What to take on a bareboat sailing trip in the Caribbean and still fit in a carry-on
We’ve been bareboat sailing in the Caribbean a number of times. Packing for those adventures has always been more challenging than for land-borne trips, but over time we got better at it. During the last sailing trip in the BVI we managed to fit all we needed in the carry-on luggage, and it helped make for a great vacation experience. In this article I will share some packing tips and what we learned in the process.
What you take or not take on a trip can make or break your vacation. This is especially true when going on a sailing trip. There are few stores out there to buy what you forgot, and little storage space on the boat to stash away things you don’t really need. It is key to get your packing list as close to exactly right as possible.
The art of packing is not about what you take, it is about what you leave behind. To vacation is to take a rest from the usual, including the mental baggage of the stuff you own. Leave as much as practical behind and get a break from it all.
Let’s dive in.
Clothes
Rule of thumb: if in doubt, leave it behind. Then take only half of what’s left on your list. You will still likely end up wearing only a small portion of what you took.
When bareboat chartering in the Caribbean, you will spend most of your time barefoot and somewhere between your swimming outfit and a single set of casual shorts with a T-shirt. Long sleeve shirt and pants are mostly useful for sun protection and the occasional cooler evenings, especially in the winter months. The swimming trunks, reef shoes, hat, long sleeve shirt, few T-shirts, hat, gloves, and shorts did not make me feel I was missing anything at any point during a two-week long trip.
When traveling to your sailing destination from a colder climate (e.g. Seattle), it is key to be thoughtful about dressing for the travel. These clothes will likely get only used during the flight, and will need to be stashed away for the rest of the trip, next to the bilge pump. If you are tactical, you can plan for your travel outfit to double as foul weather gear, Caribbean edition:
Interestingly, during our last BVI trip we experienced a full day of driving rain when sailing along the northern coast of Tortola towards Jost Van Dyke. The jacket above probably saved me from a mild hypothermia. The cup of hot tea after dropping the anchor at Machioneel Bay on Little Jost Van Dyke was the most memorable simple pleasure I enjoyed during this trip.
Equipment
Sailing is equipment- and gadget-rich activity, leaving skiing in the dust. It does not help if you also need to take a portable office with you. (Yes, I committed the travesty of lugging my laptop along). It is necessary to be selective in this phase of packing. In a vain attempt to remain gender neutral, let me just say choosing clothes can be as challenging to some as selecting electronics and gadgets to others.
What have we got here?
- Snorkeling gear. Most charter boats will be equipped with these, but you would not use a stranger’s toothbrush, would you? The diving gloves are useful if you want to touch things that do mind to be touched underwater.
- Camera and underwater housing. We took our Canon G12 with an underwater housing to take pictures while snorkeling. It worked well, but was bulky. Next time I would probably research a solid housing for the iPhone. If you do take a real camera, make sure to also take circular polarizer. This is how you take the Caribbean pictures that make your neighbors hate you. Also, the pictures just look nice.
- Charts and guides. Paper charts (darn, I just realized my mid-life crisis is overdue) and an iPad with iNavX app plus charts for the area. The iPad needs a sturdy housing to survive a sailing trip — I had great experience with a waterproof, hard-case Pelican model. Also, the Cruising Guide to the Virgin Islands, paper edition, aka “the Bible”.
- Binoculars, GPS. You never know what you will find on a charter boat, and these two can be indispensable. Waterproof Barska 7x50 binoculars and a handheld Garmin GPS (which I also use for mountaineering) never failed me.
- Lights, batteries. Headlight for each crew member, standing light, and spare batteries. The advantage of a headlight over handheld torch on a sailboat is that it gives you back one hand (the one that makes the difference between staying on board vs going overboard). The standing light doubled as an anchor light for us once we found out the masthead anchor light was malfunctioning.
- Cables, chargers. These are the shackles of modern civilization. Most boats have 12V power, so taking a 12V inverter has always proven useful. (Run your diesel when using the inverter). In addition, plan for any AC electric plug converters you may need. If traveling to the BVI from the US, you don’t need any.
- Light backpack. For those dinghy rides to shore and lightweight resupply trips, or land-borne hikes. Indispensable.
- The portable office. It is individual, and hopefully unnecessary. In my case it was an iPhone, a MacBook, and a Huawei MiFI device, all packed up in a sturdy Pelican case. Probably the common denominator for everyone is internet connectivity. Make sure your modem works well with the data frequencies wherever you go. I highly recommend a MiFI device. When attached to the main halyard and pulled up to the top of the mast, it dramatically increases coverage. All the BVI are belong to you.
What not to take
There are several thing that seem reasonable to pack when you are at 47degN, which turn out to be poor choices once you are down there.
Unless you plan to mingle with the beautiful people, leave the jacket, tie, and pressed trousers behind. No, you are not going to need that collared shirt. On the other end of the spectrum, also scratch the foul weather gear from your packing list except when entertaining the idea of an esoteric suicide during the hurricane season.
There are several things we made the mistake of taking with us on the first sailing trips in the Caribbean that turned out dead ballast:
- Extra pairs of shoes. Most of the time on the boat you are barefoot. You need reef shoes for swimming, and the rest of the trip is well covered with sturdy sandals (the Keen kind).
- Heavy duty rain gear. You are going to vacation in a place where rain belongs to the category of pleasure rather than something one needs to protect themselves from. If you are from Seattle you know what I mean, we’ve got skin.
- Long sleeve tops. Beyond what’s needed for sun protection or travel there and back, the temperatures rarely require more than a T-shirt.
- Jeans. No. Just no.
- Overabundance of shorts or T-shirts. Whether it is island time, or vacation, the end result is that you spend most of the time in 1–2 sets of shorts and T-shirts (for the occasions on the more formal end of the spectrum).
- Socks. They don’t go well with sandals, and are contradictory to going barefoot.
Last time we went on a 2 week sailing trip to the Caribbean, we planned on one visit to the laundromat. Not only did it cut our list in half, it also added to the color of the experience.
The borderline things
There are always a few items that are borderline: to take or not to take. (And I don’t mean clothes — these are clearly in the no-take camp). The choice of those is usually individual, and they need to go into the checked in luggage.
For us, if we break the carry-on-only rule, it is only for things that won’t affect the core vacation experience if the airline looses or delays them (and it will). Flippers, life vests, and sleep-on-deck blankets are in this category.
Most charter boats will be equipped with snorkeling gear for adults. If you travel with kids you need to come prepared. This is why we alway bring snorkeling gear and life vests that fit our kids.
Sleeping on deck as opposed to the cabin is not what many people do, but I always enjoy this experience immensely. You would not believe how the night sky can look like, especially at one of those secluded anchorages in the BVI. To pull this off you will need a lightweight, fleece sleeping bag or blanket. The trade winds can feel a bit chilly at night, even in the Caribbean.
But then, the morning comes and you can warm up…
