PORTLAND BOAT TOUR FIELD GUIDE
True North: A 40‑foot Jeanneau Built for Open‑Water Bareboat Sailing out of Portland
A bareboat charter aboard a 40' Jeanneau with three cabins and modern navigation — this guide explains what the boat provides, what you must bring, and how to qualify as skipper.
True North: A 40‑foot Jeanneau Built for Open‑Water Bareboat Sailing out of Portland.
Adventure brief
True North: A 40‑foot Jeanneau Built for Open‑Water Bareboat Sailing out of Portland
True North is a roomy, modern 40‑foot Jeanneau designed for adventurous groups who want the freedom of a bareboat charter: three cabins, sleeping space for eight, two heads, and a galley equipped for extended days and evenings on the water.
Set sail from Bayfield, Wisconsin, on a spacious 40-foot Jeanneau sailboat named True North, and discover a new way to experience Lake Superior’s vast and rugged beauty. Bayfield, located on the southern shore of this Great Lake, offers an ideal launching point for sailors seeking both tranquility and excitement on the water. The True North stands out as an exceptional bareboat charter with three cabins, modern amenities, and advanced navigation gear, making it perfect for friends or family groups ready to take command of their own maritime journey.
Lake Superior is known for its dramatic shorelines, clear waters, and unique geological features—granite cliffs and ancient volcanic rock formations punctuate the landscape, while protected coves and islands provide quiet anchorages. Sailors can chart courses toward the Apostle Islands, where sandstone caves and sea arches invite kayaking and shore excursions. The lake’s cool, often brisk breezes demand attention and respect but reward skilled sailors with invigorating days on the water.
True North’s design balances comfort and performance, with ample below-deck living space that includes sleeping quarters and a functional galley, allowing multi-day trips with ease. Its modern instrumentation suits new sailors looking to navigate confidently in these vast inland seas. Bayfield itself is a hub for outdoor recreation and often considered the gateway to the Apostle Islands National Lakeshore, making this charter a unique way to combine sailing adventure with the natural and cultural highlights of northern Wisconsin.
Whether you seek a day trip to nearby islands or a longer journey tracing Lake Superior’s rugged shores, True North positions you to fully embrace the lake’s unparalleled character and challenge—a standout option for water-based adventure in the upper Midwest.
Route Schematic
Typical route schematic
The charter experience moves from marina departure into open‑water sailing and returns to a mooring or marina; plan for provisioning and responsible anchoring.
Portland departure
Board from the operator in Portland; complimentary boarding is available any time after 6:00 p.m. the night before your charter begins.
Open‑water sailing
Sail aboard the 40' Jeanneau using the furling mainsail and headsail with onboard navigation systems guiding your passages.
Anchorage or return to marina
Operate to a chosen mooring or return to the marina at the end of your charter; note that camping on islands while chartering is not permitted.
Skipper and crew should be prepared to handle a vessel of this size; the operator will review your boating resume and may require evidence of recent experience or certification before allowing bareboat operation.
What the day feels like
What this charter feels like
A bareboat charter aboard True North feels like having your own floating base camp: expansive cockpit and furling sails for straightforward sail handling, a compact but capable galley for onboard meals, and cabins that allow a mixed crew to rest between watches and day trips.
THE BOAT
Spacious cruising platform with three cabins
At just over 40 feet, True North sleeps eight across three cabins with two heads, a full galley and an independent heater — the layout is built to keep a cruising crew comfortable for multi‑day trips.
THE GEAR
Galley, deck systems and safety already aboard
The boat comes fitted with a top‑load refrigerator, microwave, two‑burner propane stove and oven, LP BBQ grill, electric windlass and required U.S. Coast Guard safety gear — everything required to provision and cruise without major extras.
THE NAV
Modern navigation and autopilot for confident passage making
Electronics include depth sounder, knotmeter, GPS radar plotter and autopilot — tools that make single‑skipper or shorthanded passages more manageable on open water.
Suitability
Who it's for
Who this boat and charter are best for — and who should think twice.
Practical planner
Details to review before reserving
Pack soft luggage only: sleeping bags, pillows and towels (linens not provided), warm clothing, rain gear, sunscreen, non‑marking deck shoes, motion‑sickness remedies and food/seasonings/drinking water. The operator supplies a complimentary consumable kit and required safety gear.
Complimentary boarding is available any time after 6:00 p.m. the night before your charter begins; boats do not come with linens, towels or food seasonings.
Bring your own food and soft coolers only; tents, kayaks and hard coolers are not allowed onboard while chartering. Smoking is not permitted.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
Are bed linens and towels provided?
No. Boats are not equipped with bed linens or towels; guests must bring sleeping bags, pillows and towels.
What time can I board the boat before my charter?
Complimentary boarding is available any time after 6:00 p.m. the night before your charter begins.
What qualifications do I need to be the skipper?
To qualify as skipper you should have recent charter experience aboard a similar vessel, ownership of a similar boat, or completion of a qualified charter certification program; the operator requests a boating resume to determine skill level.
Can I bring my pet or a hard cooler?
No. Pets are not allowed and only soft‑sided coolers are permitted onboard while sailing; hard coolers are prohibited.
Is smoking allowed onboard?
No. Smoking is not allowed on the vessel.
What safety and navigation equipment is on board?
The boat is equipped with required U.S. Coast Guard safety gear, depth sounder, knotmeter, GPS radar plotter and autopilot.
How this guide was prepared
This field guide is synthesized using verified supplier specifications, route descriptions, and destination data. Some booking links may generate affiliate revenue for ADV Guides.
- Verified: 2026-08-26T20:28:41.295Z
Some booking links may generate revenue for ADV Guides or The Adventure Collective.
Availability, pricing, schedules and operating details can change.
Trip details and contextual sources were reviewed by ADV Guides Editorial.