We decide that today calls for a road trip. So after a quick breakfast we pack up and head across the street to a local rental car agency. Cars aren’t cheap on Vieques, so after checking out a collection of different beat up old vehicles, we settle on the one that looks the least likely to fall apart but still has air conditioning. Even then, it’s $60/day for a ride that looks like what a high school kid might drive (although a regular high school kid, not any self-respecting kid from Redmond), but we need transportation, so it’s Econ 101 at its finest.

The gas tank is pretty much empty, but there is a town on the other side of the island and we figure we’ll get there easily enough (the island is only a couple miles wide after all). This decision will prove unwise, but for now we are finally free of the hotel and on our way to nicer beaches on the Caribbean Sea side of the island.

On the way, we pass through the town of Esperanza. It is clearly the more tourist-oriented town of the two that are on Vieques, with a string of restaurants along the waterfront and a few shops selling activities. Were I ever to come back to the island, this is where I would stay, as on a relative basis, this is Disneyland compared to where we are. What they don’t have, unfortunately, is a gas station.

The warning light hasn’t been on long, so rather than cross all the way back over (it’s not too far as the crow flies, but with a fairly twisty road going up and over the ridge, it takes a fair amount of time), we decide to press onto Red Beach, which the rental car clerk told us was the best one to visit. It is definitely a step up from the beach at the W, with much calmer water and much softer sand. We’re totally unprepared to be on a public beach compared to the people that have shown up with chairs, umbrellas, coolers, and barbeques, but we’re lucky enough to wander by one of the covered picnic tables just as a group is leaving so get a place to set up out things out of the sun.

We spend a few hours playing in the sand and the water before deciding to check out Black Beach. I’m willing to just keep driving, but despite all her other charms, Angela makes a horrible Louise to my Thelma, so before going anywhere, she wants gas. As it turns out, there are only two gas stations on all of Vieques, both run by the same company, and strategically placed a block apart. It is Sunday though, so only one station is open, meaning there is a line of cars down the street like the oil embargo is still in full swing.

With no other option, we wait our turn in line, happily learning when our time comes that on Vieques, gas is a cash only business. Our cash however, is securely locked up in the hotel safe, and the best we are able to scratch together is $3. We sheepishly pump our ¾ of a gallon of gas, which at least gets us back to the hotel, where we pick up some cash and retake our place again at the back of the line.

Gas problem solved, we continue on our quest for Black Beach. It’s fairly prominently marked on the map, but we can’t find anything other than a faded sign nailed to a tree, so we decide to head on a bit further to Long Beach. It’s much more deserted than Red Beach and the water rougher, but the waves give the boys something new to do and they spend a good hour or so honing their body surfing skills.

It’s getting late in the afternoon, so we decide to pack up and head back towards Esperanza to find a place for dinner. Passing the tree sign for Black Beach, we see a car parked in the turnout, which piques my curiosity enough to stop and take a look. As I am parking the car, it makes an unnatural sounding clunk, followed by the entire passenger side corner sinking down several inches. My spidey sense tells me this is a bad thing, so I put the car in park and get out to assess.

The wheel tilting out from the car and the big metal bar hanging down into the dirt seem to indicate a problem (the dented bumper was a previous customization), so we call the rental office for roadside assistance, and are soon rewarded with the arrival of a sweaty 400 pound man who speaks no English. He takes us back to the office (across the island again) where our sweet ride is replaced with another high-end automobile.

We’re mostly adventured out by this point and only interested in dinner. Of course, no restaurants on this side of the island, so up and over we go again. The meal is a little uninspiring, but at a food cart we discover Pinchos, which are skewers of meat grilled up and topped with a piece of garlic bread. For $2, they are good value and the high point of Puerto Rican cuisine for us so far.

While my trusty sidekick makes a great traveling companion, the one area that sets us at odds is the relationship between vacations and mornings. She is firmly in the camp that says vacation is for relaxing, and relaxing means not feeling obligated to get out of bed until you are damn good and ready. I live on the other end of the spectrum, which says if you are going to stay in bed all morning, you don’t need to fly to a place 10 hours away to do that.

With the boys trending towards their Mom (most notably our soon to be teenager), it is nearly 11 before all hands are ready to leave the room (some of us significantly grumpier about it than others). Any organized excursion has long since departed by that time, so we again head down to the beach for a repeat of yesterday’s action.

After a few hours, the kids are begging to go back to the room, in part because they are bored, but more to get their hands back on their electronic devices, which they are starting to show signs of withdrawal from.

There’s no conceivable way I can sit in the room all day, so figuring that, with it being Saturday, the island will be busier, and a bright idea would be walking to town to see what there is to do. It is a couple miles away, but Ang and I decide it will be good to get a bit of exercise and that it will be fairly easy to get a cab back out to the hotel, hopefully with something we can feed the kids a bit more exciting than turkey sandwiches.

The walk in goes more or less as planned, but as we get to town, we realize things are beyond dead. Any place that might have been open is in the process of closing by the time we roll in around 4 pm. Looking at the number of vacant shops and the condition of many of the buildings, I’m not sure how jumping the place might be on a regular day, but today, tumbleweeds blowing down the street wouldn’t be out of place.

Fortunately, the grocery store is still open, so we pick up a few things (mostly nice, heavy liquids which feel great in my backpack) and head back to a pizza place we spotted on the way in. We figure we’ll get a hot pizza, jump in a cab with the heavy pack and be back at the hotel before it gets cold.

As it turns out, William’s Pizza is out of pizza today (huh?) and there isn’t a single cab to be found. Two miles sounds a whole lot less appealing now than it did on the way in, but with no other options, we suck it up and start back.

The one place with signs of life on this day is the chicken boxing stadium about halfway between our hotel and town, and shortly after passing it, we finally come across some cabs (no point waiting for a fare in town when everybody is at the fights). The driver wants to charge us the same price we paid yesterday to go all the way from town, but by this stage we’re in no place to argue, so climb aboard for the short drive.

Not surprisingly, the boys are exactly where we left them – Nick hunched over his Kindle, Joey with the iPad, and Sam watching some mindless cartoon. Video games and TV on vacation rank up there with sleeping in for me (and fortunately my other half concurs with me on this one), so come hell or high water we’re getting out of the hotel in the morning and finding something to do.

Today we are off to Vieques. From what we can determine, most tourists take a short flight from San Juan, but at $100 a person each way (times 5) the ferry holds a certain quaint appeal. The downside is time-based, as with the 60 mile drive to the port, 90 minute wait in the terminal, and 90 minute crossing, it is close to 3 pm before we arrive at the hotel.

Until recently, nearly half of Vieques was used as a naval bombing range, so unlike most of Puerto Rico, it is very undeveloped. With few hotels on the island, we tried to find a house for rent, but the combination of short notice, mixed with a dose of apathy, put us squarely on the day of departure with nowhere to stay. Under duress, we finally booked a few nights at the W, which, as the only real hotel on the island, smugly charges more for a room than I have ever paid when not on Goldman Sachs’ expense account. After factoring in the cleaning fees and extra person charges, it doesn’t end up being much more than a house would have cost, but I still feel a burning pain in my left front pocket.

As hotels go, it is nice, but the whole concept of the W is a little more trendy than suits us. There are not a lot of kids around, so we feel constantly on guard to make sure our little entourage doesn’t crank up the volume to eleven. And likely by design, it is quite secluded, so the options for walking to anything close by are quite limited (the harder it is to get somewhere else, the easier it is to sell you a $15 hamburger). Undaunted, we bring our full Clampett game, and quickly replace the $5 Cokes in the mini fridge with our collection to sliced sandwich meats, cheeses, and juice boxes.

Being on the Atlantic side of the island, they tell us the beaches are generally too rough for swimming, but today the water is quite calm, so we spend the rest of the afternoon watching the kids build castles at the tide line and plaster each other with sand balls.

We’re not really sure what we want to do here, other than I have heard the diving is quite good, so tomorrow maybe we’ll try and come up with a plan. While just relaxing by the pool is a perfect vacation for some, I go stir crazy easily, and as big as the resort is, I can already feel the walls closing in.

Joey and I are up early today (what’s new?) so rather than wait for the rest of our pathetically lazy gang to get ready, we decide to head out on our own and explore the old city a bit. There is a strange yellow ball in the sky that’s hurts our eyes if we look at it, but no one here seems to notice – or care as the case may be – so in the interest of blending in, we just pretend its not there.

The area where we are staying is inside the defensive walls and full of old cobblestone streets and restored buildings painted in an array of vibrant colors. It has a very Caribbean feel to it, and once she is out of bed, Ang finds it enough to her liking that she gives me false hope she could live here in one of them. We spend the rest of the morning just wandering around along the waterfront, on the wall and through the different neighborhoods before settling down for lunch and some much needed air conditioning. Not really knowing what kinds of food Puerto Rico is famous for, we try a couple of different things, but don’t come across anything that memorable.

In the afternoon we walk over to El Castillo, which is the main fort that used to defend San Juan from seaborne invaders. It takes about three hours to explore it all (including some time for a pre-scheduled conference call – sigh), so by the time we finish, the boys are ready to get back to the hotel for a bit of a break and some time in the pool.

We finish our day with a stroll back through the old town where we come across a city park swarming with pigeons. One of the locals has a bag of feed and is kind enough to give each of the boys a handful, which immediately gives them avian rock star status.

After a shot break at the hotel, we head back out to find a restaurant for dinner. There are much fewer places to eat than we seemed to recall from earlier in the day, but we finally come across a gritty looking place full of locals and decide to give that a try. We don’t really recognize any of the items on the menu, but the little people are all good sports about trying some new things, and even though they didn’t end up liking much, the all get a solid A for effort.

Tomorrow we are headed to a small island to the east called Vieques, so after setting up some transportation for the morning, its time to call it a say.

With the rain coming down relentlessly (Ang says we are just having a “bad spring”, but if that’s true, then how many years do I have to live here to see a good one?), and our plans for India on hold due to some unreliable babysitters (seriously, what kind of excuse is heart surgery?), my mental health hinges on synthesizing some vitamin D. So after digging around a bit for some travel options, we settled on taking the entire horde to Puerto Rico for two weeks.

Now normally this wouldn’t be on my hot list of destinations, but with two of the boys’ passports in for renewal, our choices are limited to the U.S. So bags in hand, we leave the house at 5 am for the airport.

In the interest of efficiency, I’ve blended this trip together with a work trip to New York and Toronto, so while our route from Seattle to JFK and then onto San Juan isn’t the most direct, it gets me where I need to be on time and at the cheapest price (while it costs almost $500 to fly TO New York, it turns out that for $350 you can fly THROUGH New York, travel 1,500 extra miles, and get two weeks of beach time in the mix – go figure).

Against my better judgment, I’ve also been convinced to use my last 3 American Airlines upgrades to get 3 seats at the front of the plane for the outbound flight. Somewhere along the line it became unacceptable for the Roberts boys to fly coach, so instead of coming home from Toronto in comfort, I’m looking forward to a middle seat back near the bathrooms.

Other than settling the arguments of who gets to sit in the upgraded seats when, the flights are fairly uneventful, although all in, they make for a pretty long day. It is definitely worth it though, as walking out the airplane door feeling the 80 degree weather reaffirms we’re not in Seattle anymore.

As travel destinations go, this one is a breeze. No customs to clear, and a quick cab ride gets us to our hotel. Our first few nights are booked in Old San Juan so that we can explore the original city and the forts that defended it. That will have to wait though, as with the time change, we are checking in close to midnight and headed for bed.