First, this is a long list, meant to cover just about anything.  But they're suggestions, I don't believe you need to buy specialized clothing or gear for a sail trip; choose what works for you. Much of it is common sense, but some things, like ear plugs, you may not think of, and may be glad you brought!

Second, start thinking about it and organizing now, and pack at least a week early.  This will take away last-minute stress, keep you from taking too much, or forgetting something.  The best advice I’ve heard is to set out everything you think you’ll need on a table or bed to get the overall picture, then take half.  I’ve been traveling for a month or more with one backpack for years, yet still manage to always bring something I don’t wear.  You can re-wear items-- we won't tell-- and you can wash and dry on board-- we have natural drying lines!  I'll bring clothes pins.    I will buy a marine-safe soap for cleaning and showering (typically Joy).

You MUST bring a personal water bottle. Nothing blows into the water faster than an empty plastic pint-sized water bottle, so I don’t buy any.  We refill.  Watch a few seconds of this: https://m.youtube.com/watch?v=iwqi0lER7e8

Unfortunately, the advice below did not recommend marine-safe shampoo or sunscreen. Please bring these. I've been asking for years without much luck, but now it's the law, punishable by fines, in many places (including places in the U.S. such as Hawai'i and Key West).  Everything you use goes directly in the ocean, even if you don't, when showering.  BTW, this is true for island hotels, too.  I’ve added the suggested brands below.  Your hair will survive a week without its favorite brand.  Dr. Bronners’ is the most famous example of an all-around shampoo/soap/toothpaste (many toothpastes have plastic beads in them). Often these items come in bottles larger than the 3.4 oz allowed by TSA, and there isn't the counter space to set out toiletries, anyway.  Consider using hang-up toiletry bags and GoToob-type travel bottles (below). They work great and have flip-tops, an important feature-- the only time we’ve ever had a clogged head aboard ($200), it was a screw-off bottle cap that fell in. You don’t want a clogged head.

Bring any personal favorite item that one would typically not find on board.  For example, if you're not fond of plain water, maybe powdered drink mix.

Finally, consider travel insurance, depending on the coverage you may already carry. It can be quite inexpensive if you're sure you're going and don’t need the cancellation insurance; i.e., mostly medical coverage. I typically pay $30 - $70 for as much as six weeks coverage, using either insuremytrip or squaremouth.

Capt'n Ed

My Comments in blue:

9 Tips to Finally Stop Overpacking

“I never wear this at home, so now’s my chance to get some use out of it!” … “What if I get invited to a fancy dinner?” If this is how you think when you pack, it’s no wonder you wind up with an overweight bag and an injury from hauling it around.

Here are nine tips to help you finally stop overpacking.

Pack Anti-Stink Clothes

Look for fabrics like Merino Wool, Polygiene, or ones woven with silver, all of which are designed to inhibit the growth of odor-causing bacteria. This will allow you to re-wear items without having to do laundry or worrying about smell. Brands like Smartwool, Patagonia, and Under Armour use this technology in many of their active wear clothes. [you can also pack dryer sheets or small soaps in your luggage.

Plan an Outfit for Every Day

Go over your itinerary day by day and lay out a complete outfit for each one. This will give you a better idea of what you’ll actually use and wear, rather than just packing a bunch of jumbled together items you think you might need.

Pack Multipurpose Shoes

If you work out when you travel, pack a pair of shoes that can withstand a run, but will also work for casual sightseeing.  [non-marking soles, please; deck shoes with siping are ideal, flip-flops are not. Keens/kayak shoes that can be worn in water work well.  I also always bring aqua socks for anytime I'm in the water, they protect your feet from rocks, sea urchins and while wearing fins!]

Coordinate Items with Your Travel Companion

Traveling with a buddy? Decide ahead of time who will bring which toiletries, like toothpaste and sunscreen, so that you don’t double up.

Only Pack for Definite Plans

If you do get an impromptu invite to that fancy party or the most amazing secret swimming spot, take it as an opportunity to go shopping. Whatever you buy locally will wind up being a memorable souvenir.

Pack Items That Go Together

Try to stick to one neutral color palette when packing, so that you can mix and match tops and bottoms to vary your outfits while still packing minimally. A good rule of thumb is to only pack items that you can wear with at least two other pieces in your suitcase.

Pack Your Favorite Things

If you never wear it at home, leave it behind—or better yet, just donate it. Pack items that you know are comfortable and make you feel confident, not things you rarely wear because they pinch, irritate or just don’t look the way you want them to.

Do Laundry  

If you’re staying in a vacation rental with laundry, it’s free and easy to do a quick wash halfway through your trip, so you can pack much less. Check the listing before you book if that’s important to you.

If you don’t mind hand-washing a few things in order to pack less, pack a small travel clothesline and a packet of laundry detergent (I like these laundry soap sheets because they’re solid and won’t spill or cause TSA concern) to make it easier.

Start Small

Pick a small and lightweight suitcase. If you start off with a big bag, you’re likely to fill it up with things that you don’t need, just because you have the space. You’ll regret it when it’s time to carry that bag through the airport.  [should be soft-sided for stowing]

Packing for a Caribbean Bareboat Charter

It was my first charter, and since I only had daysailing experience, I struggled with what to throw in the suitcase (mistake number one). Now, after living onboard my own sailboat for four years, I know exactly what’s necessary and, just as importantly, what’s not.

First, think lean.

Limit yourself to one carry-on sized bag — and don’t worry. Your basic daily uniform will be a bathing suit and shorts.

Second, think easy-to-store.

What’s smaller than a bread box? The storage space on a boat. Use a soft bag, not a hard-sided suitcase. A duffel can be rolled up and stowed away. A hard suitcase will be your bunk mate.

Third, think low-maintenance.

A sailboat is a damp environment. The faster your clothes dry, the more comfortable you will be. Ideal clothing should be quick-dry (no denim) and wrinkle resistant (no 100% cotton). [i.e., a jacket, not a sweater]

Now, let’s do some packing!

 Clothing

2 bathing suits — one to wear, one to be drying. For my taste, the fewer ties and strings, the better. Slip on and go! Remember that you’ll be jumping in and out of the water, swimming, snorkeling, hiking, climbing ladders and in and out of the dinghy. Comfortable, low-maintenance coverage is key. [I bring only bathing suits with zippered pockets.]

1 bathing suit coverup or summer dress — This should be something you’d be comfortable wearing to a beach bar and durable enough to withstand the active lifestyle. Extra points if it’s fabulous.

1 going-out outfit — Keep it on the casual side –a nice pair of khakis and a collared short sleeve button up shirt is all men need.   Ladies may choose to wear a nice summer dress or a casual skirt and blouse.  Dining in the islands is almost universally shorts and t-shirt as the norm.  So if you don’t have to, leave your dress clothes at home.

Underwear – Bring four sets.  Wash them on deck in salt water, rinse them in fresh water to get the salt out and dry them on the lifelines as needed.  Stay away from cotton underwear.  You want wicking, fast drying undergarments to maximize comfort which are available for men and women.

2 pairs of shorts — Avoid denim. It takes too long to dry. Any high-tech fiber or cotton/rayon blend is better.

1 skirt — I like Patagonia’s knit skirts. They are hardy yet feminine, roll up small and don’t wrinkle.

4 or 5 shirts — These should be comfortable and not snug. A little air flow keeps you cooler. Ideally your shirts will match your skirts, shorts and your bathing suits for maximum mix-and-match options.

2 bras that go with all the shirts.

5 pairs of non-cotton underwear. Quick-drying is key.

A few scarves — Scarves elevate a tank top and shorts to an outfit. They are easy to pack and can serve other useful purposes. (See below.)

Don’t forget your deck shoes. My favorite Adidas.

Toiletries/Personal

Sunscreen — While this seems obvious, don’t forget SPF lip balm. Break yourself in slowly. If you get burned on the first day, the rest of the week will be miserable. Wear your highest SPF the first day and then ease off. Double up on your nose.

Lotion — Your skin will take a beating between sun, salt, sand and water. Give it some TLC at night.

Water bottle — The elements are harsh on the rest of your body as well, so make sure you stay hydrated. Extra points if your bottle has a carabiner clip. Collapsing bottles that roll up when empty don’t take up any space when not in use.

Go Toobs — These travel bottles have many great features, but my favorite is that they float. If you want to shampoo your hair in the sea (and then fresh water rinse), these little bottles will float right next to you.

Personal wipes — With a limited water supply, long showers are not an option. Wipes are great for keeping you fresh in between. TIP: Baby wipes are much less expensive than ‘personal’ wipes.

Hats/Hair ties — Funny thing about sailing, there’s always wind. You’ll want to tame your hair, so it won’t get in the way of important things — like seeing while you’re lowering the anchor or raising a sail. Hats are also good for protecting your hair and shading your face.

Sleeping pills — If you’re a light sleeper, some mild sleeping pills can help you relax and ignore the new sounds and motion. Mid-Nite brand is good without leaving you feeling drugged. [eye masks and ear plugs, too]

Bug spray — If you are susceptible to bites, take some.

Other

A flashlight or head lamp — For those nights you stay a little too long at the beach bar, a light will help you make your way back to the boat. It will also come in handy if there’s an issue above decks at night. As a bonus, shine it in the water at night, you’ll get a peek at night time sea life. If you are light sleeper, do not leave behind the earplugs or eyeshades.

A dry bag — Transportation between the boat and shore is a small, open boat. Things can easily get wet. A Ziploc bag works (known as a sailor’s wallet), but, if you have something valuable like an SLR camera, a waterproof bag is a good investment.

Spare batteries.

Sailing-specific gear

Polarized sunglasses — Sailing in shallow water that is full of reefs, you’ll need to read the water. Polarized sunglasses cut the glare, making the underwater world more obvious. The ocean floor is littered with expensive sunglasses. A lanyard strap will keep yours from joining them.

Deck shoes — If you’re serious about sailing, you probably already have some. Take them.

Handheld GPS — If you own one, it will come in handy. Make a waypoint on your boat before going exploring in the dinghy. It helps you find your way back, especially after dark.

Windbreaker — These are thin and can roll up small. If you have one, you’ll probably wear it. 

Sailing gloves — Again, if you have some, you’ll want them with you. [weightlifting and cycling gloves also work]

Seasickness pills are also a staple, especially if one of your crew is known to have a rough time on the water.  [Scopolamine patches are also good]

Do not forget the sunblock! This will most likely be a sun-filled vacation, and burns are never fun. Try to avoid using tanning oil on deck as it can stain the wood or fabric on the boat.  [same for spray-on-- too windy and slippery!]

“Eighty-five percent of the Caribbean coral reefs died before 1999 or 2000. That wasn’t global warming. It’s pollution.”

More on Avoiding Chemical Sunscreens

It’s important to avoid chemical sunscreens even if, like me, you don’t spend much time in the ocean. Coral reefs are the canary in the environmental coal mine, says Caroline Duell, founder of the Safe Sunscreen Council and CEO of mineral sunscreen maker All Good. We shouldn’t feel comfortable using chemical sunscreens anywhere, Duell believes. (Our testers thought All Good’s lotion was better than average, but it wasn’t a top pick.) These chemicals pollute lakes and streams when we wash them off, and that water eventually flows to the ocean anyway.

Nor are chemical sunscreens good for us. When they soak into our skin, they may disrupt hormone production. “Coral are animals and their systems are not completely unlike ours,” Duell says.

Recommendations:

https://www.travelandleisure.com/style/beauty/reef-safe-sunscreen#raw-elements

There’s even a brand of lotions, conditioners, etc.:

https://www.girlsthatscuba.com/2017/07/03/let-s-talk-about-reef-safe-skin-and-hair-products/

https://www.consumerreports.org/sunscreens/the-truth-about-reef-safe-sunscreen/

http://safesunscreencouncil.org/

Fun Things

Now that you have all the practical necessities in your bag, leave a little extra room to bring some fun things along for your charter. Firstly, make sure you bring some music. [Most new yachts have mp3, or bring a Bluetooth speaker] Playing cards are also a great thing to have when lounging around on deck or at night. It is common for sailboats to fly a flag of where they come from, so if you have a country/state/school flag, bring it along! It is always a great conversation starter with the other sailboats.  Hammocks and inflatable floats are fun too.

Sport-specific gear

Snorkel mask — The charter company will provide snorkel gear, but if you have your own mask and/or fins, they’ll be much more comfortable. If you use the charter company’s gear, take your time selecting it. The better your mask and fins fit, the happier you will be in the water.

Ankle socks — It might not be the height of fashion, but worn with fins, socks will keep you from getting blisters. [aka aqua socks]

Long sleeve rash guard — Sometimes you just want a little coverage, protection from cool water and blazing sun.

Underwater camera — Some of your best vacation photos just might be below the surface.

Strap and float for camera — Don’t let your best vacation photos end up on the ocean floor. A float will not prevent you from taking it under but will keep it from plummeting if you drop it.

Walking shoes — Islands provide a welcome opportunity to stretch your muscles. They tend to be rocky and hardscrabble, sometimes with low-growing cactus, so flip-flops offer no protection.

Sun hat with a tie/lanyards for sunglasses, too. 

What NOT to take:

A lot of jewelry. As mentioned above, you shouldn’t wear it while sailing. In the water barracudas have bad eyesight and eat shiny fish. Get it?

Lots of electronic devices. 1. Energy consumption is limited. 2. Look at the scenery, not a device. 3. Take a paperback, not an e-reader. Finish it? Trade with someone else. 4. The fewer devices you have to worry about in a rough environment, the better. [There’s always a wait to charge devices]

Gobs of makeup. Foundation makes fantastic sunscreen, because it’s made to stay in place. Keep all else it to a minimum – and enjoy! Face wipes are good for removing the foundation without using precious water supply.

Electric hair implements. There is not enough power on a boat to run blow dryers, curling irons and straighteners. Au natural is beautiful. Embrace it.

General tips:

Favorite herbs & spices (in a pill organizer or zip lock bags) to add zing to simple dishes.

Plastic zipper bags — You’ll find many uses for these, from keeping your money dry to packing a bathing suit that’s still wet when you leave.

Tie one of your colorful scarves on your dinghy. All charter dinghies look alike. You’ll need to identify yours easily.

Take something along to mark towels (earring-style wine charms, safety pins and fabric). Charter company towels are typically all the same color. It is much easier to keep track of your own if you can mark it.

NEVER use your bath towel to dry saltwater. The towel will never be dry again! The salt absorbs water. Don’t lie on your sheets with saltwater on your body for the same reason.

A mini first aid kit can be useful. Sailing is a rough and tumble business, and it’s not unusual to get cuts and scrapes. Some ointment, bandaids, aspirin, antiseptic and an antihistamine for allergic reactions can save the day.  [but the yacht will have a kit]

Take a photo of your face every day and watch as the stress falls away. Mother Nature runs an extraordinary spa.

Fair winds!

Some others’ suggestions:

        •      Little 12v dc to 110v AC inverter if you want to charge iPod, cell phone etc that need 110                    volts.   

•    A 12-volt splitter. This allows multiple 12-volt plugs to allow multiple devices to be charging at one time. Very important if you’re taking more than a few people on the trip. Everyone thinks their cell phone/iPod is more important than everyone else’s. You’re a hero when you pull one of these devices out of the bag.

•    European to American style plug adapter. (Many charter boats are made in Europe and thus have round style ac plugs. Check this but most of your chargers these days take 230 or 110 volts input so you’ll just need an adapter and not necessarily a transformer)

•             iPod

•             Book of knots and short piece of line – for entertainment of the crew.

•             Deck of cards.

•             Other Fun stuff

 Other special interest ideas:

•             Mesh holder with suction cups to hold binoculars, GPS, VHF, sunglasses, etc. within reach of the helm.

•             Nutmeg Grinder.

•             Powder Gatorade.

•             Benadryl for allergic reactions.

•             Super Glue

•             Microfiber towel – they dry quick.

•             “The Neat Sheet“, a ground blanket for the beach that can also be used as
               additional shade.

•             Yacht Ensign.

•             Salt water soap. A bio-degradeable one. We usually just use the outdoor fresh water                 shower, not salt water, to shower in.

•             Glow sticks. To hang in the rigging before going ashore. Makes your boat easier to                     find at night in a crowded anchorage.

•             Fish identification book. It’s fun to look up what you saw while you were diving or                   snorkeling.

 Pre-Departure Notes

A few other things to remember before your leave for your charter, be sure to bring your passports as well as photo-copies of them. Also, print out your base information to show to any taxi drivers, especially if traveling in a non-english speaking country. If you plan to fish during your charter, check to see if you need to obtain a fishing license first.

Credit Cards – Take both a debit and a credit card with PIN numbers for cash withdrawals from ATMs.  Be sure to call your credit card company and bank to let them know you are traveling outside of the country so they don’t think your card has been stolen and block it when you go to use it.

Prescription Medications – Be sure to bring enough quantities.  As with your passport, scan your written prescriptions and save them in your drop box account – www.dropbox.com, or another secure cloud based account. This way you can access them anywhere you have an Internet connection.  Also, if you are not absolutely sure you don’t get seasick, pack sea sickness medication, prescription or over the counter.  All medications should be in their original labeled containers so as not to have issues when clearing customs.

Prescription Glasses – If you wear them, bring a back-up pair just in case your primary pair is lost or damaged.

Cell Phone Calling – If you feel you will need to use a cell phone while on vacation or just want it as a back-up you have a few options.  You can contact your carrier and have an international calling plan added for the period of time you are away, or you may be able to purchase a SIM card upon arrival.  If you are going to switch out your SIM card call your carrier and confirm your phone is not ‘locked’, which would prevent you from using another provider’s SIM card.  If you use your own smart phone be absolutely sure your data is turned off (tablets too).  You can create a very large phone/data bill if you’re not careful and end up using roaming data from a local phone company.

With these packing and pre-departure notes in mind, you should be in shape for a worry-free and enjoyable sailing vacation!

How to pack; the "ranger roll":

https://www.thrillist.com/travel/nation/how-to-pack-a-suitcase-army-backpack-packing-tips

https://thepointsguy.com/news/army-packing-technique-saves-money/