Natural Scenery

9 Reasons To Charter A Boat To Explore The San Juan Islands

“Is that a fin?”

Coming up the stairs from the sailboat’s salon, I could see past Captain Mike’s shoulder as he stood at the wheel. For just a moment, I thought I saw a narrow black triangle — a male orca’s dorsal fin can be up to six feet tall — above the water in the opening between islands that led to Boundary Pass. The wide channel marks the boundary between the U.S. and Canada. 

I grabbed the binoculars, and sure enough, the black fin rose from the water as the orca (also known as a killer whale) took a breath before sinking again beneath the waves. 

“Orcas!” I called down to the salon, setting off a flurry of motion from four teenage boys as Captain Mike turned the wheel and pointed the boat toward the resident orca pod cruising by in Boundary Pass. 

That’s just one of the things our family enjoys about chartering a boat in Washington state’s San Juan Islands: A change in plans is as simple as turning the boat around. There’s no set itinerary, no timetable to adhere to, and the islands are close enough together to make it easy to sail or motor from island to island. 

Charter companies in Anacortes and Bellingham, Washington, make it easy to cruise the islands on a rented boat for a week, with or without a hired captain. Another option is to take a week-long, hands-on, live-aboard course to learn the necessary skills. San Juan Sailing even offers women-only courses. 

Here are nine reasons to charter a boat in the San Juan Islands on your family vacation:

Ferry leaving Friday Harbor in Washington
Friday Harbor (Photo Credit: © June Russell-Chamberlin)

1. A Multitude Of Islands

Ferries run only to the four largest of the 172 named islands, islets, rocks, and reefs in the San Juan Islands. Lopez, Orcas, and San Juan Islands — where the ferries dock — are known for their picturesque villages, farmers’ markets, quality restaurants, fields, historical parks, and farms. They’re worth a visit, but they’re not the only islands with attractions worthy of dropping anchor. Each island is unique, and 11 are designated marine parks (accessible only by private boat and often uninhabited). Over the course of a week (the typical length of a charter), we usually enjoy experiences ranging from dining and shopping in town to roasting marshmallows over a campfire and strolling on deserted beaches. 

Kayakers at sunset near Matia Island
Matia Island (Photo Credit: © June Russell-Chamberlin)

2. Escape The Crowds

Summer is the busiest season on the islands, but it’s not difficult to escape the crowds even then. Once you leave the marina or town, the other tourists and boats disperse. It’s not uncommon to hike or walk the beach virtually alone on marine park islands such as Stuart Island or Cypress Island. Matia Island is perhaps the least crowded; Matia cove will only accommodate two or three boats. Even on a populous island such as San Juan, you’ll likely have the national historical park sites all to yourself. 

Pro Tip: The best time to explore the islands is from May to September (winters are wet and windy). Summer days are often cool in the morning, but warm in the afternoon. If you want to sail, bear in mind that warmer weather typically means less wind. 

Sailing near the San Juan Islands
© June Russell-Chamberlin

3. Set Your Own Itinerary

A boat in the islands gives you the freedom to choose your destinations and explore at your own pace. Cruising guidebooks (available at can help you discover what’s on each island, and the charter company staff can also offer suggestions. One book we often use to discover under-the-radar anchorages is the Dreamspeaker Cruising Guide: The San Juan Islands. San Juan Sailing’s guide to the islands provides a sample itinerary, and the ActiveCaptain Community anchorage reviews can help you choose a safe place to drop the anchor. Don’t forget to take into account currents and up to 13-foot tidal changes as you plan your course and anchorages. 

© June Russell-Chamberlin

4. Food And Lodging Go With You

A cruising boat (motor, sail, or catamaran) is like a floating RV or vacation cottage — beds, bathrooms (known as “heads”), the kitchen (galley), and living areas go wherever you go. It’s the perfect COVID “bubble.” The boat gives you the freedom to drop anchor in a secluded cove or spend the night in a marina with equal ease. A fully equipped galley with a stocked refrigerator keeps the crew and guests fed wherever you wander. We often set sail in the morning while other crew members (who stayed up late playing games) sleep in, and everyone grabs breakfast or snacks whenever they’re hungry. There’s plenty of room to relax or play games, both indoors and outside on the deck. 

Pro Tip: Plan your meals and buy what you need on the mainland or in larger towns such as Friday Harbor. Some smaller marina stores only get deliveries once a week and might be out of whatever you’re seeking. For example, on one occasion the dockside store was out of cheese and milk, so we had to settle for beer, cookies, and ice cream. Some charter companies will offer you a provisioning list to choose foodstuffs and will stock the boat. 

Sailing Boundary Pass
© June Russell-Chamberlin

5. Share It With Friends and Family

When we first started exploring the islands by boat more than a decade ago, it was just our immediate family. But we soon discovered that it’s more fun to take a boatload of family and friends, making for a lively, multigenerational crew. The youngest crew member began cruising with us at six years old; the oldest is more than 80. Common sense safety rules keep even the youngest crew members safe. Good balance and some agility are required to get in and out of the dinghy and kayaks, as well as to move about the boat while sailing. Stairs are standard on sailboats between the salon (living room) and the cockpit, although catamarans don’t have stairs except to sleeping quarters. 

Pro Tip: Bring your own life jackets, especially for children. The universal adult-size life jackets will keep adults afloat, but they often don’t fit well on teens or smaller adults. The charter company usually provides life jackets.

A beach on Jones Island
© June Russell-Chamberlin

6. Unplugged Family Time

Though Wi-Fi is becoming more common on boats, many charter boats still offer an unplugged vacation in the islands. Our crew members entertain themselves with cards, board games, books, birdwatching, wildlife spotting, and adventures ashore. One frequent activity is poring through cruising guidebooks to find our next destination. 

Stuart Island hiking trail
Trail on Stuart Island (Photo Credit: © June Russell-Chamberlin)

7. Adventures Ashore And Afloat

Hiking, kayaking, and raiding the local ice cream shops top the list of our activities, but we also visit whatever shops, lighthouses, beaches, tide pools, and historic sites the islands have to offer. Bicycles, mopeds, and scooters are available for rent in the larger towns and make it easy to wander the rest of the island. Kayaking is an excellent way to explore the shoreline, sneak up on wildlife, and linger in areas too shallow for the cruising boats. You can also take the dinghy ashore. 

The various state parks and 11 marine park islands all feature hiking trails, though on the smaller islands the trail may only make a simple circle. One of our favorite hikes leads past the teacherage museum and school on Stuart Island to the historic lighthouse. On Cypress Island, the trail to 600-foot-high Eagle Cliff rewards hikers with panoramic views of the neighboring islands. 

Friday Harbor on San Juan Island boasts the widest selection of shops and restaurants, and we often pick up provisions, pastries, and even shoes there. Roche Harbor, a resort and marina on the other side of the island, has some of the best ice cream around, as well as an outdoor sculpture park, intriguing memorial, gardens, and a spa. Don’t miss the local artisans selling their goods near the docks. 

Sucia Island at sunset
Sucia Island (Photo Credit: © June Russell-Chamberlin)

8. Photo-Worthy Scenery

The San Juan Islands enjoy the rugged natural beauty that has become synonymous with the Pacific Northwest. From clear green seas to forested mountains and rocky shores, the islands reward visitors with stunning scenery. Summer sunsets and sunrises are incredibly colorful. 

Among the most scenic islands is Sucia, famous for its sculpted sandstone galleries and rosy sunsets with views of Mt. Baker. James Island and Matia Island offer unspoiled nature. Photogenic lighthouses dot the islands, such as those at Patos Island and Turn Point on Stuart Island. 

Deer at Jones Island
Deer at Jones Island (Photo Credit: © June Russell-Chamberlin)

9. Wildlife Watching

Wildlife abounds in the islands, both on land and at sea. Bald eagles, great blue herons, seals, and deer are common, but you might also glimpse porpoise, raccoons, oystercatchers, and otters. Starfish, crabs, oysters, and other underwater creatures are also common. 

The most famous animals in the islands are the endangered Southern Resident pods of orcas. It’s thrilling to see them in the wild. Unfortunately, the population of orcas is dropping; at last count only 75 remain. If you do cross paths with a pod of orcas, Be Whale Wise and help protect them by keeping a respectful distance and using binoculars instead. 
Pro Tip: The easiest way to spot the resident orcas is to join a whale watching tour at Friday Harbor. You also won’t want to miss the Whale Museum to learn more about these iconic creatures.

Boat charter options are numerous and varied:

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