Working While Cruising

Our thoughts and experiences over the past two seasons

We get a lot of questions about what it’s like to work and cruise, especially from others who are considering this lifestyle. It’s sparked some interesting discussions between the two of us, and we wanted to share some of that with you. These are our honest, unvarnished experiences, but we don’t pretend to be experts nor do we think there’s a one-size-fits-all answer. 

Q: Do your employers know you’re cruising?

M: Absolutely, and I think it’s key to being able to do this. While we always do our best to avoid having our lifestyle interfere with work, there are practical exceptions. We monitor weather carefully and try our hardest to plan to already be somewhere safe when inclement weather is in the forecast, but we’ve had a few occasions where we’ve needed to take off at the last minute to prep for a storm or move the boat. Being upfront with our employers means that we don’t have to make up excuses when we need to deal with the unexpected.

C: Yes. I changed jobs while we were preparing to depart and made my employer aware of my plans during my interview process. I am always upfront about where I am and what my plans are. Most of the time during my Monday meetings the first question is “Where in the world are you today?”. Part of the reason this works so well for us is that we are both extremely careful about our work habits being beyond reproach. We make sure to always be on and immediately available, to put in a little extra time without question and to be upfront on the rare occasions we might not be available. In my view it is my responsibility to make sure my employer stays comfortable with the situation since I am the one with an exceptional lifestyle. So far it has worked well and there has been absolutely no pushback from work.

Q: Do you get to see the places you sail to?

M: Some places more than others, and more so now than when we had Silent Sky. Since Windara is faster and we’re making longer offshore passages, we’ve had less need to push hard to get south. That’s meant we’ve often had at least part of the weekend we arrive somewhere to explore, plus a down weekend in that place as well. Now that we’re back in The Bahamas, we’ve got another layer of flexibility – we can decide when and where we want to move since we don’t HAVE to be anywhere. That said, we cover much less ground than our retired cruising friends, and we’re not able to explore as in-depth as they can. However, it’s a tradeoff worth making. 

C: Mixed. The first year we did this on Silent Sky I really only saw the places we were stuck in for an extra week due to weather. Since the boat was a little slower we would push hard every Saturday and Sunday, then Monday through Friday I would do my best to see the place via morning walks and dinghy rides and our Thursday night date night. This year with a faster boat and making offshore passages I’ve seen a lot more of each place because we typically have either Saturday or Sunday as a down day to explore together.

Q: Do you miss out on social opportunities?

M: To some extent, sure. We’re heads-down during the day Monday – Friday, so when our friends are off exploring, we can’t join in, and we don’t get to socialize as much with our dock neighbors. Even so, we’ve been able to meet lots of people and make some really good friends, and we have plenty of opportunities to join people for sundowners, meet up for dinner, and hang out on weekends. I think it would be a bigger deal if we had kids, but since it’s just us, it’s fine. We actually have more of a social life now than we did when we were fully land-based!

C: We miss out on some, but still meet a lot of great people and have made some wonderful friends. We miss a lot of the chatting on the dock / in the anchorage during the week since we are working but we still meet people over the weekends. It helps a lot that Melissa has a little bit more flexibility than I do because she will occasionally meet people during the week. This has been easier in the Bahamas and Florida than along the coast because typically cruisers move during the week to avoid the weekend boat traffic and stay put during the weekend. We have no choice but to do the opposite. Once we arrive in Florida it is easier because there are more people who are staying put for a while.

Q: What do you do for connectivity? 

C: In our first year we used a 100 GB data plan from Cricket Wireless along with a WeBoost Drive Reach Extreme cellular booster. We used the 100 GB plan instead of an ‘unlimited’ plan because unlimited plans typically get rate limited during peak hours after somewhere between 15 and 30 GB. Given that I spend most of my time on Zoom in peak hours, that doesn’t work for me. The Cricket plan lets me get full bandwidth and add more data on the months when I need it. The downside is that it really limited the places we could be during the week since good cell coverage was a must. Also, we found some of the areas with bad cell coverage or congested networks surprising – the north shore of Long Island for example. In The Bahamas we switched to the tab140 plan from Aliv, which was fantastic. This year we’ve bought a Starlink, which is great most of the time. We also keep a data plan for the times when it isn’t great. Examples of places it isn’t great: marinas with lots of really large boats or buildings blocking the sky, places where the Starlink map shows ‘waitlist’. In those areas we could probably get away with just using Starlink, but we get lots of drops during meetings, which goes against our ‘making sure our work habits are beyond reproach’ philosophy.

M: One thing we’ve consistently found is that we can’t rely on marina Wi-Fi. Very few marinas are set up to handle heavy traffic, and the networks aren’t reliable enough for uninterrupted service all day.

Q: How do you get electricity? 

C: We have four electricity sources: solar, wind, diesel generator, and when we’re on the dock shore power. Most of our power off the dock comes from solar, but we’re finding that our refrigerator on Windara is a bit of a power hog, and so is Melissa’s laptop, which is ancient. That means that we typically have to run the generator for an hour or so a day when we are on the hook, unless it is also really windy, which is rare in our anchorages. We’d like to not run the generator except for cloudy days, but to do that we’ll need a lot more solar and some more efficient appliances so that is a project for when we get back.

M: And if we get REALLY desperate, we still have the small, gas-powered Honda generator that we used as our back-up on Silent Sky. We intend to sell it, but it did save us when we first got Windara. Between system failures (alternator & generator issues) and weather challenges (cloudy, inconsistent wind days), our batteries were dangerously low. It was a little bit ridiculous – we had to throw out everything in the fridge because we couldn’t power it for something like four days, but we still managed to work, firing up the portable generator for a couple hours a day.

Q: Do you always have to stay on the dock?

M: No – because we have solar, wind and a diesel generator, we’re able to pick up moorings or spend time on the hook, provided we’re in an area with good all-around protection from waves or are within a short sail of a place where we can find good protection. A good example is when we were in the Abacos last year, we’d occasionally spend a few days on anchor off Elbow Cay, Lynyard Cay or Marsh Harbour. Each of those anchorages was well-protected from certain wind directions but not others. However, we were within a couple hours’ sail of spots where we had excellent protection (like Hopetown Harbor on Elbow Cay or the mooring field inside Man-O-War Cay), which meant we could get up early and be in a better spot by the time we needed to begin our work day.  

C: Exactly.

Q: What happens when there’s bad weather? 

C: We are obsessive about checking weather and planning our lives around it. As an example I write this from the marina we pulled into because of a significant wind event at the end of last week. I prefer to be anchored out as much as possible, but again, in the spirit of our work habits being beyond reproach, if there is a question of work being interrupted by weather we come to the dock early to make sure that doesn’t happen. Not ideal, but I consider it part of the trade I have to make for the privilege of living this lifestyle. That being said, we’ve definitely had bad weather interrupt work but it happens with about the same frequency as our colleagues who work from their houses. Part of that is because if we are somewhere that has a power or internet outage we’ve got several layers of redundancy before it impacts us.

M: What he said.

Q: When do you move the boat? 

C: We mostly move on weekends. I don’t like to take days off to move since we have limited vacation, which I’d rather use once we are in our destination. We will occasionally move before or after work when the days are longer and we are somewhere that the arrival time is *very* predictable – The Abacos are a good example. We time our moves to coincide with the best weather of the weekend which means that sometimes we’ll close our laptops on Friday evening and head straight offshore, other times we’ll leave on Saturday. The one thing we never do is plan to arrive on Monday morning. It is too hard to predict arrival times accurately, and we’d be too tired. The tough thing about this is we have a balancing act to perform – too long in the north and the winter storms start rolling through too frequently making it difficult to find safe weekends to move, head south too fast and we catch the tropical systems. All east coast cruisers deal with that trade, but it is a little more acute for us since we have the extra constraint. What that means in practice is that we’ll sometimes leave in weather that I wouldn’t otherwise. As an example we left Beaufort, NC on a Friday after work this year on the tail end of a system where we saw 25 kts, gusting 35 and 7′ seas on our first night out. It got better, as the forecast said it would, but if I didn’t have to work on Monday I would have just waited and left the following day. We won’t leave in conditions that I consider dangerous given our boat and our experience level, but I will leave in conditions that I consider uncomfortable.

M: Sometimes we do have to take a bit of vacation or holidays to make progress. Last year, we found ourselves leaving Hilton Head on Thanksgiving Day to make it to St. Augustine by the time we needed to be back at work on Monday. And we took a week off to leave The Bahamas and make it as far north as possible in the spring. We made Charleston, but it was a PUSH; however it bought us an extra three weeks in The Bahamas. 

Q: How do you handle provisioning and boat work? 

M: Fortunately I have a little more flexibility in my schedule, so I’m usually able to either go to the store or arrange grocery delivery (Instacart has been a lifesaver while we’re traveling in the US), run errands and deal with most of the regular boat maintenance tasks (getting pump-out, rinsing the boat down, metal polishing, interior cleaning, etc.). Occasionally we’ll dedicate anywhere from a few hours to a full weekend to bigger projects. We keep a running list of known maintenance items and tackle things as we can, prioritizing as we go, and hiring people if a project is too critical to ignore but too time-consuming to address without spending extra time in port. We avoid that as much as we can, but sometimes we don’t have the time, tools, or patience.

C: Melissa saves us there. I spend probably 30 hours a week on Zoom and the rest with my head in code so Melissa uses her flexibility to get the provisioning done and the regular boat tasks. I’ll take on most of the larger one off tasks that I can do at night or over the weekend like taking apart sanitation systems, running wiring, fiberglass repairs, and installing new hatches. I’ll also do the mechanical maintenance – oil changes and such. The other thing is that we do pay someone else to do more things than we would otherwise like to. For example, we often pay to have the bottom cleaned, and we’ve paid for sanding and painting of the bottom the last few times.

Q: What is your office set up?

M: One of the things that lead us to upgrade from Silent Sky was that being on Zoom calls at the same time was a struggle – it was hard to find comfortable space far enough apart that we weren’t interfering with each other’s meetings. On Windara, our forward stateroom is comfortable enough to take meetings from and is far enough from the nav station (where Chris usually works) that we aren’t in each other’s way. When I’m not on calls, I typically work from one of the settees or up on deck (although we each occasionally take meetings on deck too). The only time our current work set-up is a challenge is when I need to access our electrical panel and Chris is in a meeting since the panel is directly behind his desk.

C: We are fortunate to have a full nav station, which I use as my desk. I have two laptops – one for personal projects and one for work. I also have a tri-screen for my laptop: https://www.thexebec.com/ 

I don’t use it often, most just when we are both on a dock and I’m writing code, which is unfortunately rare these days. When I do, it is really handy to have the extra screen real estate.

Q: What’s the most frustrating thing about working while cruising? 

C: I think it is the relative lack of flexibility. One of the joys of cruising is the ability to go with the flow a little bit more and to live a life that is more attuned to the natural world. We lose a lot of that by working since we are locked into the same 9-whenever grind as we were back home. That being said, I’d much rather take the trade we have and work while cruising than put this off for another 20 years and hope that everything falls in place so that we can still do it.

M: For me, it’s being tied to a place Monday – Friday. If there’s a good weather window midweek, we can’t take advantage of it. If making our next port means departing in less-than-ideal conditions, we’re departing in less-than-ideal conditions. And as I mentioned before, we don’t get to explore our destinations in the same way as our retired friends do. That said, the positives absolutely outweigh the negatives – spending the majority of the year surrounded by palm trees and crystal blue water, the opportunity to meet new people and experience another culture, and the ability to do this now instead of waiting for “someday” make up for the challenges that working while cruising introduces.  

Q: Would you recommend cruising while working? 

M: Yes, but with some caveats. If you’re new to cruising, I wouldn’t recommend it. Learning how to cruise while working is a lot to juggle, and it can be overwhelming at times. If rigid schedules are your thing, this may not be for you (honestly, cruising in general may not be for you). By the same token, if you’re not a planner, you’ll struggle. We’ve had times where we’ve made split-second decisions to depart, and both a willingness to be flexible and the fact that Chris had already planned ahead made that choice possible. It helps if at least one person on board has some flexibility in their schedule. Things aren’t always open past traditional working hours, and you can’t plan on waiting for the weekend to run errands and travel at the same time. 

THIS IS HARD. If you have a romantic notion of beautiful, sunny-day sails capped off by sundowners, remember that that’s only part of the equation. The YouTube channels don’t show much of the bad parts – mostly because when shit gets real, no one’s filming. And sometimes, shit gets real on a work night, meaning however little sleep you may have gotten, you still need to be online at 9am. 

C: Depends. If you are already comfortable with the basics of cruising, and if you are able to be honest about it with your employer then maybe. If you aren’t able to confidently answer ‘yes’ to either of those questions though I wouldn’t do it. Working while cruising takes two difficult things and combines them in a way that makes both of them harder than they would be alone. I’d advise you to think hard about your personal ability to deal with stressful situations and keep going. Yes, we see beautiful places, have amazing experiences and get to know a whole range of places we never knew existed. We also have to show up for work in the morning after having our anchor drag when we get hit by a microburst in a severe thunderstorm the prior evening. The rewards are fantastic and you can absolutely experience them now, when you know you can vs someday, when it may or may not be possible. Also remember that doing it this way is definitely NOT the nearly complete freedom sold in magazines and on YouTube. If that is what you are looking for, quit your job and cruise for as long as you can. If you are looking for balance and something that you might be able to make permanent, give working while cruising a try.

Other thoughts:

M: We cruised Silent Sky in Long Island Sound for 7+ seasons before we decided to do this. In that time, we experienced a variety of conditions and challenges over weekends and 2-3 week cruises. While it wasn’t nearly as rigorous as cruising full time, it gave us a glimpse into what this lifestyle entails.

We also kept our apartment for the first year. I’ve heard of several people who’ve cut all the cords and cast off the lines only to decide this lifestyle is not for them. I doubted we’d fall into that category, but I didn’t want to feel like we were backed into a corner with no reasonable out should that end up being the case. I realize not everyone can manage the expense of maintaining a home while cruising full-time, but it was an option for us and I was glad to have the safety net of a place to return to if boat life didn’t work out.

Working is hard. Cruising is hard. Combining the two doesn’t make either any easier. What’s been key for us is being flexible in our expectations, working together to make big decisions, being equitable in our division of labor, and constantly practicing communication. We do date night most weeks, and our first season, we dedicated part of the conversation to checking in on how we were feeling about the trip. Having a regular forum for open, honest communication was really important, and talking through the bad weeks made it feel easier – I didn’t feel like I had to pretend I was loving every minute, and these conversations were removed enough from the actual event to be objective and productive.

C: Thinking back on our experience I don’t think this would have worked if we hadn’t built up cruising experience through at least a few years of part time cruising before we left. The mechanical parts of this lifestyle: how do we anchor securely, how do we sail from point a to point b, how do we take care of the boat, etc. are really the easy part when compared with the logistics of living this lifestyle, especially while working. If we still had to think about the mechanical parts it would have just been too overwhelming.

If there’s anything else you’d like to know about our experience, leave a comment below and we’ll be happy to answer. And let us know if there are other topics you’d be interested in seeing us take a deeper dive into!