Big Connections Start Small: A Q&A with Deborah Hoskins on Meetings in the San Juan Islands

While massive conferences have their place, oftentimes smaller gatherings make for more meaningful connections. And that’s where destinations built for smaller gatherings are having a moment. The San Juan Islands have long specialized in intimate retreats and meetings where attendees can step away from daily distractions, reconnect with colleagues and leave feeling refreshed.

We spoke with Deborah of the San Juan Islands Visitors Bureau about why the islands are attracting planners looking for something different, how groups navigate transportation and the experiences that keep attendees talking long after the meeting ends.

Q&A with Deborah Hoskins, Executive Director of San Juan Islands Visitors Bureau

Meeting Northwest News: The San Juan Islands aren’t the first place many planners think of for meetings. What types of groups are the best fit for the destination?

Deborah: Groups looking for a unique small meeting or retreat experience are our best fit. They’re able to be productive while also enjoying an inspiring, calming setting. Attendees leave with a sense of accomplishment and delight after being surrounded by nature and immersed in our welcoming island communities.

Meeting Northwest News: More organizations are choosing smaller, more meaningful gatherings over large conventions. Are you seeing that trend firsthand?

Deborah: Absolutely. Smaller meetings and retreats allow teams to get to know one another on a more personal level, which often leads to stronger collaboration and productivity once they’re back in the office. We’re even seeing smaller wedding groups. I think organizations are being more intentional with both their time and budgets.

Meeting Northwest News: How does being surrounded by water change the way groups connect and collaborate?

Deborah: Many groups enjoy waterfront meeting venues, and attendees are always eager to get out on the water for team-building activities. Popular options include whale and wildlife watching, sea kayaking, hiking, biking, art classes, winery, cidery and distillery tastings and farm-to-table dinners. Some groups even partner with local land management organizations for beach cleanups or trail projects. These shared experiences naturally bring people together in a relaxed setting.

Meeting Northwest News: Accessibility is often one of the first questions planners ask. What would you tell someone considering their first meeting in the islands?

Deborah: We help planners connect with local transportation providers, so their main responsibility is getting the group to the Washington State Ferries terminal in Anacortes. From there, attendees can walk aboard the ferry, arrive on San Juan, Orcas or Lopez island and be greeted by a pre-arranged shuttle, van or trolley. We also work with mainland motorcoach companies, and smaller groups can arrive by scheduled or charter flights, including seaplanes.

Meeting Northwest News: What advantages do smaller destinations have over larger convention cities?

Deborah: Smaller destinations create a sense of belonging. Even if visitors are only here for a few days, they feel like they’re part of the community. There are fewer distractions, but that doesn’t mean there’s less to do. Our islands are filled year-round with restaurants, bakeries, coffee shops, boutiques, art galleries, museums, community theaters and endless opportunities for outdoor adventure.

Meeting Northwest News: What experiences outside the meeting room tend to make the biggest impression on attendees?

Deborah: Simply embracing “island time” makes a difference. Whale and wildlife watching is unforgettable, and the San Juan Islands are one of the best places in the world to see whales in the wild. Groups can also enjoy sea kayaking, including seasonal bioluminescence tours, with many outings designed for beginners and kept close to shore.

Meeting Northwest News: If a planner told you they wanted attendees to leave feeling like they’d experienced something they couldn’t find anywhere else, what would you recommend?

Deborah: I’d send them out on the water. Whether it’s a whale-watching excursion or a guided sea kayaking trip, there’s something magical about exploring these waters. You never know what you’ll encounter, from jellyfish and sea lions to whales, and those experiences are often what attendees remember most.

Meeting Northwest News: Anything else planners should know?

Deborah: The San Juan Islands are awe-inspiring whether you’re visiting for a meeting, retreat or vacation. If you’re planning an event here, I always recommend arriving early or extending your stay for a few days. Once you experience island life, you won’t want to leave.