This amazing journey from Texas to Maryland will take you from the banks of the San Antonio River to the bustling streets of Baltimore. As you travel across the country, you'll witness a stunning array of diverse landscapes. Rolling hills and verdant plains will give way to towering mountains and enchanting forests. Along the way, you'll have the chance to explore vibrant cities and charming towns, each with its unique character and attractions. From the vibrant culture of Texas to the rich history of Maryland, this adventure promises an unforgettable travel experience.
As you traverse this vast and varied land, you'll encounter a kaleidoscope of cultures and traditions. You'll have the opportunity to sample delicious regional cuisine, meet friendly locals, and learn about the distinctive heritage of each place you visit. Whether you're marveling at the architectural wonders of iconic cities or discovering hidden gems off the beaten path, this journey will provide a deep immersion into the very heart of America. Embrace the spirit of adventure and prepare to be captivated by the beauty and diversity of this incredible country.
As you approach the Eastern seaboard, the landscape transforms once again. The gentle hills give way to a sprawling coastal plain, dotted with sparkling rivers and vast estuaries. The air fills with the salty tang of the Atlantic Ocean, signaling your arrival in Baltimore. This charming city, steeped in history and culture, beckons you to explore its cobblestone streets, historic landmarks, and renowned culinary scene. Let the vibrant spirit of Baltimore welcome you to the East Coast, marking the culmination of your extraordinary cross-country adventure.

San Antonio

San Antonio to Baltimore

Spas & Wellness

Nightlife

Museums

Fun & Games

Food & Drink

Shopping

Traveler Resources

Concerts & Shows

Sights & Landmarks

Tours

Nature & Parks

Baltimore

Get ready for an unforgettable adventure as you embark on a journey from the vibrant city of Chicago to the historic streets of Baltimore. This epic road trip will take you through diverse landscapes, from bustling urban centers to serene countryside vistas. Along the way, you'll encounter a rich tapestry of cultures, indulge in delectable culinary delights, and create memories that will last a lifetime.
Your adventure begins amidst the iconic skyscrapers of Chicago, where you'll soak in the breathtaking views from atop Willis Tower. As you leave the city limits, the landscape transforms into rolling hills, dotted with charming towns and picturesque farms. You'll have ample opportunities to stretch your legs and explore hidden gems, immersing yourself in the heartland of America.
As you approach Baltimore, the Chesapeake Bay beckons with its shimmering waters. Take a leisurely stroll along the waterfront promenade, savoring the salty breeze and spotting majestic ships. Delve into the city's rich history at Fort McHenry, where the Star-Spangled Banner proudly waved during the War of 1812. From the bustling Inner Harbor to the quaint cobblestone streets of Fells Point, Baltimore offers a captivating blend of past and present, ensuring an unforgettable conclusion to your epic road trip adventure.

Chicago

Chicago to Baltimore

Outdoor Activities

Classes & Workshops

Get ready for an epic adventure as we embark on a journey from the bustling metropolis of Chicago to the charming town of Poughkeepsie! Along the way, we'll traverse vast landscapes, witness breathtaking landmarks, and encounter friendly faces that will make memories that will last a lifetime.
Prepare to be amazed by the vibrant cities and quaint towns that dot our path. We'll marvel at towering skyscrapers, explore historic streets, and soak up the local culture. The journey itself will be an adventure, as we wind through majestic mountains, roll through rolling hills, and glide along sparkling rivers.
Picture yourself surrounded by breathtaking scenery, from shimmering lakes to lush forests and everything in between. We'll have plenty of opportunities to stretch our legs, breathe in the fresh air, and capture the perfect shots to share with friends and family back home. Get ready for an unforgettable journey filled with laughter, discovery, and memories that will be cherished for years to come!

Chicago to Poughkeepsie

Other

Casinos & Gambling

Poughkeepsie

Get ready for an epic adventure from the bustling streets of Chicago to the vibrant shores of Oakland! This cross-country journey will take you through diverse landscapes, spanning the vast Midwest, the rugged Rocky Mountains, and the serene Pacific coast. Along the way, you'll witness the grandeur of nature, explore historic cities, and discover hidden gems.
Prepare to be amazed by the towering skyscrapers of Chicago, the rolling hills of Nebraska, and the breathtaking vistas of Wyoming. As you venture westward, the majestic Rockies will unfold before you, offering unparalleled views from winding mountain passes. Embrace the thrill of traversing the Continental Divide and the awe-inspiring beauty of the Great Basin Desert.
As you approach the Pacific Ocean, the terrain transforms into a lush coastal paradise. California's fertile valleys and verdant hills will greet you, leading you to the vibrant city of Oakland. Here, you'll soak up the Bay Area's unique culture, explore its thriving arts scene, and revel in the beauty of its natural surroundings. Get ready for an unforgettable journey that will leave you with lasting memories and a profound appreciation for the wonders of America.

Chicago to Oakland

Water & Amusement Parks

Oakland

Miami

Miami to Philadelphia

Philadelphia

Hop aboard and get ready for an unforgettable adventure as we set off on an exciting rail journey from the bustling streets of New York City to the charming coastal town of New Haven. Along the way, we'll glide past picturesque landscapes, witness the changing scenery from towering skyscrapers to quaint villages, and soak up the vibrant culture that makes this route so unique. Our comfortable train will whisk us through a tapestry of landscapes, from lush forests and rolling hills to sparkling rivers and serene coastal views. As we journey, we'll delve into the rich history of the region, uncovering hidden gems and stories that have shaped this beautiful part of the world.
Our journey will be filled with opportunities to embrace the local flavors, indulge in culinary delights, and discover hidden treasures. We'll have the chance to sample mouthwatering delicacies, from fresh seafood caught just off the coast to artisanal treats crafted by local artisans. Along the way, we'll uncover charming towns and vibrant cities, each with its own unique character and captivating charm. From bustling markets to historic landmarks, there's always something new to explore and experience around every corner.
As we approach New Haven, the scenery transforms into a coastal paradise, where the salty tang of the ocean air fills our senses and the sound of crashing waves creates a soothing symphony. We'll disembark in the heart of this vibrant city, eager to explore its rich maritime heritage, delve into its renowned culinary scene, and embrace the youthful energy that makes New Haven a hub of innovation and culture. Our rail journey from New York to New Haven promises an unforgettable adventure filled with stunning scenery, captivating history, and a vibrant tapestry of flavors and experiences.

New York

New York to New Haven

Boat Tours & Water Sports

New Haven

Prepare yourself for an unforgettable journey from the bustling metropolis of Chicago to the sun-kissed shores of Fort Lauderdale. Immerse yourself in the vibrant culture of these two iconic cities as you embark on an adventure filled with endless possibilities. Explore the Windy City's towering skyscrapers, marvel at its world-class museums, and indulge in its delectable culinary scene. Then, escape to the Sunshine State, where you'll be greeted by pristine beaches, swaying palm trees, and endless opportunities for relaxation and adventure.
As you journey from the Midwest to the Southeast, let the breathtaking landscapes captivate your imagination. Observe as the urban sprawl gives way to rolling hills, lush forests, and sparkling rivers. Witness the gradual transformation from the city's hustle and bustle to the tranquil serenity of the coastal haven. Allow the gentle rhythm of the train to lull you into a state of tranquility as you soak in the ever-changing scenery.
Upon arriving in Fort Lauderdale, embrace the coastal charm and vibrant energy that permeates the city. Discover its picturesque waterways, explore its eclectic neighborhoods, and bask in the warm sunshine that has made this destination a beloved retreat for generations. From thrilling water sports to cultural attractions and culinary delights, Fort Lauderdale offers an array of experiences that will create lasting memories for travelers of all ages.

Chicago to Fort Lauderdale

Fort Lauderdale

Escape to the bustling metropolis of New York City, where skyscrapers pierce the heavens and vibrant streets throb with life. Immerse yourself in iconic landmarks, indulge in world-renowned cuisine, and witness the dazzling spectacle of Broadway. Embrace the vibrant energy that courses through the heart of this urban jungle.
Venture beyond the concrete jungle as you journey to the historic city of Boston. Step back in time as you wander cobblestone streets, marvel at architectural wonders, and delve into the rich tapestry of American history. Explore the birthplace of the American Revolution, where the seeds of independence were sown. Discover the charm of quaint neighborhoods, where tradition intertwines with a modern spirit.
Indulge in the flavors of New England, where culinary delights await at every turn. Savor the freshest seafood, succulent meats, and delectable pastries. Embark on a culinary adventure that will tantalize your taste buds and leave you craving for more. Embrace the art of fine dining or savor the simplicity of local favorites.

New York to Boston

Boston

Hop on board and join us for an unforgettable adventure as we embark on a scenic journey from the bustling metropolis of Chicago to the charming town of Riverside. Along the way, we'll traverse a tapestry of landscapes, each with its own unique character and beauty. From the vibrant streets of downtown Chicago to the serene banks of the Mississippi River, we'll witness a kaleidoscope of sights and sounds that will captivate your senses.
As we journey through rolling hills and lush forests, you'll be treated to breathtaking views of nature's artistry. The gentle breeze will carry the sweet scent of wildflowers, while the rustling leaves of towering trees will serenade you with their gentle symphony. Along the way, we'll make stops at historic landmarks and hidden gems, where you'll have the chance to delve into the rich tapestry of the region's past and present.
Our destination, the picturesque town of Riverside, awaits us with open arms. Nestled amidst verdant parks and charming Victorian architecture, Riverside offers a tranquil escape from the hustle and bustle of city life. Here, you'll have ample time to explore its quaint streets, admire the stunning architecture, and soak up the friendly atmosphere that permeates every corner.

Chicago to Riverside

Riverside

Escape the bustling streets of New York City and embark on an epic road trip to the vibrant city of Cleveland. This adventure offers a captivating journey through diverse landscapes, from rolling hills to sprawling farmlands, unveiling the hidden gems and vibrant cultures that lie between these two metropolises.
Along the way, immerse yourself in the rich history and heritage of bygone eras as you traverse charming towns and historic landmarks. Discover the captivating stories that shaped the nation's past and present, and uncover the unique character of each destination. Indulge in culinary delights, savor local flavors, and connect with the welcoming communities that make this journey so memorable.
As you approach Cleveland, feel the energy of a thriving city on the rise. Explore its vibrant downtown, lined with world-class museums, theaters, and art galleries. Delve into the city's proud industrial heritage and witness the transformation it has undergone, embracing innovation and sustainability. Cleveland beckons you to discover its vibrant arts scene, savor its diverse culinary offerings, and experience the warmth and hospitality of its residents.

New York to Cleveland

Cleveland

Get ready for an epic adventure from the bustling city of Dallas to the heart of our nation's capital, Washington, D.C.! This captivating journey will take you through a diverse landscape of vibrant metropolises, rolling hills, and historic landmarks. Along the way, you'll discover the rich tapestry of American culture and history, with each stop offering its own unique charm. From the vibrant music scene of Austin to the serene beauty of the Ozark Mountains, every mile will unveil a new chapter in this unforgettable road trip.
As you venture further east, the landscape transforms into a rolling expanse of lush greenery, dotted with charming towns and historic sites. Immerse yourself in the vibrant atmosphere of Memphis, where the legendary rhythms of blues and soul music fill the air. Continue your journey through the picturesque hills of Tennessee, where history whispers through the hallowed halls of plantations and battlefields. As you approach the Blue Ridge Mountains, prepare to be awed by breathtaking vistas and the allure of nature's grandeur.
Finally, as you enter the bustling metropolis of Washington, D.C., you'll find yourself surrounded by monuments and memorials that pay homage to the nation's past and present. Explore the halls of power at the Capitol Building, marvel at the towering Washington Monument, and soak in the poignant atmosphere of Arlington National Cemetery. This journey from Dallas to Washington is not merely a road trip; it's a pilgrimage through the heart of America, connecting you with the threads that weave together our diverse nation's identity.

Dallas

Dallas to Washington

Washington DC

Hop on board for an unforgettable adventure as we embark on an epic rail journey from the vibrant metropolis of Chicago to the charming New England town of New Haven. Along the way, we'll traverse a tapestry of landscapes, from rolling hills and verdant farmlands to bustling cities and picturesque coastlines. The rhythmic click-clack of the tracks will provide a soothing soundtrack to our journey, as we marvel at the ever-changing scenery and the stories it holds.
Our train will glide past historic landmarks and architectural wonders, whispering tales of the past. We'll catch glimpses of iconic skyscrapers, grand bridges, and sleepy towns frozen in time. The vibrant colors of nature will paint a breathtaking canvas, with fields of wildflowers swaying in the breeze and shimmering rivers reflecting the golden rays of the sun. As we approach our destination, the salty tang of the ocean air will invigorate our senses, signaling the end of an unforgettable chapter and the start of a new adventure in New Haven.
This grand rail odyssey promises to be a symphony of sights, sounds, and emotions. Whether you're a seasoned traveler or embarking on your first adventure, this journey will create lasting memories that will warm your heart and spark your imagination. So, settle back, relax, and let the rhythm of the rails carry you away on an unforgettable adventure from Chicago to New Haven.

Chicago to New Haven

Hold on tight as we embark on an exciting adventure from San Jose to Richmond! This journey will be filled with stunning landscapes, thrilling experiences, and countless memories. Along the way, we'll explore vibrant cities where history and culture come alive. Get ready to witness towering skyscrapers, bustling streets, and captivating museums that tell the stories of the past. But that's not all! We'll also venture into breathtaking natural wonders, where towering mountains meet sparkling lakes and lush forests beckon us to explore.
As we make our way, we'll uncover hidden gems and off-the-beaten-path destinations that will leave you in awe. From charming towns with cozy cafes to secluded beaches with crystal-clear waters, every stop on our journey holds a unique surprise. We'll embrace the local flavors, indulge in delectable cuisines, and immerse ourselves in the vibrant cultures that make this region so special. So, buckle up, pack your sense of adventure, and get ready for an unforgettable journey that will create memories to last a lifetime!
And remember, this is just a sneak peek of the incredible adventures that await us! As we embark on this journey together, we'll uncover even more hidden treasures, encounter unforgettable characters, and create memories that will be cherished for years to come. So, grab your loved ones, your sense of wonder, and get ready for the adventure of a lifetime from San Jose to Richmond!

San Jose

San Jose to Richmond

Richmond

Escape from the hustle and bustle of the city and embark on a thrilling adventure. Our journey will take us along a scenic route, where we'll have the chance to admire stunning landscapes and discover hidden gems. As we cruise along, we'll uncover the rich history and captivating stories that have shaped these lands.
Along the way, we'll encounter friendly locals who will share their unique insights and traditions. We'll savor delicious local cuisine, immersing ourselves in the region's vibrant culinary scene. Whether it's exploring picturesque towns or discovering breathtaking natural wonders, this trip promises an unforgettable experience for travelers of all ages.
Get ready to embark on an extraordinary journey, filled with adventure, discovery, and memories that will last a lifetime. As we traverse through diverse landscapes and encounter fascinating people, we'll create a tapestry of experiences that will forever enrich our lives. So, buckle up and prepare to be amazed by the wonders that await us on this unforgettable road trip.

Philadelphia to New York

Get ready for an exciting adventure from the vibrant city of Philadelphia to the bustling capital, Washington, D.C.! Our journey will take us through a tapestry of landscapes, from rolling hills to bustling urban centers. Along the way, we'll discover the rich history, iconic landmarks, and hidden gems that make this trip unforgettable.
As we embark on our adventure, we'll explore the vibrant streets of Philadelphia, where the echoes of history resonate through every cobblestone. We'll delve into the hallowed halls of Independence Hall, where the seeds of our nation were sown, and marvel at the Liberty Bell, a symbol of freedom that has inspired generations. From there, our journey will continue towards Washington, D.C., passing through picturesque countryside and charming towns.
As we approach the nation's capital, the skyline will transform, revealing the iconic monuments and majestic buildings that have shaped the course of history. We'll stand in awe at the towering Lincoln Memorial, marvel at the grandeur of the Washington Monument, and explore the halls of the Smithsonian museums, where the world's wonders await our discovery. Whether you're a history buff, a culture enthusiast, or simply seeking an unforgettable adventure, this journey from Philadelphia to Washington, D.C., promises an experience that will ignite your imagination and leave a lasting impression.