Private Sailing Experiences
Your Private Georgian Bay Escape
Blend hands-on sailing with the freedom of a relaxed day on the water. These are fully private sailing experiences, just your group, a beautiful boat, and some of the most spectacular freshwater sailing on the planet.
Depart Parry Sound and explore the iconic 30,000 Islands at your own pace.
Fully Private — Your Group Only · Certified instructor · 30,000 Islands · Departing Parry Sound, ON
Day Experience
Full-Day Private Sail — 6 Hours on Georgian Bay
$1195
Depart Parry Sound harbour and sail into the Big Sound, threading through islands and open water as the mainland falls away behind you. Anchor in a hidden cove for a swim, explore the shoreline, and enjoy the simple pleasure of moving through water under sail.
The day is yours to shape. Take the helm, trim the sails, drop the anchor — you'll have a day you won't forget.
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6 hours on the water
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Private — your group exclusively (max 6 people)
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Parry Sound, Ontario
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40' Beneteau sloop, North 45°
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Safety equipment, PFDs, non-alcoholic refreshments
Sail Canada Introduction to Boating certification of completion
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Catering, charcuterie boards, custom refreshments
What to Bring
Comfortable, weather-appropriate clothing
Non-marking shoes or bare feet
Warm layer and light rain jacket
Sunscreen, hat, and sunglasses
Camera
Bathing suit and towel for the swim stop
Lunch and snacks (or pre-arrange our catering add-on)
Optional Catering Add-Ons
Enhance your day with curated onboard refreshments, arranged in advance after booking.
Light Lunch — fresh, simple meals perfect for a day on the water
Charcuterie Board — a selection of meats, cheeses, and accompaniments
Snacks & Non-Alcoholic Beverages — assorted selections
Custom Requests — celebrating something special? Just let us know
You're always welcome to bring your own food and beverages.
Weekend Experience
Weekend Sailing Experience — 3 Days, 2 Nights
Disconnect completely. Spend two nights aboard a comfortable, well-appointed 40' Beneteau and let Georgian Bay do the rest. Explore anchorages that most people never see, swim in water so clear you can count the rocks below, and fall asleep to the sound of water lapping at the hull.
This is the cruising life, and it's more accessible than you think.
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3 days, 2 nights live-aboard
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Private — your group exclusively
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Parry Sound, Ontario
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40' Beneteau sloop, North 45°
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Private forward cabin — queen berth
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All meals, bedding, towels, paddleboards, dinghy, safety equipment, PDFs
Sail Canada Introduction to Boating certificate of completion. Option to upgrade to Sail Canada Start Keelboat Standard certification course
Sample 3-Day Itinerary
Every voyage is guided by the wind, weather, and your preferences. The below is a representative outline.
Day 1 — Cast Off & Coastal Discovery
Depart Parry Sound and sail into the Big Sound after a brief orientation. Get hands-on at the helm or simply relax as North 45° glides through scenic island passages toward your first anchorage.
Introduction to the boat and onboard systems
Island cruising and informal navigation
Sunset at anchor and a relaxed evening aboard
Day 2 — Island Exploration & Cruising Life
Sail deeper into Georgian Bay and find the rhythm of life on the water. Swim, explore quiet shorelines by dinghy, and take the helm if you like.
Extended sailing through iconic 30,000 Islands landscapes
Swim stops and shoreline exploration
Informal coaching: sail handling, anchoring, navigation
Evening in a secluded anchorage
Day 3 — Return Sail & Reflection
A slow morning at anchor before sailing back toward Parry Sound, with time to take the helm and savour the final hours on the water.
Morning sail and optional skill-building
Scenic return through the Big Sound
Wrap-up of your Georgian Bay experience
Extend Your Experience — 5-Day Option
With additional days, your voyage becomes even more unhurried and immersive. Venture farther into Georgian Bay, linger at favourite anchorages, or explore more remote passages.
Access to additional remote anchorages and hidden coves
Longer stays in especially beautiful or peaceful locations
More time to relax, swim, and fully embrace the cruising lifestyle
Includes, Sail Canada Introduction to Boating certificate of completion. Option to add the Sail Canada Basic Cruising Standard certification course
One-Way Adventure Option
For a more adventurous itinerary, choose a one-way passage, for example, Parry Sound to Killarney, with stops at iconic destinations such as the Bustard Islands or the French River's Bad River anchorage.
Extended exploration across a broader stretch of Georgian Bay
Access to iconic and less-travelled cruising grounds
Comfortable return transportation by car arranged for you
Includes, Sail Canada Introduction to Boating certificate of completion. Option to add the Sail Canada Basic Cruising Standard certification course