Trips in 2023, 2024

Click linked titles for further details.
Key: Blue = Club Sponsored Trips                   Green = Sailing Opportunities

Sailing Open House

Upper Minnetonka Yacht Club and Sailing School

Friday, May 26, 4-8 p.m.

Enjoy this opportunity to try sailing an MC racing scow or a comfortable keelboat. Your family and friends are invited to meet our instructors, members and racers.

No reservation necessary, but you may call to reserve a sail time. Sails are every ½ hour from 4 p.m. to 7:30 p.m. Free event with $5 tax-deductible donation suggested.

Call to reserve your ride time, or sign up at the event.

Contact: Capt. Joan Gilmore 612-871-8101

Upper Minnetonka Yacht Club Marina, 4570 Enchanted Point, Shorewood, MN 55384

Sailing Saturdays
from Park Point in Duluth, Minnesota
June 17, July 15, August 19

2 boats with 4 sailors each will sail the harbor and surrounding waters, cruising under the famous lift bridge.
Cost is $27.50 per person for 4 hours, plus $5.00 per person per hour after that.
Food and lodging are on your own.
Skippers and first mates must be approved by the Duluth Superior Sailing Association, and skippers should have ASA 103 and should furnish a sailing resume.

To reserve a spot contact trip chair Jerry Sicard,, 612-940-7403

Day sailing in the Duluth/Superior Harbor and near shore of Lake Superior

Members who are experienced keelboat sailors can be certified to use the DSSA’s larger cruise boats with auxiliary motors. Cruise boats are available for day sailing in the Duluth Harbor and the near shore of Lake Superior

J-Fore: In 2014 we were blessed with the donation of a Cal 24. This 24′ fixed keel cruiser is in great shape and is a joy to sail. She is equipped with a electric tilt 4 stroke and a roller furler for ease of use. She has a magnificently well balanced helm and sails well.

Over Easy: Our Catalina 25, is a spacious boat and a joy to sail. It has a swing keel and very easy to handle. It has a 4 stroke outboard engine and is sure to be very comfortable for outings.

Contact DSSA directly: 

Wednesday to Wednesday, June 21-28, 2023

Questions? Contact Jerry Sicard - 612-940-7403

March 7, 2023 update: 

We have rented boat #2.  Paul Ciernia will be the skipper.

There is one vee-berth cabin available suitable for couple and two cabins with 2 single/twin beds side by side with isle in between suitable for singles.  Each cabin has its own head.  If you go to the LeBoat link below you can "jump aboard" and take a virtual tour of the boat and its cabins.

The cost per person is $1750.00. The cost is per person, not per cabin. 

If you think you might be interested check out these links:

Remote Borders Sailing
July 7—July 15, 2023

Anchor near unique rock formations and waterfalls. Visit eagle nesting grounds. Find hidden water falls. Enjoy a shore bonfire. Experience Lake Superior as the Native Americans did. Legendary Canadian Saunas. Two overnights at Isle Royale.

$1,350/person covers everything except your share of the groceries.
$500 deposit by May 1 or upon reservation.

Contact Reeve Hutchinson: 612-805-1938,

Isle Royale National Park
July 27—August 5, 2-23

Explore abandoned Minong copper mine. Visit the Wolf Moose Study camp. Tour the oldest lighthouse on the island. Overnight at Rock Harbor resort. Hike to Lookout Louise and Monument Rock from Duncan Bay. Tour an original fish camp. Moose sightings. Spectacular stargazing.

$1,500/person covers everything except your share of the groceries.
$500 deposit by May 1 or upon reservation.

Contact Reeve Hutchinson: 612-805-1938,

Tour Copper Country
August 31—September 9, 2023

Travel the entire length of the Keweenaw waterway. Visit deserted Manitou Island. Spend a night in the hidden harbor of Lac LaBelle. Dinghy to historic Fort Wilkins. Hiking or Biking outing. Go down into the historic copper mine. Experience a spectacular sunset on tip of Mr. Brockway. Lots of "free time" sailing with no agendas.

$1,580/person covers everything except your share of the groceries.
$500 deposit by May 1 or upon reservation.

Contact Reeve Hutchinson: 612-805-1938,

ASA 118 - Docking Endorsement

Taught by Captain Joan Gilmore, Sail Away Sailing School, LLC,
on a 34' Catalina

Location: Bayport, MN on St. Croix River

Dates: August 29-30, Tuesday & Wednesday from 9-5 each day

Learn straight and slip docking. Single-handed docking, backing into a slip. Standing turns. Understand and control the 4 forces on your boat.

Included: Textbook and certification upon successful completion.

NLSC Member price - $579.
To Register contact Captain Joan at or 612-871-8101
More info:

ASA 105 - Costal Navigation

Taught by Captain Joan Gilmore, Sail Away Sailing School, LLC,
151 Glen Creek Road NE, Fridley, MN 55432

10 a.m. - 2:30 p.m. on Saturdays: October 21, October 28, November 4,
November 11, November 18 - Exam

This challenging 20-hour classroom course is certified by the American Sailing Association (ASA) and taught by ASA Instructor Evaluator, Captain Joan Gilmore. Gilmore has a master’s degree in adult learning styles and gets excellent reviews from her Coastal Navigation students. You will learn how to navigate using a chart and nautical instruments. You will learn advanced skills, such as lines of position, running fixes, calculating danger bearings, distance off, tides and currents and 3 ways to calculate set and drift. This course is valuable for both power boaters and sailors. Allow for 20+ hours of homework time.  Included in course fee: textbook and class materials, training chart, exam, and ASA 105 certification upon successful completion.  

Please bring to class: pencil, eraser, calculator, dividers ($15-$25), parallel rulers ($17-$25). See to purchase. Registered students get 30% discount. 

This course is a prerequisite, along with ASA 104-Bareboat Chartering, in order to take ASA 106 - Advanced Coastal Cruising.

Questions? Contact Captain Joan at or 612-871-8101. 

Please register by September 15th. $349 per person. Registration Form

Sail in the ABACOS in 2024

Feb 3- Feb 10, 2024 (Early boarding 4pm Feb 2, 2024 included) 

(3 boats full, wait list available)

Boat, Fuel, and Carefree Pkg $1440/person
($1440/person based on 8 people) 

Carefree Pkg Includes: damage waiver insurance/full coverage, welcome pkg, final cleaning, bed sheets & towels, dinghy, outboard motor & fuel, propane gas, full water tanks, snorkeling equipment. Other expenses- provisioning, mooring balls, airfare.
Optional: restaurant meals, hotels, personal trip insurance 

Enjoy beautiful white sand beaches,
crystal clear water, snorkeling,
swimming pigs, and so much more.  

Interested? Questions? Send an email to:
Marilynn Kaplan 

Corsica and Sardinia

September 7, 2024  through  September 21, 2024

Join us for a 14 day adventure sailing around Southern Corsica and Northern Sardinia.

Corsica is the fourth-largest island in the Mediterranean and has over 620 miles of coastline that is best explored by sea. Despite being French territory since 1768, it retains a distinctly Italian feel with some beautiful quaint medieval ports. Other highlights include unspoiled nature reserves, excellent food and reliable winds.

Sardinia is the second-largest island in the Mediterranean behind Sicily and is an Italian territory. It is approximately 168 miles long and 90 miles wide. The island is rugged and the highest point is 6,017’ above sea level. The island has over 1,100 miles of coastline. With its white-sand beaches, turquoise waters, rugged coastline, ancient archaeological sites and fascinating culture, Sardinia is waiting for you to come and explore.

You will be sailing aboard either a Bali 4.3 or Bali 4.1 Catamaran. The boats are the 4 cabin, 4 head design and outfitted with the usual amenities you would find on a charter vessel of this size. The boats are berthed at the Tino Rossi Port in Ajaccio, Corsica.

The cost for the boat will be $1935 per person and does not include food, fuel, port/mooring fees, national park fees, transportation, or incidentals. An initial deposit of $700 will hold a spot on the trip. The cheapest airfare I found the other night was $1643 out of Minneapolis. Although this trip will be classified as a sailing opportunity, NLSC trip rules will apply.

Once your initial deposit is accepted, you are liable for the boat cost of $1935. Refunds will be honored if a replacement crew member is found. Trip insurance is highly recommended.

If you are interested in participating please send a check for the initial deposit made out to Jay A. Biggs. Please send the check to: 1590 110th Court West, Inver Grove Heights, MN 55077.

If you have any questions feel free to email me at: If you are planning on participating please email me of your intentions.

Fair winds! Jay