Sailing Outfit Ideas – What to Wear to a Yacht Party?


When you’re getting ready for a sailing adventure, choosing the right outfit is crucial. If you’re getting onto a yacht rental, your clothes should strike a balance between looking good and being practical.


First off, it’s important, especially while sailing on a boat rental, to never ignore safety. This means putting on footwear that is appropriate for a boat surface.

  • We recommend a non-slip white-soled deck shoe, which is always a reliable option. These shoes offer the necessary grip on a boat’s slippery surfaces, keeping you steady. If you’re feeling more relaxed and carefree, you can always go barefoot.


Since yacht parties are about enjoying open waters and chilling out, it’s important to place comfort high on your list of fashion requirements.

  • We suggest wearing fabrics such as cotton or linens, as they are light and easy to wear.
  • Men’s fashion options: lightweight shorts or chinos paired with a button-down shirt or a polo.
  • Women’s fashion options: sundresses, maxi dresses, or shorts with a loose-fitting blouse.

Being outside on the water means the weather can change on a dime. Even in hot, humid weather, it’s always wise to bring along a lightweight cardigan, a sweater, or a windbreaker. If the rain starts pouring down, it’s better to have something to cover up with.

Hanlan’s Point

When sailing in the Toronto harbour, there’s a chance you may head over to Hanlan’s Point, a clothing-optional beach on the Toronto Islands. Just remember to respect the guidelines set by the yacht rental organizers!

  • Beach-wear and easy-to-remove shirts are recommended here.
  • Tearaway pants, shorts, and bathing suits are always a good idea for a place like Hanlan’s.

Protecting Yourself

While all of these are great fashion options for sailing, it’s also very important to think about your health, even while sailing. This means covering up and protecting your body from the sun. You’ll be spending a lot of time out on the open water with no shade, and that means there’s a good chance you’ll get a sunburn if you don’t cover up.

  • We recommend a baseball hat or wide-rimmed hat to shield your head, face, and neck.
  • Bring a pair of comfortable sunglasses to wear on your yacht rental trip, as sunlight may beat down onto the water and reflect back into your eyes.
  • Apply sunscreen, whether it’s overcast or shining. Use SPF 50 or higher on every part of your exposed skin, re-applying sunscreen every few hours out on the water.

Nighttime Sailing

If you’re out on a night boat rental and the sun goes down, that warm weather you had during the day may change quickly – especially if you’re on the water.

  • Bring along an extra windbreaker or light jacket, especially if the wind picks up. You may be surprised by how cool the weather gets on the water, even during the summer months.

Dress Like a Pirate!

Here’s another fun option for fashion while sailing – why not dress like a pirate? Yes, a pirate. Hey, you’re on the water already! Why not embrace looking like an old-time sailor, wearing some older clothes and goofy accessories that show off a unique side to your sailing personality?

Going on a yacht rental call for selecting clothes that match your style but also prioritize comfort and safety. You and your friends will already have a great time on the water, but it’s that old phrase “looking good means feeling good” that applies even on a boat rental. By following these guidelines, you’ll be dressed to impress and have lots of fun on your sailing adventure!

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When considering chartering a yacht in Canada, we know you have many options. Some of these options look super exciting and at ridiculously great prices. Recent trends in the industry have opened the door for many unqualified individuals to purchase boats and offer charter services to the unsuspecting public. It’s easy to create a website and even easier to just list a boat on sites such as Facebook Marketplace, Kijiji, Getmyboat, Boat Setter and many others.

Unfortunately, many of these operators are NOT licensed, insured or qualified to accept your trust on the water.

In order to be licensed and insured a number of items MUST be in place. Listed are just a few.

  • The operator must be licensed by Transport Canada with a commercial license known as either:
    – Limited Master under 60tonne.
    – Small Vessel Operators Permit (SVOP).
  • The name of the vessel must be visible on the stern (back) or the registration number beginning with the letter “C” must be visible on the side of the vessel near the front. Boats with a registration number beginning with “ON” are not licensed for passengers.
  • If the vessel is under 12m (40’) it should participate in the Transport Canada Small Vessel Compliance Program and display a “Blue Decal” and have corresponding certificate.
  • If the vessel is over 12m (40’) or carries more than 12 passengers, it MUST BE INSPECTED by Transport Canada and have an inspection certificate on board.
  • All vessels must have commercial liability insurance and coverage specifically for the number of passengers approved to be carried on board.
  • The vessel must comply with commercial safety requirements beyond recreational standards. Many of these illegal operators do not have the proper training, carry proper safety equipment, nor do their recreational boats meet the design/construction requirements of a commercial, passenger carrying vessel. These illegal operators try to stay under the radar of Police/OPP/RCMP/Transport Canada by:
  • hiding the name of their vessel by hanging items over the stern
  • not letting you know where they will have you board until just before the start of your charter.
  • pick you up at a public park (where docking is not permitted).
  • suggest to you that you are friends of the owner/operator out for a ride and not a paying customer.
  • allow you to drink alcohol while the boat is underway (illegal-same as a car) but tell you to hide your bottles etc.
  • insist on a cash transaction or part of it as a way of defrauding the internet listing company.
  • Make you sign a “Charter Agreement” just before you board without giving you details of the document beforehand.

    Over the last few years there have been a number of deaths and even more accidents resulting from these types of operators. Be safe and know who you are getting on a boat with. All licensed operators should willingly display their credentials, and most are members of the Passenger & Commercial Vessel Association (PCVA).

    Link to Global News Report on Charter Accidents

Check before you book
Know before you Go!