It’s a deep winter’s night…You’re enjoying dinner with another couple and it’s going swimmingly. You couldn’t be more compatible. You know each other’s politics, religion, social sensibilities and wit. You’re in the same tax bracket. You have kids the same age. You consume alcohol at the same pace and volume. And as the dinner candles flicker in the joyous white noise of the evening…someone pipes up and says: “Hey, we should do the Caribbean together!” For a millisecond the table goes quiet as you glance at one another to see if this is an “aha!” moment, or if it’s just the wine talking. It’s a little of both. “Yes! A boat…we could get a boat!!” Whoa…hang on. What ‘s a trip like that gonna cost? What kind of boat? Would we need a captain? Where in the Caribbean? How long should we stay? Do we take the kids? And after fawning over the sun-baked possibilities…you stand united: We’re not getting any younger; let’s look into it.

Allow me. I’ll break this down into 4 segments for you: Experience, Agenda, Logistics and Tricks of the Trade. We begin with the obvious…. Do you know anything about boats? Meaning: Does your experience go beyond childhood fishing trips, that sunfish you sailed at camp for 5 minutes or the jet-ski your obese neighbor let’s you take for an obnoxious spin around the lake? It’s okay if the answer is “no”…we just need to establish some parameters.

So let’s say you know next-to-nothing about boats, but you’d really like to experience that post-card perfect Caribbean that you’ve seen splashed on the cover of all those travel mags. Not a problem…but you’re gonna need a captain. Charter boat companies offer these aplenty. Boat captains typically (but not always) come with a chef. More often than not, this will be a husband/wife duo…but marriage doesn’t necessarily bond them. Now before you turn your nose up at the thought of spending time in close quarters with 2 complete strangers, let me assure you that this is not their first rodeo. Through the course of their numerous charters, captains and cooks have encountered every personality trait known to man. They’ve seen and heard it all. Because of this, they are supremely adept at handling ANYthing human nature can throw at them. So if you’re worried that you might get stuck with a dud captain, or your polar opposite …you needn’t worry. I assure you, the captain of your boat will be so charming that by day’s end you’ll feel you’ve found a friend for life. (and you may have) Charter captains are truly invaluable…they keep you and your crew safe, entertained, comfortable and informed. They know when, where and what you’ll like…but here’s the kicker: It’s your cruise. If you have a plan in mind or if you’d prefer to sit in a picturesque harbor and do absolutely nothing for a solid week…so be it. He’s your captain; he works for you. She’s your chef; she cooks for you.

Some charterers may prefer a captain, but no chef….and some (though less common) may prefer a chef and no captain. For the inexperienced boater you’ll want both. The captain commands the ship and the chef commands the galley. Weeks before you board your boat, you will have filled out a provisions request sheet. This allows you to apprise the cook of your favorites, your dislikes, your special needs (allergies) and general preferences for all of your meals, snacks and beverages. Be advised though, it’s the Caribbean…not everything you have at your hometown grocery store is gonna be available, so if you want Grey Goose Vodka, that may be doable… but don’t ask for little Timmy’s favorite Cupcake Confetti Pop-Tarts and expect them to be onboard when you arrive. Rest assured though, you’ll enjoy terrific cuisine and you’ll not go hungry. You’ll also not wash a single dish. Sooo worth it.


Now let’s address the experienced and the semi-experienced skipper. Those of you who would prefer to forego a captain & chef in lieu of putting your own seamanship on display for all to marvel (or condemn). Item #1: Every charter company requires that you submit your boating resume’. You don’t have a Captain’s License, but you will need to catalog your experience. Perhaps you’re a boat owner, or you worked on boats or you’ve sold boats…Whatever it may be, put it in writing. Mention things like scuba certifications, life-guard jobs, fishing experience, CPR certifications, etc… The Charter companies have an obligation to make sure you’re up to the task of commandeering one of their boats, but they’re also deeply committed to bringing you into the fold. That said, padding your resume’ is one thing, fudging it is quite another. Charter companies have been at this a long time and they know an under-qualified patron when they see one. So don’t show up thinking you’re gonna fool anyone into just taking your money and handing you the keys…it doesn’t work that way. But remember, every bare-boat charterer was once a first-timer. So if you’re borderline qualified…or you fall well below the threshold for competency, don’t sweat it. Most charter companies will provide you with a skipper for a half-day, full-day…or how many days it takes to get you up to speed on every aspect of the boat…and then you’re on your own. Obviously, there’s a fee for this service but think of the payoff: Yourself and your crew are at ease AND you’re already “in” for your next charter.


                                                             Can you handle it?

Since experience is relative, you’ll need to use the charter fleet as your barometer.
The Moorings, the undisputed king of Caribbean charter companies, offers sailboats ranging in size from 38′ monohulls to 58′ catamarans and power-cats ranging from 39′ to 52′. So say the size of your crew dictates that you’ll need to charter a 47′ catamaran… you gotta ask yourself how comfortable you’re gonna be handling a boat that size. Please note: The question isn’t “Are you comfortable driving a boat that size?” Regardless of the proficiency of your crew, as captain, you’ll be responsible for much more than just setting a heading and pushing the throttle. Consider running rigging, navigation, anchoring, mooring, docking, dinghying, provisioning, fueling and securing….almost always with an audience. You (the Captain) are responsible for everything and everyone on the vessel. Sure, there’ll be a division of labor…but there’ll be only one responsible party onboard. Case in point: If you were to go from the BVI to the USVI…only the captain is allowed to disembark and enter the Custom’s Office. After he has tediously registered the boat and each crew member, paid fees and passports have been stamped..then the crew may follow. So while your crew may be diving into the rum, you’ve got to keep your wits about you.


Okay, so one way or another, you’re qualified. Bareboating, as opposed to “crewed chartering,” means you’re responsible for provisioning your boat. Yes, the charter company can and will have your boat stocked and ready prior to your arrival if you wish…but you’ll pay a premium for this service and you’ll no doubt need to augment their shopping with specialty items and the list of things that you forgot to include.

If you’re planning on bareboating with another family, it’s right about here that I’m going to save your marriage…so read intently. Vacations, as wonderful as they are, can be recipes for disaster. There’s a boatload (pun) of planning, prepping, packing, scheduling and maneuvering that has to happen before you can rush out the door at 5 a.m. , succumb to a TSA cavity search and strap yourself into a repulsively undersized airline seat. Add to this an agitated spouse, a few kids bouncing off the walls with excitement or the couple you’re traveling with seems to be in the silent throws of a full-blown divorce…there’s the Customs & Immigration protocol, semi-oppressive tropical heat, a raging period, a cramped and thoroughly nauseating taxi ride from the airport to the harbor…and that, my friends, is how you anger the Gods of Harmony.

We’ve been bare-boating for over 20 years and it took my travel buddy and I five of those years to figure out how to avoid the angst of multi-family travel. The secret is simple: He and I go down a day ahead of time and take care of everything…(check-in, mandatory boat inspection, mandatory chart-briefing, all provisioning, squaring away of cargo, cooler acquisitions, liquor run, fins/snorkel gear checkout, ice, etc..)…everything. The next day, the only thing the wives and kids have to do is show up…and shove off. It’s a beautiful thing. Initially, he and I thought we were the beneficiaries of their absence …turns out their travel was exponentially less stressful without manly spouses prodding them at every turn. Win / Win! There are a couple of ways to accomplish this marriage saver: #1 Charter companies offer what they call “Sleep Aboards”…wherein you may take possession of your boat but you can’t leave the dock. NOTE: Depending on whether your Charter Company charges by the person or by the daily charter rate, “Sleep Aboards” are not cheap. Which brings me to #2 In some cases you can get a room at a nearby hotel (for a fraction of the Sleep Aboard rate) and get much of the same prep work done. Another benefit of arriving early is that you get to see the condition of your boat as its prepped for charter. You can see if the servicemen are working on the refrigeration or one of the heads or the dinghy motor…all important information to note before heading out. More on Sleep Aboards later….and remember, if you’re chartering a crewed boat, none of this applies to you. Your captain and cook will have taken care of everything for you.


You don’t look a day over “Rid hard and hung up wet.”

As previously stated, The Moorings are the gold standard by which all other charter companies are judged. Typically, you will find their fleet to consist of the cleanest and best maintained boats in the industry. Their main hub is located in Road Town on the island of Tortola in the British Virgin Islands. This hub underwent a major renovation a few years back and it’s a truly impressive facility. In addition to convenience (dockside grocery, restaurants, showers, hotel, pool), location, aesthetics, and security…The Moorings is enhanced by a professional staff. That said, there are lots of other players in the Charter game…notably, Dream Yachts, MarineMax, Sunsail, Footloose, TMM, Horizon and a host of others. With the exception of Dream Yachts and MarineMax…the thing that separates these charter companies from The Moorings is the size and age of their fleet. Age of the vessel is the single most important factor to consider when bareboat chartering. So let’s go there.

The newer the boat, the higher the charter rate. Charter companies aren’t just going to assign you a boat based on the luck of the draw. The larger charter companies will tier their boats into 3 age groups…often using such terms as “Club” level, “Premier” and “Executive.” The lowest (oldest) tier will consist of boats less than 5 years old…the next being less than 2 years old and the newest being 1 year or brand new. Smaller companies do this too, just on a smaller scale…maybe only 2 tiers (2-4 years and 4+). You should know that many of the boats offered by the smaller companies may be hand- me-downs that have aged out of the larger company’s fleet. Smaller companies can’t afford to inventory new boats, so they take older boats…refit them from stem to stern with service, repairs, updated rigging, paint and more. The end result is a really decent fleet at a substantial savings to the charterer. You can actually do quite well by the lesser known charter companies, and many people feel they offer more personal service. So why all of this talk about the age of a fleet? Because 2 years in a charter program is equivalent to 6 years of private use. As soon as you step off, another giddy vacationer is stepping on…and so it goes for months on end. Boats in the fleet are constantly being serviced for a reason…they need it. I’ve chartered boats that were only 3 years old, but looked and smelled like they’d been alternative housing for a fraternity. Trust me, you’ll want to charter the newest boat you can afford….especially if it’s your first charter. Nothing’s gonna spoil your mood like walking your clan past a pristine sister-ship on the way to boarding your boat…the ugly step-child of the fleet. You’ll hate yourself…and your crew will silently join you.

Does this boat make me look fat?

Age is key…but so is selection. We’re zeroing in on the British Virgin Islands because it’s far and away the most popular charter destination. More on that later, but for right now…know that the further off the beaten Caribbean path you venture, the fewer the charter opportunities…the smaller the fleet (selection) and the older the boats will be.

Obviously, boat preferences are going to vary as widely as personalities….so there’s no hard and fast rule here; but there are a few things worth considering. First and foremost, your crew. Are you high maintenance? Granted, “high maintenance” is a relative term so we’ll address it (honestly) in relation to boating by asking these questions:

  • Is anyone packing a hair-dryer?
  • Is a tropical breeze part of the adventure, or is A.C. an absolute necessity?
  • Are the kids young enough to enjoy the ride, or are they mopey tweens bored to tears by the thought of no wifi for hours on end?
  • Does someone like to cook, or will you be going ashore to dine most nights?
  • Will you be the only one aboard with sailing experience?
  • Is sailing part of the adventure, or would you prefer to just power on to your next island destination?
  • Is a monohull cozy, or will you be longing for some room to spread out after a few days?
  • Can you adjust to a rolly anchorage, or would you prefer the stability of a catamaran?
  • Does everyone need their own bathroom, or can kids and parents share?
  • Isfuelcostaconcern?
  • Are you cheap?

My wife, kids and I have chartered with another family for 10 consecutive years. There are a myriad of reasons why our families should not have made a good travel match. We live 2 hours apart and rarely see one another. Our kids are not the same age. Our parenting styles aren’t in sync. He is a highly educated, highly successful businessman, and I have been jobless for as long as I’ve been employed. Still, we are the foursome that I described earlier…spilling wine by candlelight …talking politics, religion and reveling in all of the psycho-babble that rears its philosophical head after midnight. On our first charter we feared spousal conflict or exposing some embarrassing character flaw…. ten days and nights is a long time to be confined to a boat, after all. Turns out we blended famously. Perhaps much of it can be attributed to each of us making a concerted effort to avoid conflict and going out of the way to be accommodating. Whatever the catalyst, our first charter became the first of many. About half of them have been sailboat charters and half power-boat charters. They’ve all been catamarans, because they’re ideal for 2 couples with kids. One family takes the port side berths and heads and the other takes starboard. Yes, we pack hair-dryers. No, (aside from grilling some meat) we don’t care to cook. Yes, we need AC. No, we’re not concerned with fuel costs. –- Point being, we now know the answers to each of the questions above. And while you can’t be expected to know exactly how your crew will meld over the course of your excursion, just pondering these questions beforehand will save you some angst while underway.

That’s all well and good, but suppose you’re not interested in cruising with another family? Suppose you’d prefer to do your own thing, as a couple…or just your neat little brood? That works too, and there are some palpable advantages to that plan. You won’t need as big a boat. ($$$avings) Your preferred agenda doesn’t yield to a vote (You’ll get your way!). There’ll be no surprises (You know you.). You can tell your Ps&Qs to take a hike and not wash your hair for a day or two. You can walk in your boxers… and fart.

I’ve done the “couple thing” and the single-family thing…both have been great. Personally, I prefer the company of good friends…it just seems to energize the interaction of the entire crew…and as a result, the entire cruise. (But that’s just me.)



Okay, we’ve got you qualified (or not). You’ve determined your crew (for now). You’ve decided what size/type boat you’d prefer (pretty sure). Now we just have to figure out where you’re going. I’ve based most of this article about The Moorings and the British Virgin Islands for a reason…It’s the mecca for crewed and bareboat chartering. It’s a huge aquatic playground with plenty of room for everyone. It’s line-of-sight navigation… meaning, instead of punching waypoints into a GPS, you can just point and say: “See that island over there…the big one to the left of the two smaller ones that look like rabbit ears? Head for that.” Another really nice thing about the BVI is water depth. You can snuggle into some “skinny” harbors, but your main passages are plenty deep and plenty wide with lots of room for error. Your channels are clearly marked and there are literally hundreds of mooring balls at your disposal on a first come / first served basis. The islands themselves range from touristy to quaint, to ritzy to rustic…but enough about the BVI. You can find a plethora of information about these islands, as well as the USVI, online. The reason I bring them up is to stress the fact that we’ve gone about this bassackwards. Your destination (not your boat or crew) should be the first thing you consider. Deciding on your destination, when you can go and how long you can stay will determine which charter company you use, which boats are available and what the costs will be.

Pick your dates. The usual suspects (Christmas, New Years and Easter/Spring break) will be the most popular (expensive)…so plan ahead. Plug those dates into the charter company’s website to see which boats are available. (Remember to look closely for the age of the boat….they tend to hide this information.) Tentatively reserve the boat that best suits your needs for the dates that best suit your calendar….and then immediately start checking flights. Yeah, good luck with that.

Before you nail down your flights, you’ll need to work backwards again. Only regional jets fly into Tortola, so you’ve either got to fly a major airline to a different island (San Juan, for example) and then hop over to Tortola…or…You can fly directly into St. Thomas and grab a ferry over to Tortola. Problem with the latter being you have to work backwards from the ferry schedule for transport from St Thomas over to Tortola. Having fun yet?

If you’re chartering a crewed boat, lucky you…you can disregard the following pain in the ass (that’s salty talk) and just join up with your captain whenever you feel like it. For you bare- boaters, no such luck…read on.

It’s extremely difficult to arrive in Tortola early enough to get everything done in time to shove off the same day. In fact, I’m going to go on record as saying it can’t be done. There’s just too much to do before casting off. Which is why the aforementioned “Sleep Aboard” option is made available. It’s also why the “marriage saver” plan is so brilliant…and it gets brillianter! When my buddy and I fly down the night before and take care of all the formalities…the 2 of us can shove off the next morning and shoot for St. Thomas to pick up the rest of our crew….saving them the hassle, time and expense of taking the ferry over to Tortola. They simply take a (10 min.) taxi to the town dock in St. Thomas, hop aboard…and off we go. Otherwise we’re killing another day waiting for them to get to Tortola.

Alas… You’ve qualified. You’ve picked a destination, a company…and a boat. Time for some tricks of the trade:

  • Flying sux…especially when you’re holding a fist full of passports. My wife (the organized one of us) assumes the task of keeping up with everyone’s (2 adults and 3 kids) passports and boarding passes. Thumbing through each one to find the rightful owner in a harried effort to stay in step with the conga line of flying imbeciles can fray your nerves. Do this: Take a silver Sharpie and write the first letter of each family member’s name on the back of their passport.
  • Clearing Customs sux too…especially when you’re the captain and you have to clear in your entire crew before they can disembark. Rest assured the islanders employed there take great pleasure in watching you stare blankly at the procedure. They’ll help you…but only after silently assuring everyone in the room that you’re dumber than a bag of hammers. The paperwork is not that difficult, but it is tedious. Typically there are 8 of us on our bareboat charters. That’s 8 passports I have to riffle through in order to locate and transcribe each individual’s immigration info. Do this: Before leaving home, lay out all of your family’s passports (open to the photo page) and frame them in one shot. If you’re traveling with another family, get them to do the same and have them email the pic to you. Now print both pages (1) Your family photo IDs (2) Additional crew’s photo IDs ….place them back to back and laminate them. (or don’t and wish you had) Now instead of 8 passports you have one water-proof sheet with everyone’s information readily accessible.


  • Could you repeat that? During your boat briefing your attendant will be conveying a “boat-load” of information. You’ll be inclined to just nod your head so as to project an air of competence. Trouble is, the generator only shuts down in the middle of the night…and the water-maker only needs attention when you’re 4 rum drinks into your afternoon….and the briefing was 3 days ago. Do this: Use your iPhone to video record the technical points of your boat briefing. You won’t believe how smart you’ll look when it’s time to reset the A.C.


  • It’s okay to feed the Pelican. You’ll be gangly stepping off of a rolling boat and into a bobbing inflatable dinghy. You’ll come and go this way at least twice daily…and at least once while inebriated. Do this: Pack a small Pelican® case for phones, wallets and valuables. This case will double as your document box (passports & boat info) when you clear in and out of Customs/Immigration.


  • Your boat stinks. Seriously, it’s nasty…smells like someone placed a humidifier in your holding tank. Unless you charter a brand-spanking-new boat, this stench is more the rule than the exception. You’d like to think it will dissipate once you open up all of your hatches and get a good breeze flowing. Yeah….naw. Do this: Pack (or purchase) a small bottle of vanilla extract. Place a few drops on the floor of each berth and each head. Give it 30 minutes and voila!…your boat smells sweet.


  • Your boat ain’t rocking. The chances of you boarding a charter boat that has a fully functional stereo is on par with the pending success of your modeling career. Do this: Pack a small Bose boombox.


  • Pack Lifesavers. If you’ve got little ones you know how contagious their discomfort can be. (If baby ain’t happy, nobody’s happy.) Do this: Bring a comfy life-preserver. The charter company may (or may not) have the size/style you need…and you don’t want to be caught in the unenviable position of having to purchase one. (a) They’ll be difficult to procure. (B) They’ll be expensive. — In Antigua I had to fork over $140 USD for a kid’s life jacket…and the lady looked at me as if I was an idiot for questioning the expense.


  • Don’t pack towels. In fact, don’t pack much of anything. You’ll likely be purchasing Tee-shirts at every stop and on the odd chance you should need a blouse or dress shirt for fine dining…you’ll be able to find both ashore. Do this: Pack some colored safety pins. Boat towels (provided) get dropped, hung and clipped all over the boat. Attach pins and use them to identify their respective owner.


  • No one’s watching. Don’t be intimidated by the gabillion dollars in boats crowding the harbor. Your charter company will skipper your boat out of the harbor, then jump off and leave you in command. Same upon your return.
    Do this: Call the dockmaster on your VHF radio and let ’em know that you’re ready to depart. Give ’em 10 minutes notice if you’ve got an antsy crew.


  • Hold the mayo. When you’re provisioning your boat with groceries for the week, you’ll be tempted to stock up on sandwich bread, hot-dogs, deli meat, PBJ and the usual suspects in the condiment department. Go easy on this stuff…you’ll just leave it behind at trip’s end. Double up on your snacks and apps instead. Do this: Mid-day is about the time you’ve reached your destination and decided to go ashore to check things out. You’ll be hard pressed to find someone in your crew willing to forego an inviting restaurant (replete with conch fritters and icy rum concoctions)…in lieu of piling back into the dinghy and returning to the boat to fix sandwiches for all aboard. Just hand over your wallet and think of all the money you saved by not buying that extra loaf of bread.


  • Leave your bling at home. Theft isn’t really a problem for charterers, but there’s no upside to bringing your fine jewelry.


This is getting personal.

FYI: We don’t purchase trip insurance. Our thinking is that having trip insurance opens up a plethora of excuses to bail on the trip: Aunt Sadie could die any day now… the other couple’s son chipped his tooth… our cat’s sick… Aunt Sadie kicked… Timmy can’t miss band practice…things are crazy at the office… our dog’s got strep throat… our baby-sitter (Aunt Sadie) cancelled. Conversely, when you know you’ve got a significant investment at risk: You’re going. End of discussion.

Most people charter for a week. We typically charter for 10 days (Friday – Sunday). Whereas a week would leave us wanting more and 2 weeks would allow room for confrontation….For us, 10 days is the perfect duration.

Regardless of when you go, how long you stay, who you go with, what size boat you charter or if you go bare or crewed…do yourselves a favor and have the safety talk. Don’t be a goober…Nothing lengthy and mundane that’ll bore everyone to tears, just some simple guidelines will do. Like the “3-point” rule, head counts and after-dark protocol. We’ve gone 20 years without incident, except for the one pharmacy search and one Medac trip for a cut foot… so odds are you’re gonna have a terrific (incident free) vacation. But as charter boat captain, the crew (and crew’s safety) is under your command, so earn your stripes and remain vigilant.

Lastly, we’ve bare-boat chartered year after year. We’ve done the the Outer Banks, Whitsundays, Antigua, Les Saints, Bahamas, BVI, USVI, the Grenadines, St. Barts and lots of spots in between. Almost all of these were with another family…dear friends we now consider family. We would not have done these trips had they not been an absolute blast. Our kids were tiny then and now they’re in high school and college. I tell you this so that you’ll more fully grasp the urgency of my plea: Go. Schedule the charter and go. You’ll love it…and it’ll be wonderful channel marker along this voyage we call life.

Captain Ron

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