Itineraries | Visit Southwest Michigan

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How to Spend A Holiday Weekend in Southwest Michigan with Lydia Knoll

This itinerary makes a fun-filled day in Southwest Michigan, visiting multiple wineries and breweries.

Nov 28, 2025
Wedding Guest Itinerary

In town for a wedding? Fill your spare time with local favorites — beach time, golfing, wine tasting, great food and more in Southwest Michigan.

Oct 27, 2025
Makers Trail Fall Itinerary

Spend a weekend on the Makers Trail with tastings, hikes and fall views in St. Joseph, Benton Harbor and beyond.

Oct 6, 2025
3 Days of Family Fun with the Midwest Nomad Family

Plan a fun-filled family getaway to St. Joseph, Michigan with this 3-day itinerary featuring beaches, kids’ museums, downtown shopping, outdoor adventures and more.

Aug 19, 2025
The Perfect Summer Getaway: 3 Days in Southwest Michigan with Rachel Kawate

Follow along with Chicago Travel & Lifestyle content creator, Rachel Kawate on her 3-day summer visit to Southwest Michigan.

Jun 2, 2025
Play the Best Golf Courses in Southwest Michigan

This two-day Southwest Michigan Golf Itinerary introduces you to exciting courses, delicious libations, regional foods and fun times with friends.

Sep 12, 2024
Nature and Winery Adventure in Southwest Michigan

Spend a romantic afternoon and evening with your significant other in the gorgeous lakeside town of St. Joseph and the surrounding area.

May 6, 2024
St. Joseph & Benton Harbor For Couples

Spend a lovely spring day in St. Joseph and Benton Harbor with your significant other with this 1-day itinerary.

May 2, 2024
A Day of Nature, Mural Art and Craft Brews in Southwest Michigan

A full spring day in Southwest Michigan with Travel & Lifestyle content creator Laurel Wilson.

Mar 6, 2024
Girls Weekend Getaways

Treat yourself to a girls weekend getaway with your closest friends in beautiful Southwest Michigan. Enjoy good food, drinks, shops and company.

May 9, 2023
Fresh Air Fun in Southwest Michigan

Find fresh air fun in Southwest Michigan with this self-guided, three-day itinerary that gets you outside on an adventure!

May 3, 2023
Cannabis & Nature Itinerary

Visit Southwest Michigan to explore recreational cannabis paired with unmatched nature hikes, botanical gardens, beach views and more! Relax here.

Apr 30, 2023
History & Architecture Tour in Southwest Michigan

This self-guided history & architecture tour in Southwest Michigan teaches you about our region’s past, present and future with fascinating exhibits.

Apr 24, 2023
Spring Blossom Itinerary

Explore the beautiful colors on our spring blossom tour and indulge in delicious wines, ciders and smells of the season.

Mar 20, 2023
Southwest Michigan Self-Guided Brewery Tour

Set out on this two-day, self-guided brewery tour to taste the best pints in Southwest Michigan.

Mar 14, 2023
Empty Nester Activities

It’s time for mom and dad to vacation without the kids. These empty nester activities are bound to be so much fun, your children will be jealous!

Feb 25, 2023
Arts & Food Tour

Spend a day exploring the arts and food of Southwest Michigan on this self-guided, two-day tour full of inspiration!

Feb 1, 2023
Romance & Cultural Tour in Southwest Michigan

Get away together with this romance & cultural tour in Southwest Michigan! Reignite the spark and make new memories with your love.

Dec 14, 2022
Dog friendly fun

Take this self-guided dog friendly tour with your pup for a Southwest Michigan vacation you will both enjoy!

Nov 30, 2022
Heritage Tour in Southwest Michigan

Take this self-guided Heritage Tour to Southwest Michigan for a blast into our region’s past!

Sep 27, 2022
Fall Color Itineraries in Southwest Michigan

Follow these fall color tours in Southwest Michigan to see our beautiful leaves changing, savor seasonal eats and hike under the leaf canopies.

Sep 22, 2022
Lakeshore Art Tours

Take the lakeshore art tours to witness the best local and regional talent on display, then create your own art to take home.

May 23, 2022
Family Fun Trip in Southwest Michigan

Enjoy this self-guided family fun trip in Southwest Michigan. It has something for all ages of your crew!

Apr 21, 2022
Creators & Makers Trip

Witness our talented creators and makers as you go behind the scenes to watch them at work, taste their craft beverages and absorb their creative arts.

Apr 8, 2022
Wine & Chocolate Tour

Pack your sweet tooth for this wine and chocolate tour exploring award-winning creations and delicious chocolate treats.

May 27, 2021

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