I’ve had some pretty not so great bags over the course of a variety of years. And some good ones. Lately I’ve been looking to find a one that could do double duty; work + outdoor would be ideal but is a long shot.

For work, generally, I use a Filson, which is canvas and leather, doesn’t look like a backpack (a plus) and works fine. One of my best purchases was made a decade ago; a Mandarina Duck bag I scored while in Italy. From what I could tell they don’t make it anymore — it’s a black duffel that has hidden shoulder straps if you want to carry it on your back. I think I used those once in ten years (shoulder strap is fine).  I have this thing about luggage-on-wheels. I understand that it’s practical, but I can’t pull the string. I dunno, if it’s too heavy to carry then unload it and try again. Seems a little geriatric.

It’s about time to retire the Duck, but not critical. Sailing is. So I’ve tried a couple bags sailing. And by sailing lets say day-sails, racing, or even long weekends — nothing major. Ideally, this new bag would work as a day-pack as well. For overnight outdoors I have an old (decade) Marmot Shooting Star (3500 Cubic inches), another bag no longer in production.

I’ve looked at the usual bag suspects and have included a bunch of links. But I saw only few good choices for sailing. Most “sailing” bags are 100% waterproof which is kinda important, but most of the time your bag won’t get wet. I think waterproof bags/sacks inside a water resistant bag is fine, so I went with it. For interior waterproof bags I use Pacific Outdoor drybags with an airvent (pneumo) that allows you to compress the air out of the bag easier than a regular roll-top. They’re great.

So after looking at:

Motorcycle pack: Ergon

Sailing Packs/Bags: Harken

Kayak/Messenger: Sealline (which I like)

Patagonia Duffle (too expensive)

Trendy Master Piece Fade Black (ehh…too expensive a little too big)

Another Motorcycle Pack: Kriega

and even classic Fjallraven – not practical for sailing

and even more not worth mentioning, I went with Ortovox, (pictured above) why?

Made for skiing, its pretty water resistant (has not arrived yet so this is a guess). So will work for skiing, fine for outdoors, should be fine for boating, and maybe even for trips (like vacation if I can squeeze one in). In any case will update as I get insight and am, you know, looking…

A North U (university) sailing seminar looks something like this picture. Less than riveting. Looks aside the time spent was solid. It’s hard to learn sailing in a classroom or by reading a book.

But it’s is part of what you need if you want to push sailing skills forward. There are some basic parts of sailing that are best introduced in a class and then repeated again (and again) on the water. Instructor, Bill Gladstone was great and while sharing theory preached to simply “sail fast.” Sounds obvious, but that simple statement is what racing trim is all about.

Why do you want a “twist” in the mainsail? Because you go faster. And we could spend hours discussing the aerodynamics involved, but we stopped with fast. The best resources I found getting me started in sailing was taking an ASA course, “Introduction to Keelboat Sailing” while on vacation in Miami. If I were to do it over again I would opt for the same course given by US Sailing, but the learnings are the same.

And there are no shortage of boat owners (Captains) who need crew. It’s a challenge to round up three or four people every time you want to take your boat out, so it’s an opportunity to learn. There is a unique zen-like connection to the elements when sailing that I haven’t felt in any other sport (err…maybe kayaking, maybe even scuba diving, and xc skiing but different zen). Zen or adrenaline, looking forward to warm weather…being back on water if/when schedule works with the wind…humbling being around these coaches and teachers though, so much to learn, so much to know…

My first international sailing adventure ended as pictured above. I was crewing. That was in 2003. Well before this unhappy ending I had a bad feeling. As our sail progressed from St Lucia deep in the Caribbean to Panama I felt there were too many factors starting to work against our success. And after two weeks of mishaps, I got off the boat in the San Blas Islands two days prior to this picture (and flew back from Por Venir Island (Youtube video of “airport” not mine). Learned a lot.

As additional background — the boat was a 42 foot Ketch-rigged “cement” boat. There were three of us including the Captain for the roughly 1400 miles from St Lucia to Panama. The watch system is key and was rotating with one on, no overlap, every 6 hours and with three of us we would not have the same watch every day. The “crew” Michael and I had limited experience then, Michael really none but a lot of enthusiasm and experienced world traveler, and me some sailing and a little less enthusiastic as I started to question the occasional odd decision.

What broke on the boat before the sailboat itself: the Spinnaker, the electricity generator, most importantly the propeller shaft (thus the Colon stop as opposed to the Canal), the wire running up the mast to the VHF antenna was severed in towing attempt; towing also produced a very audible cracking sound but no damage found on visual inspection (tow in the middle of nowhere is another story — see PDF at bottom if interested). Fresh water was limited to the sulfur-laced water from volcanic St Lucia as the tanks were filled from the boat-wash hose at the Marina, becalmed for several days so food choices were limited; fruit gone, etc. Just to reiterate, without the propeller shaft we were purely sailing, no margin there.

I came up one night after hearing the curious sound of breakers to see that we were desperately sailing away from what would have been somewhere/nowhere in Columbia — where we could see the Palm Trees on the beach with the moonlight. We were sailing away from the beach at more or less 0.5 knots. Long night. Other than that we were fine.

My important take-aways:

1. Hard sometimes as crew, but try and do a boat inspection before getting on a sail boat for the trip. If you have ANY issues you may want to not go.

2. I always rent a Satellite phone when sailing, now. We were late in getting access to communication and folks were worried. It’s not that expensive and could be life saving.

3. You’re on your own. Be prepared to save your own existence whatever that means to you because it may come to that and don’t expect that someone you just met is going to be as concerned as say…you are about your own life.

4. Food is key. Bring something you like. Water very key, but unlikely you’d be in my situation — you should check though and maybe bring a couple bottles (not glass) of something that will get you through a tough spot.

5. Your life is in Captain’s hands – be comfortable with that. You can have input or opinion on weather-routing, sail plans etc, but usually that’s all — you’re kind of along for the ride, so knowledge and experience at the helm is pretty much key.

These are just a few big issues. In retrospect, I loved the experience of this trip, though there were times that I hated it. I wrote the whole story as a PDF here. The Captain got a replacement and continued his around-the-world journey and is in Asia, my crew-mate, Michael now has 2 kids, no plans to sail and lives in the Pacific NorthWest.

San Blas Islands, Panama (where I exited via 10 mile dinghy ride)

Big Wave

I wouldn’t recommend not watching where you’re going. But it’s hard to get away from the office — especially with a start-up like Voyage.tv — or any start-up for that matter. But I try to find a balance even if tied to a Blackberry (and an IPhone).

We leased a 32 foot Bennetau this past season (wife would surely say “I” as opposed to “we”). And is a challenge to make a boat pay off especially if you’re busy. Better to learn this now for sure. With a 2 year-old son, and a months-old business I should have known. Now I understand why so many sailors are retired. Couple suggestions for NYC sailors based on my limited experience:

1.  Make sure you have friends who sail or want to learn. You’ll need crew — lots — since most non-sailing friends will show up a couple of times for the novelty, trust that docking is no fun without help. Find additional friends.

2. Pay attention in NY Harbor. Picture aside, there is a lot of traffic — besides planes falling out of the sky. Also there are several sailing schools, so while you might expect someone to bear away, toss expectations and get out of the way.

3. Use the relatively protected area (as oppossed to the ocean) to get comfortable with your gear. When you lease a boat you’re rolling with whatever the boat has. Get your own VHF, GPS, charts, and apparel appropriate for the weather. I tested inavx.com as an iPhone App and its a pretty good secondary chart/GPS; for your primary you’d want something bigger; and a device more rugged than the iPhone. I like the app though and it keeps getting better. Not a bad idea to carry a Garmin or similar though if you’re in the ocean (and a paper chart). I rent a satelite phone if I’m on the ocean overnight – could be a lifesaver and cost about $5/$6 a day.

4. Speaking of weather — avoid weather (rain, wind, etc). Get accurate info from NOAA. Before your leave. Easy to avoid in NYC harbor a little more challenging on a trip — but you know that.

5. Watch the tides — NY Harbor has some pretty serious tides — especially around the infamous Hells Gate. It has the name for a reason. If you can only go 5 knots and you hit a current of 3 knots — well you have some issues. Worse in some ways is if you’re moving with the current and now 8 knots and you can’t accelerate out of turn. Don’t want to kiss the bridge. Another great iPhone app AyeTides can keep you out of trouble.

6. Make sure you can actually leave the office (and leave it behind at least for a few hours). Mission not accomplished there for me, but baby business is demanding. Your call if you can swing it.

That said, sailing overall is declining. Even before the recession. Sure it’s expensive to “own” a boat, but you can sail for free if you’re crew — the NY Times covered crewing and if you’re up for it, it’s one way to learn. It’s really how I took my first deep dive in sailing — crewing 1500 miles from St Lucia to Panama.

The above are just a couple thoughts…see you out there….

First time out this weekend on a Shields 30. Pretty exciting on a windy day. 4 boats (all Shields), 12 or so crew (one down for stitches after a boom/accident). Stepping on a boat you don’t know (especially for a race) is always a little nervy. You get about 10 minutes of instruction, given while you’re getting underway, over the noise of the wind,  and then you’re off.

We were doing three person crews generally with the buoys laid out earlier than the 10AM start and the committee boat standing by. First call was there was too much wind for Spinnakers (gusts probably to 25 maybe 30 knots I dunno).

I was on the Main Sheet, so was in the very small cockpit between the helmsman and Kirk working the jib. Kirk then jumped (literally) to the committee boat to assist getting Bernie to the hospital — leaving just the two of us. And as two we won the first two.

The jib was very unlike the bigger boats as you’re really releasing with one hand and trimming with the other — hopefully at the same time. There’s kind of an art to this while ducking under the boom. Good bit of water coming over the bow as well. And loud (wind).

In good wind the boat comes about quickly and heels so the rail is in green water before you know it. In wind. All good — nothing like a few hours in the wind to make you forget anything else but wind and water. I don’t even really know where this nautical fascination came from — think it’s all part of a general wanderlust. Is perfect for now. The boats are courtesy of Oak Cliff Yacht Club (more on Oak Cliff here: http://very.fm/little-rainlittle-fog).

With both my parents from the Caribbean (Trinidad and Jamaica) I’ve probably spent more time there than many. But Turks is different and great. For me. Small and manageable with beautiful water and great diving (DIDN’T make it this trip). So this was one for the family — no diving or sailing or anything that required more than flip flops.

And if you want to slow down, Turks is perfect — we got there the week before Labor Day so the height of both the off season and  hurricane season as well. Sure there were a couple of suspicious systems that could have developed, but the family was oblivious as I checked NOAA daily. I would def recommend the island and the hotel — Gansevoort. Great service and beautiful property. Rented a car for a couple of days just to see the place, and my minimal left-hand side driving skills were sufficient.

The island sports the 3rd largest barrier reef in the world so I will be back. Do want to hop on a boat as it’s pretty close to lots of interesting places. I posted a bunch of pictures on Flickr, and they tell just a part of the story. Consider the destination and the property highly recommended.

I have road tested the iNavx iPhone nav app in both a 400+ mile sailing trip from Ft Lauderdale, and weekly out on the Hudson — pretty impressive what you can do with a GPS-enabled iPhone. Hoping to do get a bit further off the grid though. At least for a few days.

Voyage.tv is still so early stage that I’m not so enamored with leaving the development to whoever is next in line. As with most start-ups there really is no next in line as everyone is fully embroiled and slightly overwhelmed in their own efforts. And vacations. We are a travel/experience video-enabled platform, so here’s to testing some product before the streets ice over.

Took the boy (2 years old) to the Beach to see the big waves today, but he slept through them. They were impressive — to me. We made it out to Captree – a place that conjurs foggy memories ( a growing category for me). But I grew up on Long Island and some of the less-known beaches like Gilgo and Tobay were more a mainstay than Jones Beach or Robert Moses. And Captree. Can’t say I would recommend it if you don’t share the nostalgia.

Rehabbing the leg for the Nike Human Race in October and anything else I can find time for. I the meanwhile will be at my desk.

And there is just so much to know, and Tayana Captain (friend) is a fantastic sailor. There’s so much to know on a boat and any time with someone who’s sailed probably 35,000+ miles is really like Gold.

INavx worked well — hard to keep an iPhone on deck in wet environment though Aquapack can help. Still need a bigger electronic chart on the computer and ideally the same as what’s on the iPhone. Again ideally you’d want to plot waypoints on the bigger screen of laptop and upload them to iPhone, but can do on phone with patience. In any case, good to have another chart on board (and GPS). Just took ASA 105 which is kind of a throwback Navigation class — lots of pencils and erasers….but it all helps…especially blue water…harbors too.

Trip was 400 miles — did 10 knots with the help of the Gulf Stream and was back at desk on Wednesday.

Short story. I could say the Atlantic wins, but that would imply Branson loses. And sailing is complicated. He demonstrated the judgment that has helped him amass a fortune; sure you take risks, but you have to know when to fold. And with two of his adult children on board the boat I’m sure his risk aversion was only heightened.

Still, the thought that the Atlantic ocean can send a world-class yacht back to port is on one level amazing. That they lost a life raft and a sail can be said of many a long sailing trip — something always breaks. Chalk up one more of many for the Atlantic. Reassuring, for me, to know that adventure is still just as close as the beach.