Let me tell you something about the San Juan Islands: the ferry is a lie. Well, not exactly a lie, but it’s like watching a movie trailer and thinking you’ve seen the film. You get the highlights, sure. But you miss everything that happens in between—and that’s where all the good stuff is.
I’ve watched people step off the ferry in Friday Harbor, spend four hours wandering around, and leave thinking they’ve “done” the San Juans. Meanwhile, there’s this entire world of hidden anchorages, tide pools teeming with life, and oyster farms you can only reach by boat that they’ll never see. And honestly? That kills me a little bit every time.
That’s why we do what we do at Roam Charters. We’re not running a ferry service. We’re giving you the keys to actually explore this place the way it deserves to be explored—on your schedule, following your curiosity, with the freedom to say “let’s pull in there” when something catches your eye.
Roche Harbor: Where History Meets the Water
First time I pulled into Roche Harbor, I couldn’t believe a place like this actually existed. It’s like someone plucked a New England fishing village, gave it a Pacific Northwest makeover, and dropped it on the edge of the Salish Sea.
The marina is world-class (seriously, the facilities here rival anything you’ll find in Seattle or Vancouver), but it’s what surrounds it that makes it special. You’ve got the historic Roche Harbor Resort right there—this isn’t some rebuilt tourist trap, this is the actual 19th-century resort that hosted wealthy lime barons and their families back when this was the most important port in the islands.
Walk through those English gardens—and I mean actually walk through them slowly, don’t just snap a photo—and you’ll find rose varieties that have been growing here for over a hundred years. The head gardener once told me they have to protect some of the older plants with special coverings in winter because there’s literally no way to replace them if they die. That’s the kind of place this is.
Then there’s the Flag Ceremony at sunset. I know, I know, it sounds touristy. But they’ve been doing this exact same ceremony since 1909, and there’s something about watching the flags come down while the sun sets over the harbor that just… gets you. Even if you’re not usually into that kind of thing. Bring a glass of wine, stand on the lawn, and just be present for it.
Pro tip: If you’re docking here on a summer weekend, call ahead. The marina fills up fast, and they can’t always squeeze you in. Weekdays are much easier, and honestly, more peaceful.
Now, if crowds aren’t your scene at all, here’s the move: skip Roche Harbor Marina entirely and anchor at Reid Harbor on Stuart Island instead. It’s maybe 20 minutes away by boat, completely protected, and on a weeknight you might be the only vessel there. I’ve spent nights there where the only sounds were the water lapping against the hull and the occasional seal popping up to see what we were doing. That’s the San Juans most people never experience.
The Oyster Stop That’ll Ruin You for Life
Okay, real talk: Westcott Bay Shellfish Co. is going to ruin oysters for you everywhere else. I’m sorry, but it’s true.
Here’s the thing—these aren’t oysters that got pulled yesterday, trucked to Seattle, distributed to a restaurant, and served to you three days later. You’re eating oysters that were in the water this morning. Sometimes, depending on when you show up, they were in the water an hour ago. The difference is… I don’t even know how to describe it. They just taste like the ocean in the best possible way.
Pull up to their dinghy dock (it’s tiny, so if someone’s there, you might have to wait a few minutes), and head into the farm store. The staff there actually work the oyster farm—these aren’t retail employees, they’re the people who grow and harvest what you’re about to eat. Ask them questions. They’ll tell you about the tides, the water temperature, why this year’s crop is different from last year’s. It’s fascinating stuff if you’re into it.
If you time it right and the Tide Tables restaurant is open (it’s seasonal and weather-dependent, so check ahead), get a table. It’s nothing fancy—picnic tables, plastic cups, that vibe—but you’re sitting right on the edge of the bay eating the freshest seafood you’ve possibly ever had. Last time I was there, I watched them pull oysters, shuck them, and serve them to the table next to us in what couldn’t have been more than 10 minutes.
Try the Pacific Oysters if you’re new to this. They’re sweet, creamy, and not too briny—even people who think they don’t like oysters usually come around on these. If you’re already an oyster person, get a variety tray and taste the difference between their different grows. The staff can explain why oysters from different parts of the same bay taste completely different. (It’s all about the minerals in the sediment, apparently. Who knew?)
Insider tip: Bring a cooler and some ice. You can buy oysters to take back to the boat, and there’s nothing better than shucking fresh oysters on your deck at sunset with a cold beer. They’ll even give you a shucking knife if you don’t have one.
What You’re Missing If You Never Leave the Boat
Look, I get it—the whole point of chartering is the water. But you’d be crazy to dock at Roche Harbor and not explore a little bit on land too. Some of this stuff is legitimately unique.
Actually Getting Around
Kayaking the easy way: Right at the Roche Harbor dock, there are outfitters who’ll rent you kayaks and paddleboards. This is clutch because you don’t have to haul your own kayak on the charter, and the waters around the harbor are perfect for beginners—protected, calm, and scenic. Paddle over to the oyster farm if you want. Make a morning of it.
Scooter life: Here’s what locals do when they want to see the island quickly—rent a scooter in Friday Harbor. It’s about a 25-minute drive from Roche Harbor, so you’ll need a ride or to call a taxi, but once you’ve got a scooter, the whole island opens up. There are only about 40 miles of roads total, so you can cover a lot of ground in a few hours. Plus, it’s just fun. Wind in your hair, coastal roads, stopping whenever something looks interesting. The island’s speed limit tops out at 35 mph anyway, so you’re not exactly road-racing here.
Just be careful on the scooters if the roads are wet—they can get slippery. And wear the helmet even if you feel dorky. I’ve seen too many people learn that lesson the hard way.
Hiking that’ll kick your ass (in a good way): The trail system around Roche Harbor is no joke. Over nine miles of connected paths through Douglas fir forests, wetlands, wild pastures—it’s beautiful and surprisingly varied for such a small area. The trails connect to English Camp at the San Juan Island National Historical Park, which is cool on its own (British soldiers were stationed here in the 1860s during the Pig War—yes, there was actually a war over a pig, look it up).
But the real prize is Young Hill. It’s a steep climb—bring water and don’t attempt it in flip-flops—but when you get to the top, you can see the entire archipelago spread out below you. On a clear day, you’ll see Mount Baker to the east, Vancouver Island to the west, and all the islands in between. It’s one of those views that makes you just… stop and stare. Give yourself at least 2-3 hours for the full hike up and back.
Lime Kiln: The Whale Park
The west side of San Juan Island is where things get really special. Lime Kiln Point State Park—everyone calls it Whale Watch Park—is legitimately one of the best places in the world to see wild orcas from shore.
From about May to September, the Southern Resident Orcas (these are the iconic black-and-white orcas, not the offshore ones) cruise past this point hunting for salmon. And I’m not talking about distant specks you need binoculars to see—I’m talking about orcas passing 100 yards offshore, close enough to hear them breathe.
Timing matters here. The whales follow the salmon, and the salmon follow the tides and currents. Your best bet is to check the Whale Museum’s sighting network or ask locals where whales have been spotted recently. Early morning and late afternoon tend to be good times. And be patient—this is wildlife, not SeaWorld. Sometimes you’ll see five pods in an hour. Sometimes you’ll wait all day and see nothing. That’s the deal.
The lighthouse itself (built in 1919, still operational) is this classic red-roofed beauty perched on the rocks. In summer, you can sometimes get tours inside, which is worth doing if you’re into maritime history. The interpretive center is small but really well done—they explain the different orca pods, how to identify individual whales by their dorsal fins and saddle patches, and the history of the lime kiln industry that gave the point its name.
There are about 1.6 miles of trails here, both along the rocky shoreline and up through the forested areas. The views across Haro Strait to Vancouver Island are stunning, especially at sunset. Pack layers—the west side gets windy and it’s always cooler than you think it’ll be.
The Mausoleum That’ll Give You Chills
This one’s weird, I’m not going to lie. But it’s the kind of weird that sticks with you.
Walk through the old Roche Harbor Cemetery—it’s peaceful, well-maintained, nothing creepy—and follow the path to Afterglow Vista. That’s the polite name. Most people call it the McMillin Mausoleum.
John McMillin was the lime baron who basically built Roche Harbor. Made a fortune, built an empire, and apparently had some very specific ideas about death and family. He designed this open-air memorial before he died, and it’s loaded with Masonic symbolism that goes deep if you’re into that sort of thing.
The centerpiece is this limestone table (symbolic of the “broken column of life”) surrounded by six concrete chairs. Each chair contains the ashes of a family member—John, his wife, their sons. The whole setup represents the family reuniting around their dinner table in the afterlife. The chairs even face specific directions based on the family members’ roles and Masonic symbolism.
Seven columns surround the structure (representing the seven liberal arts and sciences in Masonic tradition). The entire memorial is aligned with specific astronomical and cardinal directions. There’s a lot going on here, and if you’re into symbology or architecture or just unusual historical sites, you could spend an hour here reading all the details.
It’s beautiful and haunting and peaceful all at once. And the walk there through the cemetery and woods is lovely. Just… maybe don’t go at dusk if you’re easily spooked. The atmosphere gets thick.
Eating Beyond Oysters (Though, Why Would You?)
If you manage to pull yourself away from the oyster farm long enough to want other food:
Farm dinners—but plan ahead: A few times a year, local farms and restaurants host these incredible farm-to-table dinners. Wild Berry Farm does them, Coho Restaurant in Friday Harbor sometimes hosts them at partner farms. We’re talking 5-7 courses, everything sourced from the island or surrounding waters, often paired with local wines or beers. They’re magical—you’re eating at long communal tables in a field or barn, watching the sunset, meeting other food-obsessed travelers and locals.
But here’s the catch: they sell out fast. Like, within-hours-of-announcement fast. If you know you’re coming during summer, check the restaurants’ websites or social media a few months ahead and grab tickets the second they’re available.
Friday Harbor’s food scene: When you make it to the main town (and you should, at least for an afternoon), the dining is better than you’d expect for a place this small.
Downriggers is right on the water—get a table on the deck if you can, order the fish and chips or the Dungeness crab melt, and watch the seaplanes come and go. It’s classic Pacific Northwest waterfront dining done right.
The Restaurant at Friday Harbor House is the fancy option. Pacific Northwest ingredients, beautiful presentations, excellent wine list. Go here for a special occasion or when you want to remember why eating local and seasonal matters.
San Juan Island Brewing Co. is where you go when you want good beer, casual food, and to hang out with locals. The fish tacos are surprisingly good, and they usually have 8-10 of their own beers on tap. Grab a flight, sit outside, and eavesdrop on the locals—you’ll learn more about the island in an hour there than reading any guidebook.
Coffee that’s actually good: Rocky Bay Cafe in Friday Harbor. Don’t skip it. Get the breakfast burrito and a real espresso drink. Thank me later.
Here’s Why This Actually Matters
Look, I could keep listing cool spots for another 3,000 words. But here’s the real point: the San Juan Islands aren’t a checklist. They’re not a place you “do” in a day.
The magic happens in the moments between the destinations. It’s pulling into a quiet cove and having lunch while harbor seals pop up to investigate. It’s changing your plans because the sunset looks incredible from where you are right now. It’s taking the long way back because someone mentioned there’s a bald eagle nest on the north shore. It’s having the flexibility to say “let’s spend an extra day here” because you’re not ready to leave yet.
That’s what chartering gives you. That’s what Roam Charters is designed for—not rushing you through someone else’s itinerary, but giving you the freedom to discover this place at your own pace.
Ready to actually see the San Juans? Let’s talk. Tell us what you’re interested in—wildlife, food, history, just peace and quiet—and we’ll help you plan something that’s actually yours.
Shane Moa
Founder, Divine Marine