Wi-Fi day, and both are needed badly. We haven’t done laundry since three islands back (3-4 weeks) and, yes, you can tell. We have a quick breakfast and head into town, dinghy piled high with fat laundry sacks. We find a laundromat near the docks, but the machines cost $10 per wash and $10 per dry cycle. We exchange our $20 bills for a plastic solo cup full to the brim with quarters and get started. We find a coffee shop nearby and take turns dashing back and forth to switch around laundry loads while taking advantage of its mediocre Wi-Fi. Just another day in paradise!

12:00 p.m. – We’re done with laundry and head back towards Sonder. It’s hot and we’re adequately sweaty by now. The best way to get cool is to just jump in the water, so we do. We find the water clarity around the boat is actually amazing right now and grab our dive masks and fins. We keep going and snorkel and freedive out around the rocks at the edge of the bay. We see turtles, stingrays, countless fish, and some colorful coral. These are the impromptu moments we live this lifestyle for. 

“These are the impromptu moments we live this lifestyle for.” 

I glide weightlessly underwater, following an electric blue fish through an outcropping of rocks. Two years ago, at this very moment on a weekday afternoon, I would probably be sitting at my desk stressed about the string of back-to-back meetings ahead of me. What a difference a couple of years make. 

6:10 p.m. – We watch the sun slowly set from the deck of Sonder, Cuban rum cocktails in hand courtesy of bartender Phil. This is how we’d like to spend every day at sunset, but in reality it’s a treat when we actually make a proper sundowner happen. It’s easy to take for granted these moments of beauty, so we pause to toast our good fortune and hard work. “Well, this doesn’t suck.” I remark casually. We’ve been saying this a lot since moving on Sonder.

10:00 p.m. – It’s a Saturday night, Sunday in Asia, so all is quiet on the business front. Finally. We take the opportunity to settle in with a movie on our little TV in the salon, tonight we’re watching Pirates of the Caribbean. Yes, a little trite, we know. Normal moments like this, curled up on the couch, feel like we could be back home in Boulder, living solidly on land. A sudden tropical rainstorm hits and then we’re running around frantically closing all our hatches and windows, breaking the illusion in an instant.

DAY FIVE

9:15 a.m. – I get out of bed and see I have an email from my brother—he’s just been laid off from his job. He was also working remotely full-time while traveling, but for a medium-sized SaaS (software as a service) company in the US. I feel the pit of my stomach drop. The feeling is mostly empathy for what my brother must be feeling right now. We always knew choosing an alternative lifestyle had some inherent risk, but moments like this hit on just how fragile it can be. 

12:40 p.m. – We inflate our stand up paddleboards (SUP) and paddle in to the beach. There’s a trendy beach club here with a coffee shop and fancy rum bar sprawled along it. We stow our SUPs under some palm trees and head for the coffee shop. We buy a couple iced lattes and casually ask for the Wi-Fi password (eternally trying to make it seem like it’s not the only reason we’re patronizing a place). I sit down in the shade and immediately FaceTime my brother to see how he’s doing.

2:00 p.m. – We’re on our second round of overpriced coffee now. Phil and I find ourselves talking about where we’re “at” right now. We talk about fall-back plans. What if our sales plummet, or our business fails tomorrow—what would we do? We do this sometimes, get stressed out and worked up wondering if we’re making the right choices. 

“We talk about fall-back plans. What if our sales plummet, or our business fails tomorrow—what would we do? 

3:10 p.m. – On our way back to the SUPs we run into an older retired couple who also live on their boat. We get to talking and just before we part ways they tell us, “We just so wish we’d started doing this at your age!” They say goodbye and walk away, having no idea the impact that statement left on us. It can be easy to forget sometimes just how fortunate we are to be here. Maybe we’re on the “right” path, maybe not. One thing’s for sure: We are exactly where we want to be right now, regardless of the risk.

7:30 p.m. – Over dinner we slowly download the latest weather forecast from our satellite phone. To our surprise, there’s a change of wind direction coming in a couple days. This is probably our best opportunity to make it further south. Our next island destination, Grenada, is 390 miles away. At an average sailing speed of 6.5mph, it should take us a little less than three full days to get there. This means sailing nonstop through the night, taking alternate shifts to keep watch and navigate. We decide to do it and start making plans. Time to get to bed—tomorrow is going to be busy.                        

DAY SIX

7:30 a.m. – We wake to an alarm and get busy packing up the cabin. Anything that can possibly fall, break, or leak has to be put away or secured. While sailing, the boat can rock, buck, and lean heavily to either side… it’s kind of like preparing for an earthquake. 

Early on in living on Sonder we made the mistake of underestimating the importance of this step. After a few especially bad experiences (such as taking a wave through an unlatched window and completely soaking our bed in saltwater, or a metal rack flying from the oven and taking out a big chunk of the interior woodwork) we now take this task very seriously. 

12:00 p.m. – After stowing as much as possible, we sit down to figure out what we need to do in order to be offline for the next 3 days while we are on passage. The word “offline” gives me a bit of a skin-crawling feeling. Not because we’ll be away from Instagram, Netflix, and the daily news cycle—that’s often a bit of a relief, actually. I’m just dreading the inevitable time-sensitive business tasks we’re going to have to figure out.

“It’s kind of like preparing for an earthquake.”

3:45 p.m. – I set up an out-of-office message on all our email accounts and laugh to myself—if only people knew just how out-of-office we really are. While at sea we’ll have a satellite phone that will allow us to slowly download tiny weather forecast files, which are only about 10kb on average. We can also send and receive short text messages, but it can be somewhat unreliable. Generally, my mom monitors our email accounts while we’re on passage and then texts me if she sees anything urgent come through. If she does have to respond to an email on our behalf, she’ll tell people she’s our company’s “office manager.” Moms are just the best, aren’t they?      

7:30 p.m. – We’re tired and decide to eat out for dinner so we can avoid having to deal with dirty dishes and more cleaning tonight. We find a decent looking place on TripAdvisor and head over in the dinghy. I remembered the flashlight this time and use it to guide us through the dark maze of boats, mooring balls, and bouys in the harbor. Dinner is at a Thai place and we talk over our curries about what to expect from the passage and anything we have left to do. We need to leave at first light tomorrow, so we head back to the boat and go straight to bed. This will be our last full night of sleep for a few days.  

DAY SEVEN

6:00 a.m. – Another alarm. Time to go. We check our emails one final time before sliding out of bed to face the day. We raise the anchor and start slowly motoring out of the harbor. When we’re a little way out we point into the wind and hoist our sails. As we point south, towards our destination, the sails fill with wind and become taut and smooth. Sonder is eager to go. The auto-pilot is turned on and starts steering the boat to our compass course (the auto-pilot is honestly our MVP). I make some toast, but the rocking of the boat keeps me from making much more for breakfast. 

10:30 a.m. – The winds are stronger than predicted so far. It’s a wet ride as we fly over and through the waves. Constant sea spray makes our lips taste salty. I just realised I forgot to download any audio books on Audible. Guess I’ll be hunting through Phil’s books on board for something to read. He teases me about preferring audio books, but I like hearing stories in a voice other than my own. My favorite narrator, Imogen Church, could read me the dictionary for all I care. There’s not much to do for now but trim the sails and hang on. 

2:10 p.m. – The winds have calmed considerably now, it feels more like sailing and less like riding a mechanical bull. We make an easy lunch of sandwiches and sit in the cockpit. Land is still in sight in the distance behind us, but barely. I repeatedly resist the urge to check my phone, we haven’t had any service since about 8 a.m. anyway. The first and last day on passage always seem the longest—land withdrawal and anticipation I think. Everything in the middle flies by.

“Falling overboard can mean being left behind—for good.”

5:50 p.m. – The sun is starting to set. We put on our life vest PFDs (personal floatation devices) and attach our tether to it. Tethers are like dog leashes, but for humans, and keep you attached to the boat for safety. Falling overboard can mean being left behind—for good if you’re not found quickly. It’s my #1 fear out here,  but I try not to dwell on it. The sun just dipped below the horizon to the west, in 12 hours it’ll appear again on the opposite horizon—one thing, at least, we can always count on out here.

8:15 p.m. – We decide to make pasta for dinner. Phil leans over the side and scoops seawater into a pot to boil it in, no need to add salt this way. We both sit in the dark cockpit while we eat. I usually hate eating in total darkness, but looking up at the incredible stars splayed above us more than makes up for it. We also see sparkles of bioluminescence in the water as Sonder slices through the waves and disrupts whatever must live there. I turn on the satellite phone and check for texts, but none come through. Guess things are going OK out there on land.                 

11:55 p.m. – We started our night shifts at 10 p.m. Probably should have started earlier, but neither of us felt like sleeping yet. I’m on watch now—night shifts usually last around 3-4 hours. I planned to sit and read, but can’t get motivated to go below to search for a book. I sit quietly in the dark, and my mind wanders to the future. It might sound far-fetched now, but in a few years we’ll likely have access to high-speed satellite Wi-Fi out here in the ocean (courtesy of Elon Musk of course—Google it). We could be out here doing our normal jobs, hundreds of miles from land. Our lifestyle probably won’t be so niche anymore, in this “connected-everywhere” future I’m imagining. With more affordable, reliable connectivity everywhere on the planet, more office-based workers could choose to live nomadic lives like ours. No commute to consider when buying a home, no reason to live somewhere you don’t love. I don’t know, maybe this is all just an exhaustion-fueled futuristic dream—but, we’re living it now.