if I was going to plan that trip for someone else I would have to ask a few questions. How do you feel about anchoring over night? How often do you need a shower? (Even three days does me fine when boating). Do you want to cook on the boat or eat out? Do you like art and shopping or history? Are you going to fish?
We try to stay on the anchor whenever we can and pull a day stop or anchor near a place to shower every third day. We like to look at art galleries and museums but hate shopping and crowds. We love Ice cream and good food but eat on the boat most days. And we love to fish and crab. Do you want to see wild life? We always do. Do you like to hide way and read? Are you bringing a dog? Do. Not the first time.
So here’s my two week run to see the most. First off make sure you can go to Canada. Well worth it and you will get bored in the san juans in two weeks, well maybe.
Starting at les's for a training session and leave early afternoon for James Island. Short run from cornet bay, well protected and the dock should be empty in September. Hike over the island at dusk to the east side and watch the ferry go by in the dark. Love it. Do not leave any food on the deck including the ice chest unless you can lock it. James has the biggest fearless raccoons in Washington. You will be boarded by a raiding party.
Day two head to Friday harbor but make a lunch stop at Spencer spit. Anchor out and row the dinghy in. (if you don’t have one for the trip I will lend you one) go for a walk around the salt water pond and the spit itself. Then head to Friday harbor for the night. It's the heart of the san juans and you should see it once. Go to breakfast at the little place next to the theater, long line great food. Only place I will wait in line for food, ever.
If you want to see killer whales on your trip then in the morning you should go on a guide boat to see the whales. They will get you on the whales 80% of the time, which is better then you will do yourself unless you know how. Pm me if you want to know how. There is even a 25 c-dory, soul mate, that guides as a whale watching boat. Really nice guy, look him up online. The whales are worth the money for the guide boat or the gas in your tank if you want to do it in your boat. Just allow a whole day for this either way. Then run to British camp before sun set to anchor in garrison bay.
Day four. In the morning you can walk the old British fort and the surrounding trails. After lunch make the short cruise to Stewart Island and stay at the dock or anchor out. Hike the trail around the island to the light house at turn point. It’s a good hike with some hills so take a snack and water. From turn point look out you can see a good bit of Canada and the gulf islands.
Day five. I say go to Canada, go west young man. I would really think about going to Canada. Lots to see and do. It’s a really short run across the border to Sidney to clear customs. I pick Sidney for a few reasons. It's close and easy to get too. If you cannot get around to Victoria because of wind you can take the bus from Sidney to Victoria. Only takes a half hour and your right in down town Victoria. I would prefer to take the boat to the Victoria water front and spend two days going to the museums and watching the street performers (love the Darth Vader playing a fiddle on the side walk) and eating at the shipping container. Best fish and chips anywhere. They only serve lunch and its all take out. its a shipping container behind the customs dock that turns into a kitchen for three hours a day. Love it.
From Sidney or Victoria you can take a bus to Buchard Gardens. Plan to spend most of the day. Its a wonderful and amazing place. A old quarry that was turned into a example of floral overload. You have to see it. If you go on Saturday night they have fireworks in the summer. You can also take the boat around to Sannich inlet and anchor right behind the garden and dinghy in to the dock to enter the gardens if you wish. We have done both.
While in the Sidney area spend the night in Sidney spit. It's a marine park on the end of a island near Sidney. Lots of wild life and trails to walk. Visit the east side of the spit at low tide. Lots of pools and birds to see . We have seen eagles, marsh hawks, deer, kingfisher, seals, egrets, etc etc.. Just a wonderful place to stay and relax. You can anchor or stay at the dock or even a mooring buoy.
Now its day 7 or 8 depending on how much you did in the Victoria area. Time to head north. I would head to Ganges harbor for at least a day trip if not overnight. You can go there and then run to Montague harbor to spent the night on anchor or at the dock. If you do stay at Ganges do not stay at the city dock or salt spring marina. One is unsafe and the other is owned by aholes. But that’s just my opinion. We loved End of the harbor marina. Its a little farther away for town, another 200 yards, but they are really nice folks. Clean showers, laundry, and they rent scooters. A scooter ride is a great way to see all of salt spring island in one day.
From here on you can go to a lot of different towns or harbors. Chemainus is one of my favorites; they have ice cream, with its 40 or so wall murals. Great place to walk town but I would leave and over night at Thetis island, Go to the marina in the back. or head up to lady smith. Or, there are a lot of or's at this point, Wallace island or De courcy island. Both have several nice anchorages, some with docks.
Now in the morning you can head thru Dodd narrows to Nanaimo. I would get a dock spot at New Castle Island and take the shuttle boat to down town for the day and then come back to the quieter and peaceful marine park docks at new castle. The enter harbor docks can be busy and noisy. If its a weekend the ferry from the dinghy dock pub on Protection island can be noisy until early in the am as the last ferry does not bring back the singing drunks until 3am. They are not on key, hell they can’t find their keys, which is a good thing as they should not drive.
I forgot what day it is but who cares your on vacation. Get up early and listen to the vhf to see if whisky gulf is open or closed. If it’s open to traffic get going and cross the straits of Georgia before A) the wind comes up or B) they start to shoot torpedoes. Either way you are better off crossing the gulf early and head to the east side. You can go to smuggles cove, Pender harbor or Egmont for fuel Fill up before you head to chatter box falls. I like to stop at Egmont and hike the trail to Skookumchuk Narrows to watch the tide change and see kayaks surfing the 8 ft standing waves just off the rocks. Fun to watch and looks scary to try. After that you can run for the inlet and the entrance to chatter box falls. Try to time your arrival for the entrance for just before the slack tide hi or low. Stay the night hell stay two nights and just sit and read and relax.
Now you can go home by going back thru the islands or down the coast. I would run back to Winter cove in the gulf island or even tumbo island if the weather is nice. Both are great places to anchor and spend the day walking the shore and looking at wildlife. One day this year while in winter cove I took a dinghy ride with the camera. At one point I was looking at a family of river otter, a seal, two eagles , a blue herring, a kingfisher, three deer and a group of buzzards. Ok the buzzards where weird but all this was from the dinghy at the same time. love it.
Now you have to cross back to the USA and clear customs at Friday harbor or Roche harbor. I would pick roche and then head north around orcas and stay at Suica or that other island I can’t remember right now. Stay the night and go for walks in the morning. From here it’s a few short hours to cornet bay down the east side of orcas or take another day and hit anyone of 30 more bays, islands, docks, ice cream shops. You get the idea.
Well that was longer then I planned. You can do all or some at any time. You can cut out parts due to weather and hit places closer. Just remember to have a plan and except that you will have to break it at any time due to wind rain fog or people. You may not be able to get the dock you want and the next place to dock is a hour away. Try to plan to be secure for the day at least a hour before dark. The san juans are not a place to be traveling after dark even if you know your way around.