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Wine Trails & Shopping: RoadTrips USA Adventures through California, Oregon, New York, Pennsylvania & more!

Grab your credit card and a thirst for adventure and indulge in these epic road trips through the mighty USA, combining wine, culture and endless fun!

Grab your credit card and a thirst for adventure and indulge in these epic road trips through the mighty USA, combining wine, culture and endless fun!

More than just dynamic metropolises, jaw-dropping natural beauty and Southern Charm – the United States also boasts some of the world’s best wine and shopping!

Come with us as we explore the country’s top wine regions and shopping hotspots on these epic road trip adventures.

Ready to sip, shop, and savour your way through the USA?

Let’s go!

Road Trip #1: Pacific Northwest Wine Trails

Duckhorn Vineyards, Napa Valley
Visit Napa Valley as you follow trails to vineyards and wineries throughout California and Oregon ©Brand USA

Fast facts
  • Starts: San Francisco, California
  • Ends: Portland, Oregon
  • How long: Allow 7 days
  • Distance: 1,093km

Sample some of the USA’s best food and wine on this tantalising journey along the West coast!

Beginning in gorgeous San Francisco, snap that iconic selfie on the Golden Gate Bridge at Battery East Vista for the ultimate Instagram moment, and then hop across to Sausalito for some quaint Mediterranean vibes before heading into Napa Valley.

Rise and shine – it’s time to explore Napa’s renowned vineyards! Start your day at Domaine Chandon, where you can sip sparkling wine amidst stunning landscapes. Next up, St. Helena beckons with V. Sattui Winery’s delightful tastings and artisanal deli offerings.

But wait, there’s more! Don’t miss the architectural marvel that is Opus One Winery in Oakville. Trust us, it’s a feast for the senses!

Onward to Redding, California! But first, indulge in Calistoga’s mineral hot springs for a relaxing soak. If you’re feeling adventurous, why not tackle the Mount St. Helena hike for breathtaking views before treating yourself to local vino at Indian Peaks Vineyards and Moseley Family Cellars.

Crossing into Oregon’s Rogue Valley, you’ll be captivated by the artsy charm of Ashland. Wine lovers will love Irvine & Roberts Vineyards where pinot noir flows freely against a backdrop of scenic splendour.

Before reaching Eugene, make a stop at Del Rio Vineyard Estate for a picturesque picnic. And don’t forget to experience the mind-bending Oregon Vortex before indulging in wine and dine delights at Schmidt Family Vineyards.

Prepare for a day of wine and wonder in Eugene! But first, a side trip to marvel at the breathtaking beauty of Crater Lake National Park is an absolute must.

Back on the wine trail, Silvan Ridge Winery awaits with its exquisite pinot noirs. Follow it up with a visit to Sarver Winery for a taste of Oregon’s finest, paired with gourmet treats. Round off your day with a visit to King Estate Winery for a culinary journey that’s as unforgettable as the views.

Next, venture into the heart of the Willamette Valley where Pfeiffer Winery beckons with its intimate tasting experiences and Pinot Clinics. Walnut Ridge Vineyard charms with its rustic ambiance and panoramic views. And cap off your day with a fine dining experience at The Painted Lady, where farm-to-table fare takes center stage in a Victorian setting.

Cottage Grove, Willamette Valley
Pedal to plate: take a ride on the Willamette Valley Scenic Bikeway ©Brand USA

Your journey concludes in the vibrant city of Portland. But not before indulging in tastings at Sokol Blosser Winery and Domaine Serene’s Clubhouse. As you bid adieu to your wine-filled adventure, treat yourself to the culinary delights of Olympia Provisions Southeast—a fitting finale to an unforgettable journey! Cheers to the memories made along the way!

Road Trip #2: Northeast Wine Trails

Brooklyn Bridge, New York ©Brand USA
Follow the Northeast USA’s wine trails to tasting rooms, attractions and cities starting in New York City ©Brand USA

Fast facts
  • Starts: New York, New York
  • Ends: New York, New York
  • How long: Allow 10 days
  • Distance: 1,231km

Embark on a wine-filled journey from the bustling streets of NYC to serene wine country. Savour tastings, explore charming towns, and indulge in fine dining along the way.

Let the adventure begin!

Spend your last evening sipping on some fine wine while enjoying live music in the heart of NYC at City Winery New York in Soho. This winery brings the charm of wine country right to the bustling streets of the Big Apple and is the perfect introduction of what you’re in store for over the next 10 days…

The next morning, we’re hitting the road south to New Jersey wine country! But not before a pit stop in Princeton. Dive into a late breakfast at Jammin’ Crepes and explore the vibrant Princeton University Art Museum. Then, it’s off to Amalthea Cellars Farm Winery for a taste of southern France right in Jersey! Keep the adventure going with stops at White Horse Winery and Hawk Haven Vineyard and Winery in Cape May, where you’ll be surrounded by stunning coastal views and Victorian charm.

Cape May Lighthouse ©Brand USA
At the tip of southern New Jersey’s Cape May Peninsula, Cape May is known for its grand Victorian houses and the Cape May Lighthouse, which provides views across the bay and ocean ©Brand USA

From there, we’re off to Kennett Square, Pennsylvania, aka the “Mushroom Capital of the World.” Explore its quaint streets, taste some local wines, and enjoy a fabulous dinner at Portobello’s – delish!

The next day is all about exploring the beautiful Brandywine Valley. Marvel at the botanical wonders of Longwood Gardens before indulging in tastings at Galer Estate Vineyards, Penns Woods Winery, and Va La Vineyards. Don’t forget to check out the boutiques in West Chester before a delicious steak dinner at Pietro’s Prime!

Then it’s on to Lancaster, Pennsylvania, where you can grab a bite at the Java Junction Coffee Bar before exploring the rich history and cultural attractions of Pennsylvania Dutch Country. After that, drive to Hershey, the sweetest place on earth, and learn about this great American chocolate bar before visiting Cullari Vineyards and Winery and settling in for the night.

Ready for more wine? Awesome! Today we’ll explore the Hershey and Harrisburg wine regions, with stops at Armstrong Valley Vineyard & Winery, J & P Winery, and Cassel Vineyards. Top it off with a fine dining experience at Char’s Tracy Mansion in Harrisburg.

Next, we’re heading northeast to the Finger Lakes region. Make a pit stop at the Corning Museum of Glass before arriving in Ithaca, where you can explore the stunning waterfalls and indulge in wine tastings along the Seneca Lake Wine Trail.

New York State
Continue to the heart of the Finger Lakes Wine Country in Ithaca, New York ©Brand USA

Then spend the next one or two days exploring Finger Lakes wineries like Lamoreaux Landing, Dr. Konstantin Frank, Belhurst Castle, and Hermann J. Wiemer. Even more wine adventures await around Cayuga Lake, like Sheldrake Point Winery, Thirsty Owl Wine Company, Hosmer Estate Winery, and Buttonwood Grove Winery. Wrap up the day with Italian cuisine at Mercato Bar & Kitchen.

Sadly, it’s time to head back to the Big Apple, but not before soaking in the beauty of upstate New York and enjoying lunch in the Pocono Mountains.

Road Trip #3: Shopping USA

Wynwood Market, Miami ©Brand USA
Explore the boutiques and markets in Miami including Wynwood Marketplace ©Brand USA

Fast facts
  • Visits: Arizona, California, Florida, Illinois, Massachusetts Nevada, Pennsylvania, New York, New Jersey, Texas
  • How long: 1-3 Days, depending on city

Who needs a therapist when there’s retail therapy! No matter where you are in the USA, shopping adventures await around every corner, such as these, spread out amongst 10 great states.

Phoenix/Scottsdale, Arizona

First up, dive into designer discounts at the Phoenix Premium Outlets and Arizona Mills, and then unwind with lunch and gaming at Wild Horse Pass Hotel & Casino. Don’t forget to soak up the desert vibes with a spa session or a round of golf before calling it a day. The next morning, enjoy luxury shopping at Biltmore Fashion Park and Scottsdale Fashion Square, and then chill in Old Town Scottsdale’s charming boutiques and eateries.

Los Angeles, California

Hunt for bargains at outlet malls, buy haute couture from designers and seek out specialty items at locally owned shops in Los Angeles ©Brand USA
Hunt for bargains at outlet malls, buy haute couture from designers and seek out specialty items at locally owned shops in Los Angeles ©Brand USA

With your credit can in hand, shop till you drop at Del Amo Fashion Center and The Outlets at Orange, and then head to Anaheim for more bargains. Then, cap off the afternoon with eclectic dining and Disney-themed shopping at Downtown Disney District. Keep your eyes peeled for celebrity sightings while indulging in fine dining and exploring Hollywood’s iconic landmarks. The next day, do a little seaside shopping and dining in Santa Monica, perhaps at Big Dean’s Ocean Front Café?

San Diego, California

Score deals at Las Americas Premium Outlets and Fashion Valley before diving into the vibrant nightlife of Gaslamp Quarter. Then, drive north to Carlsbad Premium Outlets for even more discounts and enjoy lunch with ocean views in Carlsbad Village. The following day, visit Westfield UTC for upscale shopping and dining, or dine in La Jolla overlooking the Pacific. Don’t miss out on exploring Seaport Village and the world-famous San Diego Zoo for some extra fun!

This city break package including accommodation and car hire is bookable through Infinity Holidays!

San Francisco, California

Start your retail therapy at Union Square for some upscale shopping. Then, take a cable car ride to Fisherman’s Wharf for waterfront views and Ghirardelli Square treats. The next morning, drive south to Half Moon Bay, and then east to Palo Alto’s Stanford Shopping Center. Proceed to Milpitas for some shopping at the Great Mall, and end at Stoneridge Shopping Center in Pleasanton for even more “therapy.” Finally, make the trip to Napa Valley for wine tasting and scenic picnics before wrapping up your day with a delicious dinner overlooking the Bay Bridge.

Miami, Florida

Kick off your shopping spree at Miami International Mall where you can explore 140+ stores like Macy’s and H&M. Then check out Miami Beach for a little poolside relaxation or spa indulgence. Suitably recharged, go and explore The Falls and Miracle Mile for even more fabulous finds before venturing north to Dadeland Mall and its 180+ stores, including Urban Outfitters and Microsoft. End your day at Miracle Mile in Downtown Coral Gables for upscale shopping and dining experiences. Before leaving, visit Sawgrass Mills, one of the largest outlet malls in the USA, with over 350 stores like Prada and Adidas.

Accomodation, car hire and tours are included in this Infinity Holidays package bookable today!

Chicago, Illinois

Macy's Chicago Water Tower ©Brand USA
See the best of Chicago while embarking on an exciting shopping excursion ©Brand USA

Start your retail adventure at Gurnee Mills. Explore this vast outlet mall with nearly 200 stores, and then consider a visit to Six Flags Great America for thrill rides or Illinois Beach State Park for a serene day. Then, explore the Magnificent Mile for luxury brands before wrapping up your trip at the Fashion Outlets of Chicago for some last-minute steals, conveniently located just five minutes from O’Hare International Airport!

Check out this awesome city break package including accommodation through Infinity Holidays!

Boston, Massachusetts

Begin your retail rampage at Copley Place, a hub of luxury shopping and dining in Boston’s historic Back Bay area. Then use the skywalk to access the Prudential Center Boston for more shopping and dining options. The next afternoon, enjoy lunch at Legal Sea Foods or The Cheesecake Factory before exploring nearby attractions like Boston Common and the Freedom Trail. On your last day, check out Faneuil Hall, a historic marketplace filled with shops and restaurants near the Boston Waterfront, and then set sail on a Boston Harbor Cruise to learn about local history and enjoy city views. End your day with a seafood dinner at Boston Sail Loft on the waterfront.

This accommodation and tour package by Infinity Holidays is perfect for this shopping adventure!

Las Vegas, Nevada

Surround yourself by designer names in Las Vegas ©Brand USA
Surround yourself by designer names in Las Vegas ©Brand USA

As a special welcome treat, embark on a thrilling helicopter tour from Las Vegas to the Grand Canyon before discovering designer labels at The Shops at Crystals and Miracle Mile Shops. Then, catch a show and indulge in world-class cuisine for dinner along the Strip. The next day, try your luck at the casinos for the ultimate Vegas experience and do some more shopping at The Grand Canal Shoppes at The Venetian. Whilst there, admire the replica of St. Mark’s Square and enjoy a gondola ride along the canals. End your evening with a ride on the High Roller at The LINQ for stunning views of Las Vegas.

Philadelphia, Pennsylvania

Embark on a shopping extravaganza just an hour from downtown Philadelphia at the Philadelphia Premium Outlets in Limerick. Boasting over 135 stores with renowned brands like Nike, Levi’s, and UGG, it’s a retail wonderland! Then, explore the King of Prussia Mall, one of the nation’s largest, before calling it a day. Rest and recharged, get a morning dose of retail therapy at Macy’s Center City, and immerse yourself (and your credit card) in Rittenhouse Row’s chic boutiques. Complete the day with dinner at The Good King Tavern or aboard the Moshulu ship restaurant.

Book this accommodation and tour package by Infinity Holidays today!

New York City, New York

Revel in some tax-free shopping at three vibrant shopping hubs – Newport Centre, Newport Crossing, and Newport Plaza – all easily accessible via the PATH train from Manhattan, before visiting the 9/11 Memorial & Museum and grabbing dinner at a West Village eatery like Morandi. The next day, visit Woodbury Common Premium Outlets which boasts over 220 prestigious store, before driving back to the city through Bear Mountain State Park and Hudson Valley. On your last day in the Big Apple, go on an iconic shopping spree along Fifth Avenue and discover luxury brands at Bergdorf Goodman and Henri Bendel. Enjoy a bite to each at the Time Warner Center before strolling through Central Park’s landmarks. End the day with a Broadway show and dinner at Sardi’s in Times Square.

Dallas-Fort Worth, Texas

Begin your Fort Worth shopping exploration at The Shops at Clearfork where luxury brands like Neiman Marcus, Louis Vuitton, and Burberry jostle for your attention. Next, head to University Park Village for Banana Republic and Apple before experiencing the Fort Worth National Stockyards Historic District for some local rodeo action and local shopping. After a well-deserved rest, discover Grapevine Mills’ 180+ stores and family-friendly attractions like the Sea Life Grapevine Aquarium, and then spend the rest of the day on a wine tour along the Grapevine Urban Wine Trail. Don’t leave the city without checking out even more shopping options at Galleria Dallas and Highland Park Village or visiting Dallas landmarks like The Sixth Floor Museum.

Houston, Texas

Texas is a great place for Western wear, boots, cowboy hat and more! ©Brand USA
Texas is a great place for Western wear, boots, cowboy hat and more! ©Brand USA

Start your retail therapy by perusing through over 375 stores at The Galleria – which also boasts 30 eateries and even an ice skating rink! Then head to Space Center Houston for a glimpse into space exploration. Up early the next day, explore River Oaks District for luxury boutiques like Dior and Hermes before enjoying a gourmet dinner at Steak 48 or savouring Parisian vibes at Toulouse.

Register for the USA Discovery Program and start your journey to become a USA Specialist.

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Brand USA and Infinity Holidays are proud to partner to showcase even more of the USA and the endless possibilities for your clients. For more information on the fully bookable and customisable USA Road Trips itineraries and USA City Breaks go through HELiO, here.

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