3-Day Bayfield, WI Itinerary: Kayaking, Wine, and Island Vibes
Bayfield, Wisconsin is a charming harbor town on the shores of Lake Superior, best known as the gateway to the Apostle Islands and Madeline Island. With its quaint downtown, stunning lake views, and one-of-a-kind local spots, it’s the perfect escape for those seeking nature, food, and a little adventure.
This Bayfield, WI itinerary is based on two visits we made, and combines the best of both trips into a 3-day guide you can follow loosely or make your own. Whether you decide to kayak the sea caves, hop on the ferry to explore Madeline Island, or sip cider and wine at a family run orchard/winery, Bayfield is a destination you’ll want to return to again and again.
Bayfield, WI Itinerary Overview
Escape to Bayfield, WI for a charming 3-day getaway filled with kayaking the Apostle Islands, sipping wine, and exploring Madeline Island. This itinerary blends outdoor adventure, small-town charm, and great food, all set with the stunning backdrop of Lake Superior.
➡️ Trip Length: 3 Days, 2 Nights
➡️ Great For: Couples, solo-travelers, outdoor enthusiasts
➡️ Best Time to Visit: Late spring through early fall (especially during Bayfield in Bloom, the Festival of Arts, or Apple Fest)
➡️ Where We Stayed: Old Rittenhouse Inn
➡️ Must-Do Activities: Kayaking the Apostle Islands, visiting Madeline Island, Bayfield Winery & Blue Ox Cider
➡️ Food Highlights: Good Thyme Restaurant, The Fat Radish
Day 1: Getting There + Madeline Island Adventure
Ease into your Bayfield adventure with a scenic drive along the North Shore before catching the ferry to Madeline Island. This day is all about laid-back island vibes, exploring by scooter, and a cozy night back on the mainland.
Morning
If you’re coming from the Twin Cities, stop for breakfast in Duluth around 8 AM. I recommend Duluth Grill or At Sara’s Table. It’s the perfect fuel for your road trip north.
Afternoon
Plan to arrive in Bayfield by 11:30 AM to catch the 12:00 PM Madeline Island Ferry. I don’t recommend taking your car across, instead, rent scooters from Motion to Go for a fun and breezy way to explore the island. Stop into the shops near the dock, or make your way out to Big Bay State Park for hiking and beach time.
Before heading back, grab a drink at Tom’s Burned Down Café, a must-see quirky bar made from the remnants of a building that literally burned down. It’s iconic and unforgettable.
Evening
Check in to the Old Rittenhouse Inn. We love the charm of this historic inn, and the included breakfast is a huge perk.
Dinner tonight is a quick 15-minute drive at The Fat Radish, a cozy local spot offering seasonal ingredients and creative dishes. Reservations are a good idea in high season.
Day 2: Kayaking the Apostles + Local Wine & Cider
Get ready for a day of adventure on the water followed by a relaxing afternoon at one of our favorite wineries in the area. You’ll wrap up the day with a memorable dinner in a charming, historic setting.
Morning
After breakfast at the inn, head to Lost Creek Adventures for your 10:00 AM kayaking tour of the Apostle Islands. They provide everything you need and transport you to the launch site. It’s a peaceful way to see the area’s famous sea caves and learn about local history from your guide.
Afternoon
Post-kayak, do a quick clothing change, and head to Bayfield Winery & Blue Ox Cider. This spot holds a special place in our hearts. We first visited in 2019 and met Phil, who, at the time, was running tastings and dreaming of launching his own cider line. When we returned in 2022, that dream had come true and he is now the proud owner.
They now offer live music, cheese & charcuterie plates, and dinners once a month. Don’t miss trying the Forager Cider or the Sparkling Brianna, they’re doing incredible things with low-intervention styles and modern blends.
Evening
Dinner tonight is at Good Thyme Restaurant. It’s set in an old house with a wraparound porch, and the cocktails are just as good as the food. Make a reservation if you can, they fill up fast.
Day 3: Coffee, Hiking, and the Scenic Route Home
Soak up your last morning in Bayfield with a peaceful trail walk and a great cup of coffee before hitting the road. If you have extra time, squeeze in a scenic hike or cruise to end the trip on a high note.
Morning
Before heading out, grab one last breakfast at the inn and check out by 10 AM.
Late Morning
Take a short stroll to the Iron Bridge Nature Trail, tucked right in town. It’s surprisingly expansive and a great way to stretch your legs before a travel day.
Pick up coffee from Wonderstate Coffee before hitting the road, it’s our go-to for something warm and delicious to sip on the way home.
Optional Add-Ons Before You Leave
- Houghton Falls or Meyers Beach: Both offer beautiful hikes just outside of Bayfield.
- Apostle Islands Cruise: If weather permits, it’s a relaxing way to see more of the area from the water.
- Duluth Pit Stop: Break up the drive home with one last stop in Duluth. We love stopping at Wild State Cider where there is usually a food truck, but don’t leave without getting an ice cream cone!
Where to Stay in Bayfield, WI
Bayfield offers a mix of cozy inns, lakeside rentals, and charming B&Bs, but our top pick is the historic Old Rittenhouse Inn.
🛏️ Old Rittenhouse Inn – Ideal for couples or those wanting an elegant, B&B-style experience with breakfast included. Conveniently located in the center of Bayfield.
🏕️ Big Bay State Park (Madeline Island) – Great for campers looking to stay on the island.
🏡 VRBO – There are plenty of charming rental properties and cabins nearby if you want something more secluded.
FAQs
Planning a trip to Bayfield comes with a few common questions, like when to visit, how to get to Madeline Island, and what to pack. Here are answers to help make your getaway smooth and stress-free.
- Is Bayfield dog-friendly?
Yes! Madeline Island and many hiking trails are dog-friendly, but be sure to double-check individual businesses and park rules. - Do I need to book the ferry in advance?
No, but it’s smart to check the schedule and arrive early in peak season. - What should I pack?
Layers (weather can vary), water shoes for kayaking, and a day bag for exploring the island. - Can I do Bayfield in a weekend?
Absolutely. This 3-day itinerary is designed for a long weekend and leaves plenty of room for customization.
Bayfield, WI Itinerary Final Thoughts
Bayfield has a magical mix of lake life, local charm, and unique adventures that make it a one-of-a-kind destination in Wisconsin. Whether you’re there for the kayaking, the cider, or the quirky cafés, you’ll find something to fall in love with by following this Bayfield, WI Itinerary.
Safe travels,
Jacki
Grab your free one-page itinerary below, as described in the post above—just drop your email and let the planning begin!