Savor History, Indulge in Luxury, and Toast to Adventure in Virginia’s Wine Country! 

August 17-21, 2025
5 days / 4 nights

Overall Trip Highlights

• Trump Winery Private Tasting & Tour – Explore Virginia’s largest vineyard, savor award-winning wines, and enjoy an exclusive behind-the-scenes look at winemaking. The estate is situated in the heart of Jefferson’s Monticello Wine Trail, a region envisioned by Thomas Jefferson as America’s premier wine country.

• Luxury Stay at The Forum Hotel – Experience a modern yet charming retreat in the heart of Charlottesville, located near the historic University of Virginia. The hotel’s botanical gardens and refined ambiance provide the perfect setting for relaxation after days filled with exploration.

• Exclusive Falconry Experience at Boar’s Head Resort – Witness the ancient art of falconry, a practice that dates back over 4,000 years. Learn how birds of prey were once essential to medieval hunting traditions and their continued importance in conservation today.

• Thomas Jefferson’s Monticello Tour – Walk through the iconic home of America’s third president, a UNESCO World Heritage Site, and learn about Jefferson’s architectural innovations, scientific curiosity, and impact on early American history.

• Exploring the Blue Ridge Mountains – Take in breathtaking views and uncover the region’s rich history. The Blue Ridge Mountains, first mapped by European explorers in the 17th century, are home to some of the oldest mountains in the world, dating back over 1 billion years.

• Historic University of Virginia Tour – Founded by Thomas Jefferson in 1819, the University of Virginia was designed to embody his vision of higher education and remains the only U.S. university designated a UNESCO World Heritage Site.

• Charlottesville Historic Downtown Mall – Stroll through one of the longest pedestrian malls in the country, featuring 19th-century architecture, boutique shops, and charming cafes. Once a key stop for travelers in the 1800s, this district remains a cultural hub of the region.

• Elegant Dinner at The Mill Room at Boar’s Head Resort – Dine in an iconic setting with a history dating back to the 1750s, when the land was home to Terrell’s Ordinary, a stagecoach stop along Virginia’s colonial trade routes. Today, it offers a refined dining experience with locally inspired dishes.

• Ancient Weapons and Axe Throwing Experience – Engage in a hands-on session where you can learn about and try your hand at ancient weaponry, including axe throwing, providing a unique and thrilling connection to historical combat techniques.

• Poolside Cocktails & Farewell Dinner at Albemarle Estate – Unwind with a refreshing drink while enjoying the scenic estate before indulging in an elegant farewell dinner at the prestigious Albemarle Estate at Trump Winery, blending historic charm with modern luxury.

Step Into History, Savor the Moment, and Explore Virginia’s Timeless Beauty.

Every Beatrice Bradley trip is crafted to maximize the experiences had during the trip.
The itineraries are specially made to allow time for engaging in conversation and having belly laughs with a new friend. We hope that the activities and experiences may allow you to come out of your comfort zone and to try new or unique things.
These trips are made to replicate a ‘friends get-away trip’. 

*Itinerary subject change

Day One: A Warm Virginia Welcome Under the Setting Sun

As you arrive in Charlottesville, the rolling hills of Virginia wine country set the perfect stage for a romantic and luxurious adventure. The evening begins with a refreshing welcome drink on the terrace, where you can sip and unwind while soaking in the picturesque Blue Ridge backdrop. After checking into the elegant Forum Hotel, a gourmet dinner awaits, setting the tone for an unforgettable journey. Afterward, enjoy a peaceful stroll through the enchanting arboretum and botanical gardens, where golden-hour sunlight bathes the landscape in a warm glow, creating a serene and picturesque ending to your first night.

Highlights

• Check-in at The Forum Hotel – Settle into your luxurious accommodations at this modern yet charming retreat.
• Welcome Drink on the Terrace – Relax with a refreshing cocktail or wine as you take in the stunning views.
• Dinner at The Forum Hotel – Indulge in a chef-curated meal at Charlottesville’s newest luxury destination.
• Evening Arboretum & Botanical Garden Walk – Stroll through beautifully curated gardens as the evening sun lingers in the sky.

Fun Fact: Charlottesville’s Botanical Garden of the Piedmont is part of a regional conservation effort that protects Virginia’s native flora. The Blue Ridge Mountains boast one of the most biodiverse ecosystems in North America, with over 1,600 plant species thriving in its rich soils.

Day Two: Walking in the Footsteps of History

Today is dedicated to immersing yourself in the rich history of Charlottesville, from the homes of America’s Founding Fathers to the university that shaped generations of leaders. After a delightful breakfast at the hotel, the day unfolds with a series of guided tours that bring the past to life. From the iconic estate of Thomas Jefferson to a deep dive into the history of the University of Virginia, each stop offers new insight into the figures and moments that shaped America. The day concludes with an interactive Unlock History experience, bringing history to life in an engaging and unforgettable way.

Highlights of the Day:

• Breakfast at The Forum Hotel – A fresh, locally inspired start to the day.
• Visit Highland – Tour the historic home of James Monroe, America’s fifth president.
• Explore Monticello – Step inside Thomas Jefferson’s legendary estate, a UNESCO World Heritage Site.
• University of Virginia History Tour – Walk the grounds of the prestigious university designed by Jefferson himself.
• Dinner in Town at a Local Hot Spot – Unwind with a delicious meal in a lively, historically rich setting.
• Unlock History Experience – A hands-on, interactive journey through the region’s past, offering a fresh perspective on the people and events that shaped the nation.

Fun Fact:

The Rotunda at the University of Virginia, inspired by the Pantheon in Rome, was personally designed by Thomas Jefferson and remains one of the most recognizable symbols of higher education in America.

Day Three: Adventure and Elegance in Virginia’s Countryside

Today is all about embracing the natural beauty and outdoor traditions of the Blue Ridge Mountains while indulging in unique, hands-on experiences. After a hearty breakfast at the hotel, venture to Boar’s Head Resort, where the ancient art of falconry awaits. Continue the excitement with an Ancient Weapons and Axe Throwing Experience, where you’ll test your skills with traditional weaponry. Then, take to the water for a serene flatwater kayaking adventure before setting off on a scenic hike through the breathtaking Blue Ridge landscapes. As the sun sets, unwind with an elegant dinner at The Mill Room, where fine dining meets Virginia’s rustic charm.

Highlights of the Day:

• Breakfast at The Forum Hotel – A fresh and energizing start to the day.
• Falconry Experience at Boar’s Head Resort – Get up close and personal with majestic birds of prey in an ancient hunting tradition.
• Ancient Weapons and Axe Throwing Experience – Step back in time and test your skills with traditional weaponry, including axes, spears, and bows.
• Flatwater Kayaking – Paddle through peaceful waters, taking in the lush Virginia scenery.
• Exploring the Blue Ridge Mountains – Breathe in the fresh mountain air and enjoy sweeping panoramic views.
• Dinner at The Mill Room – Conclude the day with a refined dining experience featuring locally sourced ingredients.

Fun Facts:

Axe throwing dates back to medieval times, when warriors used it as both a hunting tool and a weapon in battle. Today, it has become a popular sport and skill-based challenge, allowing participants to experience the precision and technique of ancient warriors.

The Boar’s Head Resort sits on land that was once home to Terrell’s Ordinary, an 18th-century inn and tavern along a major stagecoach route. In the early 1800s, travelers—including some of Virginia’s most influential figures—would stop here for rest and refreshment before continuing their journeys through the Blue Ridge foothills.

Day Five: A Grand Trump Finale of Beauty and Elegance

Your final day in Virginia’s stunning countryside is filled with scenic beauty, refined luxury, and a perfect farewell toast. Start the morning with a leisurely breakfast before taking a peaceful stroll through the Arboretum and Botanical Gardens, enjoying the vibrant landscape and fresh morning air. The afternoon is dedicated to Trump Winery, where a private tasting and exclusive tour of the estate grounds offer an intimate look at Virginia’s premier wine country. As the sun begins to set, relax with cocktails poolside, soaking in the estate’s elegance. The trip concludes with a formal farewell dinner at the Albemarle Estate’s Dining Room, a final chance to indulge in fine dining and celebrate the unforgettable experiences shared.

Highlights of the Day:

• Breakfast at The Forum Hotel – A relaxed start to the final day of the trip.
• Explore the Arboretum & Botanical Gardens – Enjoy a peaceful morning among the lush gardens and scenic trails.
• Trump Winery Private Tasting – Sip and savor a selection of expertly crafted, award-winning wines.
• Private Tour of the Trump Winery Grounds – An exclusive behind-the-scenes look at the vineyard’s history, winemaking process, and breathtaking estate.
• Cocktails Poolside or Explore the Grounds – Unwind with a refreshing drink and enjoy the elegant surroundings.
• Farewell Dinner in the Albemarle Estate’s Dining Room – A luxurious, chef-prepared meal to end the trip on a high note.

Fun Fact:

The Trump’s Albemarle Estate at Trump Winery, where your final dinner takes place, was originally designed as a private mansion and is now one of the most prestigious winery estates in the country, offering a perfect blend of historic charm and modern luxury.

Day Five: Farewell to New Friends and Virginia’s Charm

As your unforgettable journey through Virginia’s wine country and Blue Ridge beauty comes to an end, take one last morning to soak in the serene surroundings. Enjoy a final breakfast at the hotel, reminiscing about the memories made, the history uncovered, and the friendships forged along the way. With bags packed and hearts full, it’s time to bid farewell—but the experiences shared and the bonds formed will last a lifetime.

Highlights

• Final Breakfast at The Forum Hotel – A relaxed and reflective morning before departure.
• Time for Last-Minute Goodbyes – Exchange contact information and memories with new friends.
• If Time Allows, Explore the Famous Charlottesville Historic Downtown Mall – One of the longest pedestrian malls in the country, featuring charming shops, cafes, and historic architecture.
• Depart with Lasting Memories – Take one final look at the rolling hills and vineyards before heading home.

Fun Fact:  The Charlottesville Historic Downtown Mall spans eight blocks and is home to more than 120 shops and restaurants, housed in historic buildings dating back to the 1800s. Once a bustling trade center, it has evolved into one of the most unique and vibrant pedestrian areas in the country.