The Complete Sailing Trip Packing List: Here’s What to Pack

I recently dusted off my sailing trip packing list for a bareboat charter trip to Key West. We’ve picked up more than a few packing tips over the years.

This list assumes you are heading to a warm, tropical destination such as the caribbean.

You probably have heard, but if it’s your first time, it’s a good idea to bring a duffel bag as your luggage. Space is at a premium on board, and you’ll be thankful you don’t have to find a place to store hard luggage.

There are some items on this list that you would have to go through airline checked luggage. If you are carry on only, plan to buy those items in country, leave them at home, or consolidate so only 1 bag needs to be checked amongst the crew.

Here is what to bring on a sailing trip – the obvious, and maybe not so obvious. I’ve made a few specific recommendations with our affiliate links where I think the brand matters!

Clothing & personal sailing packing list items

  • Swimwear / swimsuits – you don’t need one for every day, but they don’t take up much space!
  • Long-sleeved cover ups – there will be a point each day where it may be difficult to re-apply sunscreen. It’s usually because you are wet – rain, sweat, dripping from a recent dip, etc. Having a couple of these sun shirts is a great idea to keep you protected from sunburn. For the guys, Florence Marine X – John John Florence’s new brand – puts out a great SPF hooded shirt
  • T-shirts/tank tops
  • Shorts
  • Sarongs for the ladies
  • Dad hats for the guys
Yacht warriors dad hats
We made our own custom dad hats in 2021
  •  Lightweight rain coat or windbreaker – we usually encounter a squall or two and someone still has to drive the boat! These aren’t bad either for a nighttime dinghy ride into the wind.
  • Sweater – it can feel chilly at night at times
  • Theme night – we usually pick one night to dress up and have some fun: Luau Night, Dinner with the Captain (think Master and Commander), etc.
  • Polarized sunglasses – all the crew should bring polarized shares. They are helpful to read the water and see potential obstructions. My favorite brand recently is Electric – the Knoxville Sport model is a perfect everyday pair. Get them in Blue Polarized Pro for your boat trip.
  • Snorkel & mask – I highly recommend bringing your own. Snorkeling gear is usually available from the charter company, but it gets a lot of use. The quality is not usually great either. Spend the money and invest in your own. I learned to scuba dive in 2008, and I am still using the same snorkel/mask. They will last you for years if taken care of. Another reason to bring your own is that, due to Covid, some charter companies are no longer providing masks (although you can still get fins from them).
SwimStar Sorkel Mask Combo (Amazon)

This SwimStar model is an affordable option. We definitely recommend bringing your own set.

  • Fins – if you have them and have space, bring them. Otherwise, the fins from the charter company will usually be just fine.
  • Walking/hiking shoes – these are usually the pair I wear on the airplane.
  • Flip flops
  • Water shoes – optional, but they can be helpful. For example, jumping in the water to beach your dinghy.
UBFEN Aqua Shoes (Amazon)

These water shoes are great. They're affordable and will give you great traction/protection on slippery surfaces.

  • Boat shoes – you definitely do not need these. I think most people that wear boat shoes have never been on a boat. I’m always barefoot when we are on the sailboat.
  • Quick dry towels – most charter companies don’t provide beach towels, so plan to bring your own. Since they might get multiple uses every day, we like quick dry options. This type of towel also won’t take up as much space in your bag.
  • Sunscreen lotion – if you can find it, bring a reef friendly option. Reef Safe Sunscreen is a bit more expensive, but it’s worth it to help protect the reefs.
Reef Safe Sunscreen (Amazon)

SPF 50, kid, and ocean friendly.

  • Personal toiletries – toothbrush, toothpaste, lip balm, deodorant, shampoo/conditioner (the boat will not come stocked with this), etc.
  • Electronic chargers

Things to bring for the crew

Divide and conquer – split these items up amongst the crew.

  • Fishing gear and tackle – check out our sailboat fishing guide for all the details.
  • Group flag – such as our Yacht Warriors flag! I ordered a custom burgee from bestflag.
Yacht Warriors custom burgee flag (I need to find a better picture!)
  • First-aid kit – your yacht will have one, but we’ve found it can be helpful to bring some supplemental items. Sometimes the boat kit is incomplete
    • Dramamine for seasickness, extra band aids, neosporin, aloe, etc.
  • Cash – it’s a great idea to have a couple hundred bucks for each person. You’ll need it for purchases such as mooring ball fees, trash pickup fees, and some restaurants might be cash only.
  • Extra zip lock bags of various sizes
  • Board game, playing cards, or dominoes – whatever the crew likes if games are your thing
  • Floats – if you can rent them, we’d recommend just going that route. You can pack your own, but they take up space and are likely going to be thrown out at the end of the trip. I’ve taken a MONSTER float on a couple trips, but it always becomes way more work than it’s worth.
  • Flashlight or headlamp – bring a headlamp if you have one, but if you need one, your smartphone flashlight will probably be fine for the boat. You might want a real flashlight if you plan to take the dinghy ashore for dinner and return after dark.
  • Collapsible cooler – for those shore excursions or storing extra ice on the boat. For some destinations, you could also pack meat in dry ice to bring with you. I like the TOURIT coolers. It’s soft, so it can be packed or used as a carry on. They are also much more affordable than higher end coolers like Yeti or RTIC.
TOURIT Cooler Backpack (Amazon)

Fits 30 cans for excursions ashore. Can also function as your flight carry on.

  • Waterproof speaker – believe it or not, some sailboats don’t have external speakers that you can hear well while underway. You’ll want a waterproof, portable speaker so that you can also take your sailing tunes ashore.
  • Reusable drink cups, such as Yetis (get them personalized for a great trip souvenir)
  • Dry bag – you don’t need anything big, just something to fit phones in for a dinghy trip ashore. I’ve had a Sea to Summit dry bag for years – a 4L version should be perfect.
Sea to Summit Lightweight Dry Sack (Amazon)

My Sea to Summit sack has lasted over 10 years now. This 4L is the right size for your trip.

  • Paracord (550 cord) – you will find some many uses for this: securing fishing poles, tying on flags, making croakies for your sunglasses. Lots of color options are available online.
  • Spices – we always bring a basic assortment, salt and pepper at a minimum
  • Hot sauce – I always pack some of my favorite all around hot sauce – Marie Sharp’s. In Texas, I can get it at the local supermarkets, but you can also pick it up online.
Marie Sharp's (Amazon)

2-pack of the good stuff.

Fresh caught ono poke bowl
Marie Sharp's on the fresh caught wahoo poke bowl from our recent Exumas trip
  • Duct tape
  • Charts and cruising guides
  • Fishing licenses (check local regulations)
  • Drone (optional) – you won’t regret it. I recently upgraded to the new DJI Air 2S. It is compact and takes stunning pictures – check out recent trips to the Exumas, Bahamas or Key West and the Dry Tortugas for some examples. I also post these pictures on our instagram profile.
DJI Air 2S Combo (Amazon)

The Air 2S is one of the newer models. It takes stunning pictures and has several flight modes that make it easy to use aboard a sailing yacht.

  • Chefs knife or knife sharpener (optional) – this might sound silly, but I usually pack a well-sharpened kitchen knife since we are usually checking luggage for our fishing gear. We do a lot of cooking and working with a dull knife is the worst (and also dangerous)!
  • Projector (optional) – OK hear me out. Yes I know we are going on a boat trip to cut the cords and enjoy the islands. It is sooo much fun, however, to watch Master and Commander or another favorite sailing movie (Captain Ron perhaps?) on the boat. We don’t do it every night, but once or twice is fun! We hang up a sheet with duck tape and connect the projector via bluetooth to the boat’s sound system. Check out our projector setup on our recent Exumas trip.

First time on a boat trip? For more tips, check out our bareboat charter guide for beginners.

Our Favorite Secret BVI Anchorages: Escape from the Crowds


When we go on bareboat sailing trips to the British Virgin Islands, I love to find off the beaten path anchorages. While you will be sure to find me with a painkiller at the busy Soggy Dollar Bar, I enjoy a secluded anchorage with an epic Caribbean sunset even more.

BVI lays claim to to tagline Nature’s Little Secrets, but each visit it seems to get crowded. That is, unless you know where to look.

I’m going to share three of my secluded anchorages where you are most likely to enjoy the view all by yourself. I have a few more, but I can’t give away all of my secrets! If you are looking for the more popular British Virgin Island anchorages, check out my recommended itinerary for a perfect week in the BVIs.

  1. Eustatia Sound
  2. Muskmelon Bay
  3. Benures Bay
  4. Key Bay

As always, confirm with your charter company during your boat briefing whether some of these areas could be red-lined and therefore, off-limits.

Eustatia Sound outside Virgin Gorda Sound

Eustatia Sound Anchorage
Beautiful sunset at secluded Eustatia Sound

There is plenty of room for everyone in North Sound, but if you want to get away from the crowds, check out Eustatia Sound between Prickly Pear Island and Eustatia Island.

Take note that this area is redlined by several charter companies – make sure you confirm during your boat briefing. If it is off-limits, you can still explore this area with your dinghy from North Sound.

This peaceful area is usually one of the first stops on our BVI sailing trips. It gets me perfectly settled in vacation mode every time. It is also a convenient jumping off point for the offshore crossing to Anegada.

Eustatia Island is a high-end, water sports focused resort. You might see some of the guests kitesurfing nearby.

Sunsets here are excellent, and there is a nice reef with good snorkeling just to the north. We often take our dingy over in calm conditions.

You get the added benefit of gazing upon two islands owned by billionaires – Eustatia Island is Larry Page’s. His neighbor, Sir Richard Branson, owns the luxe resort Necker Island which he lives at for a number of months each year.

North Sound is a short dinghy ride – you can still get a piece of the action at some nearby beach bars and restaurants. Our picks would be Saba Rock and the Bitter End Yacht Club.

Eustatia Sound Anchorage in BVI
Eustatia Island, Eustatia Sound, the snorkeling reef, and proximity to North Sound (source: Eustatia Island)

Eustatia Sound Anchoring Guide

There are two approaches to reach Eustatia Sound. The easier route is to continue past the channel markers outside of North Sound and enter the wide channel on the east side of Prickly Pear Island from the north.

Your other option is to enter North Sound and continue east towards Saba Rock. Use the channel markers, keeping Saba Rock to port. You’ll see Eustatia Island to port as well. Proceed carefully around the reef, giving yourself plenty of space.

Anchor west of Eustatia Island in about 10-15 feet of water. The bottom is sandy and your anchor should set well.

This spot is exposed to northerly ground swells, so make sure you try this one in settled conditions. They are well-forecasted.

Muskmelon Bay at Guana Island

Muskmelon Bay Anchorage
The rugged geography of Guana Island with our catamaran at Muskmelon Bay

We like to stop here for lunch at Muskmelon bay on our way back from Anegada. Muskmelon bay is located at the northwest part of Guana Island, near Long Point. The entire island is a very private luxury resort and nature sanctuary.

This spot is incredibly picturesque and is swarming with marine life. Cliffs near the anchorage site make for some spectacular scenery. Truly a BVI secret. 

The coral reefs are well developed and it attracts plenty of baitfish. This, in turn brings the birds – what a show the they put on! I’m not much into bird watching, but it is a lot of fun to see them diving for fish at close range.

You’ll definitely want to hop in for a snorkel – you won’t have to swim far from the yacht. Expect to see lots of fish, rays, and a few turtles on most days.

The anchoring location is quite close to shore at Muskmelon Bay

Muskmelon Bay Anchoring Guide

I view this as a day anchorage only and there are no moorings available. The anchoring area is quite small, so I’d suggest you move on if there is another boat occupying the space.

Drop your anchor in the patch of sand about 400 feet south of the rocky beach visible on satellite in the NE corner of the bay. You’ll be fairly close to shore.

Backwinding is a concern here and is why I wouldn’t want to be here overnight unless in very calm conditions. If you aren’t as familiar with the concept, I talk about it in my BVI weather post.

Benures Bay at Norman Island

Benures Bay Sunset at Norman Island, British Virgin Islands
Not another boat in site at Benures Bay

(Update – since I wrote this, I’ve learned several mooring balls were installed, which is disappointing. You may not find solitude in this anchorage anymore.)

This peaceful bay is quite the opposite of the Bight with rowdy Willy T on the other side of the island. The shoreline is rocky and there is some interesting snorkeling in the bay.

If you like hiking, you can access the Norman Island trail system from the middle of the bay. It is easily visible on satellite imagery. Check out this article for tips on other ways to experience Norman Island

Pro tip: start early and hike over to the Pirate’s Bight restaurant for a nice lunch or dinner. It’s about a mile over to the Bight. If you go for dinner, make sure you make it back in time for sunset at Benures! Take a look at your sailboat lying in the bay below.

It is also a short dinghy ride over to the Bight. Make sure conditions are calm so you don’t get wet.

Benures Bay is another fantastic place to grab a sundowner and watch the beautiful show. The Indians and US Virgin Islands provide an outstanding backdrop.

Benures Bay, Norman Island British Virgin Islands
Another view of Benures Bay at Norman Island

Benures Bay Anchorage Details

The approach is straightforward and the bay is fairly deep in the middle. Aim for the north east side of the bay. The bay should have enough room for 4 or 5 boats, so don’t worry if you have to share.

Depths get shallow quickly as you get closer to shore. Drop the hook in ~20 feet of water and deep sand. Holding is excellent.

Be careful not to anchor to close to shore since backwinding can occur at Benures. Leave yourself enough swinging room.

Key Bay at Peter Island

The legendary Willy T, now an artificial reef at Key Bay | Source: Beyond the Reef

Key Bay is a wonderful, seldom used (in my experience) anchorage on the south side of Peter Island. It’s small, with only room for 2-3 boats – but that is what makes up it’s charm. It’s not possible for this one to get crowded.

Given it’s proximity to the marinas at Tortola, it can be a convenient first or last night stop for your sailing trip.

In 2019, Beyond the Reef successfully sunk the Willy T at Key Bay. Willy T was beached nearby at Norman Island after Hurricane Irma.

Beyond the Reef turned it into an artificial reef, and had some fun with a pirate theme. You can see it if you snorkel (the top mast is at about 30 feet), but it is really intended for divers.

They ask for a $5 donation if you use their mooring ball which will go towards supporting local kid’s swim programs.

Key Bay Anchorage Details

If there is any wind out of the south, this anchorage should be avoided, since swell will wrap it’s way around Key Cay. No one likes a rolly night.

The approach is from the SW and you’ll want to get close into the NE corner. Depths are around 15 feet with some sand, but also a lot of sea grass. Choose your spot carefully as there is also some coral in the area.

My BVI Beginner’s Guide has some useful information on other more popular anchorages in the British Virgin Islands.