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The Sailing Club, Inc.

On The Water TrainingThe San Juan Islands consist of hundreds of islands, ranging from small rocky outcrops to large, mountainous and forest-clad behemoths. The waters are teeming with marine life, from the edible salmon, rockfish, and Dungeness crab, to the much larger seals, sea lions and the infamous orca. The area has much to offer, and you may want to add a few days to explore.

We’ll sail through pristine waters and explore some quiet anchorages, as well as spend two nights in slips – one in Friday Harbor, the hub of the San Juans, and one in Rosario, home to a locally prominent resort. There should be plenty of opportunity to spot orcas, as most days are short enough to enjoy unhurried sailing to the next destination, or mill about while wildlife spotting.

The trip begins on the afternoon of September 9th, when we’ll board the boats, do food shopping, and dine at one of the many excellent restaurants in Anacortes.

The following itinerary is what we hope to do. Wind and waves may necessitate changes.

September 9 (Saturday) – Pre-board
In the late afternoon, pre-board the boats at Anacortes Marina. Boarding will be after the skippers do a check-ride with the charter company. The afternoon can be spent provisioning at the local Safeway and other markets. Dinner ashore.

September 10 (Sunday) – Sail to Lopez Island
After any last minute provisioning and vessel checks, it’s off to Lopez Island, where there are several decent anchorages. The first choice is Aleck Bay on the southeast side, as this provides the best start for the next day’s long sail. Dinner aboard.

September 11 (Monday) – Sail to Garrison Bay on San Juan Island
This will likely be the best day to spot orcas. This twenty-five mile leg will pass to the west of San Juan Island through Haro Strait, on the way to the north end and Garrison Bay. This is where the British fleet was anchored during the Pig War. Tomorrow there will be time to go ashore and visit English Camp, part of the San Juan Islands National Historical Park, where you can learn all about this odd, peacetime conflict. Dinner aboard.

September 12 (Tuesday) – Short Sail to Reid Harbor on Stuart Island
In the morning, dinghy in to see the Park. Stop in at the Visitor Center to learn how the conflict started (you won’t believe it), and how long it took to achieve peace. Then it’s a quick stop in Roche Harbor before heading to Stuart Island, about three miles away, all the time watching for orcas. Dinner aboard.

September 13 (Wednesday) – Sail to Friday Harbor on San Juan Island
The hub of the San Juans, Friday Harbor is the busiest port, but that means that there’s a lot to do. Since arrival will likely be in the late afternoon after a fifteen mile sail, there will be time the next day to explore. This is also a good place to re-provision, as we will be in slips for one night. Dinner ashore.

September 14 (Thursday) – Time in Friday Harbor, then to Blind Bay on Shaw Island
Explore the town of Friday Harbor in the morning. Be sure to check out the Whale Museum, and learn all about orcas (which aren’t actually whales). When re-provisioning, be sure to check out the Friday Harbor Seafood market right on the main dock. They will even cook the Dungeness crab for you. After lunch, it’s off to Blind Bay, a mere ten-mile jaunt around the east side of Shaw Island. Dinner aboard.

September 15 (Friday) – Sail to Rosario Resort and Spa on Orcas Island
A leisurely start is in order today as this leg is only six miles. The resort was once the home of shipbuilder Robert Moran. It looks it, with lots of teak and brass. The mansion itself is also a museum, with a slide presentation on the history of the resort, with accompaniment performed on a room-sized Wurlitzer pipe organ. The show begins at 4:00 p.m. and is worth it. Dinner ashore (reservations recommended).

September 16 (Saturday) – Sail to Hunter Bay or Spencer Spit on Lopez Island
Our last full day on the water, we’ll head to the east side of Lopez Island, and either anchor off of Spencer Spit (seven miles) or in Hunter Bay (ten miles) depending on wind and current. Capping off the trip will be a traditional must-go party. Dinner aboard.

September 17 (Sunday) – Return to Anacortes
The return to Anacortes is about fifteen miles. Everyone needs to be off the boats by 1:00 p.m

The boats (both have two cabins and two heads):

Harriet Tubman (Caliber 40) Orcastrate (Jeanneau 44)

The nearest commercial airport to Anacortes is Seattle (SEA), and is served by all major airlines. From there, the best option is Bellaire Airporter Shuttle, which runs between the airport and Anacortes on a regular schedule. Individual round-trip fare is $102 (Seniors - $98).

The cost of this event is $1,525.00 per person. (Skippers and Trip Leader - $779.00). This price includes charter fees and slip fees for two nights (Wednesday and Friday nights). Provisioning, fuel, pump-out (other than the final one at the charter base), other mooring fees, dinners ashore, airfare, and other incidentals are additional and will be handled by each boat’s crew.

The deposit for this trip is a non-refundable $200.00.  Please make your check payable to The Sailing Club, Inc. and mail it, along with your completed two-page Reservation/Release Form to Craig Gill at the address below. Reservations will be processed beginning April 10, 2023 with a random draw of those received by that date. All reservations received after that date are on a first-come, first-served basis. A final payment of $1325.00 is due on July 12, 2023. Cancellations made within 45 days are not refundable, unless a replacement is found.

Travel insurance is NOT included in the trip price. Confirmed participants should make their own decisions regarding insurance that would provide coverage appropriate to their needs and that they feel best protects them in their individual situations. Two useful resources for comparing plans are and As always, read all policy terms and conditions carefully.

A pre-trip meeting will be held before the trip, at a time and place to be announced. All crewmembers should make every effort to attend in order to meet your crewmates, plan your meals, and make travel plans.

Trip Leader

Assistant Trip Leader

Craig Gill
10 Spencer Drive
Morristown, NJ 07960

Steve Krakauer
11 Clark Ct.
Basking Ridge, NJ 07920

Please note that sailing conditions are dynamic, that your safety, and that of your crewmates, depends on your good physical health and agility.



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