Puget Sound Anarachy

Chris in Santa Cruz CA

Super Anarchist
6,879
1,654
earths surface
Lasal's suggestion looks like your best option for that many people. I've chartered trawlers, sail and taken my own boat up there a few times. Really enjoyed the area. I think a trawler is a great way to go with the very light and fickle wind. But it's not likely you will find a bareboat trawler to accommodate that many people.

Do you have a Waggoners guide? If not get one.

Some of my favorite memories involved:

Holly B's on Lopez

Rosario

Riding a bike to the vineyard on Lopez

Walking to the school house on Stuart, is it still open?

Sucia

So much to see and do, have fun.
My cousin, Holly, is Holly B. :)

The butter horns and cinnamon rolls are epic, especially if you love butter!

 

Hawaiidart

Anarchist
613
86
Anacortes, WA
That's a busy itinerary. You might consider spending two nights in one place. Here are my thoughts in no particular order.

Anacortes: don't know what they're doing during Covid times but Dad's Diner serves an excellent breakfast that'll hold you all day.

Rosario: I'd recommend a hike up the hill above Rosario at least to the lake. Take your bathing suits if it's hot, the swimming is great. If you're feeling ambitious and have time, go all the way to the falls.

Roche: visit the outdoor sculpture garden and hike up through the old cemetery to the McMillin Mausoleum. 

Sucia: no matter where you anchor, you can't go wrong from a scenic standpoint but I tend to prefer Fossil Bay. It's protected from north winds, which tend to be predominant this time of year. The entry is dramatic and the bay itself is very quiet.

Friday Harbor: I really have no use for it. Ferries coming and going, lots of people and noise, not-good food. And I say this as a person who tends to like crowds. I'd much sooner spend the day at Eastsound on Orcas.

FWIW. 
All of the Anacortes restaurants and bars are open in some capacity for dine-in/take-out/dine and drink outside/etc.  Dad's Diner included.  However, by mid-August who knows?  There are three takeaway food vendors adjacent to the parking lot at Cap Sante for a quick al fresco lunch: Mexican, Chinese buns, and a great hot dog/chile/clam chowder place.  There is plenty of seating there or at tables scattered around the marina.

 

hobot

Super Anarchist
As to my earlier suggestion....this was on the county scanner a bit ago...

Double Drug Overdose in a vehicle at the top of Cap Sante Lookout: PD/EMS en route #scanner.

Okay, it's still a good little hike from the marina with a great view of the area, just keep your radar on I guess.

:(

 

Left Shift

Super Anarchist
10,528
3,275
Seattle
That's a busy itinerary. You might consider spending two nights in one place. Here are my thoughts in no particular order.

Anacortes: don't know what they're doing during Covid times but Dad's Diner serves an excellent breakfast that'll hold you all day.

Rosario: I'd recommend a hike up the hill above Rosario at least to the lake. Take your bathing suits if it's hot, the swimming is great. If you're feeling ambitious and have time, go all the way to the falls.

Roche: visit the outdoor sculpture garden and hike up through the old cemetery to the McMillin Mausoleum. 

Sucia: no matter where you anchor, you can't go wrong from a scenic standpoint but I tend to prefer Fossil Bay. It's protected from north winds, which tend to be predominant this time of year. The entry is dramatic and the bay itself is very quiet.

Friday Harbor: I really have no use for it. Ferries coming and going, lots of people and noise, not-good food. And I say this as a person who tends to like crowds. I'd much sooner spend the day at Eastsound on Orcas.

FWIW. 
Too busy an itinerary.  

Be aware that with Canada closed, the US boats are packing the marinas.  Last I heard Roche and Friday were operating at 50% occupancy.  I doubt you'll find indoor dining.  Outdoor and takeout yep.  

Do you have a dinghy or kayaks?  Rowing or paddling around is a number one activity.  

Dress in layers.  Always expect the temperature to change.  

Stuart Island:   Hike out to the lighthouse with a picnic lunch.  Be prepared to anchor.

Orcas:  East Sound is a real small town.  Less traffic, fewer tourists, short walk to the northshore.

Roche:  Second on the sculpture garden.  

Friday :  Rent bikes if you can and head south or west until you run out of land.  

Lopez:  Try Fisherman's Bay if the depth is OK.

Whales:  Best place is either in Haro Strait or outside of Cattle Pass.  Keep an eye for for other boats going slow or acting funny.  Obey the rules.  The poor buggers are getting harassed.

 

pbd

Super Anarchist
1,400
313
Ca
That's a busy itinerary. You might consider spending two nights in one place. Here are my thoughts in no particular order.

Anacortes: don't know what they're doing during Covid times but Dad's Diner serves an excellent breakfast that'll hold you all day.

Rosario: I'd recommend a hike up the hill above Rosario at least to the lake. Take your bathing suits if it's hot, the swimming is great. If you're feeling ambitious and have time, go all the way to the falls. 

Roche: visit the outdoor sculpture garden and hike up through the old cemetery to the McMillin Mausoleum. 

Sucia: no matter where you anchor, you can't go wrong from a scenic standpoint but I tend to prefer Fossil Bay. It's protected from north winds, which tend to be predominant this time of year. The entry is dramatic and the bay itself is very quiet. 

Friday Harbor: I really have no use for it. Ferries coming and going, lots of people and noise, not-good food. And I say this as a person who tends to like crowds. I'd much sooner spend the day at Eastsound on Orcas.

FWIW. 
Good input thanks for playing along

 

wristwister

Super Anarchist
1,084
40
The Salish Sea
Sounds like a fun itinerary. Some comments:

Day 1 Anacortes to Blakely Island

             You're right, absolutely nothing to do at the Blakely Island Marina. There's even no trespassing signs bordering the marina so there's really nowhere to go. But ... still an excellent stop, especially for your first night. Picturesque, low key friendly marina with a cute little store that serves beer, ice cream, pizza, and great breakfast burritos. I assume you'll be leaving Bellingham mid-day, so you won't get there till evening. But if you can leave earlier, I recommend a stop at either Eagle Harbor or Pelican Beach on Cypress Island on your way. Do the fantastic hike up to Eagle Cliff.

Day 2 Blakely to Rosario Beach on Orcas Island

           That's a tight little marina, and you're going to attempt it in a 51' sailboat you're not real familiar with. Good luck! Fortunately, they employ lots of dock hands who are well versed at roping and wrangling errant charter boats before they turn into insurance claims.

Day 3 Orcas to Sucia Island

              My favorite is Shallow Bay, the sunsets can't be beat! But with 7' draft you'd want to stay to the center of the bay, maybe not feasible if it's too crowded in there.

Day 5 Sucia to Roche Harbor

              You've already reserved your slip, so that's cool. However, my favorite way to do Roche is to either anchor out or guest dock, explore and hike around, then motor around to Garrison Bay for the night, probably my favorite spot in the islands.

Day 7 Friday Harbor to Lopez Island

              I assume your slip is in Fishermans Bay? With 7' draft, don't attempt that anywhere near low tide! Seriously, the local entertainment is to hang out at the entrance at low tide and watch boats ground. In fact, some charter companies flag Fishermans Bay as a red zone, might want to check on that. But ... if you do go there, then yes, renting bikes and exploring is the hot ticket. 

 

pbd

Super Anarchist
1,400
313
Ca
Sounds like a fun itinerary. Some comments:

Day 1 Anacortes to Blakely Island

             You're right, absolutely nothing to do at the Blakely Island Marina. There's even no trespassing signs bordering the marina so there's really nowhere to go. But ... still an excellent stop, especially for your first night. Picturesque, low key friendly marina with a cute little store that serves beer, ice cream, pizza, and great breakfast burritos. I assume you'll be leaving Bellingham mid-day, so you won't get there till evening. But if you can leave earlier, I recommend a stop at either Eagle Harbor or Pelican Beach on Cypress Island on your way. Do the fantastic hike up to Eagle Cliff.

Day 2 Blakely to Rosario Beach on Orcas Island

           That's a tight little marina, and you're going to attempt it in a 51' sailboat you're not real familiar with. Good luck! Fortunately, they employ lots of dock hands who are well versed at roping and wrangling errant charter boats before they turn into insurance claims.

Day 3 Orcas to Sucia Island

              My favorite is Shallow Bay, the sunsets can't be beat! But with 7' draft you'd want to stay to the center of the bay, maybe not feasible if it's too crowded in there.

Day 5 Sucia to Roche Harbor

              You've already reserved your slip, so that's cool. However, my favorite way to do Roche is to either anchor out or guest dock, explore and hike around, then motor around to Garrison Bay for the night, probably my favorite spot in the islands.

Day 7 Friday Harbor to Lopez Island

              I assume your slip is in Fishermans Bay? With 7' draft, don't attempt that anywhere near low tide! Seriously, the local entertainment is to hang out at the entrance at low tide and watch boats ground. In fact, some charter companies flag Fishermans Bay as a red zone, might want to check on that. But ... if you do go there, then yes, renting bikes and exploring is the hot ticket. 
Thanks for the great info.

 

sledracr

Super Anarchist
5,123
1,192
PNW, ex-SoCal
Day 1 Anacortes to Blakely Island

Day 2 Blakely to Rosario Beach on Orcas Island

Day 3 Orcas to Sucia Island

Day 4 Sucia to Stuart Island

Day 5 Sucia to Roche Harbor


Day 6 Roche Harbor to Friday Harbor

Day 7 Friday Harbor to Lopez Island

Day 8 is back to reality
My two cents:

-- there's really not much at Blakely Island.  Hiking, yes, but no real facilities except the marina store, and that's really only interesting for the donuts.  Recommend skipping Blakely and doing a second night at Rosario.  The grill is open (and good), it's a very relaxing peaceful little place, with stuff to do (hikes, the mansion, etc)

-- if either Sucia or Stuart don't work out, you could bail to Deer Harbor on the west side of Orcas.  quiet little place, almost always has capacity, the restaurant at the Inn is pretty good, and stuff to see/do in the area.

-- Friday Harbor (as others have said) is busy and crowded and noisy.  Might skip that one and spend two nights at Roche.  Still pretty busy, but shops and stuff along the pier, the restaurant at the hotel is good, and lots of stuff to hike to.

-- Lopez (as others have said) the entrance to Fisherman is *very* shallow.  I draw 6 feet and have bumped the bottom 2 hours after a zero low.  For-sure check your tides, stay in the channel, and as someone once told me, "if you stick, you'll have plenty of time to think about the fact that you did it in front of the whole town".  Holly B's is good, there is also a decent breakfast place to the south of the marina (I don't remember the name).  Lopez Island Resort claims to have a phenomenal prime-rib dinner, but it's not worth it IMO

-- take your time, enjoy the sights, smell the flowers.  Frenetically going point-to-point-to-point is a good way to miss out on the magic of the San Juans.

 
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steele

Super Anarchist
1,798
266
Land of the locks
I talked to a knowledgeable sailor today, who is also runs a very good sail loft. He backs up Left's report of the San Juans being very busy. I suspect you will still have fun, but plan to anchor rather than pick up a mooring in some areas. Do some research so you have back up options for nights you do not have a reserved spot, and if you end up in good place or score a park bouy, consider spending an extra night. I would rather spend 2 nights at Sucia or Stuart than one in Friday Habor.

 

IStream

Super Anarchist
11,021
3,200
Day 2 Blakely to Rosario Beach on Orcas Island

           That's a tight little marina, and you're going to attempt it in a 51' sailboat you're not real familiar with. Good luck! Fortunately, they employ lots of dock hands who are well versed at roping and wrangling errant charter boats before they turn into insurance claims.
Rosario's tight but it's a lot better than it used to be since they re-modeled the marina and built the linear dock:

image.png

Our 50'er fit nicely tucked in to that NW corner behind the linear dock (no issues with the 6' draft):

/monthly_2018_09/large.IMG_20180808_094750.jpg.c130e3daec84766dd37b833ae975c49b.jpg

 
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