What To Do While Staying At
The Bluff House

There are many wonderful things to do all time of year while staying at The Bluff House. Located in beautiful Rolling Bay, your rental property is centrally located to many activities for all ages. Check out these guides as examples of the kinds of adventures waiting for you!


9am – Take your morning coffee out to the deck… look at that view!

10:30am – Enjoy a mid-morning walk up to Rolling Bay. It’s a pleasant short walk, but it gives you chance to stretch your legs, breath in the fresh air and enjoy the trees.

11am – Pop your head into one of our oldest, most treasured shops on the island. Bay Hay and Feed is a fabulous store that includes a local food market, an extensive plant nursery, and many wonderful gift options for souvenirs. This is a great place to shop for your local eggs, diary, and wine!

2:30pm – Stroll back towards the house. Take a right on Manitou Beach Dr and walk towards the water. Manitou Beach welcomes you with one of the best views of the Seattle skyline the island has to offer! If it’s a clear day, you will also see Mt Rainier! You can sit on the bench to take in the view or walk farther down the beach to gain access to the sand. Low tide offers interesting exploration of tide pools. Bring your camera and be prepared for fun exploration!

5pm – Head back to the house for a family dinner, board games located in the guest room and great views of Puget Sound. Look for whales and eagles! Don’t feel like cooking? Order take out to be delivered at the house! Islandbite offers delivery for most all of our island restaurants. Check out their website for menus.

The Bluff House

Rolling Bay Hay and Feed

Manitou Beach


9am – Walk or drive to carly’s Rolling Bay Café for fresh brews and backed goods. Sharing the building with Bay Hay and Feed, you can sit outside or stroll among the beautiful plants of the nursery. Bay Hay doesn’t open until 10am, but this would be a great opportunity to pick up local delicacies for later today.

10am – Get back to the house to prepare for a picnic – remember to pack your layers and your sunscreen.

11am – Jump in your car and drive the three miles to Fay Bainbridge Park. The park is a locally operated public recreation area situation immediately south of the Point Monroe sandspit on the northeast tip of the island. With over 1400 feet of saltwater and sand shoreline, the park offers sweeping views of the Sound, the Cascade Mountain range. Be on the lookout for Mount Rainer and Mount Baker! Enjoy your choice of picnic tables for your relaxing picnic. There are volleyball courts and horseshoes for those athletically inclined, as well as a fabulous Pirate Ship play structure for the kids. Bring a chair for enjoying the sun while reading with your toes in the water- the kids can climb on the washed-up logs and driftwood. This is another great photo opportunity place!

5pm – Make your way back to the house to clean up and enjoy a wonderful dinner together. Light the firepit outside – and don’t forget the s’mores!

Fay Bainbridge Park


10am – Prepare a nice breakfast before you leave.

11am – Head over to Meadowmeer Golf Course for 9 holes of golf (reservations in advance available by phone or on-line). With plenty of personality and challenge at each hole, Meadowmeer is a well-maintained par 72 course that is always in great shape. Don’t have your clubs? You can rent them, along with a cart at the office.

3pm – Enjoy a burger and a drink at the Meadowmeer Grill. With a fantastic view of the 9th hole, the deck is a fabulous place to enjoy happy hour daily from 3-5pm for discounted drinks and food. They also offer lunch all days and dinner most days.

Not a golf fan? Grab any of the various sports courts at Battlepoint Park – tennis, soccer, softball, basketball, disc golf… even a rink for skating.  BYOB- bring your own ball!

6pm – In the mood for relaxing after your active day? Grab some popcorn and a drink and head into the Historic Lynwood Theater on the south end of the island. The theater specializes in showcasing independent and foreign films and has been open since 1936! Looking for new releases? Watch those at our pavilion off Madison Avenue closer to Downtown Winslow.


9am – Beat the weekend rush by popping in your car and heading over to the Streamliner Diner in Downtown Winslow. For over 20 years, the Streamliner is the place on the island for an amazing breakfast. Fresh pastries made daily, egg scrambles, pancakes and hot coffee. It’s the perfect way to start the day!

11am – That full belly will come in handy as you head back north to visit the world famous Bloedel Reserve. One of the best examples of Pacific Northwest beauty, and named one of the 10 Best Botanical Gardens in North America, Bloedel is 150 acres of curated gardens, structural features and distinctive landscapes. Enjoy the stunning Japanese Garden, the mysterious Moss Garden and the peaceful Bird Marsh.

3pm – How about some local culture? Head over to Downtown Winslow to enjoy the latest art exhibits at the Bainbridge Island Museum of Art. This contemporary art museum rotates exhibits every quarter and offers something for everyone. Visit their gift shop for souvenirs and gifts.

4pm – Ready for a little libation? Walk next door to Bainbridge Island Brewery’s Alehouse for a fresh pint. They serve up light snacks and peanuts to accompany your brew. Sit outside on the patio for the best people watching. Beer not your thing? Head next door to the tasting room of Fletcher Bay winery. If you’re lucky, their patio rooftop is open for great views of Eagle Harbor and Winslow!

6pm – Stroll down the street to the food scene of Downtown Winslow. Delight in some Vietnamese Asian Fusion at BaSa. Scissor cut your pizza at Pacific Northwest inspired pizza at Bruciato. Get your English fish and chips on at Proper Fish. Or scoot down to the waterfront at the end of Madison and enjoy some amazing views of Eagle Harbor over your bowl of famous clam chowder at Doc’s Marina Grill. Reservations are recommended for most places.


10am – Time to get our blood pumping! Take a hike through the beautiful Grand Forest. The Grand Forest encompasses 240 acres across three parcels, with 8 miles of trails and a beautiful lush hilltop that divides east from west.  With dense fir and cedar trees along mostly moderate walking trails, the Grand Forest is the jewel of hikes for Bainbridge Island – not to be missed!

Grand Forest

12pm – Drive into Winslow and grab a delicious lunch at Red Cedar Café. You can enjoy a cup of soup, a variety of salads or a delicious handcrafted sandwich while sitting under their bright umbrella tables on their patio. Or bring your food over the gazebo at the corner of Winslow Green for the best views of Downtown Winslow.

1:30pm – Walk or drive down to the other end of Winslow to Ericson Avenue to get to the Historical Museum. No island visit is complete without a visit to this 1908 schoolhouse packed with artifacts, photos and hands-on exhibits retelling the island’s past. Learn about the Japanese American Exclusion in WWII, the most product sawmill in the world, the mosquito fleet that served 30 small communities, the teen music scene and the invention of Pickleball!

Bainbridge Island Historical Museum

3pm – Complete your island history lesson by driving to the other side of Eagle Harbor to visit the Japanese American Exclusion Memorial. This sobering exhibit commemorates our island residents who were one of the first in the country to be asked to leave from their homes during World War II. With beautiful views of Eagle Harbor, the area is an opportunity for reflection and thought. Don’t miss neighboring Pritchard Park, which includes a beautiful beach for walking and great views of the ferries as they arrive and leave from the island!

5pm – Before heading back to the house, swing by the Town and Country market to pick up the makings for dinner. This delightful neighborhood market dates back to 1957 and offers local fresh food as well as your favorite national labels. Grab some fresh local salmon, chicken, steak and veggies.

5:45pm – Get that barbecue grill and the fire table lit for a cozy evening at the house. How about those Puget Sound views?!

Japanese American Exclusion Memorial


9am – Beat the weekend rush before the boat arrives by getting to Blackbird Bakery early. This quaint bakery offers craft coffee drinks, pastries and cakes (why not for breakfast? You’re on vacation!). They also offer hardier soups, breads and tarts. Enjoy a seat outside on Madrona Way under an umbrella table- it makes for excellent people watching.

10am – Check out the Bainbridge Island Farmer’s Market! Held Saturdays from 10am-2pm at the Town Square at City Hall, just walk up the hill from the bakery and you’re there. Enjoy all island grown food and flowers as well as local artisan crafts and treats. While you shop, you’re often serenaded by the music of local bands. This is a season event held for most of the year- check their website for schedules.

Bainbridge Island Farmer’s Market

11am – You’re still beating a lot of the ferry crowds if you hit Downtown Winslow in the morning for the various shops and galleries. There is so much to check out and many souvenir and gift ideas, too!

1pm – Head back north with your purchases from today and make a pit stop back home. Grab a sweater and a vessel for water.

1:30pm – It’s a good time to get that body moving again by taking a hike in Historic Port Madison. Pop back in the car and park on the shoulder of Euclid or on the corner of Hidden Cove and Phelps. This is an easy 2.1-mile walk. Get a feel for the historic bay by visualizing black canoes- visitors from the north. Can you imagine what it would have been like to inhabit the few houses that remain from the old milling days? The houses uphill from the water along Washington and Euclid were built in the early 1900s. You can extend this walk from the East Euclid part of the loop by flowing Lafayette east .2 miles to the historic Kane Cemetery, founded in 1860.

Port Madison

3:30pm – It’s time to head over to Rolling Bay Winery for an amazing tasting flight of wine! Meet winemaker Alphonse, your super friendly and knowledgeable winemaker, who will undoubtedly offer you a tour and a barrel tasting. Light snacks are available. The summer months often include outdoor tables and local musicians! Reservations in advance required. But don’t overindulge, because…

6pm – Time for dinner! Pop over to Via Rosa 11 Italian Market and Kitchen for a delicious and relaxed meal. Seating is available both indoor and outside on their patio. Order an incredibly fresh dinner at the counter: roasted vegetables, meatballs, salads, house made pastas of all kinds, soups and wood-fired pizzas. Your whole family will enjoy this incredible meal.


9am – Grab your layers, sunblock, sturdy footwear and a hat and drive into Winslow early to beat the crowds.  Park in front of the Winslow Mall to enjoy another delicious bakery stop, this time at Coquette! You will not be disappointed in their piping hot coffee and incredible selection of super fresh and delicious bakery selections. Think croissants of all kinds, muffins and tarts… amazing! Grab a table in the mall while you eat and enjoy the people watching and window shopping.

10am – Walk or drive down to the city dock at Waterfront park with your gear. It’s time for your Kayak rental with Exotic Aquatics! They offer rentals of kayaks for an all-day adventure on the water. Spy eagles, fish, sea lions and- if you’re lucky- whales! They provide all the equipment you’ll need for a day full of fun. They also provide tours and training for brand new kayakers. Book your reservations ahead of time.

Exotic Aquatics, Eagle Harbor

3pm – Enjoy a little more nature time by hopping in your car to head over to Halls Hill Lookout and Labyrinth. Based on the 13th Century French Chartres Cathedral labyrinth design, Halls Hill Labyrinth is a secret destination for visitors “in the know.” Garden designer and stone artist Jeff Bale created the intriguing mosaic using color, symbols, patterns, and numerology with stones found on Bainbridge Island beaches. It’s a perfect place to slow down, breathe, and quietly meditate. As you leave, embrace the energy and ring the bronze prayer wheel.

Hall Hill Labyrinth

Seasonal Activities


February, May, July & November