After running crewed yacht charters on our sailing catamaran throughout Florida, the Virgin Islands, and the Grenadines for 9 seasons, we’ve become experts on what to bring, and what not to bring.
Packing for a sailing trip isn’t like packing for a typical vacation. Here’s the ultimate packing list for a week-long sailing trip in the Caribbean, based on what actually works onboard.
Soft-sided duffle / collapsible bag – carry-on friendly and easy to store on board
Packing cubes – keep small cabins organized and make unpacking quic
⛵How Packing for a Sailing Trip is Different
Storage space for personal items is limited. Your yacht is already packed with linens, kitchenware, water toys, provisions, and maintenance items. Floor space is minimal, unlike a hotel room, so hard-sided luggage simply doesn’t work.
You realize quickly how little you actually need when “your hotel” rooms moves with you.
Pack light, pack smart, and avoid first-timer mistakes with this liveaboard packing guide.
Lightweight long sleeve and pants – for wind and cooler evenings (skip heavy sweaters and jeans)
2 sundresses – versatile for daytime coverups and evening wear
1-2 nicer shirts – evening attire for men
1-2 sleep / lounge sets – you’ll live in this more than you expect
Daily personal undergarments
Fresh water will be your best friend. A quick fresh water rinse after every swim/splash keeps your clothes fresh enough to wear. Skip the freshwater rinse, and your cabin, and clothes, will start to smell fast. This is why quick-dry fabrics matter so much onboard.
👙 Swimwear (You’ll live in this)
3 swimsuits – rotate between wet, dry, and semi-dry
Body/face lotion – you’ll want this after sun exposure (and your feet will thank you)
Toothbrush, toothpaste, floss
Deodorant
Lip sunscreen – high SPF lip balm is one of the most forgotten essentials
Bug spray – needed on shore (hello no-see-ums), but usually not onboard with the breeze
First Aid + Medications – seasickness, antihistamine, headache, stomach, plus hydrocortisone for bites
Travel RX Medicine Kit – pre-packed options are great for saving space and covering the basics
Swimmer’s ear drops (if prone)
Hand sanitizer – because who travels without hand sani these days?!
Personal medications/glasses/contacts
Keep everything travel-sized and reef-safe. “Boat hair, don’t care” is real life out here. Even the “fine dining” spots in cruising areas know their audience. Sundresses and salty hair are welcome. Don’t overdo it.
🪪 Essentials
Passport – valid at least 6 months beyond your travel dates
Travel insurance + required documents – includes visas, island entry forms, and any charter paperwork
Credit cards – bring at least two and notify your bank before traveling
Cash (small bills) – essential for moorings, tips, beach bars, and taxis
Visa and Mastercard are widely accepted, while AMEX, Discover, and Apple Pay are often not. Power outages are common, so carry backup cash. Even at places that accept cards, tips are usually cash only, and many small businesses don’t take cards.
US dollars are widely accepted across the Caribbean, regardless of the local currency.
🔌 Electronics + Practical Gear
Phone
Portable charger
Noise cancelling headphones – a must-have I never travel without
Charging cables + wall blocks – don’t forget both
Outlet adapter / converter – check outlet types for your yacht and destination
Sleep eye mask – sunrise is early and bright out here; this is another must-have for me
Important: Avoid bringing power strips or extension cords unless approved by your captain. Boats operate on limited electrical systems, and adding extra load can create safety risks.
💧 Waterproof & Boat-Friendly Gear
Waterproof phone pouch + daypack – the dinghy will be your main transport, and beach days are a big part of the trip
GoPro / underwater camera – don’t skimp here if you want to capture the water time
Snorkel mask (optional) – if you prefer your own fit
⚓ Bareboat Sailing Trip Essentials Most People Forget
(Skip this if you’re on a crewed charter, as these are usually provided.)
These are the small extras we often see experienced bareboat crews bring that make life onboard easier. This will likely require a checked bag.
Headlamp / flashlight – essential safety gear for dinghy rides after dark
Small waterproof speaker
Reusable water bottle – safe the sea turtles, avoid single use plastics
Playing cards / small games – simple entertainment for evenings onboard
Clothesline clips – necessary for hanging wet clothes along the lifelines. This is what keeps everything dry, fresh, and rewearable all week long
Sharp kitchen knife – much easier (and safer) than relying on dull ones onboard
Small spice kit (ziplock sized) – salt, pepper, and your favorite basics go a long way with onboard meals
Travel-size baby shampoo – great for defogging snorkel masks
🚫 What NOT to Pack for a Sailing Trip
Hard suitcases – they don’t store well onboard (and yes, we’ve seen one end up in bed with a kid)
Too many outfits
Denim – heavy, slow to dry, and just not practical onboard
High heels / fancy shoes – heals are safety concern on the boat and island surfaces
Bulky toiletries
Nice or sentimental jewelry – best left at home
Towels – these are provided
Spray or tinted sunscreen – makes decks slippery and unsafe or will stain
Food or drinks – crewed charters are fully provisioned with no extra storage space (even for that “must-have” diet raspberry Snapple)
Bulky toiletry bags and small bathrooms don’t mix. We’ve seen items fall straight into a used toilet thanks to overstuffed hanging bags…not something you want to deal with on vacation.
⚠️Important reminders
Weapons – not permitted onboard
Illegal drugs (including marijuana in any form: CBD, gummies, and vapes) – not allowed on any maritime vessel, regardless of local laws
🌴 Respect the Destination
One of the biggest misconceptions is that you need to bring everything with you because it’s “too expensive” or “not available” locally.
A sailing vacation isn’t about recreating your home, and it’s also not meant to bypass the places you’re visiting. Local markets, shops, and ingredients are part of the experience. Support the community, shop local, and enjoy what’s available.
🎉 Fun Things to Bring (If you have space)
Items for theme nights – pirate, Captain Ron, Gilligan’s Island, 80s disco, white night
Personal flags – sports, state, alma mater, custom
🧠 Final Tips: How to Pack Smart for a Sailing Trip
Pack light – you’ll use less than you think
Choose versatile pieces – items that can be worn multiple ways
Re-wear outfits – totally normal (and expected) onboard
Prioritize function over fashion – that sequin dress won’t survive Caribbean humidity
Adjust expectations – this is not Below Deck or Yacht Week in the Mediterranean. Caribbean sailing is relaxed, casual, and often barefoot
If you take one thing from this guide, let it be this: pack less than you think you need.
Life onboard is simpler. You’ll wear less, need less, and spend most of your time in a swimsuit, salty hair, and bare feet which is exactly how a Caribbean sailing trip should be.
The British Virgin Islands are one of the world’s best sailing destinations, and it is easy to see why. We have traveled extensively throughout the Caribbean, and nothing compares to the ease of sailing and countless protected anchorages in the BVI. Even in peak season, you can still find quiet, tucked-away bays if you know…
