Telecommuting while island/coast hopping

[irishgigantor]

I currently live in the Washington DC suburbs and am extremely bored. I've just been certified in the past year and have done 8 dives on Grand Cayman since getting my card.

I've been joking with my boss for years about telecommuting full-time though I have never done it. At most I have spent a month away from the office.

For various reasons I am considering making the plunge into full-time telecommuting and I would like to use this freedom to visit a variety of destinations for a few weeks or a month at a time.

Essentially the only absolute requirement is that I have reliable internet access wherever I am and it isn't too difficult to get back to DC if I need to. For now that leaves out the Asian destinations. I will still be earning my current salary, so I am not relegated to budget locations. I can afford to rent a furnished apartment for $1500 US a month if I need to.

Things I would *like* to have in each destination:
- Housing close to or on the beach
- Other travellers/backpackers/transients around to have a beer with or trade stories.

I have travelled extensively around Europe and Australia for long periods, so I already know that being 'away from home' won't be an issue.

Reading these boards I have gleaned a ton of useful information from trip reports about places to go and what to expect.

My goal is to be able to dive at least once or twice during the week along with some weekend dives, either with a boat charter, or shore diving with a buddy depending on actually job schedule.

To start out with, I was thinking of going to the following places:
- Key Largo
- Somewhere in CA to dive the kelp forests
- Maui
- St Croix
- Utila
- Domenica

I suppose my main question is, has anyone here done this before? Most reports on this board seem geared towards week long vacations, and not actual non vacation living. I have gotten a lot of info related to moving to island nations from other sources, but nothing seems to marry the moving/living (slightly) longer term with the diving.

Also if anyone else is in a similar position and wants to talk about maybe planning something together, that would also be welcome. I am looking to start this trip in August 2011 when my lease expires.

 

[ColoDale]

I telecommute full time but in the U.S. I have supported companies with overseas sites and a few who accessed their work from their home in other countries. We did not support that kind of WFH access for them.
There are some technical challenges that you will face in general.
1. The IT infrastructure in foreign countries may not be that good. Their main connections out of the country may have very limited bandwidth. You have to share that with everyone in that country (assuming you spend time accessing international resources, logging into international servers, etc). The local infrastructure (cables, servers, circuits, etc) may or may not be good and the maintenance questionable in addition to getting good customer service if you have a problem. Hopping from place to place may add to the problem. Local ISP and VPN issues can easily arise such as supported protocols.
2. Local support for hardware such as your PC/laptop and local router. If you need your company PC/laptop re-imaged it can be difficult if not impossible. Most things like that have to be done by your deskside personnel at their site. Shipping you machine back is a huge hassle not to mention it may disappear (foreign location).
3. Security - I don’t know what proprietary information you will access or send but there can be significant security holes in provider networks especially wireless.
4. Most companies have limited support for remote users via their IT department. They may support the VPN client on your machine and everything past VPN (or dial up modem banks) into their network but nothing in between i.e. the ISP. That makes you the troubleshooting person who has to deal with whatever ISP you use if everyone else says it’s not their technical problem (which ISPs will do as well).
5. This is the short list.

I am not sure about the questions about living and diving. You do your work and go diving in your spare time. If your company offers flex time schedules ( 4 tens, am or pm work) then take advantage of that.

If you work on a team and take off for a month at a time with flex schedules, there has to be a lot of coordination and access/communication back and forth especially for availability or I guarantee you will have ticked off coworkers who may view your telecommuting as company paid vacations. That is, unless your work is totally independent - I don’t know what you do.

I cannot address other parts of your post as I have not worked this way.

 

[DeputyDan]

ColoDale - very good post!