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Sailboat anchored at sunset in Prince Edward County, Ontario

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Welcome to Your Sailing Adventure

Prince Edward County — Eastern Lake Ontario Base Guide

Welcome Itinerary Getting There Accommodation Restaurants Area Guide Textbooks Sea Sickness Insurance Packing List Contact

Welcome Aboard

Congratulations!

Welcome and congratulations on taking the next step in your sailing journey! We are excited to welcome you aboard for our Prince Edward County — Eastern Lake Ontario adventure.

This trip combines the experience of living aboard with hands-on sailing education as we explore the beautiful coastline of Eastern Lake Ontario. You'll gain confidence, build skills, and make lasting memories while discovering one of Ontario's most stunning sailing regions.

Your Journey

Itinerary

Our itinerary is weather dependent and may be adjusted for safety and conditions. We also visit alternative anchorages such as Big Sandy Bay, Wemp's Bay, Marysville, and Bath depending on the winds for that week. Here is a typical route through Eastern Lake Ontario.

Each day includes sail training, theory sessions, and hands-on learning. You also gain access to online learning modules to help you prepare for your exam.

Day 1

Picton to Prinyer's Cove

First sail, anchoring practice, settle into life aboard
Day 2

Prinyer's Cove to Little Bluff

Coastal navigation, swim stop, scenic anchorage at the bluffs
Day 3

Little Bluff to Main Duck Island

Open-water crossing, remote island exploration (weather permitting — easterly winds may redirect to suitable anchorages)
Day 4

Main Duck Island to Kerr Bay

Sail along the coast, sheltered bay anchorage
Day 5

Kerr Bay to Glenn Island

Island hopping, final evening under the stars
Day 6

Back to Picton — Disembarkation

Return to port, pack up, and say farewell

Getting There

Arrival & Parking

Our meeting point is at 80 Cleave Avenue, Picton, Ontario. When you arrive, you'll find free parking at the foot of Cleave Avenue. Walk just past the Claramount Club along the boardwalk to reach us at the dock.

Most of our students drive in from the GTA, Ottawa, Montreal, or are locals to the area. Picton is roughly a 2.5-hour drive from Toronto and about 3 hours from Ottawa or Montreal.

We'll coordinate details through a WhatsApp group closer to departure so everyone has the latest information and can connect with fellow students.

Meeting Point

Where to find us on arrival day

  • Address: 80 Cleave Avenue, Picton, Ontario
  • Parking: Free parking at the foot of Cleave Avenue
  • Directions: Walk past the Claramount Club along the boardwalk to the dock

Where to Stay

Accommodation

If you're arriving the night before or extending your stay

Picton Harbour Inn

Right on the harbour, walking distance to the dock and downtown.

The Royal Hotel

Boutique hotel on Main Street with acclaimed farm-to-table restaurant.

The June Motel

Retro-chic motel in Prince Edward County with a fun, colourful vibe.

Mattinson Hosted Homes

Several hosted accommodation options throughout the county.

Tip: Airbnb has many options in the area, and Bed & Breakfast PEC lists charming local stays throughout the county.

Where to Eat

Restaurant Suggestions

In Picton

The Royal $$$

Upscale farm-to-table with own-farm ingredients. Michelin Key awarded.

Harbour Inn $

Beloved home-style breakfast and brunch right on the harbour.

Bocado $$$

Spanish-inspired tapas, charcuterie, and craft cocktails on Main Street.

The Acoustic Grill $

Best burgers in town with live music. 14 beers on tap, great value.

The Blue Sail $$$

Seafood-focused restaurant and market with fresh, high-quality catches. Casual atmosphere.

Around Prince Edward County

Stella's Eatery $$–$$$

Indigenous-inspired seasonal farm-to-table, sharing plates, natural wine. In Waupoos (~20 min).

Flame + Smith $$$

Sustainably-minded woodfire cooking, rustic fine dining. In Bloomfield (~10 min).

La Condesa $$

Authentic Mexican cuisine with tequila and mezcal cocktails. In Wellington (~15 min). Walk-in only.

Darling's $$

Wood-fired pizza and Italian-American fare. Voted top 10 new restaurant in Canada. In Bloomfield (~10 min).

Explore

Local Area Guide

Prince Edward County is Ontario's premier wine and culinary destination, surrounded by the waters of Lake Ontario and the Bay of Quinte. Beyond the sailing, there's plenty to explore if you're arriving early or extending your stay.

Wineries

Norman Hardie

Acclaimed Pinot Noir and Chardonnay with vineyard views.

Karlo Estates Winery

World's first certified vegan wine producer.

Sandbanks Estate Winery

Fantastic outdoor atmosphere with multiple tasting bars.

TerraCello Winery

Hidden gem with wood-fired pizza and a vineyard patio.

Breweries & Cideries

Parsons Brewing Company

Large outdoor space with live music and fire pits.

The County Cider Company

Best views in the county, overlooking orchards and the lake.

Matron Fine Beer

Small-batch craft brewery with creative, flavourful brews.

Beaches & Outdoors

Sandbanks Provincial Park

Largest bay-mouth sand dune formation in the world. Three stunning beaches.

North Beach Provincial Park

Quiet and scenic, one kilometre of beautiful sand.

Millennium Trail

35+ km cycling and hiking trail on an old railway line through the county.

Taste Trail & Arts Trail

Self-guided routes through wineries, breweries, restaurants, galleries, and studios.

Prince Edward County is a destination in itself. Whether you're into wine, food, beaches, or cycling, there's no shortage of things to do before or after your sailing adventure.

Prepare

Reading Your Textbooks

We'll be getting your textbooks in the mail to you as soon as possible. If you are completing the Basic Cruising level, please read "Basic Cruising Skills" by Gillian West before the trip. If you are registered for the Blended or Intermediate Cruising level, we recommend supplementing your knowledge with the Intermediate Cruising Notes.

PLEASE read through these at least once before the trip! This is an intensive course, with a lot of skills and material to cover. You will significantly increase your chance of passing each level of certification if you read your material in advance.

We find that students who prepare ahead of time come aboard far better equipped, learn more quickly, and ultimately end up being able to enjoy the course more. The more prepared you are, the more time you'll have for fun.

Health

Sea Sickness

If you are prone to sea sickness, it's best to plan ahead so you can fully enjoy your time on the water. A few simple steps can make a big difference:

  • Stay well hydrated and get plenty of rest before sailing
  • Avoid alcohol, caffeine, and greasy foods
  • Spend time above deck, keep your eyes on the horizon, and take the helm if you're comfortable — it often helps to steady you
  • Let your crew and instructor know if you're not feeling well so we can support you

Over-the-counter or prescription remedies can also be effective if you know you are prone to motion sickness. Sometimes seasickness occurs on the first day and your body acclimates to the rhythm of being at sea.

Note for Lake Ontario: While much of our sailing is in sheltered bays and along the coast, Lake Ontario can produce significant swells, especially with strong winds. Open-water crossings to places like Main Duck Island can feel quite different from nearshore sailing. Being prepared ahead of time ensures you'll spend more time enjoying the adventure.

Important

Travel Insurance

The course is non-refundable. If you need to transfer your spot to another participant, there is a $150 CAD administration fee.

We recommend checking whether your existing health insurance or travel insurance covers activities on the water. If you're travelling from another province, your home province health plan may not fully cover you in Ontario — supplemental travel insurance is recommended.

Travel insurance can help protect you in the event of medical emergencies or unexpected trip interruptions. Having coverage means peace of mind for you and your crew, and ensures that your investment in this adventure is protected.

Tip: If you have questions about the best insurance for you, please inquire with Cathy Davis when booking.

Get Ready

Packing List

Please pack all items in soft-sided, collapsible luggage like duffel bags or backpacks. No wheeled luggage — there is no place to store it on the boat. Everyone will have shelves and a closet in their cabin to unpack into.

Clothing

Essentials

Gear

Course Materials

Highly Recommended

Questions?

Get in Touch

Email us at hello@happysailing.ca for any concerns or suggestions.

Contact Us
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