Explore the Apostle Islands: Unforgettable 3-Day Overnight Sailing Adventure
Difficulty
moderate
Duration
3 days
Fitness Level
Participants should be in good physical condition for light to moderate activity, including some standing, walking, and basic sailing tasks.
Overview
Sail through the Apostle Islands on a captivating 3-day overnight trip from Bayfield, Wisconsin. Experience rugged sandstone cliffs, hidden sea caves, and pristine wilderness aboard the classic schooner Dream Catcher Sailing.
Overnight Highlights – 3 Day Sail Trip
Complimentary boarding offered the evening PRIOR to your first day of sailing.
Select participants and date
Adventure Photos
About This Adventure
Embark on a unique multi-day sailing adventure where you can learn sailing skills tailored to your interests. Enjoy courtesy boarding the night before, explore stunning caves and beaches, and relax in serene anchorages. Each day offers opportunities for swimming and exploration, making this trip an unforgettable experience on the water.
On this trip, you can really get the feel of the boat with as much sailing instruction as you want. Learn sailing, seamanship, boat handling, navigation, and anchoring. The specifics of this multi-day sailing trip are worked out with your captain. Considerations include weather, your interests, and lake conditions.
Additional Information
With courtesy boarding the evening before the trip, you can sleep in the boat in the harbor the first night and walk to dinner and breakfast in town within a couple blocks of the boat. Depart Bayfield in the morning of the first day of sailing and several stops at caves, sand spits, pristine beaches, or lighthouses. At the end of each day, you will sleep aboard the boat in a quiet cove or one of many harbors in the Apostle Islands.
During each day of sailing, you might anchor in a calm, natural anchorage to enjoy the views, or play in the dinghy pulled behind the boat – explore caves or peaceful beaches. The last day might be spent sailing, swimming (in season), and exploring before returning to Bayfield by 3 p.m.
You will need to prepare for meals by bringing meals for your group and the Captain. Guidelines/suggestions are included with your confirmation. The galley will be available for all passengers.
Adventure Tips
Prepare for Variable Weather
Lake Superior’s weather can change rapidly; bring layered clothing and waterproof gear.
Book Early for Summer
Summer trips fill quickly—reserve your spot months in advance to secure dates.
Bring Motion Sickness Remedies
Open waters and shifting sails can cause seasickness; pack medications if you're prone.
Respect Wildlife Distance
Observe eagles and loons from afar to avoid disturbing their natural behaviors.
Local Insights
Wildlife
- Bald Eagles
- Common Loons
History
The Apostle Islands National Lakeshore protects over 20 islands known for their cultural history related to the Ojibwe people and 19th-century maritime trade.
Conservation
The trip operators prioritize low-impact sailing practices to protect fragile island ecosystems and Lake Superior’s water quality.
Select participants and date
Adventure Hotspots in Bayfield
Frequently Asked Questions
Recommended Gear
Waterproof Jacket
Protects against lake spray and sudden rain showers.
summer specific
Non-Slip Deck Shoes
Ensures safety on wet boat surfaces.
Warm Layers
spring specific
Sun Protection Kit
Sunglasses, hat, and sunscreen to shield from reflective sunlight on the water.
summer specific