Not intended for navigation. Routes and distances are approximate and are determined by each skipper based on conditions and preferences.
This leisurely adventure is a great two-week itinerary for sailors, or those boating in trawler-style yachts, or anyone wanting to avoid long days at the helm.
This cruising itinerary extends the route of our 7-Night Perfect Sail and Trawler Cruise to allow for nearly a week to explore the Gulf Islands in Canada, as well as eight stops in the San Juan Islands.
The leisurely pace allows for casual cruising days for those favoring ‘getting there’ a bit more that ‘being there’. Just relax and enjoy the ride.
14-Night / 15-Day Itinerary
Day 1Anacortes to Deer Harbor
Cruising miles: 20
One of the most well-equipped marinas in the San Juan Islands, Deer Harbor is a great place to start your adventure. You’ll find top of the line facilities here, along with shopping, dining, water sports and more.
Day 2Sidney
Cruising miles: 18
Port Sidney, located at the southeastern tip of Vancouver Island, is a quaint village offering easy access to the world famous Butchart Gardens. Despite its proximity to the large city of Victoria, Sidney has retained its small town charm while offering best-of-breed modern facilities. You’ll find shops, museums, a seaside walk and much more.
Day 3Victoria to Port Sidney Marina
Cruising miles: 12
As you venture up the eastern side of Vancouver Island, you’ll find Cowichan Bay. This long and protected bay is a sometime haven for Orca, so keep your eyes open! Tucked in the northeast corner of the bay is Genoa Bay. This very well protected harbor offers both dock and mooring space. Once a lumber camp, there are some wonderful hiking trails on the shore, as well.
Day 4Telegraph Harbour
Cruising miles: 19
Located between Kuper and Thetis Islands, this is a major cruising destination with two popular marinas. Ferry service is available to the nearby town of Chemainus, for those craving a taste of ‘civilization’. For everyone else, these islands offer wonderful sightseeing, hiking and small craft adventures.
Day 5Nanaimo
Cruising miles: 19
Nanaimo is a historic mining town which has grown into one of the largest cities in British Columbia. Nanaimo’s large harbor offers sea planes, restaurants, shops, theaters and museums. The bustling waterfront district has been completely restored in recent years, and is enjoying its return to a thriving tourist destination. Don’t miss the Newcastle Island Marine Park across from the main harbor. This oasis away from the bustling marina across the channel is a wonderful must-see detour.
Day 6Montague Harbour
Cruising miles: 27
For decades, this has been one of the most popular British Columbian cruising destinations. This is where you’ll run out of film because every at every turn, in every kind of light, this place is truly spectacular! Montague became BC’s first Marine Park in 1959, and has been thrilling visitors with its pristine beauty ever since. Plan to stay at least one night here – sunsets in Montague are truly unparalleled in the world.
Day 7Brentwood Bay
Cruising miles: 21
Located at the southern tip of the Saanich Inlet, Brentwood Bay is best known as a popular sport fishing resort town, and as the entrance to the world famous Butchart Gardens. Located down the Tod Inlet (just south of Brentwood Bay), Butchart Gardens is a colossal example of the best in garden design, maintenance and creativity. Jennie Butchart began cultivating the gardens in 1904 after her husband’s cement company had excavated all of the lime from this piece of property. She transformed what was a stripped, eyesore into a ‘Sunken Garden’ which now also includes a magical fountain. Whether you’ve got a green thumb or a concrete garden, Butchart Gardens is easily one of the most impressive places you’ll ever see.
Day 8Reid Harbor
Cruising miles: 4
Reid Harbor at Stuart Island not only affords 360-degrees of protection but also boasts a comforting number of mooring buoys and floats. This is a great place for the hikers in the crew to stretch their legs in Stuart Island Marine State Park.
Day 9Roche Harbor
Cruising miles: 11
Venturing back into the USA, Roche Harbor will again be the most appropriate place to clear Customs. Tucked in the northwest corner of San Juan Island, behind Henry Island, Roche Harbor is another wonderful small seaside town with a unique personality. You’ll find ample services, dining, shopping and activities here (and this is a great place to pick up any provisions you’ve run low on).
Day 10Friday Harbor
Cruising miles: 8
Friday Harbor is the seat of the Island County government and is the most populous of the island towns. Don’t let that fool you though – this enchanting town is intimate and inviting. You’ll find wonderful shopping, dining and hiking here – along with simpler joys such as sitting on a dockside bench to read, watch birds or simply relax. Plan to spend at least a few hours here (if not longer) to truly take in all the sights.
Day 11Rosario Resort
Cruising miles: 4
Located on Orcas Island, Cascade Bay is home to one of the jewels of the islands – the historic Rosario Resort. The original mansion here was built in 1904 by a millionaire Seattle shipbuilder (Robert Moran). Anchored on bedrock, the property took six years to complete, and boasts more than fifty rooms. The architecture includes concrete walls, shipwright style doors and woodwork and inch-thick plate glass windows. Far from seeming like a cold ship, however, this is a warm, world-class resort.
Day 12Blind Bay
Cruising miles: 8
Located on Shaw Island, just opposite Orcas Island, Blind Bay offers wonderful protection from winds and weather. It can be a little tricky to get in and out of this small bay, but the privacy of this place is well worth the extra effort.
Day 13Hunter Bay
Cruising miles: 13
Lopez Island’s Hunter Bay is another small but wonderfully protected location. Crab Island at the mouth of the bay is a wildlife refuge, and offers great bird watching opportunities for everyone on board.
Day 14Eagle Harbor
Cruising miles: 9
As you wrap up the trip, a stop at Cypress Island’s Eagle Harbor is a perfect last stop. This small east-facing bay provides you with lovely sunrise views across Bellingham Channel.
Day 15Anacortes
Cruising miles: 9
Eventually, you’ll need to return to Fidalgo Island, but you’ll have time for a leisurely return while you begin working on next year’s itinerary. We look forward to seeing you next time.
Cruise Planning Tool
Destination distances in miles. Use this chart to estimate the mileage between destinations when planning your cruise.
