San Juan Islands & Victoria, BC
The Pacific Northwest is your backyard.
Sail it like you mean it.
The San Juan Islands and Victoria, BC are some of the most beautiful sailing waters in the world — sheltered channels, dramatic coastlines, charming harbor towns, and wildlife around every headland. Gypsy Wind brings it all within reach.
San Juan Islands & Victoria, BC
Your boat. Your islands. Your adventure.
San Juan Islands charters aboard Gypsy Wind are private whole-boat adventures. The yacht is reserved exclusively for your family or group — we do not combine unrelated guests. Whether you're looking for a long weekend escape or a full week exploring the islands and crossing to Victoria, we'll build the trip around you.
Charter Options
Choose Your Adventure
Weekend Charters
A long weekend on the water — depart from Anacortes, explore the San Juan Islands, and return refreshed. Perfect for families, groups of friends, or anyone who wants a taste of island life without taking a full week off.
- Departs from Anacortes, WA
- San Juan Islands anchorages
- Up to 6 guests
Week-Long Voyages
A full week to explore the islands at a relaxed pace — from the San Juans through the Gulf Islands and across to Victoria, BC. Time to anchor in hidden coves, explore ashore, and truly disconnect from the world.
- San Juans + Victoria, BC
- Gulf Islands & Canadian waters
- Up to 6 guests
San Juan Islands Private Yacht Charters Prices
3 Days / 2 Nights — Starting at $333 Per Person
Experience the San Juan Islands aboard Gypsy Wind, our spacious 72-foot luxury sailing yacht. Enjoy a private 3-day sailing adventure for just $333 per person, based on six guests sharing three comfortable double-occupancy cabins. Private Yacht Charter — $2,000 Per Day Explore beautiful island anchorages, discover wildlife, and enjoy an unforgettable sailing adventure while supporting our Sea Scout youth sailing program.
Get in TouchWhat Awaits You
The Pacific Northwest Experience
Orcas & Wildlife
The San Juan Islands are one of the best places in the world to see orcas in the wild. Keep watch for humpbacks, porpoises, harbor seals, bald eagles, and the resident pods of killer whales that call these waters home.
Victoria, BC
Cross the border and spend time in one of Canada's most charming cities. Victoria's Inner Harbour is one of the most beautiful anchorages in the Pacific Northwest — and the fish and chips aren't bad either.
Hidden Anchorages
Drop anchor in quiet coves and bays where the only sounds are the water lapping against the hull and the eagles overhead. The San Juans have hundreds of anchorages — we know the best ones.
Island Towns & Harbors
Tie up in Friday Harbor, Roche Harbor, or Deer Harbor and explore on foot. Great restaurants, local shops, and the unhurried pace of island life — a world away from the mainland.
Kayaking & Exploring Ashore
Launch the kayaks and explore beaches, sea caves, and shorelines that can only be reached by water. The San Juan Islands reward those who slow down and look closely.
Fishing & Crabbing
Drop a crab pot in the evening and pull it up in the morning. The San Juan Islands offer excellent Dungeness crab, salmon, and bottomfish — and there's nothing better than cooking your catch fresh aboard Gypsy Wind.
Season
October through June.
San Juan Islands charters run October through June, when the Alaska season is on pause. The Pacific Northwest is beautiful year-round — fall color, winter storms rolling through, spring wildflowers, and the return of the orcas. There's never a bad time to be on the water.
Food & Life Aboard
We cook together. We eat together. We share the adventure.
Just like our Alaska expeditions, San Juan Islands charters are a shared experience from bow to stern. Breakfast is provided by the crew. Lunch and dinner are a group affair — fresh crab, salmon, and whatever the day brings. Think of it less like a charter and more like a floating family gathering.
Sailing with a Purpose
Every charter supports Sea Scout Ship 226.
Charter proceeds help support Sea Scout Ship 226 and youth sailing and maritime education in Everett. When you sail with us, you're not just exploring the Pacific Northwest — you're helping give young people the opportunity to learn seamanship, navigation, and leadership on the water.
Ready to Explore the Islands?
San Juan Islands charters run October through June. Reach out to learn more about availability, trip options, or to start planning your voyage.