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Evening events typically call for more formal attire, but the Key West version of “formal” is still pretty casual. When your sail won’t be including watersports, like most sunset cruises, you won’t be needing your swimsuit and an easy throw-over – and that immediately takes your attire up a notch.
As a general rule, when drinks and appetizers are involved, you should dress up a little bit. So, the sailing outfit men choose might feature khaki or linen shorts or trousers, and a short or long-sleeved button down or collared shirt. Women may choose a dress in a lightweight fabric, cotton or linen shorts or trousers and a top, rather than a T-shirt. Denim is fine for men and women, although preferably not cut offs or ripped jeans. Hats and sunglasses are, of course, acceptable too.
When a full meal is served, especially if it’s a seated dinner, you are more likely to be expected to wear something more formal. Cocktail attire is probably best – so trousers and a blazer or a suit with or without a tie for men, and a short, mid, or long dress for women. If you’re unsure, call your host or the company you’ve reserved with for more information.
In all cases, make sure you can easily reach, take sizable steps, and maneuver in your sailing outfit. You will need step over, duck under, or reach up in order to safely navigate around the vessel.
Ok, let’s talk about which types of shoes to pack. Some boats require that you remove your shoes before coming aboard. At Danger Charters, though, we allow you to keep your shoes on. Even so, some shoes are better for sailing than others.
Heels, platforms, and boots aren’t wise footwear choices for sailing. The boat moves up and down and side to side with the wind and waves, sometimes heeling to one side (the best part!), so you want to be nimble and sure footed while on a yacht. There’s water around, so it can be easy to slip. Plus, these shoes can leave scuffs and dings on surfaces.
Better sailing shoes for women are flat – like ballet flats, sandals, running shoes, or waterproof shoes. Sneakers and water shoes are better for a day-time charter and ballet flats and sandals for a sunset cruise. Men will be most comfortable in boat shoes, slip on or lace up shoes, and comfortable walking shoes. Flip flops are fine if you’ll just stick them in your bag and opt to go barefoot, but keeping them on may tempt them to fly away with the wind!
Regardless of what footwear you choose for your cruise, you will be most comfortable if the sole offers traction, the material is water resistant or dries quickly, and you have a bit of protection for the inevitable knocks and bumps from walking across a “foreign landscape.”
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