Packing for a trip can certainly be an annoying task; you don’t want to over-pack but you still don’t want to be caught unprepared for any situation that might present itself. If you’re going on a sailing holiday this summer (lucky you, by the way) it is important to keep your luggage as compact as possible so that the boat’s storage space is divided fairly among all those aboard. However, packing lightly does not mean that you cannot have sufficient items to cover all the occasions during your trip.

We thought that it would be a good idea to share our favorite hard-working pieces that are easy to pack, work multiple ways, and are suitable for different scenarios with a bit of tweaking. We’re also including some outfit combinations using these pieces to show you how you can be the best-dressed lady onboard without the luggage overload.

Three Dresses

Dresses are the ideal items to pack when you have space limitations because they can be easily rolled up and stored in a suitcase, apart from the fact that a dress can be easily dressed up or dressed down and therefore provide endless styling options.

Four Pairs of Shoes

The good news about summer shoes is that they take up considerably less space than those clunky winter boots. However, it is still a good idea to take with you only strategically chosen options that can complement various outfits and scenarios: a cute espadrille wedge sandal will give you height, comfort, and stability (even if you’re exploring cobblestoned cities during your trip), flip flops are necessary for those days spent chilling on your sailing boat, a stylish flat sandal is great if you want to give your shorts a more polished feel and a fun high heel sandal is necessary for drinks and dinner at the more sophisticated sea front restaurants.

Three Tops

Similarly to dresses, summer tops take up little space in your suitcase and so it is possible to take a quite a few with you without taking up too much space. We suggest having a combination of solid colored options and versatile patterns to mix and match with the other pieces in your suitcase.

Two Pairs of Shorts

What would a sailing trip be with shorts? Shorts are essential to throw on while sailing or chilling on your boat but they are also perfect for those days when you’ll be doing a lot of sightseeing.

Three Scarves

Again, scarves do not take up a lot of space but will give you a lot flexibility: use a large scarf instead of a sarong, twist a square scarf into a headband on windy days, a light flowy scarf when it’s a bit breezy during an al fresco dinner or use just about any scarf to liven up a plain dress. 

Two Pairs of Earrings

Statement earrings are everywhere this summer and you can find some fun options at various price points. It’s a good idea to pack a couple of fun options with you during your trip to dress up the solid pieces in your suitcase, without taking up any space.

Three Swimsuits

Obviously, you need to take an assortment of swimsuits with you on a sailing holiday and luckily these hardly take up any space.

One Handbag 

A versatile handbag is worth its weight in gold since it can go seamlessly from sightseeing to dinner without missing a beat.