Sailing Vacation Charters

Turn your dream of a sailing vacation into a reality! Whether you want to completely sit back and relax, have your every whim catered to, participate in your adventure as crew, take the helm and skipper the boat, or learn to sail while on vacation – we’ve got a sailing vacation charter for you!

Skippered Charters

If you are new to sailing, or if you just want to sit back, relax, and enjoy the ride, then hiring a skipper is a great choice. A skippered yacht charter is nothing more than a bareboat charter with the addition of a professional skipper. It’s the perfect blend of laid-back luxury for your sailing vacation charter!


  • Operational, technical and safety aspects of the sailing yacht
  • Planning the itinerary for you or with you –  your choice
  • Sailing skills support for you and your crew

Price:  $300 (+hst) per day

Note: hired skippers require their own cabin and on-board meals to be provided.

Certification Charters

You can learn to sail anywhere in the world, so don’t let your current location or season stop you from achieving your dream! Spend a week on a sailing vacation chartered yacht with a fully qualified instructor, and you will have the opportunity to achieve your sailing certification while enjoying a unique vacation adventure.

Available courses include:

  • Sail Canada – Basic Cruising Standard
  • NauticEd – Large Sailboat Skipper, Bareboat Charter Master

The cost will depend on the course selected, the number of certification participants and travel requirements.

Note: certification skipper requires their own cabin and on-board meals to be provided.

Bareboat Charters

Want to do it all yourself? We can help you with your trip planning, boat selection and much more.

Large keelboat - bareboat charter - intermediate and advanced skills

Sailing vacations are an amazing way to combine sailing, adventure, travel and culture in one amazing trip! We can help you sort through the many choices and decisions you’ll need to make in order to plan a relaxing vacation.

  • Chartering
  • Purpose
  • qualifications
  • Pricing
  • Provisioning
  • Briefings
  • Locations
  • What to bring
  • Who to bring
  • Charter agents

Flotilla Charters

Flotillas are groups of sailboats exploring an area together. They follow the same itinerary and meet up to overnight in a bay or marina. They are a great way for larger groups to share a sailing adventure, with someone knowledgeable to lead the way. Whether there are too many people to fit on one boat, a lack or mix of experience, or a preference to have help navigating a tricky area, a professional skipper leading your flotilla will make your sailing vacation charter one to remember.

Usually, each boat is a bareboat charter, a skippered/crewed charter, or a shared boat, depending on preference and availability.

The cost for a Lead Flotilla Skipper depends on the size of the flotilla and the location.

Note: hired skippers require their own cabin and on-board meals to be provided.

The benefits of flotilla sailing include:

  • Led by an experienced skipper
  • Itinerary planning and daily briefiings
  • Local knowledge and activities
  • Organized preparation
  • Comfort in numbers
  • Nearby support
  • Meet new people
  • Fun, fun, fun!

Learn more about charter destinations and planning through our NauticEd Blog

Get Your Two Free Online Courses & Sailing Logbook Here!