Journeys Curated with Discerning Precision
“Anyone that who has a dream should go to Italy. It doesn’t matter if you think the dream is dead and buried - in Italy, it will rise and walk again.”
-Elizabeth Spencer
Each journey we craft is an artful composition—balancing iconic landmarks with intimate, hidden gems—so that every moment unfolds with curiosity and excitement.
The Gems of Le Marche Italy is an eight-day journey weaving together castles, vineyards, rolling hills, and Adriatic coastal charm, designed to reveal a more authentic and less-traveled side of Italy. Explore medieval hill towns, wander ancient stone streets, and step inside historic castles that overlook dramatic valleys and sea views.
The Gems of Le Marche Italy
Dates - May & September 2027
$ 3499
An eight-day journey weaving together castles, vineyards, rolling hills, and Adriatic coastal charm, designed to reveal a more authentic and less-traveled side of Italy. Explore medieval hill towns, wander ancient stone streets, and step inside historic castles that overlook dramatic valleys and sea views.
Women-only & Co-Ed options available
Day 1 – Arrival & Welcome to La Dolce Vita
Ease into the magic of Le Marche, Italy with a warm welcome and effortless elegance.
Settle into your accommodations—no changing hotels, as charming Senigallia will be your home throughout the journey—before gathering for a beautifully curated welcome dinner featuring wines from a boutique local winery; your first taste of the region's exceptional terroir.
This evening is a celebration of new beginnings. Meet your fellow travelers, raise a glass to the adventures ahead, and savor authentic Italian cuisine in an atmosphere filled with warmth, conversation, and the unmistakable charm of la dolce vita.
D
Day 2 – Storybook Towns & Culinary Dreams: Urbino & Truffle Hunt
Step into a Renaissance masterpiece as you explore Urbino, a UNESCO World Heritage city celebrated for its magnificent architecture, rich artistic legacy, and breathtaking hilltop vistas. Wander its elegant streets and experience one of Italy's most captivating historic towns.
In the afternoon, venture into the rolling countryside for an authentic truffle hunt with local experts before enjoying a delicious lunch showcasing the prized treasures you've helped uncover.
B • L
Day 3 – Nature & Cultural Wonders: Frasassi Caves & Jesi
Journey beneath the earth to discover the awe-inspiring Frasassi Caves, one of Europe's most spectacular natural wonders, where soaring chambers and remarkable limestone formations create an unforgettable underground landscape.
Continue to the charming walled town of Jesi for a leisurely exploration, followed by a relaxing lunch complemented by regional wines that reflect the distinctive character of Marche.
B • L
Day 4 – Timeless Tradition
Stroll through the elegant piazzas and graceful streets of Ascoli Piceno, one of Italy's most beautiful and best-preserved medieval cities, renowned for its stunning travertine architecture.
Immerse yourself in an authentic Italian tradition with an aperitivo lesson, discovering the art behind Italy's beloved pre-dinner ritual while learning to craft the perfect classic cocktail.
Pause in the picturesque seaside village of Sirolo, where sweeping views of the Adriatic coastline provide the perfect opportunity to capture unforgettable photographs.
B • L
Day 5 – Castles, Wine & Culinary Artistry
Step into centuries of romance and legend at the magnificent Gradara Castle, one of Italy's most enchanting medieval fortresses, where history and folklore come vividly to life.
Then journey into the picturesque countryside near Morro d'Alba for an exclusive vineyard experience at Antica Cantina Sant'Amico, Marche's oldest winery, where generations of winemaking tradition continue today.
Enjoy a guided wine tasting before rolling up your sleeves for a hands-on cooking class, preparing authentic regional dishes that you'll later enjoy together over a leisurely lunch filled with conversation, laughter, and the joy of Italian hospitality.
B • L
Day 6 – Senigallia: Style, Flavor & Leisure
Discover the sophisticated seaside charm of Senigallia, where elegant architecture, vibrant local life, and the Adriatic coast come together to create one of Marche's most beloved destinations.
Browse the lively Foro Annonario market, visit the impressive Rocca Roveresca fortress, and explore the newly renovated Pope Pius IX Museum, each offering a unique glimpse into the town's rich heritage.
Enjoy a guided walking tour followed by lunch at an award-winning pizzeria before visiting a carefully curated fine jewelry and antiquities boutique, an ideal place to discover a truly memorable keepsake.
Treat yourself to authentic Italian gelato, browse the inviting boutiques, or simply relax along the picturesque banks of the Misa River while soaking in the rhythm of everyday Italian life.
B • L
Day 7 – Seaside Serenity: Velvet Beach Day & Conero Riviera
Slow the pace and savor your final full day in beautiful Senigallia.
Enjoy a leisurely morning along the celebrated Velvet Beach, relax by the Adriatic, visit the iconic Rotonda a Mare, or take one last stroll through the charming streets you've come to know so well.
In the afternoon, embark on a scenic boat cruise along the spectacular The Conero Riviera where dramatic limestone cliffs, hidden coves, and crystal-clear Adriatic waters reveal one of Italy's most breathtaking coastal landscapes. It's the perfect opportunity to unwind, take in unforgettable views, and reflect on the incredible journey you've shared.
As evening falls, gather for a heartfelt farewell dinner celebrating new friendships, shared laughter, unforgettable discoveries, and memories that will remain long after the journey ends.
B • D
Day 8 – Departure
Enjoy a relaxed breakfast and a leisurely morning before departing, taking home not only treasured souvenirs but also lasting friendships, unforgettable experiences, and a deeper connection to the heart of Italy.
B
✔ 7 nights’ accommodation in a carefully selected 4-star hotel
✔ Meals as indicated in the itinerary (B = Breakfast, L = Lunch, D = Dinner)
* On Women-only tours, guests are welcome to join C.C. at dinner times
✔ Private transportation throughout all scheduled touring days
✔ All sightseeing, guided tours, and experiences included in the itinerary
✔ All entrance fees and admission tickets for included attractions and activities
✔ Expertly curated itinerary showcasing the authentic culture, history, cuisine, and hidden gems of the region
✔ Services of your Tour Host from The Diamond Journeys throughout the journey
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Please note: Airfare, travel insurance, personal expenses, meals not listed in the itinerary, optional activities, and gratuities for non-included services are not included unless otherwise stated.
What Travelers say about their Journeys with C.C.
Traveling is so much more enjoyable when you're with someone who loves planning the details, and that is exactly what it's like to travel with C.C. We often joke that I simply show up with my suitcase and everything else is taken care of. From arranging flights and accommodations to selecting restaurants based on my personal preferences, every detail is thoughtfully curated. C.C.’s planning has led to some of the most memorable experiences of my life. She is knowledgeable, organized, and incredibly thorough in her preparation. Most importantly, she genuinely cares about ensuring that everyone has the best possible experience, and it shows in every aspect of the trip.
-Nicole N.
We have had the pleasure of traveling with C.C. on three occasions, visiting Italy, Japan, and the Philippines, and each experience has been exceptional. Her level of planning and preparation is truly outstanding, always paying close attention to every detail and anticipating our needs.
C.C. takes great care in creating fun, enriching, and culturally immersive itineraries, perfectly adapting them to the interests and requirements of each traveler. Her dedication, warmth, and commitment allow you to enjoy your trip with complete peace of mind, knowing that everything has been carefully planned and organized. The experience unfolded with quiet precision; luxury revealed itself in subtle layers.
Another great advantage for us was her excellent command of Spanish. As non-native English speakers, having someone who could communicate fluently in our own language made a huge difference and allowed us to enjoy every experience with greater confidence and peace of mind.
Without a doubt, we would travel with her again and highly recommend her.
- Evelyn & Felipe S.
CC is the most well traveled and most adventurous person I have ever met. She is extremely experienced in the traveling world and has a true passion for adventure. She has an abundance of knowledge about every aspect of traveling you can think of. Whether it's where to find the best deals, fun tourist spots, safety tips or even on cultural norms to follow when visiting a country.
Whenever I am traveling somewhere for the first time I will always go to CC first for any tips I need, or questions I may have. Traveling with CC is also fun as well. She provides the perfect balance of scheduled activities and free time so that it allows for a perfectly balanced vacation. Making sure everyone is safe and is having a fun time is always the top priority for CC and whenever an issue arises she is always on top of it.
I promise if you travel with CC it will truly be a one in a life time trip you will never forget :)
-Kim R.