Pike's Peak CO
Milwaukee Bastille Days
Mississippi Valley
Lake Michigan, Shorewood WI
Maine Coast


Authentic People         Hidden Gems         Unforgettable Experiences

Travel Your Way


Our passion at Deep Travels America is crafting unique and memorable road trip experiences for travellers like you. 

We specialize in the road less travelled and diving deep to find the unique places and people that will interest you most.


Our services range from creating custom itineraries tailored to your group to serving as experienced tour guides and traveling companions who will take care of everything while you relax and enjoy some of the best North America has to offer!

Let's start planning! FREE 15-minute consultation:
Custom-crafted trip itineraries
starting at 

per day

Whether it is cultural or historical tourism, enjoying America's natural wonders, or exploring this continent's great cities, our team will work with you to craft a unique vacation tailored to you. 


We are happy to accomodate the needs of groups with children, elderly and disabled patrons.  Learn more

Every Group is Different so Every Trip is Customized.

  • Custom itineraries based on your interests.

  • For groups of up to five people.

  • Travel in the vehicle of your choosing.

  • Accommodations in quality hotels and Airbnbs.

  • Do the trip yourself or have your travelling companion guide do the driving and handle all of the logistics.
    Learn more

How It Works

What Are You Planning?

Let's turn your ideas into fun,memorable experiences for you and your traveling companions! Sign up for your free 15-minute trip planning consultation today. 

COVID-19 UPDATE (July 2021)

Thanks to the COVID-19 vaccinations currently underway in the United States, we are optimistic that we will be able to resume full operations in 2021. Until then:

  • It's never too early to plan! Contact us to create your custom itinerary.

  • Travel companion trips can resume for fully vaccinated parties. Proof of vaccination is required.

  • Current reservations will be rescheduled as soon as possible. 

  • Trips will resume when permitted by all relevant federal, state, provincial and local authorities.

Short Trips from Milwaukee, WI

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Day Trip 

Discover Milwaukee's rich history and sample some of its unique cultural offerings and local oddities.

Day Tour of
Quirky Milwaukee

Travelling Companion Guided Tour

(up to 4 people)

Day Trip

Experience Madison, Frank Lloyd Wright's Taliesin and visit New Glarus, a unique Swiss enclave in the beautiful Wisconsin countryside.

Taliesin and 
Rural WI 

Travelling Companion Guided Tour

(up to 4 people)


 2 Days

Visit Wisconsin's famed Door County peninsula and enjoy its unique atmosphere, vibrant arts scene and beautiful scenery.

Wisconsin's Door County

Travelling Companion Guided Tour

(up to 4 people)

Long Distance Adventures


Exploring the Upper Mississippi

12 Days

Travel from the headwaters of the mighty Mississippi in northern Minnesota to Memphis, TN.

Itineraries start at

$50 per day

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Around the
Great Lakes

2 Weeks

Discover extraordinary cities and natural wonders in this loop from Chicago, IL  through Wisconsin, Minnesota, Ontario, Quebec, New York, Ohio, and Indiana.

Itineraries start at

$50 per day

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New France

3 Weeks

Explore the vestiges of New France and its enduring cultural legacy on an amazing historical trip from Quebec,QC to New Orleans, LA.

Itineraries start at

$50 per day


On the Trail
of the Blues

2 Weeks

Follow the birth of the Blues in the Mississippi Delta to Memphis, TN and its northward migration to Chicago, IL. 

Itineraries start at

$50 per day


3 Weeks

Travel the spine of the Rockies from Banff, AB to northern New Mexico and explore the stunning landscapes and rich history of the Wild West.

Itineraries start at

$50 per day


Wonders of
Northwest Coast

2 Weeks

Take an incredible journey through the natural wonders of the West Coast from Seattle WA to San Francisco, CA.

Itineraries start at

$50 per day