Are you searching for a Gulf Islands sailing charter built around exceptional hospitality, a thoughtfully curated fleet, and a genuine commitment to making boating accessible for every experience level? If a week on the water in British Columbia has been on your list and you are not sure where to start, Seaport Yacht Charters in Sidney, BC is exactly where you want to begin. And after our recent week aboard a Seaport Yacht, I’m here to share all the ins and outs you need to know before you book. 

In reality most charter companies hand you a key, point you at the boat, and wish you luck. Seaport Yacht Charters — a proudly Canadian, female-owned company based at Port Sidney Marina on Vancouver Island — starts with a very different set of questions: “Who are you?” “What do you want from this week?” And “How can we make sure the boat, the itinerary, and the experience are exactly right for your family?” That approach, backed by the expertise of founder Robin McKeown, is what transforms the experience from the moment you begin the booking process. 

I spent six days aboard Simply Dreaming, a 45-foot Catalina from Seaport’s fleet, with my family in the summer of 2026. It was, without question, the best trip I have ever taken — and I say that as a travel writer who has spent months in French Polynesia, Australia, and all across Canada. What made it that is what I want to tell you about: the boat, the company, the woman who built it, and what the Seaport charter experience actually looks like from the inside.

We saw orcas on our first night in port. My teenage daughter docked a 45-foot sailboat solo on Day 5. My son, the youngest person aboard, became the strongest helmsman in the family by Wednesday. And every single morning, we woke up to a boat that felt like ours — because Robin McKeown built her company on the conviction that hospitality is not a detail. It is the epicenter for an exceptional experience. 

Quick Charter Overview

About Seaport Yacht Charters

Seaport Yacht Charters launched on January 1, 2026 — which sounds new until you understand what Robin McKeown brought to it. The small and carefully curated fleet is built from relationships with owners who trust and rely on Robin’s 25 years of work in the industry. Seaport Yacht Charters has built an elevated partnership with Voyage Makers Coastal Adventures on a shared conviction about what getting people on the water should feel like. This is not a startup. It is a career’s worth of expertise given a new name and a new home.

Seaport operates from two locations on the Saanich Peninsula: Port Sidney Marina in Sidney, BC, and North Saanich Marina nearby. From either departure point, guests have access to the Southern Gulf Islands, the American San Juan Islands, Desolation Sound to the north, and the broader waters of the Salish Sea — among the most celebrated sailing grounds in the world. The fleet spans both power and sail, ranging from 34 to 54 feet, with vessels suited to coastal day cruising, multi-day island passages, and extended offshore adventures.

Seaport offers two paths to the water. Experienced boaters can charter independently through the bareboat program — you demonstrate the required competency, choose your vessel, plan your route, and go. For guests who are newer to sailing, or who want to build their skills while exploring the islands, Seaport’s official training partnership with Voyage Makers Coastal Adventures makes an instructional charter possible: you get the boat, the freedom of a charter itinerary, and a professional instructor aboard for the week. No prior sailing experience required.

The company also provides yacht management, maintenance coordination, and owner-care services for the boats in its fleet — which matters to guests because it means every vessel is maintained to a consistent, documented standard. Robin oversees charter preparation, cleaning, mechanical inspections, and guest readiness for every booking. It is, as our Voyage Makers instructor noted unprompted after working with charter companies across the region, an exceptional level of boat care. That is not something every charter company can say.

About Robin McKeown, Founder and President

Robin McKeown is the first woman in Canada to hold the Certified Marine Manager designation. She received her CMM in 2018, and as of this writing, there are approximately four women in Canada who hold the credential. The CMM is not simply a qualification — it is a network, because to sit for the designation you must have a reference from an existing CMM holder. Mentorship is built into the credential’s structure, and Robin is known in the marine industry specifically for the people she has brought through it.

She showed me a recent example while I was at the marina. The new manager at Port Sidney Marina completed his CMM in fall 2025 with Robin as his referring CMM holder. He was hired at the marina the following spring. That is how the credential is meant to work: professionals investing in the next generation of professionals, raising the standard of an industry that — in Robin’s words — is a big business and deserves to be treated like one.

Four years ago, Robin came to Sidney to start what she calls her second act. She left a career she had spent decades building, arrived on her own, and built Seaport from the ground up. What you get when you book with Seaport is not a transaction with a company. It is access to someone who knows these waters, these boats, and quality experiences — and who built a business specifically so she could share that with guests.

Seaport Charter Services: What to Expect

Before You Even Step on the Boat

The Seaport experience begins before arrival. Robin spends time with every guest in advance: understanding your boating background, your experience level, your family composition, and what kind of week you are hoping to have. From there, she handles vessel selection, itinerary suggestions, safety preparation, local knowledge, and the kind of small details that most charter companies consider the guest’s problem. When you walk down the dock at Port Sidney Marina, the boat is ready. You just have to show up.

Bareboat Charter

For experienced boaters who want the freedom of the Gulf Islands without an instructor aboard, Seaport’s bareboat program offers independent access to the full fleet. You demonstrate your competency, select your vessel, plan your itinerary, and go. Robin provides local knowledge, routing suggestions, and the kind of pre-departure orientation that makes the difference between a smooth passage and an anxious one. The Gulf Islands, the San Juan Islands, Desolation Sound, and the Sunshine Coast are all within comfortable reach.

Instructional Charter with Voyage Makers

For guests new to sailing — or those who want to build their confidence and certification while exploring the islands — Seaport’s official training partnership with Voyage Makers Coastal Adventures makes an instructional charter possible. Your instructor joins the boat for the week, working through the Competent Crew curriculum and beyond, while the itinerary is designed around both your learning goals and the most beautiful anchorages in the region. This is the option we chose. For the full story of what the instruction looked like, see the companion Voyage Makers article.

Right on the Dock

One detail that became quietly important as the week unfolded: Seaport Yacht Charters’ office is not a phone number at the other end of a long drive. It is a door on the dock at Port Sidney Marina, steps from where Simply Dreaming was tied up. When Robin walked us through the boat on arrival day, she was not making a special trip out to meet us — she was already there, operating from the same dock where the fleet lives. 

The proximity is intentional and it matters. Questions before departure get answered in person. If anything came up during orientation, the solution was steps away, not a call routed through a booking system. There is something genuinely reassuring about a charter company that operates from the dock rather than from a distance. The support is real and immediate, which is exactly what you want on your first day aboard a new boat.

Book Your Charter: Seaport Yacht Charters is based at Port Sidney Marina, Sidney, BC. Visit seaportyachtcharters.com for fleet information and charter options. For families and beginners, ask Robin directly about the instructional charter partnership with Voyage Makers Coastal Adventures — no prior sailing experience required.

Simply Dreaming: A Closer Look at the Boat

I wanted to take this moment to share our own sailing charter in Victoria experience aboard Simply Dreaming. This beautiful 45-foot Catalina sailboat completely overwhelmed my expectations. I had seen photos, I thought I knew what to expect, and the photos did not do this beautiful girl justice! This boat is bigger, more elegant, and more genuinely comfortable than any charter vessel I had imagined. Three full staterooms. Two heads with showers. A full galley. A proper saloon with a dining table that fits a family of six without anyone feeling crowded. This is not a boat you sleep on. This is a home you happen to sail.

The Forward Cabin

The forward cabin sits in the bow of the boat and makes excellent use of the V-shaped space that is typically the most awkward part of a sailboat to furnish. Simply Dreaming’s forward cabin is a genuine double stateroom with storage on both sides, good ventilation via a forward hatch, and a privacy that makes it feel like a proper bedroom rather than a berth. If you are travelling with teenagers who value their own space — and I am — this cabin will settle the question of who sleeps where before it becomes a conversation.

The Aft Cabins

Simply Dreaming has two aft staterooms, one on each side of the boat, accessible from the saloon. Both are proper double cabins with their own storage and comfortable berths — not the narrow single berths that give live-aboard sailing its reputation for discomfort. One has a double bed and the other has a double bed with a single bunk on top. The aft port cabins are notably spacious for a sailboat of this length. Our family’s experience was that three separate sleeping spaces meant three genuinely separate sleeping situations, which on a week-long charter is not a minor detail.

The Heads

Simply Dreaming has two heads — two full bathrooms with showers — which is the detail that separates a genuinely comfortable charter from a compromised one. On a week-long live-aboard with four people, two heads means no morning queue, no negotiated schedules, and the specific domestic peace that comes from not sharing a single bathroom with your family for seven days. Both are clean, well-maintained, and fully functional. 

The Galley

The galley on Simply Dreaming runs along the port side of the main saloon and is a proper working kitchen, not a camping setup. Half-size refrigerator, cubby freezer, a three-burner propane stove, oven, microwave, sink, and enough counter space for 2 people to comfortably prepare a meal rather than battle for space with elbows up.

The Saloon: Dining Room and Living Room

The saloon is the heart of the boat — the space where everything happens that is not sleeping or sailing. On Simply Dreaming, it is a proper room: a U-shaped settee with a dining table that converts, good natural light from the ports and companionway, and enough space that six people can sit in it simultaneously without anyone’s knees touching. We ate meals and played cards, and debriefed every day’s sailing here, going over the chart and talking about what came next.

The Cockpit and Helm

The cockpit is where you will spend most of your waking hours underway, and on Simply Dreaming it is generous: a large, comfortable space with seating on both sides, a bimini overhead for sun and rain protection, and a helm position that gives the person at the wheel good sightlines in every direction. There are two full-sized wheels, the instruments are clear, and everything a new sailor needs to understand the boat’s state — wind speed, boatspeed, depth, GPS chart plotter — is legible from the helm without needing to go below. This is also where you eat dinner when you are at anchor and the evening is calm, which on the Gulf Islands is often. Highly recommend.

The Seaport Welcome: What Robin Does Before You Leave the Dock

The welcome aboard Simply Dreaming is worth describing in detail because it is not standard for a charter company and it set the tone for the entire week. When Robin walked us down to the boat, there was a beautiful welcome card in the galley with every family member’s name on it. A small vase of boat-friendly flowers — chosen specifically because they would not tip in a swell. A box of cookies from The Fickle Fig, a bakery in Sidney, with gluten-free options included. Every stateroom was made up with fresh linens, pillows arranged, everything in its place.

This is what Robin means when she says a charter begins before you hand someone a key. She had learned about our family — who we were, what we needed, what would make us feel at home — before we arrived. The result was a boat that already felt like ours. 

After the welcome, Robin walked us through the boat: every system, every piece of safety equipment, what to do if something unexpected happened, and who to call. She answered every question we had and a few we hadn’t thought to ask yet. By the time she left us to settle in, the anxiety of being somewhere new and unfamiliar had been replaced by something closer to excitement. That transition — from nervous to ready — is Robin’s particular gift.

What I Loved: The personalized welcome was specific, thoughtful, and unmistakably the work of someone who had paid attention to who we were before we arrived. The cookies from a local bakery were not a gesture. They were a detail that said: Welcome to your home for the week. I’m so glad you’re here. 

The boat was immaculate — genuinely immaculate. Our Voyage Makers instructor, who works with charter companies across the region, volunteered unprompted that Seaport’s standard of boat preparation is exceptional. That kind of third-party endorsement matters.

Proudly Canadian, Proudly Female-Owned

Seaport Yacht Charters and its training partner Voyage Makers Coastal Adventures are both proudly Canadian, female-owned businesses. In an industry that has historically been overwhelmingly male, both Robin McKeown and Tracy Sarich are doing something worth noticing: building companies of genuine quality and bringing more people — especially women and families — into an experience that has too often felt like it belonged to someone else.

Robin was the first woman in Canada to hold the CMM designation. She mentors the next generation of marine professionals. Tracy produces the seminar programming at the Vancouver International Boat Show and has spent years building the proportion of women speaking as experts from 30 per cent to more than 50 per cent. These are not incidental details. They are the context in which both companies operate, and they shape what you will find when you show up: an environment where boating is for everyone, where your questions are genuinely welcome, and where nobody assumes you already know what you are doing.

Practical Information for Planning Your Seaport Charter

Frequently Asked Questions: Gulf Islands Charter with Seaport Yacht Charters

The Gulf Islands Are Waiting for You

When someone asked our group on the last evening of the trip which was the best trip we had ever taken, I said this one. I have been to French Polynesia, Australia, and all across Canada. I meant it without hesitation.

Seaport Yacht Charters is not a big company. It is not trying to be. It is a boutique operation built on relationships — with the boat owners in the fleet, with training partners like Voyage Makers, and with every family that walks down the dock at Port Sidney Marina. Robin McKeown built it with a specific intention: to offer a more personal, thoughtful, and welcoming way to experience boating on the West Coast. After a week aboard Simply Dreaming, I can tell you she has achieved exactly that.

The Gulf Islands are waiting for you. Seaport Yacht Charters will make sure you are ready when you arrive. Your adventure, thoughtfully delivered.

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Here are some other great articles to inspire your next Victoria trips:

Family Sailing Lessons in Victoria

Sailing BC’s Gulf Islands: Why This Became Our Family’s Best Trip Ever

72 Hours Victoria

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