How to Plan the Best Girl’s Road Trip

I recently went to a creative retreat and part of it involved a fun girl’s road trip. Spending time in the car with a good friend can be the best thing for the soul.

You too can have the experience of a lifetime. Pack up your car and hit the open road with your friend(s).

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Planning Your Itinerary

While we were on a mission to get from Chicago to Dallas, your summer road trip could be planned for just about anywhere.

It’s a good idea to decide how many days you want to be gone before you plan your trip. 400-600 miles a day is a good goal depending on the stops you want to make along the way. You should also buffer in some time for those gift shops or antique stores you just can’t pass up.

Depending on where you live and what you want to see, you might be looking a flying to your starting point and renting a car for your trip.

Some suggestions:

  • The East Coast
    • New England, New Hampshire, Vermont, Maine
    • New York City
    • Boston, Cape Cod, Martha’s Vineyard, Nantucket
    • Washington DC, Virginia, North Carolina,
    • South Carolina, Georgia, Florida,
The Bilmore Mansion in North Carolina
Photo Credit Stephanie Klepacki

The East Coast is steeped in history. Whether you’re looking for great beaches, meandering off the beaten path through small towns, taking a Historic tour, or enjoying the bright lights of Broadway and nightlife of the Big City; the sky’s the limit on the East Coast.

  • The West Coast
    • Southern California – San Diego, Los Angeles, Santa Barbara
    • Northern California – Napa Valley, San Fransisco,
    • Pacific Northwest – Oregon, Washington State

There is so much to see in California and you could take days discovering each city. Driving the Pacific Coast Highway should be a bucket list for everyone and some of the most beautiful beaches are on the Pacific Ocean. Santa Barbara and Napa Valley are my two favorite places in California.

Highway in the Pacific Northwest
Photo Credit Joe Gardner

While I’ve never been to Washington State or Oregon, I’ve always wanted to go. When you see beautiful gardens in magazines, they are almost always in the Pacific Northwest.

Holy Hill Basilica in Wisconsin
Holy Hill Basilica in Hubertus Wisconsin
  • The Midwest
    • Michigan – Lake Michigan Shore, Mackinaw Island
    • Wisconsin – Door County, Milwaukee, North Woods of Wisconsin
    • Upper Midwest – Minnesota, the Dakotas, Montana, Wyoming

Living in northern Illinois, Michigan, and Wisconsin are my stomping grounds and great places to go for a quick weekend road trip. Mackinaw Island is a trip back in time. while Door County and the North Woods is a way to slow life down and just wile away the days.

A trip I went on with my parents several times was to the upper Midwest. It’s not just for kids. This would be a fun trip if you wanted to do some glamping. Imagine how much fun it would be to stay at a dude ranch and enjoy horseback riding, hiking, and all things outdoors.

Photo in Wyoming
Photo Credit Bryn Gibson

There is a lot of history and mother nature to be found in the upper Midwest.

  • The South
    • Tennessee, Mississippi, Louisiana
    • Texas, New Mexico, Arizona

A fun couples road trip that I went on with “Handy” and another couple was when we headed south through Memphis Tennessee and then skirted the Mississippi River down to New Orleans. We saw a lot of Civil War History. We stayed in Antebellum Plantations and enjoyed all the amazing food and nightlife of New Orleans.

A great trip starting in San Antonio, passing through Austin, Waco, and on to Dallas would round out some of the Texas highlights. Then a drive through New Mexico, with the Grand Canyon in Arizona as your final destination. That would make a great southwest road trip.

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Planning Your Budget

When you’re planning your budget you’ll need to take into account the following:

  • Cost of Gas and Vehicles miles per gallon
  • Lodging (Hotels are great for quick overnight stays but Airbnb or Vrbo are great home-away-from-home ideas for extended stays with friends)
  • Meals (You’ll need to budget for meals in a restaurant unless you are staying in a home rental where you can prepare some of your meals)
  • Entertainment (Tickets, Entrance Fees, Shopping etc)
Our Hostess Michele Howell from @vintagehomedesigns

Prepping to Go

Before you leave on a road trip some things need to be done ahead of time.

  • Make any necessary reservations (lodging, attractions, etc)
  • Have your mechanic give your car a once over. It won’t guarantee that there might not be issues but it’s a great piece of mind knowing things should be fine.
  • Make sure your car has some basic necessities stowed away.
    • Jumper Cables
    • Umbrella
    • Current Map
    • Flash Light
    • Garbage Bag
    • Snacks and Bottled Water
  • Create a packing list based on your road trip activities. Purchase any items that you might need.
  • Instructions for house or pet sitters.

You might consider joining AAA (Triple A) as a safety net for unseen vehicle emergencies.

I also had my car detailed before I left so it was clean and shiny for my travel companions.

What’s in My Car

Car Fun

While you will probably enjoy the drive while chatting and fixing the problems of the world, you might also want to plan some fun things to do in the car.

  • Listen to Podcasts
  • Listen to an Audiobook
  • I’m a huge fan of the license plate game
  • Have a Road Trip Playlist for added fun.

If you’re a friend of Living Large in A Small House, you have access to my FREE Resource Library.

NEW in the Library is my Road Trip Playlist!!

It’s also fun to plan some stops along the way so you don’t always have full days of driving.

Elkhorn, Wisconsin Flea Market

Car Trip Rules for a Long Drive

  • Make sure you plan out your gas situation so you’re always sure to have enough fuel to make it to the next stop.
  • Don’t make gas stations your only stop. Rest stops are great places to stop to use the bathrooms or just to walk around a bit and stretch your legs.
  • Switch out drivers. Let everyone take a turn at driving.
World's Largest Truck Stop in Iowa

Road Trippin’ Isn’t Just for Girls

While a great road trip with your friends can be so much fun, so can a couples road trip with your spouse or partner. “Handy” and I love to take a long weekend to Door County in the winter. Snuggling up in front of a wood fire at a romantic Airbnb isn’t just for kids!

Wisconsin in the Fall

Best Time to Travel

Obviously, the warmer months are the best time to travel so you don’t risk bad weather. July is the most popular vacation month so be prepared for traffic and things to be crowded.

A beautiful time to travel the northern states is in the fall. Fall in New England, Upper Midwest, or Wine Country in the West is simply breathtaking.

No matter when or where you plan your trip, be sure to have a great time.

Peace and Love,

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All of my friends who were on our girl’s retreat are writing about different aspects of our trip today.

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WELCOME

Meet Me


After years in corporate America, I’ve channeled my interior design degree and passionate creativity into transforming our 1,300 square foot house into a cozy, inviting haven that proves beautiful living doesn’t require massive square footage.

My slight OCD tendencies fuel my love for organizing while my “Handy” husband helps bring my vintage-inspired decorating visions to life in our empty nest, where we entertain, garden, and cook from scratch.

Join me as I share practical wisdom, genuine humor, and professional insights for making the most of every square inch—because I’ve discovered that living large isn’t about the size of your home but how you fill it with style, function, and heart.

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A dark blue background with a subtle, wavy abstract line pattern running across the center, reminiscent of the flowing creativity often found when living large in a small house.
A dark blue background with a subtle, wavy abstract line pattern running across the center, reminiscent of the flowing creativity often found when living large in a small house.
A dark blue background with a subtle, wavy abstract line pattern running across the center, reminiscent of the flowing creativity often found when living large in a small house.

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6 Comments

  1. Love all these suggestions! But where are Thelma & Louise? Thought we’d get a glimpse of them.
    Thanks for the playlist–I’ll be firing that up soon I hope!
    Brings back great memories of our TX – KC leg..

    1. I gave a sneak peek of the two of us right in the beginning. You and I never got photos of us on the way home!

  2. You two are a hoot! I love that you got to road trip together! What an amazing week!!! I love all of your road trip tips! I love a good road trip!

  3. Wendy McMonigle says:

    Lynn, this was undoubtedly one of my favorite trips! Nothing could beat spending time in the car with your girlfriends. Your other road trip suggestions sound amazing. I think I see a West Coast trip in the future soon. I miss you friend and our sweet chats along the highways.

  4. Michele - vintage home designs says:

    There are SO many great road trip suggestions here! This makes me want to pack up the car right now and hit the road out of this Texas heat!!

    So glad you road tripped to Texas for our amazing retreat week!

  5. Great tips Lynn! I especially love the idea of a playlist for a road trip! I’m partial to your East Coast suggestions since I’m from Delaware. The East Coast is full of historical places to see! It was great to spend time together with everyone and work during the retreat! Great post!