Guided Flotillas!
You can explore new cruising grounds with confidence, having an expert flotilla leader and the camaraderie of fellow sailors, or share familiar cruising grounds with the companionship of new faces! Our flotillas give you as much privacy or togetherness as you like. Each day you can cruise together with the flotilla or separately. You are welcome to raft to other boats in the group, or seek solitude in your own corner of an anchorage. You can join your cruise mates for evening hors d’oeuvres after exploring shore-side trails, poking your dinghy (or a kayak) into tiny inlets, or enjoy a relaxing evening watching the shadows of the evergreens stretch into the water.
What are the benefits of flotilla cruising?
Flotillas are an ideal setting to gain confidence and familiarize yourself with new cruising grounds, while enjoying the camaraderie of fellow cruisers. Your flotilla leader serves as a knowledgeable guide, providing skills “coaching” and docking or anchoring assistance as needed. Have a question? Assistance is always there.
In addition to safety and guidance, your flotilla leader(s) provide history and in some cases naturalist briefings on each cruising area. For example, each day’s cruise begins with a weather report and a chart briefing. They’ll review your destination and course and highlight both hazards and special natural scenes en route. In addition you’ll have the opportunity to learn about the history of each area, the original peoples, the Spanish and English explorations of the region, and even anchor in the same coves as George Vancouver.
In other words, it’s the best of both worlds as we help one another moor, point out wildlife, avoid rocks and reefs, and share prawns, oysters and crab straight from the sea.
Spring Guided Flotilla: Princess Louisa Inlet & British Columbia's Sunshine Coast
10 days. May 10 – May 19, 2025
10 days. May 21 - 30, 2025 (This flotilla is currently full. Please contact us for waitlist.)
("10 Days of Charter for the Price of 7 Days"... a 43% added value!)
Late Spring is the perfect time to visit the "Sunshine Coast". Days are long, breezes are kind, waterfalls are running strong and wildlife is abundant. This relaxed 10-day flotilla takes advantage of our “10 days for the price of 7 days” Spring Special...a 43% added value...and spring charter rates that are 12.5% less than our summer rates! Your flotilla leader will guide you along BC's Sunshine coast (the eastern shore of the Strait of Georgia), into Jervis Inlet and through Malibu Rapids to spend two nights at Chatterbox Falls. (Spend the day in between exploring Princess Louisa Inlet, relaxing, or hike to the top of the falls, and for the really ambitious, continue on with the 2-hour hike up into the forest to explore the Trapper's Cabin.) Other stops on this flotilla include protected Garden Bay (Pender Harbor), quiet Secret Cove, labyrinthine Smuggler's Cove, quaint Gibson's Landing, and historic Snug Cove (Bowen Island).
(read more)
Spring Guided Flotilla: Barkley Sound
10 days. May 31 – June 9, 2025 (This flotilla is currently full. Please contact us for waitlist.)
This trip takes advantage of one of our "10 Days of Charter for the Price of 7 Days" special date sets!)
Join us for a special adventure out to Barkley Sound. Located on the west coast of Vancouver Island, Barkley Sound is an intricate warren of island clusters, including the Deer Group, the Broken Group, and the Pinkertons. They are a wild, rugged and incredibly scenic part of the Pacific Rim National Park. Join us as we travel together to visit remote anchorages, explore uninhabited islands, and try to spot local wildlife (whales, bears, wolves, sea lions and eagles).
As Barkley Sound is 140 nm from Bellingham, transit legs to get up there and back will include some legs with +60 nm days. For that reason this trip is limited to any powerboat in the fleet or any sailboat that is at least 40' long and able to cruise at least 7 knots under engine power. Sailing is always encouraged although on the long legs the wind/current may make it necessary to spend part or all of the day under power. At the end of each day, the entire flotilla will arrive at the same destination so you will never be alone or out of touch.
(read more)
Summer Guided ASA Flotilla: Cruising the Gulf Islands
7 days. June 21 - 27, 2025
Join fellow sailors in cruising the charming east coast of Vancouver Island and the beautiful Gulf Islands. These islands boast sheltered waters, magnificent marine parks, quiet villages and welcoming marinas. Wildlife abounds on the land and in the sea, with deer, bald eagles, sea otters, seals, sea lions and orca whales commonplace.
On this flotilla you'll depart Bellingham and sail through the San Juan Islands to clear customs and overnight at the quaint seaside town of Sidney, BC. As you cruise through the Gulf Islands, and along Vancouver Island, you'll visit several iconic destinations:
- Montague Harbor Marine Provincial Park (Galiano Island), known for wooded trails, a white sand beach, and the option to catch the fun and eclectic pub bus to the Hummingbird Pub
- Charming and welcoming Maple Bay (Vancouver Island)
- Quiet and unspoiled Thetis Island
- Visit Vancouver Island's Saanich Inlet (likely Tod Inlet) and spend a few hours exploring Victoria or the enchanting Butchart Gardens.
Summer Guided Flotilla: Desolation Sound
14 days. June 21 – July 4, 2025
Take this opportunity for an early summer exploration of Desolation Sound, enjoying the long, sunlit days around the summer solstice. Your flotilla leader will guide you through the San Juan and Gulf Islands, along BC's Sunshine coast (the eastern shore of the Strait of Georgia), and in to Desolation Sound and the Discovery Islands. 14 days allows us time to explore, discovering the nature and history of this incredible cruising ground along the way. A couple of lay days will allow time to relax, explore in depth, hike, or simply watch the sun move across the sky. The last night of the flotilla will be planned close enough to Bellingham that those who prefer to do so may return to the dock on July 3 (for holiday travel reasons). If you'd like to enjoy the 4th of July festivities in Bellingham, booking a room at one of our waterfront hotels (Hotel Bellwether or The Chrysalis Inn & Spa) for the night of July 4 will allow for a front row seat to the Bellingham fireworks show! This flotilla takes advantage of our multiweek discount.
(read more)
Summer Guided Flotilla: Independence Day Celebration
7 days. July 5-11, 2025
Enjoy summer cruising in the picturesque and beautiful Salish Sea. Arrive early for your preboard on Friday, July 4, and enjoy the 4th of July harbor festival, before completing your onboard checkout and watching the waterfront fireworks from the deck of your boat. On Saturday morning we'll cruise north from Bellingham to enjoy a beach BBQ at Sucia Island Marine Park. Then we'll cruise down to vibrant Victoria BC, where we'll spend a lay day exploring this vibrant city. In addition to browsing museums and shops, sampling restaurants, and watching the talented street performers, there will be an option for a side trip to visit Butchart Gardens. Then back to the San Juan Islands to clear customs and anchor at Garrison Bay (San Juan Island), where we'll visit Westcott Bay Oyster Farm and learn a bit about local history at English Camp. On Wednesday we head through the islands to stately Rosario Resort (Orcas Island) where we'll enjoy a group happy hour and smores. Thursday we'll raft in Pleasant Bay, have a bit of fun with blindfolded dinghy races, and spend one last evening enjoying each other's company before our return to Bellingham.. A truly memorable flotilla experience!
(read more)
Summer Guided Flotilla: San Juan Islands
7 days. August 23 – 29, 2025
This late summer flotilla explores classic destinations throughout the San Juan Islands. While we cruise among evergreen-studded islands we will keep our eyes peeled for eagles, herons, seals and sea lions, try to spy some orcas and do some hiking. If you have not cruised these islands before this will be a great introduction. Mixed in with all the beauty will be the opportunity to socialize with other boaters as we raft up for the night.
Enjoy daily history, weather, route, and naturalist briefings, occasional "rafting" and the camaraderie of your fellow boaters.
(read more)
Fall Guided Flotilla: Sailing the San Juan Islands & Saanich Peninsula (Sail Only)
7 days. September 6 – 12, 2025
Looking for a chance to enjoy a flotilla environment while focusing on sailing? This one's for you! This flotilla is timed to take advantage of the nice weather and uncrowded anchorages typical of September in the Salish Sea. The intent will be to sail from destination to destination (though you can motor if you want). First we'll head through the northern San Juan Islands to anchor at Sucia Island and enjoy a group BBQ. Then on to Bedwell Harbor (S. Pender Island), to clear customs and enjoy Poet's Cove Resort (pool, hot tub, spa, restaurant and cocktail bar). Then a peaceful night at anchor at Princess Cove (Wallace Island) before heading to explore the shops, galleries and restaurants at vibrant Ganges Harbor (Saltspring Island). From there we'll sail back to the US, clear customs, and head for Gatsby-era Rosario Resort and Marina (pool, hot tub, spa, restaurant & bar). Finally, we'll sail across Rosario Strait and anchor our last night at Chuckanut Bay, where we'll cap the trip with the lighthearted fun of blindfolded dinghy races. Sorry, sailboats only on this flotilla.
(read more)
Fall Guided Flotilla: Desolation Sound
14 days. September 6 – September 19, 2025 (This flotilla is currently full. Please contact us for waitlist.)
14 days. September 20 – October 3, 2025 (This flotilla is currently full. Please contact us for waitlist.)
Discover the joys of exploring Desolation Sound at the end of the season, when the crowds have left and the air turns crisp. From Bellingham journey through the San Juans, Gulf Islands, and Sunshine Coast to Desolation Sound. 14 days allows us time to explore, discovering the nature and history of this incredible cruising ground along the way. Serving as guide, naturalist and local historian, your experienced flotilla leader will help you discover an enriched cruising experience among these beautiful and diverse inlets and islands. Charter one of our well-maintained yachts or, if you prefer, we often have several by-the-stateroom rental options available.
Enjoy daily history, weather, route, and naturalist briefings, occasional "rafting" and the camaraderie of your fellow boaters.
(read more)
Fall Guided Flotilla: End of Season Hoorah!
10 days. October 8 – 17, 2025
("10 Days of Charter for the Price of 7 Days"... a 43% added value!)
This flotilla is designed to be a relaxed exploration of our favorite locations in San Juan Islands and Gulf Islands. Time to unwind and enjoy the crisp final days of the fall cruising season. Our route will remain somewhat flexible to accommodate weather. Possible destinations include:
- Blind Bay (Shaw Island). This protected, scenic anchorage, is the perfect place for dinghy exploration and watching ferries come and go.
- Rosario Resort (Orcas Island). Gatsby-era resort offering a restaurant, pub, pool, hot tub and spa. Take some time to explore the museum and take in the pipe organ concert/history slide show. Hikers and runners will enjoy access to the Moran State Park trail system.
- Watmough Bay (Lopez Island). This cove offers a beautiful view of Mount Baker, public beach access, and several hiking trails.
Special Opportunities
| Courses & Stateroom Bookings | Spring & Summer Guided Flotillas | Fall Guided Flotillas | |
|---|---|---|---|
| Stateroom Bookings | 10-Day Sunshine Coast | 7-Day Independence Celebration | 7-Day San Juans & Saanich |
| 2-Day Sailing Courses | 10-Day Barkley Sound | 7-Day San Juan Islands | 14-Day Desolation Sound |
| Women-Only LNC | 7-Day Cruising the Gulf Islands | 10-Day End of Season Hoorah | |
©Copyright 2023 San Juan Sailing | All Rights Reserved | This Website was Handcrafted by the Staff at San Juan Sailing
View Our Sitemap
