Sailing, BVI

What do you do when your life partner asks/insists you go on a trip that is completely dependent upon being surround by one of your biggest fears?

Attempt to convince him how great this trip could be without you? Yeah, me too.

Clearly my persuasion skills are lacking. Because guess what? I ended up on a sailboat in the ocean of the British Virgin Islands.

In my defense, those who know Jake should completely understand how I ‘lost’ in my attempts to forgo this trip.

And also, I love Jake. He’s the calm to my anxious.

And I would go pretty much anywhere with him. Even into the terrible, horrible, no good, very bad ocean.

So here I am, about to divulge information about our sailing trip in the BVIs – because it happened. And you know what?

It was mostly amazing.

But, before I get started, there are some notes I feel are necessary to mention. While all of the posts on this blog are from my (Liz’s) point of view, I feel it especially important to mention that regarding this trip. Because again, I hate the ocean. And I feel that more than most of our adventures, this one is definitely from the perspective of a woman with a fright of the ocean.

Anyways, some notes:

  • I have a decently intense fear of being in the ocean. Have I mentioned that?
  • I also hate propellers. They are the worst. Did you guys know that sailboats also have propellers? Ugh. They suck.
  • The trip was 10 days of sailing. We were out of our marina of origin for 8 days.
  • This trip was total vacation mode. So no internet connection. 10 full days of no working all day. All day freedom from government contracts and mobile internet woes.
  • This trip ended up being really ‘cheap’ – apparently our friends are not only really awesome, but also well connected. But mostly they are just really cool.
  • This blog is chock-full of half-naked (although very attractive) people. Boat life is half-naked life. If you hate bikinis and topless men, skip this one.
  • Sailing (and writing about sailing) must bring out the ‘pirate’ in me. Because I am about to swear more than typical. If you hate swears, please skip to the next blog.
  • This blog is going to be stupid long. Trying to stick to the highlights – but it’s tough when an entire trip turns into a highlight.
  • Our friend and crew mate Michelle also wrote about our trip over on her blog.

Our Crew:

Our boat, Annie Daydreaming, a 51′ Monohull chartered by Sunsail:

Annie Daydreaming had 4 bedrooms and 4 bathrooms. They were all very small. Ever slept in a coffin? Ever crapped in a refrigerator box? (I hope not, but you do you).

Only two of our toilets broke. So, I’d say things on Annie were pretty good.

Our planned route. And by ‘plans’ I mean ‘idea’. You learn that all plans are always ‘jello’ when you travel as a lifestyle.

Jake and I met up with Bob, Scott & Nicky, and Wes and Michelle at our tropical hill castle in the two days before sailing towards probable doom paradise. We had very important tasks to accomplish before setting sail. Like ravaging the property’s mango trees for any hold outs (we got em), provisioning our vessel with sundries (cheese and alcohol), and laying the foundation for all future jokes picking on Bob.

After a final rainbow viewing and puppy scratching session, we left our tropical Airbnb abode and headed to over to the store to provision. And by provision, I mean be 7 people walking around a store popping random goods into a shopping cart. We needed Janice (of Bob) for this. It was really pretty sad. Without Janice’s direction, we ended up with 18 pizza flavored gallons of water, about 10lbs of cheese, 12 different jars of spices, several bottles of wine and liquor, a flat of Carib beer, and some charcoal. You could say things were going really smoothly.

After stockpiling cheese and alcohol, we headed over to the marina to pick up our vessel. And by pick up our vessel, I mean wait to pick up our vessel. For about 7 hours. Because apparently vessels don’t decide to be ready until they decide to be ready. Don’t fret though – there was a bar at the marina.

Around 4pm, we were informed that our noble sea steed, the Annie Daydreaming, was ready to board! And board we did. We formed a human chain to pass our cheese and alcohol into the galley, where Michelle and I stored items in a manner which Bob deemed ‘no where as good as Janice, but acceptable’. I took that as pretty high praise from Bob.

We met Nevron (AKA, Mr. Ima Stealyourgirl), who walked us through the ins and out of the Annie Daydreaming – including how to work bow thrusters which we later found out were disconnected long ago (thanks anyways Nevron).

We then spent an evening in a slip in the Mooring’s Marina where we cooked some of our meat (because why save that for a night near the end of the trip where we only had cheese left?) and let Jake attempt to figure out how to repair the bow thrusters. Spoiler: the thrusters had been completely disconnected by Sunsail long ago – and were unfixable. But Jake got pretty damned close.

In the morning we all took our last real showers at the marina. Oh, did I not mention that not only would 7 of us be cramming into a 50′ hull, but we also would be conserving water for 10 days? And showers use a lot of water? No? Welcome to smelly town bitches friends!

Then, we set sail. And by set sail, I mean we started our motor because apparently you shouldn’t sail out of a marina.

And then, once clear of marina obstacles, we set sail!

And by set sail, I mean Bob realized that our main sail was tangled in some other boat shit (the boom maybe? I don’t know really – ask Bob) and wouldn’t go up the mast.

And then, we motored to our destination: The Baths.

Bob was not pleased by the no sailing.

Wes may or may have puked. (Sorry Wes – TMI?) He was the first, but he wouldn’t be the last. And during this incident we learned about scanning the horizon. SCAN THE HORIZON! So, thanks Wes.

So, our first planned ‘sail’ may have failed, but The Baths did not fail. Jacob and I had ventured to visit them the previous week (during our time with friends at an Airbnb on Tortola). Guess what? Our second trip was just as amazing. The Baths are amazing. You can climb through rock tunnels, ripping your knees open if you’re not careful. You can get lost in mazes of rocks. You can point and laugh at your friends who are shorter than you and therefore cannot stretch between rock formations to traverse sections as readily as you can (Hi Michelle). You can wade in clear, warm water while drinking a Carib (beer).  You can snorkel on tropical reefs. You can jankily lift your friends onto a lone rock in the midst of clear water and then jump off. You can eat and imbibe at the top of the Baths and overlook your vessel.

We did all of those things. Yeah, The Baths are really something.

But, you can’t moor (tie your boat up to a big ball that is attached to the ocean floor) overnight at the Baths. So after lunch, we headed to Savanah Bay, Virgin Gorda, where Bob thought we might catch a mooring ball and have decent protection from rough waters for a night or two.

We put the jib (the front, small sail) up – and Bob guided us to Savannah Bay. Plans were to wait til we were in the bay, with some shelter from winds, to try and un-ruffle the main sail.

We ended up anchoring in Savannah Bay for two nights while we waited out some weather. We were surrounded by boats from a school of  young sailors learning to sail and partaking in other horrible ocean activities such as scuba diving and parasailing and snorkeling. These kids really must have pissed their parents off to be sent on a month long sailing trip.

After a pretty calm night, most of our crew spent the day snorkeling and swimming. Snorkeling is just another ocean activity that makes me feel like I am going to projectilely vomit. But the snorkel crew (Jake, Michelle, Wes, Scott, & Nicky) found a conch shell! Which was super exciting, except that one of us knew (Michelle?, #facts) that conch shells are a endangered habitat, so they put it back. And now there is probably a really happy, delicious conch living in that shell.

I spent the day chilling on a barren beach, walking the beach (LAND!) and reading. I found a terrible tree that will kill you if you eat it’s fruit and will burn you if it’s sap touches you (#horrible). It’s called the Manchineel Tree and you should probably just stay away from it.

Bob spent the day basking in the glory of being on a sailboat. Because Bob thinks being on sailboats is super glorious.

The group (minus me – who was happy as a -insert happy animal- on land) also spent some time figuring out how to fix our sail. They fixed it. And apparently also critiqued our route plan based on the weather, which is the real boss bitch when you are living on a boat.

And Michelle also did some work. I haven’t mentioned it yet, but Michelle doesn’t mess around! I mean, she does – she’s silly – but also super professional. She runs a highly regarded blog ( and puts in serious work on it. Even during her vacation she checked in to answer questions daily – but never once complained. That girl loves her job.

After a failed attempt by the crew to find a beach bar for drinks (spoiler: there is no beach bar in Savannah Bay), we all ate cheese. And grilled meat. And drank alcohol. And jammed to Bob’s epic Caribbean sailing playlist.

Scott makes a mean Pina Colada if your stomach can handle that kind of thing.

And the next day… we sailed.

We really sailed!

Here are some fun facts I learned during our first real sail pass:

Did you know that when you’re sailing your boat tips over to the side? Because I didn’t. It’s called ‘heeling’. And it’s where the wind pushes your sails so hard that your boat damned near tips over – making the boat go fast. While basically tipping over. Bob and Wes and Michelle seemed to really love it. I think Jake and Scott and Nicky also enjoyed it. I refused to be convinced that the sailboat wouldn’t be tipping over during this activity.

Also, along with the whole ‘heeling’ thing, I also found out that sailboats don’t sail straight to their destination when under sail. Oh no. They zig zag. FREAKING ZIG ZAG! Back and forth. Look at that ship in the port! So neat! But don’t worry if you don’t take it in during your first pass by it; if you’re on a sailboat under sail, then you’ll get to see it about ten more times! Yay! The hell.

So, anyways, Bob mentioned that our destination for the day was not too many nautical miles away. “Great” I thought. “That’s not very far! We’ll be there so soon! And I can just read my book while these dweebs sail me there.”


First, heeling equals no reading – only holding on for dear life.

Second, zig zagging. Means that this trip could take all freaking day.

Third, sailing does not equal relaxing. It involves pulling lines and loading and unloading winches (similar to a wench, except not at all) and jumping sails, and looking out for other boats, and trying really hard not to get seasick.

Fourth, have I mentioned that I hate the ocean? Oh, also, I get seasick. Yep.


Bob was happy though.

Anyways, we got to Bitter End Yacht Club eventually. We found a mooring ball, hooked up Annie Daydreaming, and took the dinghy (from this point on the dinghy boat will be referred to as the ding-a-ling) to shore.

Scott, Nicky, Jake and I headed out for a hike. It was a beautiful hike. A little bit because it was on land and not water, but also because it was just seriously beautiful. After climbing some terrain which was more than likely the inspiration for the Aggrocrag and having Nicky assaulted by a rogue cactus plant, we got an epic view of Bitter End’s bay and Sir Richard Branson’s private Island. And we saw first hand why President Obama flew directly from the White House to Necker Island to hang out and kite sail and show us his presidential abs after his tenure was completed.

After hanging out for a bit on Yacht Club property, we met up with Wes, Michelle, and Bob, paid for some real showers at the Yacht Club, dressed respectably (aka, not in our bathing suits), and headed to Saba Rock for happy hour and dinner. And we all said “it is good”.

We met a giant pet lobster, drank a few too many drinks, and ate conch fritters in honor of Janice. Then the three of us girls got coerced into taking some free shots with a not-so-savory name in a ridiculous manner by the maitre-de.

In the morning the crew minus Bob (who was very happy to enjoy time on the boat) fired up the ding-a-ling, loaded up a bag of garbage, and headed back to shore – some of us for a run, and some of us for breakfast.

And then we set sail towards Anegada – with full sails up!

Our sail to Anegada was eventful.

And scary.

Have you ever watched one of those ‘Terror at the High Seas’ shows on the (old style) Discovery Channel? If you haven’t, I think the tale is also relatable to an episode of the Kardashians (aka, terrifying).

Well, I have to admit that I half expected every sail we did to be similar to an episode from one of those type shows. But up until this point, they weren’t like that. Even with all the heeling (I am still not convinced that a sailboat will not go upside down when it is heeled over so far). And all the zig-zagging. And all the ‘hey Jake – can you go below and pull the poop tanks dump handle once we get a mile or so off shore’. (Oh, did you not realize that boats dump their people poop overboard? Guess what.)

Most of our sail passes were actually pretty nice – at least until my stomach had had enough for the moment.

But, our sail to Anegada?

Yeah. That one was like an episode from a ‘Terror at the High Seas’ show.

Anegada is the most remote island in the BVIs. It has a population around 400 people. The highest point is 28′ above sea level. It is reachable by boat or very small airplane. It is famous for it’s lobster and small flock of flamingoes.

Clearly, our means of transport to Anegada was sailboat. Zig-zagging, poop-releasing, full heeled sailboat.

It was a really great sailing day, as per report from Bob and Wes. Since Wes is very crazy interested in sailing, had done that whole week of sailing school, and had been soaking up Bob’s vast sailing knowledge since well before we got on the Annie Daydreaming, it was decided that Wes would be our Captain today. Woohoo! Captain Wes!

Which left Bob to play First Mate.

And also to just play.

We learned the hard way that it’s not a good idea to let wild man Bob play. Long story shortened for trauma’s sake, Bob was playing pirate on the bow while we were at ~10knots and pretty well heeling, with Captain Wes sailing competently behind the helm. Bob fell. Bob hit his head. I screamed and froze. Jake made a flying leap through the bimini and grabbed Bob before he went overboard. Scott grabbed Jake before Jake and Bob both went overboard. Nicky grabbed Scott. Michelle and Wes stayed at the helm and tried to figure out how the hell to get the Annie Daydreaming out of the heel she was in so that our crew, who were now all clinging to the port bow, could safely return to the cockpit. I played verbal relay between Captain Wes and the clingers.

Wes was able to get us pretty upright, allowing Bob, who had come to, and the death grip crew to return to the cockpit.

Bob and Jake were pretty banged up. Battle bruises and strained tendons galore.

We did the best concussion protocol checks we knew, grabbed ice for Bob and Jake’s various body parts, and got our bearings back.

I felt pretty damned seasick after that scenario. Nothing like your main Captain, friend, and mentor and the love of your life almost going men overboard to make you forget to scan the horizon. There is a possibility that a few others of the crew were also feeling a bit queasy after that, but I won’t lie, I was too busy dry-heaving over the transom to know.

In all honesty, our mishap during our pass between Virgin Gorda and Anegada was one of the scariest moments in my life. I wish I could say I jumped to action (like Jake) and was heroic. Or that the outcome made me more confident of our abilities as humans on the ocean. My ‘flight’ instinct is really strong – something I was aware of before this incident, but was re-instilled in my awareness of self. Seeing the world, challenging yourself with novel activities and ideas, and doing new shit really helps you figure out your place in the world. I learn a little bit more about myself with each new adventure, triumph and mishap. I just wish the mishaps weren’t so completely terrifying sometimes.

But guess what?

We made it to Anegada. In one, slightly battered, crew.

After being greeted by the mooring ball bill / trash collector, we took the ding-a-ling to shore and recouped. Anegada has very little in the way of medical assistance (I guess ‘doctor’ isn’t a popular job amongst the 400 residents), so we did the next best thing to getting our crew’s wounds checked out by a doctor:

We drank. And ate lobster.

After a decent, albeit a it wavy, night’s sleep aboard Annie, we all ding-a-linged to shore decently early the next morning. Bob suggested we go spend the day over on the other side of the island at Loblolly Bay. Loblolly sounds a little like ‘lollipop’, so I was clearly in.  Jake and I decided I wanted needed to run the 6ish miles in 90º temperatures to Loblolly Bay. Jake was banged up enough from our previous day’s affair so that walking wasn’t easy for him. But Jake will not be stopped. He rented a bike and biked next to me through the roads of Anegada to The Big Bamboo, a place with a beach bar and some hammocks for us to swing in. We met road cows, steers, and goats on the way over, and we spotted the Anegada Flamingoes (from afar – they mostly looked like a big pink blob). We rolled in to The Big Bamboo drenched in sweat a few minutes before the rest of the crew, who had eaten some breakfast at the Reef Hotel before boarding a taxi to the other side of the island. It felt good to run – even in 90º, direct sunlight.

We had The Big Bamboo pretty much to ourselves all day. We spent the day straight chilling – reading, walking the beach, laying in hammocks, laying on the beach, sitting on the beach, sitting on benches at the beach, snorkeling, and drinking beers. Even I partook in the snorkeling – and I didn’t die! And also saw some really cool ocean shit.

Oh, and Jake and I got engaged.

>>Insert super romantic engagement story here. The kind where Jake has his best friend help him scope out a spot to ask Liz to marry him earlier in the day, then later has said best friend (ahem, Scott) ride rental bike with best friend’s beautiful girlfriend (ahem, Nicky) sitting on the bike handlebars on sketchy back roads to the target spot to secretly photograph the moment. Cue the part of the story when Jake asks Bob to use his drone to capture our walk down the beach, but doesn’t tell him why. Signal the part of the story where Jake decides to get down on one knee earlier than intended, just as Bob’s drone turns back towards home because it is running low on battery, and best friend is still 100 meters down the beach hiding with beautiful girlfriend in some prickly bushes. Prompt response of “Holy shit, yes! Get up!” in private moment. Enter laughter and smiles and initial celebrations – and post event photo shoot.<<

Cue: Even more celebrating -drinking & dancing- than has become typical on our sailing trip thus far. Oh, and some limboing to this really great No Mercy song on repeat for good measure. Apparently Anegada residents really appreciate the musical genius of No Mercy – specifically their song ‘Where Did You Go?’

The next morning was a little rough.

Luckily (?), the waters on our sail from Anegada to Jost Van Dyke weren’t rough. Which is because there was very little wind. Which meant that there was to be very little sailing. We spent a lot of time under motor that day.

Oh, another fun sailing fact for you. Being under motor tends to allow the boat to rock more. Which means increased risk of sea sickness! Yay!

Nicky loaned me one of her prescription nausea patches at this point. She really is a goddess amongst women.

Prescription nausea patches are really neat. And by neat, I mean they F you up pretty good. Who needs Colorado anyways?!

So, I spent most of this passage happily asleep in Jake’s lap.

Thank god for our Captain and First Mate. They carried on – and got their pretty useless crew to Jost Van Dyke without a hitch.

We made a brief stop over at Sandy Spit to say ‘hi’ to Bob’s dear friend Gordy, who left Bob’s life way too soon.

Then we motored over to and moored on the East side of Jost Van Dyke in Long Bay near Foxy’s Taboo. We ventured out in our ding-a-ling to find the hike to Bubbly Pool.

Bubbly Pool is ‘nature’s jacuzzi’. It’s an inlet of ocean water that is completely calm, and then – whoosh – in comes the ocean. And in come the bubbles!

And if Bubbly Pool wasn’t neat enough, we were gifted with an awesome double rainbow (DOUBLE RAINBOW!!) on our hike back to Foxy’s for a drink.

We decided to make dinner on the Annie Daydreaming, which I heard was delicious, as per usual. Except I was pretty F’ed up from that nausea patch, so I passed out at around 6:30 and slept so well. So well.

In the morning we set sail for a hike at the old sugar mill at Annaberg Plantation, on St. John’s Island. Which is in the U.S. But we totally did not ‘break into’ the U.S. without checking in which would be a tedious, long, expensive process, only to then have to clear back out and return to the British Virgin Islands. Nope, we totally did not just pay the national park mooring fee and hike into the old sugar mill for a few hours, then return to Annie and sail away.

We then pointed Annie towards Bight Bay on Norman Island, the home of The Willy T. The Willy T is a moored floating bar and restaurant that gives people an excuse to jump off the poop deck of a two story steel hulled boat without clothes on. In perfect honesty, our crew was a bit ‘pooped’ out on drinking, but made sure to tie the ding-a-ling to Willy T and have a drink. None of us ended up jumping topless into the ocean aside Willy T, but we were #blessed(?) to witness a few tipsy ladies and gents do it.

We decided to return to our own vessel, where we cooked and ate dinner and ended up dancing into the night, Annie Daydreaming club style.

After a quick motor trip over to the Indians, which has some of the best snorkeling in the BVIs, we were sailing again. Heeling, zig-zagging, poop releasing – you know, sailing.

All the way to Cooper Island. Where every mooring ball was full. So we attempted to anchor off in a bay to the side, but the shelter was too weak for our crew (ok, mostly me – I’m not a sailor, and I don’t think the rest of the crew wanted to smell vomit for the entire day/night). So we sailed again! To a sheltered bay off of Beef Island (real place). With no place on land to go (rocky coasts, terrifying island dogs), we spend the evening eating, drinking, and chilling on board a very rolly Annie.

In the morning we headed back to Cooper’s Island, where we miraculously found a mooring! After tying up, we spotted a few sea turtles, and everyone (even me!) popped out snorkel stuff on and jumped in to check them out. Then I saw Annie’s propeller and aborted mission pretty damned quick. But the turtles were cool.

After everyone had their fill of turtles, we ding-a-linged to shore where we were greeted by a resort with a coffee shop. Delightful iced latte consumed. We then spent a few hours sitting on chairs on land, chatting, and generally enjoying the scenery. Then we reboarded Annie Daydreaming, all shared a gigantic cheese plate, and made our final sail back to Annie’s home at Moorings Marina.

We made it back to Roadtown, Tortola. Back to where we started. And to showers with endless hot water (after you let them warm up for a good 5 minutes). And fresh towels. And fruit. And non-pizza flavored water. And LAND. Tons and tons of land. A whole island full of land!

We spent the afternoon cleaning and packing up from our 9 days on the water. Jake, Scott, Nicky and I went for a leisurely walk through Roadtown and drank some bubbletea. It was delightful.

Bob stayed on Annie – I got the feeling we were possible going to have to physically drag him off of her in the morning.

We regrouped and all ate dinner at the marina. We spent our last night aboard Annie Daydreaming in a slip – a non-rolly, very safe slip.

In the morning I ran (without forcing someone to ding-a-ling me to land!), got an ice latte from the marina coffee shop, took another hot, lengthy shower, and ditched the Annie Daydreaming to catch a taxi to the ferry boat which would take us all back to St. Thomas, were we would all board flights back to the motherland.

Parting thoughts:

  • Holy shit, the Caribbean is a beautiful place
  • Holy shit, boats really dump their raw sewage straight out of their holding tanks into the ocean
    • I bet some of that poo comes to shore before the fish can get to it… guess I should probably continue to stay away from the ocean.
  • This trip was terrifyingly delightful. So many feelings of awe and fear wrapped up into 10 days. I loved it. And I hated it. And I loved it some more.
  • Living in a 50′ space under the water line with 6 other people isn’t as bad as you might think. It kind of sucks when one of your toilets break, but luckily we are all pretty good at sharing. Also, when your toilet breaks, call the marina immediately. It might take them a little while to get out to you. And no, they won’t come out to Anegada.
  • Don’t sit too close to the guy pulling the ding-a-ling’s motor starting string.
  • Make sure you taste water before buying 15+ gallons of it. Unless you don’t mind water that tastes like pizza.
  • I’m glad that I went on this trip – but I have no desire to do it again via a sailboat. Maybe a boat with a motor? A bigger one? I can’t help it – I’m a land lubber.
  • Jake & I are going to keep living in an RV for the time being. But full support to our friends who go aquatic! Go guys go!
  • When you find good adventure friends, keep them close. They are some of the best kind of friends.




3 comments on Sailing, BVI

  • Cherie

    Congrats guys on an awesome and terrifying adventure … and the wonderful adventure to come in your partnership! I can only imagine having been in the islands so recently and shared a major moment in your lives, that the post-Irma & Maria reports are even more saddening.

    Can’t wait to have you aboard m/v Y-Not one day and show you a less terrifying adventure on water (with no poo-dumping overboard).

  • Fred

    LIZ–thank you for a great blog and wonderful pictures. I like the one of Jacob grilling.

    It must have taken a long time to put this together but remember–we all live vicariously through you and Jacob so we look forward to these blogs and photos.

    My very best to you both.


Leave a Reply

Your email address will not be published. Required fields are marked *