Guided Flotillas!

Guided flotilla rafted in Melanie Cove

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.

2026 Guided Flotillas

Sunshine Coast Flotilla Image

Spring Guided Flotilla: Princess Louisa Inlet & British Columbia's Sunshine Coast

10 days. May 9 – May 18, 2026 (This flotilla is currently full. Please contact us for waitlist.)
10 days. May 20 - 29, 2026 (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 through the Gulf Islands, 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 potential stops on this flotilla include scenic and protected Pender Harbor, cozy and labyrinthine Smuggler's Cove, idyllic Montague Marine Park (famed for its white shell beach), and the beautiful Poet's Cove Resort.

(read more)
Desolation Sound Flotilla Image

Spring Guided Flotilla: Desolation Sound

14 days. May 30 – June 12, 2026

Take this opportunity for an late spring/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. This flotilla takes advantage of one of our "10-for-7" specials.

Enjoy daily history, weather, route, and naturalist briefings, occasional "rafting" and the camaraderie of your fellow boaters.

(read more)
Sail Only Gulf Islands Flotilla Image

Summer Guided ASA Flotilla: Cruising the San Juan Islands

7 days. June 20 - 26, 2026

Join fellow boaters in exploring the highlights of the San Juan Islands during the early summer. This flotilla is timed to beat the crowds and enjoy the long hours of daylight during the summer solstice. The San Juan Islands boast sheltered waters, magnificent marine parks, quaint villages and welcoming marinas. Wildlife abounds on the land and in the sea, with deer, bald eagles, otters, seals, sea lions and orca whales commonplace.

Departing from Bellingham you'll spend the week visiting some of our favorite destinations the San Juan Islands. Likely stops include:

  • Echo Bay (Sucia Island). Sucia is considered the "jewel" of the San Juan Islands, and Echo Bay offers beautiful views of Mount Baker, beaches to explore and excellent trail access.
  • Friday Harbor (San Juan Island). Vibrant island town that offers a grocery store, wide selection of restaurants and shops/galleries.
(read more)
Independence Day Flotilla Image

Summer Guided Flotilla: Independence Day Celebration

7 days. July 4-10, 2026

Enjoy summer cruising in the picturesque and beautiful Salish Sea. On Saturday morning we'll cruise to Anacortes to enjoy the 4th of July festivities and gather for a salmon BBQ. Then over to Lopez Island (likely Watmough Bay) for a night at anchor before heading to beautiful 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 Thursday we head back through the islands to 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)
San Juan Islands Flotilla Image

Summer Guided Flotilla: San Juan Islands

7 days. August 22 – 28, 2026

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)
Salute to Summer Flotilla Image

Salute to Summer: Enjoying the San Juan and Gulf Islands

14 days. Aug 29 - Sept 11, 2026

This flotilla is designed to cruise the San Juan and Gulf Islands with more free time to pause at destinations and enjoy the lingering days of summer weather. Destinations will include a blend of marinas and anchorages offering options to explore, relax, participate in off-boat activities or simply relax during a non-transit day, what we call lay-days. Sucia, Roche Harbor, Ganges, Montague Harbour, Nanaimo, Telegraph Harbour, Sidney, Princess Cove, and others are all favorites that we'll consider as we craft a "Salute to Summer" float plan. Have a favorite place? Let us know and we'll have the flotilla leader consider it.

(read more)
Fall Gulf Islands Flotilla Image

Fall Guided Flotilla: The San Juan Islands & Saanich Peninsula

7 days. September 12 – 18, 2026

This flotilla is timed to take advantage of the nice weather and uncrowded anchorages typical of September in the Salish Sea. First we'll head through the northern San Juan Islands to anchor at Sucia Island and enjoy a group happy hour. Then on to Roche Harbor where we'll enjoy exploring the resort and plan a salmon BBQ. After that we'll cruise over to Sidney, BC to clear customs and then continue on to raft for 2 nights in Tod Inlet. A lay day there allows time to visit Butchart Gardens or take the bus down to Victoria, BC. Then we'll cruise back to the US, clear customs and spend an evening at either Friday Harbor or Rosario Resort. Finally, we'll meander through the islands and across Rosario Strait to anchor our last night at Pleasant Bay, where we'll cap the trip with the lighthearted fun of blindfolded dinghy races.

(read more)
Fall Desolation Sound Flotilla Image

Fall Guided Flotilla: Desolation Sound

14 days. September 19 – October 2, 2026 (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)
End of Season Hoorah Flotilla Image

Fall Guided Flotilla: End of Season Hoorah!

10 days. October 7 – 16, 2026

("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.

(read more)
* For private boats joining San Juan Sailing & Yachting flotillas, a $100 non-refundable reservation deposit is required to confirm your place on the flotilla. The remaining balance will be due 45 days prior to the start of the flotilla. If you cancel your participation in the flotilla within 45 days of the start of the flotilla, your flotilla fee will only be refundable (less $100) if we are able to rebook your space on the flotilla to another participant. We highly recommend that you consider Cancellation/Travel Insurance (available directly at TravelGuard, World Nomads or from your local travel agent).

2027 Guided Flotillas

Sunshine Coast Flotilla Image

Spring Guided Flotilla: Princess Louisa Inlet & British Columbia's Sunshine Coast

10 days. April 28 – May 7, 2027
10 days. May 29 – June 7, 2027

("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 through the Gulf Islands, 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 potential stops on this flotilla include scenic and protected Pender Harbor, cozy and labyrinthine Smuggler's Cove, idyllic Montague Marine Park (famed for its white shell beach), and the beautiful Poet's Cove Resort.

(read more)
Broughton Islands Flotilla Image

Spring Guided Flotilla: Broughton Islands

21 days. May 8 – 28, 2027

(This trip takes advantage of two of our "10 Days of Charter for the Price of 7 Days" special date sets, creating 3 weeks for the price of 2 weeks!)

Join us for an adventure to the pristine Broughton Islands Archipelago. Adjacent to the Northeast coast of Vancouver Island, this area is an expanse of natural beauty, secluded anchorages and towering snowcapped mountains. Be transported back in time and picture life in this sparsely populated region of the world. Witness wildlife in its natural setting. Embrace life “off the grid”, away from the hectic, modern world.

As the Broughton Islands are 250 NM from Bellingham, and we want to spend as much time up there as possible, the beginning and the end of the trip will involve lengthy transit days, including some likely 50+ NM days. Depending on the cruise speed of your vessel, that can mean days where you are underway for 7+ hours.

(read more)
Sail Only Gulf Islands Flotilla Image

Summer Guided ASA Flotilla: Victoria & the Islands

7 days. June 19 – 25, 2027

Join fellow boaters in visiting Victoria, BC (with a lay day to explore this vibrant city) plus some favorite destinations in and around the San Juan Islands and Gulf Islands. This early summer flotilla is timed to beat the crowds and enjoy the long hours of daylight during the summer solstice. The San Juan Islands boast sheltered waters, magnificent marine parks, quaint villages and welcoming marinas. Wildlife abounds on the land and in the sea, with deer, bald eagles, otters, seals, sea lions and orca whales commonplace.

Departing from Bellingham you'll spend the week visiting some of our favorite destinations. Likely stops include:

  • Roche Harbor (San Juan Island). This historic and stately resort is well loved and known for its sunset Colors Ceremony, unique mausoleum, shops, spa and restaurants, as well as for the nearby sculpture garden and distillery.
  • Victoria (Vancouver Island). A vibrant city with a European feel, Victoria offers restaurants, shopping, excellent museums, talented street performers and colorful outdoor markets.
(read more)
Independence Day Flotilla Image

Summer Guided Flotilla: Independence Day Celebration

7 days. July 3 – July 9, 2027

Enjoy summer cruising in the picturesque and beautiful Salish Sea. On Saturday morning we'll cruise to Spencer Spit to enjoy a salmon barbecue on the beach. The next day we'll head to Anacortes to enjoy the 4th of July festivities. After that, over to beautiful 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 Thursday we head back through the islands to 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)
San Juan Islands Flotilla Image

Summer Guided Flotilla: San Juan Islands & Gulf Islands

7 days. August 21 – 27, 2027

This late summer flotilla explores classic destinations throughout the San Juan Islands and Gulf 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)
Sail Only Gulf Islands Flotilla Image

Salute to Summer: Enjoying the San Juan and Gulf Islands

14 days. August 28 – Sept 10, 2027

This flotilla is designed to cruise the San Juan and Gulf Islands with more free time to pause at destinations and enjoy the lingering days of summer weather. Destinations will include a blend of marinas and anchorages offering options to explore, relax, participate in off-boat activities or simply relax during a non-transit day, what we call lay-days. Sucia, Roche Harbor, Ganges, Montague Harbour, Nanaimo, Telegraph Harbour, Sidney, Princess Cove, and others are all favorites that we'll consider as we craft a "Salute to Summer" float plan. Have a favorite place? Let us know and we'll have the flotilla leader consider it.

(read more)
Fall Gulf Islands Flotilla Image

Fall Guided Flotilla: The San Juan Islands & Saanich Peninsula

7 days. September 11 – 17, 2027

This flotilla is timed to take advantage of the nice weather and uncrowded anchorages typical of September in the Salish Sea. First we'll head through the northern San Juan Islands to anchor at Sucia Island and enjoy a group happy hour. Then on to Roche Harbor where we'll enjoy exploring the resort and plan a salmon BBQ. After that we'll cruise over to Sidney, BC to clear customs and then continue on to raft for 2 nights in Tod Inlet. A lay day there allows time to visit Butchart Gardens or take the bus down to Victoria, BC. Then we'll cruise back to the US, clear customs and spend an evening at either Friday Harbor or Rosario Resort. Finally, we'll meander through the islands and across Rosario Strait to anchor our last night at Pleasant Bay, where we'll cap the trip with the lighthearted fun of blindfolded dinghy races.

(read more)
Fall Desolation Sound Flotilla Image

Fall Guided Flotilla: Desolation Sound

14 days. September 18 – October 1, 2027

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)
End of Season Hoorah Flotilla Image

Fall Guided Flotilla: End of Season Hoorah!

10 days. October 6 – 15, 2027

("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.

(read more)
* For private boats joining San Juan Sailing & Yachting flotillas, a $100 non-refundable reservation deposit is required to confirm your place on the flotilla. The remaining balance will be due 45 days prior to the start of the flotilla. If you cancel your participation in the flotilla within 45 days of the start of the flotilla, your flotilla fee will only be refundable (less $100) if we are able to rebook your space on the flotilla to another participant. We highly recommend that you consider Cancellation/Travel Insurance (available directly at TravelGuard, World Nomads or from your local travel agent).

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 Juan & Gulf Islands
2-Day Sailing Courses 14-Day Desolation Sound 7-Day San Juan Islands 14-Day Desolation Sound
Women-Only LNC     10-Day End of Season Hoorah