Bloody Marys, Boutique Shops, and Breathtaking Views
If you’re dreaming of a girls weekend that’s equal parts scenic, spirited, and soul-refreshing, let us introduce you to the magic of Door County, Wisconsin. Here’s an itinerary for an unforgettable Girls Weekend Getaway, to keep your crew smiling from start to finish. Don’t miss our insider tips to help you plan your own adventure!
Day 1
Bloody Marys to Kick Things Off
No road trip starts without a good brunch beverage, right? Make a pit stop at Kitty O’Reilly’s Irish Pub where the Loaded Bloody Mary is next-level delicious (think mozzarella whips, beef stick, pickle, and more)!
Lunch in Sturgeon Bay
It’s always great to grab lunch at Sonny’s in Sturgeon Bay. Located right on the water with a huge menu and relaxing views, it’s the perfect way to ease into vacation mode. We also like to hit up Bridge Up Brewing Company in the lower level.
Cave Point County Park
Before heading too far north, we always stop to take in the sights at Cave Point County Park. Trust us, the dramatic cliffs, turquoise water, and crashing waves are must-see. We recommend doing this stop on your way in or out of the peninsula since it’s toward the southern end.
Scenic Waterfront Drive
Door County is known for its shoreline beauty, so we took our time cruising up the coast. Windows down, music up, soaking in the lake breeze—it’s all a part of the magic.
Sunset Dinner at The Shoreline
Always a trip highlight: dinner at The Shoreline in Gills Rock. Come for the food and drinks, stay for the best sunset view in Door County. This place knows how to set the mood.
Day 2
Lunch at Husby’s
After morning coffee and a slow start at the cottage, grab a small bite and celebratory cocktails at Husby’s, a go-to spot in Sister Bay with a fun, welcoming vibe. *Tip: be sure to also visit their Garage Bar for outdoor drinks and live musics on most nights.
Thrift Shopping
You can’t beat the thrill of a good find. Some of our favorite spots are; Summer Camp Antiques, Bargains Unlimited, Secondhand Sue’s, Reclaimed Resale and The Simple Solution – all packed with quirky, cute, and budget-friendly treasures.
Cards and Cocktails at Stabbur
A nice mid-day break is to stroll along the Sister Bay Beach and then stop at Stabbur Beer Garden, it’s a great spot play some cards or bean bags, sip local brews, and just enjoyed each other’s company. *Two Tips: The Swedish Sangria is really good and the outdoor kitchen has a great menu, especially if you want fast service.
Skip the Island? Try Pebble Beach
If a Washington Island day trip doesn’t fit into your schedule, Pebble Beach in Sister Bay is a convenient and comparable alternative. It’s quiet, scenic, and great for skipping rocks or just relaxing.
Cottage Time = Relaxation Time
Make sure to carve out time to just be. Cozy cottages are part of the Door County charm, and ours give us the perfect place to laugh, nap, recharge, and enjoy late-night card games.
Dinner at Sister Bay Bowl
For a true taste of Wisconsin, Sister Bay Bowl delivers. Their Friday Fish Fry and Old Fashioneds are iconic—don’t leave Door County without trying both. *Tip: If you’re feeling up for it, they also have an old school bowling alley where you still have to hand score your games.
Day 3
Brunch it Up
Blue Bear in Ellison Bay is the best spot to enjoy a delicious brunch to start your day. Whether you’re looking for savory or sweet, they have it all and don’t forget to try one of their great coffee or cocktail drinks.
Leave Your Mark at Anderson Dock
Join the longstanding tradition at Anderson Dock, where visitors paint their names on the historic dockside warehouse. Bring your own markers/paint and make it official!
Peninsula State Park Adventures
Spend a morning in Peninsula State Park, climbing Eagle Tower for sweeping views and visiting the Eagle Bluff Lighthouse for a peek into the past.
Lunch at Barringers
Next stop: Barringers in Fish Creek has a very fun outdoor dining space and the menu features the very best lobster roll. If you’re looking for a more casual spot, we also love Bayside Tavern.
Shopping in Fish Creek
Retail therapy is in full swing as you hit the shops in Fish Creek. From cute boutiques to artisanal finds, there’s something for every style and budget.
Cocktails at Hill Street
We highly recommend Hill Street in Fish Creek, especially their outdoor bar area. It’s a great little spot to unwind with a craft cocktail in hand. *Tip: they have the best Grilled Cheese I have ever tried.
Nature Walks at The Ridges Sanctuary
Take a break in nature and explore The Ridges Sanctuary in Baileys Harbor. It’s a serene and beautiful nature preserve, perfect for clearing your mind and connecting with nature. If you’re looking for a longer hike, we recommend Toft Point State Natural Area.
Beer & Live Music at Door County Brewing
We capped off the afternoon with craft beer and live music at Door County Brewing, another Baileys Harbor gem with a laid-back vibe and plenty of character.
Dinner at The Cleat
To end the weekend on a high note, we dined at the brand new restaurant in Sister Bay—The Cleat. Fantastic food, great atmosphere, and a fitting finale to a perfect trip.
Final Thoughts
Door County is the kind of place that wraps you up in its charm, feeds your soul, and brings friends even closer together. Whether you’re chasing sunsets, sipping cocktails, or thrift shopping your heart out, every moment feels like a memory in the making.
So pack your bags, gather your girls, and get ready for your own unforgettable weekend in Door County. 💕🍒🌅
