I used to love going on a sailing charter before we owned our own boat. Nothing is better than spending your days in the Caribbean or South Pacific sailing, diving, snorkeling, hiking, fishing and exploring little towns and villages, taking in the local culture and delights.

Whether you are going on a bareboat charter, or down to stay with a sailing friend on their boat in the tropics what to pack and bring on your trip is a tough call. Boats have a very limited amount of space for storage. Packing for a trip like this is quite different than packing for a normal vacation.

Pack as lightly as you can. Most charter guests wear only a fraction of what they bring! As far as clothes are concerned, all you really need are shorts, tee shirts and beachwear – and possibly a light wrap or sweater for the evening.

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).

When we used go on a charter we never checked luggage. There is nothing worse than lost luggage when you are getting on a sailboat and have limited communication and will be moving around an area. We took a personal item (backpack) and carry on item (duffel bag) for the overhead bin.

What to Bring

• Swimsuits (2-3)
• Shorts (2-3)
• T shirts (5)
• Flip flops or sandals

Most of the time we wear swimsuits and t-shirts on the boat. And on land we use flip flops.

Pack your items in a soft sided duffel bag if possible. Please do not use hard sided luggage, space is at a premium on a boat, duffel bags can be rolled up.

• Lightweight long sleeve shirt – After you’ve been in the tropical sun all day adventuring it is nice to have a lightweight longsleeve technical shirt that keeps you cool, but protects you from the sun.
• Lightweight buff or bandanna – same principal here, you can put this over your neck and ears for sun protection in the dinghy or on land
• Sarong – for covering up in public. Many cultures in tropical areas dress conservatively, so wearing a lightweight sarong is cool and respectful of local culture.
• Cell phone – my cell plan is the same cost domestic or international, but check with your carrier before you leave so you don’t get hit with excessive charges for being out of the country.
• USB Charger – a lot of boats have USB chargers as standard equipment.
• Handheld GPS or download Navionics to your phone or tablet – Most charter boats have dedicated chartplotters, but if you go exploring in your dinghy as we do sometimes, having Navionics on a cell phone is helpful. The app for the Caribbean is around $20 for the year.
• Handheld VHF – If you are a boater and have one of these I would bring it, but I wouldn’t purchase one just to take bareboating.
• Binoculars – Same as a handheld VHF, bring a small pair of binoculars if you have them at home.
• External charging battery – This is nice to throw in your backpack if you are out all day and need a quick boost to your cell phone to take more photos or video
• Backpack for walking around or day adventures – I am always stuffing items in my backpack to go on a dinghy adventure or going into town. A dry bag that is also a backpack is the perfect solution for this.
• Dry bag or ziplocs – everything on a boat is subject to getting wet, and in the tropics squalls and rainstorms can pop up with little notice. If you have expensive electronics you need to keep dry you will want to bring a dry bag. I use ziplocs for phones and batteries all the time.
• Wood clothespins – Everything is going to get wet, hanging it up on lifelines with clothespins is the easiest way to get clothes to dry. I use wood ones because I always seem to lose a few overboard during a trip. This is better than losing plastic clothespins overboard.
• Light for the cockpit – When you go out for a sundowner or dinner at a bar and coming back a crowded anchorage where all of the charter boats look itentical it is nice to have a red or purple LED light in the cockpit or helm area to identify your boat. Just don’t forget to turn it on before you head to land.
• Cheap thermometer for your fridge or freezer – Getting on a boat that you are not familiar with is tough in that you’re not sure how long to charge the fridge and freezer. A small cheap thermometer is an easy way to ensure your beer and provisions stay cold.
• Personal flag or burgee – Sailboats often fly flags to show where they have come from. If you have any flags that you would like to fly, from your country, state, university, favorite sports team, local yacht club, etc. feel free to bring them along! 
• Hammocks and inflatable floats are fun too if it’s not a windy day!
• Tote bags – I throw a couple of cheap tote bags in a backpack any time we are heading to the grocery store or market.
• Sailing gloves – some people like them and some don’t require them. If we are going to be doing a lot of sailing we throw them in.
• Reef friendly sunscreen – We like Raw Elements and Tropic Sport, they are in airline approved sizes so we don’t have to check our luggage.
• SPF lip balm
• After sun lotion or aloe vera – you need to take care of your skin after being in the hot sun all day. I can’t tell you how many people I have seen nearly ruin their vacation because they either got too much sun, or didn’t take care of their skin. The sun in the tropics is no joke.
• Books or books on kindle or tablet – I like paperback, but everyone has their preferences.
• Music and speaker – Most charter boats come with Bluetooth stereos nowadays, so you may not need the speaker, and most people store their music on their phones. Make sure you don’t need an internet connection for your music, you may not have a data signal at every anchorage.
• Ballcap or visor or wide brimmed hat – keeping the sun off of your face and nose should be a high priority.
• Sunglasses and strap – I like polarized sunglasses and croakies straps. My favorites are Costa and Maui Jim. The polarization helps you to see into the water, very helpful if navigating around shallow coral reefs.
• Tennis shoes if you want to go hiking or prefer the arch support on long walks.
• Boat shoes – we sail with bare feet, but some people like to wear shoes. We only use non marking shoes on deck, so pack appropriately.
• Snorkeling gear – If you don’t already have this, it might be a good time to purchase a good set if this is something you are interested in, a set should last your entire life. My three favorite brands are Scubapro, Mares, and Aqualung. I have a pair of Mares fins that I bought in 1998 and they are still great.
• Rash guard or synthetic shirt to keep the sun off when snorkeling, I prefer a rash guard, but even a t-shirt will work in a pinch.
• Wetsuit if you plan on diving or snorkeling for long periods, check water temperature before you go. I find most of the time I can get away with a spring suit in the tropics in winter. Water will sap your body heat if you are in it for hours a day.
• Local currency – check with your charter company  on this, some places take US Dollars or Euros , some it is better to get local currency before you come. Your bank can easily get foreign currency at a good exchange rate before you go. We once went to the BVI and not one ATM machine was working in the entire country. We were lucky we brought enough cash with us. Local veggie markets rarely take credit cards.
• Thin beach towel – some charter companies supply these, check with your charter company before you go. Lots of people use Turkish towels for this purpose.
• Bug repellant
• Lightweight rain jacket or lightweight foul weather gear. I only wear a rain jacket when it’s raining, I wear a swimsuit, I don’t really care if my legs get wet. Some people like to have rain pants too.
• Headlamp and spare batteries. You will want this at night especially when dinghying in the evening. A headlamp is better than a flashlight because then you have use of both hands.
• Camera, underwater camera or Go Pro or equivalent. I use my phone for most photos, but some people have expensive DSLR cameras and underwater dive cameras, etc.
• Water bottle – Staying hydrated is paramount. It is very easy to get dehydrated out in the sun all day.
• Toiletries and prescriptions
• Consider adding some melatonin if you are a light sleeper, the boat is usually gently rocking at night. For me melatonin helps me fall asleep and doesn’t leave me groggy the next morning.
• Seasickness remedy – If you get seasick, or are unsure if you do or not, it is a good idea to include some seasickness bands, Scopolamine, Bonine or Dramamine in your kit. Do some research before leaving if you are unsure, or have never used these remedies. You don’t want to use scopolamine on a boat for the first time, you want to try it out on land first. Other more holistic remedies are ginger, peppermint and vitamin B-6.
• Passport
• Credit card
• Fishing Kit – Some places are great for fishing, some are not. If I want to fish off shore I bring a handline setup on a yoyo reel with a bungee and a few lures, usually cedar plugs. This setup will catch wahoo, dorado and tuna, and is easily packable.
• Waterproof phone pouch or case – My phone is supposed to be waterproof, but I still bring a case for it. I usually wind up leaving it out in the rain accidentally.
• Condiments – Bareboats sometimes come with salt and pepper on board, but I throw in packets of mayo, mustard and ketchup so I don’t have to buy big bottles at the store. I love mayonnaise, but how much are you going to go through in a week.
• Ziplock and garbage bags. It’s not worth it to buy a whole box at the store when you are provisioning. Much easier to toss some in your luggage before you go.
• 12v charger – Most every boat has an outlet for a 12v charger like the one in your car. These are great for charging with USB cords for phones, tablets and cameras. I always bring one that has two usb outlets and a couple of cables.
• Consider travel and diving insurance – I once had a boating accident while on charter and had to be rushed to the emergency room in the middle of the night in a driving rain storm. We were a mile from the closest dock and had to dinghy it the whole way where we met the ambulance, then had to get a hotel room and emergency flight back to the US for emergency surgery. I never leave home without appropriate travel and dive insurance after that incident. There are many items your normal health plan will not cover while out of the country.

What to Leave at Home

• Fancy jewelry – Unless you really need to have expensive jewelry adorning your body as you sail around the tropics, there is little security on a sailboat. Leave this stuff at home.
• Dress clothes – even if we go out to eat, shorts and a t-shirt are fine. Don’t bring your fanciest dresses and shirts, most everyone in sailing areas will be wearing t-shirts and shorts.
• Hard sided luggage
• Hair dryers, Straighteners and Curlers – Many boat electrical systems are not set up to handle the capacity these hair implements require. Leve them at home.