Cycling Adventures on Prince Edward Island

Enjoy stunning PEI landscapes as you explore the best of the award-winning Confederation Trail, seaside paved pathways, or rusty red gravel and historic clay roads.

We have tours and services to suit riders of all levels from those prefering E-bikes on gentle surfaces to gravel enthusiasts who want as much of our famous red gravel as possible.
Woman riding on red gravel road

Tip to Tip Tours 

Ride across PEI from tip to tip in 5-7 days while enjoying quintessential PEI landscapes. Choose from four tours that cover a mix of surfaces—from the Confederation Trail to paved pathways along the North Shore to our famous red gravel roads.
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Multi-Day Tours

Spend 2-4 days riding some of the best parts of our Tip to Tip Tours. Choose from four tours that cover a mix of surfaces—from the Confederation Trail to paved pathways in PEI National Park to more challenging gravel and clay roads.
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Day Tours

Interested in one of our signature day tours? We provide shuttle transport and bike rentals (if needed) so you can enjoy a carefree ride in several beautiful parts of the Island.
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Woman riding on red gravel road

Custom Tours 

Let our knowledgeable, local staff design the perfect tour for you, whether it be on Confederation Trail, on paved bike paths by the shore, or on our unique red gravel roads and heritage roads. We'll customize it completely, right down to the scenery desired and eateries you want to visit.
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Shuttle Service 

If you've planned your own point to point cycling tour, or if you are doing the Island Walk, we can transport you and your gear to your start point and then transport you back from your end point.
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Route Planning 

Let our knowledgeable, local staff design the perfect ride for you, whether it is road, or gravel. Our staff know where the hidden gems are that will make your ride fantastic.
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Why Choose Us?

  • Part of a Bike Shop

    Since we are part of an award-winning, full-service bicycle shop, Ted's Bicycle Studio, we have professional mechanics on staff as well as all the parts and accessories on hand that are required to fix any problems your bike may have before, during, or after your tour.

  • Premium Support Levels

    For our tours, we offer all the same levels of support as our fellow tour operators. For our longer Tip to Tip Tours and our Day Tours, we offer premium ride support consisting of a support vehicle on course, nutrition stations with complimentary food, and a post-ride bike wash. This allows you to focus on the ride and enjoy the views!

  • High Quality Rental Bicycles & Accessories

    We have carefully selected and tested the bicycles and gear you can use for your ride. Ted's Bicycle Studio carefully maintains the bicycles so that you get a smoothly operating gravel or hybrid bike for your tour. If you want to try out bikepacking or touring, we have bikepacking bags and touring panniers you can select to carry the gear you need.

  • Customized Routes

    Our local staff know where the best roads, trails, and gravel is in PEI. Our staff and ride ambassadors regularly ride all over the Island and know where the hidden gems are. We love sharing our curated routes and providing recommendations on the best beaches and restaurants. Benefit from our local knowledge when you take one of our tours or let us plan a bespoke tour so that you get the features you want!
Tip to Tip Tour

Client Testimonial

"Amazing 5-Day Self-Guided Bike Tour Experience!"

"I recently booked a 5-day self-guided bike tour with Tailwind Cycling Tours, and it was nothing short of incredible. From start to finish, the entire experience was thoughtfully organized and perfectly suited for adventure lovers.
"The route was a fantastic mix of terrain—gravel roads, red clay paths, stretches of the beautiful Confederation Trail, and smooth paved roads that offered both variety and challenge. Each day brought a new landscape to enjoy, and the directions and route planning were spot on, making navigation easy and stress-free.
"One of the highlights of the trip was the accommodations. Every place we stayed in was comfortable, welcoming, and unique—clearly chosen with care to enhance the overall experience. After long days of riding, it was such a treat to relax in cozy, well-appointed lodgings.
"I really appreciated the freedom of the self-guided format while still having the peace of mind that everything was taken care of behind the scenes. The support from the company was excellent, and it’s clear they truly care about their riders.
"If you’re looking for a scenic, well-organized cycling adventure with a lot of heart, I can’t recommend this company enough. I’m already dreaming about booking my next tour with them!"

-- C.T.

Brought to you by

Tailwind Cycling Tours
41 Hollis Avenue, Unit 4a
Stratford PE, C1B 4A1, Canada

902-367-5191

info@tailwindcyclingtours.ca