San Juan to Culebra: Can’t get there from here (apparently).


I’m typing this from the anchorage in San Juan. It’s Sunday afternoon, and we were supposed to have been in Culebra by now.

We knew coming here that it would be a windward slog to get back to the Virgin Islands. It’s about 70 miles when you account for tacking angles to Culebra from San Juan. Mia and I spent most of Saturday getting the boat ready for the passage back – replacing the genoa with the smaller jib, stowing all the accumulated crap down below that inevitably gets left out after a long stay in port, removing and stowing the outboard and the dinghy, etc. etc. The plan was to depart at midnight on Sunday morning – have an early dinner, get some sleep, then high tail it out of here so we’d make it into Culebra in daylight.

I snoozed three times before finally rolling out of my bunk and making some coffee to wake up. It was 12:23. With the boat ready to sail, we hoisted the mainsail while still on anchor, raised the hook and turned downwind for the two-mile jaunt past the cruise ships and commercial freighters out of the harbor, around Fort Morro and offshore.

The small jib we’d hoisted felt tiny, and even with a full main, the light wind offshore was barely enough to keep the boat moving at five knots into a very uncomfortable, sloppy sea state. The forecast had called for 15-20 knots from the east along the north shore of Puerto Rico, with squalls and showers for the next few days.

Once we cleared the Fort and got further offshore, the wind filled in and Isbjörn heeled to the sea and started smashing her way upwind. It was fluky going for a while, with rainclouds overhead that stole the wind, then brought it back with fervor, before dying again. I cursed myself for removing the big genoa.

And then, suddenly, the wind filled in for good once clear of the wind shadow that the big island creates. The stars were out so it was a beautiful night, but man was it windy! The anemometer, which I’ve calibrated to read as low as it possibly can (I always feel like they over-estimate the wind speed), was touching 30 knots. Mia came up from her bunk (I was supposed to have the first watch) seasick and perched herself under the dodger to get some relief from the cool night air. I was at the helm taking a beating, every second wave crashing off the bow in a huge plume of spray and slapping me in the face. We took two reefs in the mainsail right away and were well cozied down. The boat was sailing great – 7 knots upwind, smashing through the seas, easy on the helm. But her crew was not. I don’t know what we expected, but it certainly wasn’t this!

By 0200 I was exhausted, my paltry four hours of sleep catching up with me as the caffeine effects of that first cup of coffee wore out. It was too rough to make more, and besides, my tender stomach at that point probably couldn’t have handled it. I has some indigestion from eating half a bag of blue corn chips – the salty crunch is a sure bet against seasickness for myself, but I ate too many of them.

I had this gut feeling that we should just go back. I’ve never done that before, gone back into port after having made a solid plan to move from Point A to Point B. I’d read that the strong high pressure over the Atlantic creating the enhanced easterly trades was going to abate by Sunday night into Monday, so why not just turn tail and wait it out?

So we did. After a quick tack we bore away, aiming again for the lighthouse on Fort Morro. Reaching now, Isbjörn took flight, making 8.5 knots with still 25 knots of apparent wind over the deck. It was remarkable how fast we sailed with such little sail area up, so it kind of reinforced our decision to duck and run.

At 0400 we rounded Fort Morro again, dropped sails and motored back into our usual spot off the small airport in San Juan. Half an hour later and after a freshwater shower to get the salt off, I collapsed in my bunk, not waking up again in 1100 this morning. Defeated, but happy to be back in familiar territory.


Thanks to our aborted mission last night, it’s now day 8 of our stay in San Juan. We arrived here without a plan besides dropping Lisa at the airport last Sunday. But I’m pretty sure the plan didn’t involve staying this long.

So Mia and I have gotten to know San Juan. The long walk to Old San Juan past busy streets and shady neighborhoods. The numerous parks along the northern shoreline and the glut of bronze statues spread around the city. The South-Florida feel of the Condado beachfront hotel area, replete with the shops and restaurants you’d expect to find there, and the requisite pasty-white tourists that frequent them. The locals neighborhood of Miramar where we ate amazing portabella burgers at an airy outdoor burger joint called ‘Yamburger’ just up behind the San Juan Bay Marina where we’d been leaving the dinghy in their secure, gated dinghy dock to the tune of $5 per day.

We’ve had a week of office work interspersed with boat maintenance and improvements and local exploration. There is a nearby Hilton hotel with a fabulous lobby where we’d been hiding out all week to get some ‘real-life’ work done – managing the World Cruising Club business since the end of the Caribbean 1500; organizing our ever-increasing list of crew who have signed up to come sailing on Isbjörn (the whole reason we’re here on the boat in the first place); publishing a few podcasts; banking; etc.

The dual-nature of our time down here highlights the contradiction that is our lifestyle right now. The Internet world of email, business and banking runs at a certain speed; it’s only possible to keep up with this speed by living a ‘normal’ life ashore, working from home with high-speed wireless connection and easy access to cars, offices, post offices, etc. We’ve given that up to come and live on the boat, which happens to be in the Caribbean due to the schedule we’ve created, but we still have to work. And it’s impossible to keep up.

Consider that just getting ashore to find good Internet is an hour-long process at best, our ‘commute’ so to speak. Install the battery on the Torqueedo electric outboard (my favorite piece of kit onboard, which I can go into detail on later), load up our backpacks in dry-bags so as to protect my literally priceless computer (my life’s work is stored there, and only some of it is backed-up), dinghy ashore at about 3 knots (we’re a quarter-mile or so from the dinghy dock, so this takes time), lock up the dinghy and then walk the mile or so to the hotel lobby where we try to act inconspicuous while we spend the day enjoying their air conditioning and their ice-cold, orange-infused water.

This works, and its part of the reason we’ve stayed here so long. To have a reliable place to get work done is valuable, so we take it in chunks, working as efficiently as we can to try and get ahead so that the following few days can be used to enjoy the cruising lifestyle as it’s meant to be (hence our plan of heading to Culebra for some exploration and R&R).

Cruising operates on a whole other pace, which Mia and I are starting to (finally) adapt to. We’ve truly got no place to be (at least until December 18, which is a long-time in our constantly-on-the-move lifestyle). So we’ve adopted the Swedish phrase ‘ingen brådska’, literally meaning ‘no hurry,’ which we say to each other several times a day to remind ourselves to slow down. It’s become a running joke aboard that started with Lisa, but it’s still true.

Boat stuff takes forever, especially in the tropics where it’s 90º every day. Mia does not do well in the heat, and I think that by being around her so much my blood has started to thicken too. Anything over 75º and I’m uncomfortable.

We ran out of underwear a few days ago so set aside a full day to get a laundry mission accomplished. The nearest laundromat was a good 3-mile walk through the South-Florida beach areas and into a more locals-oriented neighborhood. During the hike, I felt as if we’d transitioned from South Florida into Southern California, such was the vibe along the quiet streets once we left the high-rise hotels behind us. Little cafes popped up here and there, a few small surf shops on the corners, some local groceries, a vegetarian restaurant. Very hippie.

By the time we’d reached the laundromat, Mia lugging the backpack full of dirty clothes, myself carrying my backpack with my laptop inside (the laundry had Wi-Fi, so I took the opportunity to publish a podcast), both our backs were soaked with sweat. We didn’t bother washing our newly soiled clothes though – we still had to walk back.

6 miles later we hung up all the now-clean-but-still wet clothes on the lifelines to dry in the tropical sun. Laundry took the entire day. ‘Bra at det ar ingen brådska’ we said to each othergood thing there’s no hurry!


That evening was to be our last in San Juan. Mia invited me for a glass of New Zealand Sauvignon Blanc in the cockpit (Mia and I met in New Zealand, so this is always a special occasion) and a few black olives before we saddled up in the dinghy yet again, parked at the marina and sauntered 3 miles in the other direction and into Old San Juan. It was Friday night.

We were warned on several occasions that San Juan could be shady – be careful of pickpockets and don’t leave stuff unlocked, we were told. But our week-and-counting here has proven that it’s just like any other big city. 99% of the people are super friendly and helpful, and if you don’t do stupid, obviously touristy stuff, you’ll probably be fine. I don’t know the stats, but San Juan can’t be any more dangerous than the streets of New York, and I certainly have felt safe here. And as for the whiners on the cruising forums who don’t like the deep anchorage surrounded by cruise ships, commercial traffic and a noisy airport – well, I’m happy for you guys to stay away. Leaves more adventure for us to find here.

Anyhow, Mia and I stumbled upon a Friday night street party in Old San Juan. The local restaurants spilled out into the cobbled alleyways and police stopped traffic to make room for the throng of pedestrians. Local 10-piece bands took to small stages at every other street corner and pop-up bars under colorful, beer-branded tents sold drinks to the passersby. One Spanish restaurant had a hot-tub sized pan loaded with paella that the locals queued up to get a portion of. Classy white Christmas lights hung between the balconies overhead, the sole reminder of the Holiday season down here where it’s hot all year round.

At street level, the cobbled alleyways are too narrow for cars to pass, so all the streets are one-way only, the bluish-purple cobbles obviously laid long before the automobile was ever even an inkling of an idea. Shops, bars and restaurants line the ground level of the busier streets, with apartments taking up the second, third and fourth stories. Each building has it’s own uniquely colorful stone and paint work, with intricately detailed tiles on the steps and walls of most places. On the quieter, residential streets, you can often see right into living rooms and kitchens, as most people leave their windows – which are really just wooden shudders, as it’s too hot for glass – open in the evening to let in the cooler night air.

But those balconies are a magical part of the architecture of Old San Juan. Some seem close enough together, given the narrow streets, that you could jump to your neighbor’s place. We witnessed one lady three stories up lower a wicker basket down to another lady at street level, presumably filled with her lunch. Clever. Most of the railings are beautiful wrought-iron pieces with intricate floral patterns, and nearly all of them are impeccably maintained. Gazing down the streets, there are countless balconies lining the higher levels – it’s like a scene from Aladdin. So Mia and I wandered the streets that Friday night, admiring the music, the architecture, the people and especially those balconies, taking it all in one last time before our planned departure the next night.