Winnetka
Day Plans

Make the most of your day with our curated plans, packed with Winnetka's hidden gems and unique experiences!

day 1

Relaxing Beach Day

morning

:

Start your day with a visit to the beautiful Winnetka Beaches. Enjoy a walk along the shoreline and take in the fresh lake air.

afternoon

:

Spend your afternoon sunbathing or engaging in water activities like paddleboarding or kayaking. Don't forget to grab a picnic lunch from a nearby café.

evening

:

As the sun sets, relax with a beach bonfire and toast some marshmallows. Enjoy the calming sound of the waves while watching the stars come out.

day 2

Nature Exploration

morning

:

Begin your morning at the Winnetka Botanical Garden where you can walk through beautiful flower displays. It's a perfect spot for nature lovers and photographers.

afternoon

:

In the afternoon, head to the nearby Skokie Lagoons for more outdoor adventures, including hiking or biking on the trails. Keep an eye out for local wildlife.

evening

:

Wind down your day with a quiet stroll through the Winnekta Park District at dusk. Enjoy the tranquility and perhaps catch a glimpse of the sunset.

day 3

Gourmet Food Tour

morning

:

Kick off your culinary adventure with breakfast at a local bakery. Savor freshly baked goods paired with a strong cup of coffee.

afternoon

:

Explore Winnetka's diverse dining scene during lunch, trying out different local restaurants. Each eatery offers unique flavors to delight your taste buds.

evening

:

Conclude your food tour with a fine dining experience at one of Winnetka's upscale restaurants. Pair your meal with an exquisite wine to enhance the flavors.

day 4

History and Culture

morning

:

Start your day at the Winnetka Historical Society, where you can learn about the town's rich history. The exhibits offer fascinating insights into local heritage.

afternoon

:

Visit the nearby Art Institute or local galleries to appreciate the artwork and culture of the area during the afternoon. Spend time exploring various artistic expressions.

evening

:

End your cultural day with a live performance at a local theater. Enjoy the talent on display while immersing yourself in the artistic vibe of the community.

day 5

Scenic Views and Relaxation

morning

:

Head out early to catch the sunrise at the lakefront. The serene views are a perfect start to your day.

afternoon

:

Spend a lazy afternoon by enjoying a book at one of the charming lakeside parks. Bring along a light snack and enjoy the peaceful environment.

evening

:

As evening approaches, consider a sunset cruise on Lake Michigan. Enjoy the breathtaking views while relishing a relaxing moment on the water.

day 6

Shopping Spree

morning

:

Begin your day by exploring Winnetka's local boutiques and shops. You'll find unique items and handcrafted goods that reflect the town's character.

afternoon

:

After shopping, enjoy lunch at a nearby café known for its cozy ambiance. Treat yourself to a delicious meal while taking a break from your shopping spree.

evening

:

Wrap up the day with a visit to the local farmers market in the evening, where you can sample local produce and homemade treats. It's a perfect way to embrace the community spirit.

day 7

Family Fun Day

morning

:

Kick off your family day at the Winnetka Community Center, where kids can enjoy various activities. The morning is filled with fun games and sports.

afternoon

:

In the afternoon, visit a local zoo or petting farm to engage the little ones with adorable animals. Pack a family-friendly picnic to enjoy in the park afterward.

evening

:

End the day with family-friendly entertainment such as bowling or mini-golf. Share laughs and create wonderful memories together.

day 8

Active Adventure Day

morning

:

Start your morning with a bike rental from a local shop. Explore the scenic paths in the area that offer breathtaking views.

afternoon

:

In the afternoon, consider a hike in nearby nature reserves. Rejuvenate your energy by enjoying a packed lunch surrounded by nature.

evening

:

As the sun begins to set, find a cozy spot to watch the sunset after your day of activities. Unwind with a light dinner at a casual local diner.

Discover Winnetka

Read more in our Winnetka 2024 Travel Guide.

Winnetka Travel Guide