Set sail on an unforgettable journey through the breathtaking San Juan Islands, guided by expert local knowledge, detailed maps, and meticulously crafted boating itineraries. Master the rhythms of tides and currents to glide effortlessly between islands. Pitch your tent in hidden forested parks, drop anchor in pristine bays, and hike trails that lead to sweeping vistas. Wander the bustling charm of Friday Harbor and the elegance of Roche Harbor—then escape it all in a serene, secret cove where the world slips quietly away.
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Dec 7, 2025

San Juan Islands Boating Guide: Best Routes, Tips, and Weekend Trip Ideas

A Two-Day or Weekend Boat Getaway to the San Juans

Planning a quick boating getaway to the San Juan Islands sounds simple, just point the bow north, err, west, and go. But a trip to the islands demands a bit more thinking than your average lake outing or day cruise. Before you load the cooler and cast off lines, you should take a moment to make sure your boat, gear, and expectations all match what a San Juan weekend requires.

Rainbow over Brown Island in Friday Harbor, WA with kayaks and ferry
Rainbow over Brown Island in Friday Harbor
How to Plan the perfect San Juan Islands getaway

Friday Harbor Marina showing sailboats, powerboats, and the main harbor area.
Friday Harbor Marina from steps to Whale Museum

Friday Harbor marina map

Not Every Boat Is Ready for the Islands: 

click below to continue


A common misconception is that any boat can make the run to Friday Harbor or the other island towns and marine parks.  While it is probably true for the most part, that doesn’t make taking your overloaded dinghy across Rosario Strait a smart or safe idea.

lone sailboat being paddled on Lopez Sound in the San Juan Islands
Calm day on Lopez Sound is not a quick getaway,
but may be a dream vacation for this solo sailor.

In reality:

 A weekend getaway, especially a short one, should eliminate the slower and less seaworthy boat choices.


Distance matters:

From most mainland launches, it’s about twenty miles to Friday Harbor. That’s twenty miles of open water, strong currents, tide rips, and sometimes, strong winds that whip up local seas that seem to arrive from four directions at once. Most sailboats, particularly smaller ones, simply can’t maintain the speed needed to push through adverse conditions and still make the trip in a reasonable time. So, when a “quick escape to the islands” becomes an all-day battle with nature, the expected adventure and charm fade fast.

Distance chart from there to there

Full dock at James Island with campground in background
The perfect quick getaway.
James Island is only five miles from the launch ramp at Washington Park

James Island and others

Powerboat operators don’t get a free pass:

While the islands are filled with small aluminum skiffs and open runabouts, they’re often used locally, not for cross-channel hops. For a reliable weekend trip, your boat should have:

  • Modest but sufficient horsepower
  • Good freeboard 
  • A decked-over bow to punch through the occasional steep wave
  • Enough size and weight to ride comfortably in chop

If your boat is underpowered, overloaded, or rides too low, a short crossing can become uncomfortable or worse, unsafe.

what is the best boat for the San Juans?

Packing for Shore Camping

If your plan includes sleeping ashore, your gear list becomes more than just a sleeping bag. Camping gear is bulky, and boats have limits. An overloaded boat doesn’t behave like a boat anymore; it behaves like a half-submerged log.

Instead of riding up and over swells, a heavy boat plows, wallows, and waves wash over the deck. Even a light chop can become a problem in an overloaded boat. If you have to question whether you’re carrying too much, you probably are.

A good rule: pack like backpackers, not car campers.

mother of all packing lists

Day Boats Are Welcome—If You’re Prepared

Taking a ski boat or fishing skiff for an overnight trip isn’t out of the question, but taking one without proper safety gear absolutely is. Many boaters get casual about gear when they’re used to staying close to home. A trip into the San Juans is not the time to assume you know where your whistle or life jacket ended up.

Review the Coast Guard requirements for your boat, and then go beyond the minimums. For island boating, I think you should include:

  • A VHF radio (handheld at minimum)
  • GPS or a chart plotter (smart phone will do)
  • Compass (electronics fail, magnets don’t)
  • Current tide tables (hard copy)
  • Paper Chart of the islands, even if you think you know the route (I recommend NOAA chart number 18421)

Fuel:

A common practice among experienced boaters is to carry enough fuel for 75 miles of travel, even if you’re only planning a 40-mile round trip. Detours, strong tides, and weather changes can quickly expand your route.

The San Juans Reward Prepared Boaters:

A fast, seaworthy boat with proper gear transforms a short weekend into a relaxing adventure. Whether you’re sliding into Friday Harbor for dinner, anchoring in a quiet cove, or camping at a marine park, the islands reward those who are prepared and plan ahead.

Dinghies:

Don't forget the dinghy.  You need a way to get to shore from your anchored boat. Even if your plan is to use the dock at a marine park, plans change.  A cheap two-man inflatable will work, a paddleboard will work in a pinch.

The dinghy dilemma

A little preparation ensures your quick escape stays quick, enjoyable, and brings you back home with great memories rather than stories about fighting currents all day or limping back on fumes.Top of Form

 Suggested Itineraries:

Bottom of Form

  •  Assuming your boat is on a trailer, you should begin at:
    • Cornet Bay in Deception Pass Park
    • Washington Park in Anacortes
    • Squalicum Harbor in Bellingham
There are other launch sites but to keep it quick and easy, you should use one of the three.

  • Destinations:  
    • Friday Harbor  (slips or anchor)
    • Roche Harbor  (slips or anchor)
    • Rosario  (slips or anchor)
    • Jones Island  (dock or anchor)
    • James Island (dock or anchor)
    • Matia Island  (dock or anchor)
    • Stuart Island (docks or anchor)
    • Sucia Island (Fossil Bay, docks (2) or anchor)
There are many destinations to choose from, but for a quick and successful getaway, you want a tried and true location that offers various amenities.  All these locations offer protected coves, all have multiple tie-up options.  All are suitable for late or early arrival, and all are usable in inclement weather.

What Happens When You're Unprepared, or Conditions Turn Against You?

Safety first. If the weather, currents, or visibility don’t suit you, don’t push your luck. Modify your plans or cancel outright. The San Juans aren’t going anywhere, and there will always be another weekend.

A Likely Scenario.

You launch from your chosen departure point and ten minutes later find the conditions far rougher than expected. A fast-running Rosario Strait colliding with an opposing wind can build steep, uncomfortable, and sometimes unsafe waves. Waiting a few hours can completely change the sea state, but you don't have to deal with or cross Rosario Strait at all.

Simply change the plan.

Point the bow toward Cypress Island and Pelican Beach, cruise over to Saddlebag Island Marine Park, or run over to La Conner, where three public docks offer easy moorage. A simple adjustment to your itinerary can turn a stressful day into a memorable getaway.

*optional plan*



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