GETAWAYS
Apostle Islands National Lakeshore
Bayfield, WI
Aug. 10-14, 2026
Aug. 10-14, 2026
5-days
$1,625.00
Difficulty rating
Discover the stunning Apostle Islands, nestled in the waters of Lake Superior along the north shore of Wisconsin, right by the quaint town of Bayfield. This beautiful archipelago, made up of 22 islands, has been masterfully carved by the endless motion of the sea, and we get the chance to explore them up close by paddling our sea kayaks. This pristine and wild area is home to bald eagles, black bears, and abundant orchards. Every day you’ll have opportunities to be on the water paddling, sailing, or even jumping into the refreshing lake itself! Come join us on this adventure that will truly feel like you’ve discovered your own little slice of paradise.
Kayak through sea caves along the coastline of the remote and mysterious Devil’s Island.
Hike Lake Superior’s shoreline’s towering cliffs, rugged rock outcroppings and verdant forests at Big Bay State Park.
Explore Madeline Island via moped or bicycle
Optional Sailing among the Apostle Islands via True North Sailing.
Optional additional kayaking the Meyer’s caves from mainland.
Stargaze from a beach campfire
Pick fresh blueberries
A room with a gorgeous view of Lake Superior & walking distance to local shops.
Group size is limited to 10 or 12 participants plus 2 guides. Depending upon room choices.
Registration Cost
Included in booking:
2 Guides throughout the Getaway.
4 nights of “Double Accomodation” at the Pier Plaza with a room overlooking Lake Superior. (only 2 singles available for additional $450 upgrade)
5 hour Apostle Island adventure aboard the Kayak Express, for a 1.5 hour paddle. Refunds given for inclement weather.
Guided hike on Madeline Island and ferry costs to the island.
Dinner on the lawn during the “Concert on the Park”.
Beach bonfire, s’mores, and star gazing.
Services to reserve optional sailing or additional kayaking at Meyer’s Caves.
Electronic booklet full of area information, maps, detailed itinerary & more.
Park entrance fees and permits.
Amazing memories, friendships, and bragging rights.
Photos from your Getaway
Not included:
All meals, excpet one dinner is provided.
Cost of optional activities:
Sailing, 2.25 hour ($90.00)
Kayak from the mainland, 2.5 hour ($90.00)
Sip and paint ($40.00)
Single room accomodation fee ($375.00 at first come basis)
Pay a $400 deposit now to secure your registration. An invoice for $1,225.00 will be sent to you in June.
A $400 deposit will not be refunded if you cancel within 60 days of the trip, unless there's a waiting list, and someone to take your place.
Lodging details:
Trailbound has secured your accommodation at the Pier Plaza Inn in Bayfield, WI.
Bayfield is a quaint town tucked between the vast blue of Lake Superior and rolling, fruit-laden orchards. Voted a Top 10 Coastal Town by USA Today readers and proudly nicknamed the Berry Capital of Wisconsin, Bayfield blends small-town charm with big, wild waterviews.
Your reservation includes a room for double occupancy with a deck and lake view. Should you prefer a single room, please let us know, and we will invoice you for an additonal fee of $375.00. Only two single rooms available, and released on a first come basis.
Pier Plaza Lodge
15 Front Street, Bayfield, WI 54814
(715) 779-3330
What to Bring:
A full Packing list will be sent to registered individuals.
Main items:
Day pack - water bottle
Hiking boots
Swimsuit - Towel
Sunglasses
Watershoes
Hiking clothes and evening casual clothes.
Transportation
Bayfield is approximately 7 hours from Palatine, IL.
We will share registration names and phone numbers for those seeking to carpool to Bayfield.
DAY 1
Check into PierPlaza Hotel and get settled in room. Each room with incredible lake views and with walking access to town and the lakeshore.
Meet us at the Roof top bar and restaurant at the Bayfield Inn. We will be looking for you there, located right across the street from our hotel. The prefect setting to start our trip overlooking Lake Superior!
Relax and dine at one of Bayfield’s most popular restaurants, the Bayfield Inn.
DAY 2
Apostle Island Exploration!
We board the Kayak Express, a 50-foot boat that comfortably whisks us out to the outer archipelago’s breathtaking, remote Devil’s Island. Famous for its unusual carvings and sea caves carved into billion-year-old sandstone, Devil’s Island is a paddler’s paradise.
From the boat we launch tandem kayaks—no experience necessary—and spend about 1.5 hours paddling along and through these spectacular caves. The full outing is 4–5 hours and includes safety instruction, guided paddling, and time to explore. Restrooms are available aboard the Kayak Express.
*Lake Superior is know to have unexpected high winds and bad weather. Sometimes, due to safety, an alternative island is chosen, or trip could be cancelled. Safety is always the highest priority.
Dinner , picnic style, as we enjoy the “Concert in the park” on the shores of Lake Superior. Dinner will be catered from Manypenny Bistro, Tripadvisor’s #1 restaurant in Bayfield.
Commraderie continues with a walk along the harbors to admire the yachts and sailboats or getting ice cream from local shops.
DAY 3
Explore Madeline Island
We begin with a 20 minute car ferry to Madeline Island, ranked by Smarter Travel as one of the world’s 10 most secret islands.
Hike Lake Superior shoreline’s towering cliffs, rugged rock outcrops and verdant forests at Big Bay State Park. For mushroom lovers, this park has a great variety to explore. Enjoy lunch on the trail, and if you dare, take a chilly dip in the water.
Enjoy a few hours of free time on the island to either rent a moped or bike, go paddle boarding, explore the little town of La Pointe, or rest a the beach at Big Bay State Park.
Take the ferry back to Bayfield, savoring the wide open water views one more time while breathing in the cool clean air.
Dinner at Hoops for the freshest whitefish in town! Casual dining on the dock for more amazing water views!
Optional craft night in town, to sip and paint yourself a souvenir.
Sail Superior: Sail amoung the Apostle Islands, ranked by Sail magazine as sone of the country’s 10 best sailing spots. Board Ture North’s sailing charter for a 2 hour cruise. You can help hoist the sails, or sit back and relax as the captain navigates through the islands. Additional $90.00
Kayak Meyer’s Caves: For those who truly love kayaking, reserve another trip, this time from the shores of the nearby town Cornucopia, which is more protected from the winds, and less likely to have a cancellation due to weather. Meyer’s caves is a 2.5 hour paddle, and has the biggest caves off the mainland. Additional $90.00
Take a short hike: follow a gurgling creek through the woodlands to a cascading waterfall. We wil also peek at some old fishing boats in Cornucopia.
Visit Bayfield’s quaint shops: Feel the midwest coastal charm with all the unique shops and no “big box stores”. Approximately 70% of all the shops are women owned and operated.
Bike or Hike the Brownstone Trail: Bring your own bike, or rent one, to bike along Lake Superior for 5 miles.
Head back to Madeline Island: to do adventures that you missed yesterday.
Enjoy a great book on your private deck
DAY 4 - Choose your Adventure!
Blueberry picking: Truly a treat to pick fresh blueberries at the height of freshness. Bayfield boasts of the “Fruit Loop”, allowing you to visit 13 differnt orchards. Known as the berry capital of Wisconsin, these orchards also include wineries and ciders.
Dinner at the “Good Thyme”. A meticulously restored 125-year-old yellow house that serves extraordinary meals from local sources with homemade sauces, marinades and desserts.
Listen to the waves lap the shore at Bayview Beach as we enjoy the glow and warmth of a beach bonfire. With our new friendships, enjoy our last night with s’mores and star gazing away from the city lights.
DAY 5
Depart at your leisure back home.
On your car ride back, your heart will be refreshed with new friendships, a sense of accomplishment, amazing stories, and laughter.
Guides:
Kari McLennan: Aka, “ Mucky Duck”
Karen Pogalz: Aka, “ Cairn”
Cancellations & Refunds
You may cancel your Getaway to the Apostle Islands Adventure for a full refund if made 60 days in advance.
If you cancel less than 60 days, a refund will be made if your spot can be filled from a wait list.
Please consider purchasing travel insurance from Travel Guard, Allianz, or company of your choice.
**Some itinerary changes may be made due to weather. Lake Superior is known for sudden changes in weather, so safety will be our prime concern while on the water.