Travel & Leisure recently described Prince Edward County as one of the top places to travel to in the world in their annual list: ‘Cross Montauk, NY, with California’s Napa Valley circa 1970, and you get Prince Edward County, a tiny wine-producing region that’s becoming a haven for creative types.” From Toronto, the county is an easy train ride away. With over 40 vineyards (including Norman Hardie Winery, Closson Chase and Karlo Estates), and now over a dozen breweries, many with tasting rooms, this bucolic land of orchards, vineyards, stunning beaches (Sandbanks Provincial Park is unique in all of Canada), is a mecca for cycling (and eating). On our guided trip, meet our friends along the way and enjoy can’t miss dining, and tasting opportunities that you wouldn’t easily find on your own.

Only Great Explorations:

· Small groups, extraordinary guides, and authentic experiences
· Order off the menu at restaurants you won’t find in guidebooks
· Distinctive, charming hotels too small for larger groups
· We design and operate our own trips so there are only good surprises



Wellington, Prince Edward, ON, Canada

Day 1+2


Milford, Prince Edward, Ontario, Canada

Day 3 + 4


Picton, Prince Edward, ON, Canada

Day 5 + 6 + 7

What’s Included in the Cost of Your Trip?


Services of one or more experienced Great Explorations guide(s)
Support vehicle
6 nights lodging
All breakfasts, 2 lunches, and all dinners but 1
Welcome and final night receptions
Selected wine and craft brewery tastings
Entrance fees for selected historical sites and museums
Detailed maps and GPS instructions
All baggage transportation

Not Included

Bike rental




Available dates upon request. Minimum 4 to guarantee. Private and self-guided trips also available.
Please contact us at or by telephone at 604.730.1247 for details.


Available dates upon request.


4-16 participants


7 days / 6 nights


Wellington / Picton


Moderate. Average daily distance is 40 - 55 km (25 - 35 miles) with optional route extensions.


Some gently rolling hills but generally level.


Land Cost:
CAD $2,925*
Includes 6B/2L/6D

Single Supplement:
CAD $750*

Bike Rentals

Hybrid or Racing Bikes: CAD $280

E-Bikes: CAD $480*

*E-bikes are generally available but are on an ‘on request basis ‘ and will be confirmed on receipt of your booking registration. E-bikes provided are the best rentals available in the region. Our regular fleet of hybrid and race bikes are fun to ride and light and fast, but if having an e-bike will make your trip, we’ll do our best to provide. E-bike rentals are non-refundable.

*Price before tax. Trips in Ontario are subject to 13% HST.

Please note: Final itinerary is subject to revision; any changes made are done so in an attempt to provide the best possible trip given route conditions and available services. Due to the nature of our business and exchange rates, prices are subject to change. Due to cancellations and waiting lists, trip availability fluctuates daily. If you have any questions or would like to confirm space on this trip before making your reservation, please contact us at or by telephone at 604.730.1247.

Getting there

Your tour starts in the town of Wellington, about 200 km (120 miles) east of Toronto. From Toronto, trains take approximately 1h45 to Belleville. If travelling by car, it is possible to leave your car in Wellington, where you will be able to pick it up at the end of your cycling trip.


Day 1


Wellington is a lakeside village that is a short cycle away from many of the finest wineries in the County. We meet at 2pm at our first hotel and enjoy a warm-up ride. Afterwards, poke around the shops and cafes of Wellington. After a welcome wine reception, enjoy dinner at a restaurant with a deck overlooking West Lake.

Ride Distance: 28km; 40m


Day 2


Ride a loop along vineyard studded Closson Road, admiring the restored barns from the 1800’s and tasting wines that are garnering the County acclaim. Visit the Old Third, Closson Chase Vineyards, Norman Hardie Winery and Karlo Estates to name some.

Ride Distance: 36 km ; 60m or 43 km*; 100m


Day 3


From Wellington, make your way first to Bloomfield, with its eclectic shops and cafes, then along West Lake and through Sandbanks Provincial Park, with its sand dunes and stunning beaches before continuing on to our charming accommodation for the night. Dinner will be at a local restaurant in Waupoos.

Ride Distance: 54 km; 80m*


Day 4


From Milford, you have several options. You can make straight to the beaches of Sandbanks Provincial Park and loop back along quiet roads via Port Milford, where you can stop to visit the Mariners Park museum. Another option is a ride out towards Prince Edward Point to see an incredible Bird Observatory. A shorter option takes you to a secret beach that we will share with you. There is also an option to stop and taste wine on the return trip.

Ride Distance: 32km; 100m or 55km; 120m*


Day 5


From Milford, ride out to Fifth Town Artisan Cheese shop to taste and visit. An add-on option explores Point Traverse and the Prince Edward Point Wildlife Area if you didn’t do yesterday. In Picton, visit the town and settle into our hotel, steps from fabulous restaurants and home to a few craft breweries with tasting rooms.

Ride Distance: 40 km;  180m with a 39 km add-on option*


Day 6


Ride a fabulous loop out to Waupoos, with tasting opportunities at the County Cider Co. and at Waupoos Winery. Lunch will be a highlight at the Lake of the Mountain Resort, with a dreamy setting. Or ride a loop out to Big Island where you can gaze out over Massassauga Point Conservation Area from Robinson Bay. Back in Picton, we’ll dine at an acclaimed restaurant and toast our time in Prince Edward County.

Ride Distance: 40 km;  240m  or  56km; 310m  or  60km; 270m



Day 7

Departure Day

Depart. We will offer transfers to Belleville by 10am.

Wellington Willows, Wellington

This boutique B&B offers a carefully crafted blend of retro farmhouse design and modern amenities. Located a short stroll from superb restaurants, cafes and possibly the best ice-cream store in the county.
Alt: Augustus B&B

Jackson Falls Inn, Milford

Built in 1870, Jackson's Falls Inn is a former schoolhouse, combining the personalized service of a B&B with the privacy and spaciousness of a country inn. While staying here, you can dine in nearby Waupoos.
Alt: The Wilfrid Boutique Farmhouse

Merrill House, Picton

This lovely historic inn with 13 rooms boasts a superb location steps from downtown. Merrill House is furnished with a balance of fine antiques and artifacts, contemporary art and modern touches. The restaurant has a well-earned reputation as one of the best in Picton.
Alt: The Manse Boutique Inn & Spa