BAYFIELD SAILING FIELD GUIDE
Secret Caves & Windward Sailing: A Half-Day Discovery of the Apostle Islands
A 5.5-hour sailing outing from Bayfield with All Hands Sailing that tows an inflatable zodiac so you can swim, explore sandstone shorelines and small sea caves, and help sail back.
Secret Caves & Windward Sailing: A Half-Day Discovery of the Apostle Islands.
Adventure brief
Secret Caves & Windward Sailing: A Half-Day Discovery of the Apostle Islands
Turn away from busy lakeshores and into an archipelago of sheltered sandstone, where small sea caves, clear-water beaches and wind-swept sailings compose a single afternoon. On this 5.5-hour outing from Bayfield you’ll travel under sail to one of the protected Apostle Islands, anchor in a calm cove and deploy a zodiac dinghy for beach landings, shoreline exploration and optional swims before helping the crew sail back.
Experience a breathtaking 5.5-hour sailing journey with All Hands Sailing as you explore the Apostle Islands near Bayfield, Wisconsin. This private outdoor adventure takes you to hidden sea caves carved into stunning sandstone cliffs along Lake Superior’s pristine shoreline. Swim in the crystal-clear waters, relax on untouched beaches, and navigate the rugged coast in a zodiac dinghy for closer encounters with nature. Whether you're a seasoned sailor or a first-timer, the crew welcomes all skill levels and even offers the chance to assist with sailing back to Bayfield, adding a hands-on element to your trip. The Apostle Islands are renowned for their unique geological formations and rich natural beauty, making this experience a rare blend of excitement, tranquility, and discovery. Perfect for adventurers seeking a memorable day on the water surrounded by the wilderness of northern Wisconsin.
Route Schematic
Route Schematic
A typical outing sails from Bayfield to a protected Apostle Island, stages zodiac exploration at the shoreline and returns under sail.
Departure from Bayfield
Launch and sail out of Bayfield toward the Apostle Islands; the vessel heads to protected waters where the zodiac can be used.
Anchor Near an Island Cove
Weather permitting, the boat anchors in the protection of Basswood, Long, Oak or Hermit Island to stage shoreline exploration and beach landings.
Zodiac Exploration & Swim
The operator tows and deploys an inflatable zodiac dinghy to ferry guests to clear-water beaches, lake-carved sandstone shorelines and small sea caves; swimming is an option on warm days.
Sail Back to Bayfield
After time ashore, guests have the opportunity to help the crew sail the boat back to Bayfield, completing the 5.5-hour loop.
This trip is designed for people of all ability levels with an adventurous spirit; plans and exact island destinations are weather dependent and may change at the operator’s discretion.
What the day feels like
What the Afternoon Feels Like
Settle into sailboat motion for 5.5 hours as the vessel slips away from Bayfield and into the protection of the Apostle Islands. The crew anchors in a sheltered cove of Basswood, Long, Oak or Hermit (weather permitting) and lowers the zodiac for closeshore exploration—the rhythm alternating between calm swims and short, energetic outings in the dinghy, then a return to the boat where you can help trim sails for the passage back.
THE CAVES
Small, Secluded Sandstone Caves
Weather permitting, the trip anchors near one of the Apostle Islands so guests can visit smaller, uncrowded sea caves carved into the sandstone shorelines—private, intimate rock formations unlike the larger mainland attractions.
THE ZODIAC
Inflatable Dinghy Exploration and Beach Landings
The operator tows an inflatable zodiac so guests can be shuttled to surf-smoothed beaches and paddled around shorelines to explore clear-water coves and the lake-carved rock faces up close.
THE SAIL
A Hands-On Sail Back to Bayfield
After time ashore and optional swims, passengers have the chance to join the crew in sailing the boat back to Bayfield—an engaging end to a relaxed, adventure-forward half day on Lake Superior.
Suitability
Who it's for
Who this trip suits—and who should look elsewhere.
Practical planner
Details to review before reserving
Bring a cooler with food, drinks and utensils if you plan to picnic; passengers are welcome to use the boat’s galley during the trip.
The galley is available for guest use and you may bring snacks and beverages aboard; plan for sun protection and a change of clothes if you intend to swim.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is the trip?
The outing is 5.5 hours long.
When does this trip run?
Available Thursday through Saturday from 6/26–8/23 with morning and afternoon departures (example windows listed in the operator schedule).
Can I bring food or a picnic?
Yes—feel free to bring a cooler with food, drinks and utensils; the galley aboard is available for guest use.
Will there be swimming and beach time?
Yes—on warm days guests can swim and land on clear-water beaches accessed by the zodiac dinghy.
Do I need sailing experience?
No prior experience is required; the trip is suitable for people of all ability levels and offers the chance to help sail back if you wish.
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: 2026-08-10T12:58:07.951Z
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.