Frequently Asked Questions

we’re here to answer any questions you may have

  • We design intentional, personalized journeys through Italy, thoughtfully crafted itineraries that balance culture, beauty, local experiences, and seamless logistics.

  • Our experiences are ideal for couples, families, friends, and small groups seeking a meaningful and well paced journey through Italy without the stress of planning it themselves.

  • For now, yes. Italy is our heart, from beautiful coastlines to alpine landscapes. By focusing on one country, we are able to design experiences with care, authenticity, and meaningful detail. As Olèa evolves, new destinations may join our portfolio, but Italy will always be where we began.

  • An Olèa itinerary includes thoughtfully curated daily plans - accommodations that fit your style, meaningful experiences, pacing that feels natural, and notes that give context, rhythm, and confidence.

The Design Process

  • You begin by sharing your vision through our Design My Trip form. We review your details, confirm expectations and timeline, and then craft a custom itinerary tailored to your style, rhythm, and priorities.

  • Not at all. Whether you have a clear plan or simply a feeling you are chasing, we guide you in shaping an experience that feels aligned and intentional.

  • Your first draft is typically delivered within 7 to 10 days after we confirm your trip details and timeline.

  • Yes. Travel design is collaborative, and refinements are part of the process to ensure your journey feels just right.

  • Absolutely. We take dietary needs, accessibility considerations, and special celebrations into account when designing your journey, ensuring the experience feels thoughtful and well supported.

Bookings and Logistics

  • Our trips typically include locally-owned accommodation, transportation, guided tours, and some meals. Specific inclusions will be detailed in your custom itinerary.

  • Yes. We can handle bookings for accommodations, experiences, and transfers through trusted partners. We always appreciate your feedback afterward so we can continue refining the experience and maintaining strong relationships with our partners.

  • We carefully select locally-owned boutique and luxury stays that align with your preferences, prioritizing character, comfort, location, and overall experience.

  • If booking support is selected, we can arrange private airport transfers, train tickets, private drivers, or regional flights to ensure your journey flows smoothly from beginning to end.

Payment

  • Our custom design fee depends on the length and complexity of your trip. This fee covers the creation of your personalized itinerary and our planning expertise.

  • No, the comfortable budget range you share helps us design around your expectations for accommodations, transportation and experiences; airfare is considered separately based on your preferences.

  • Design fees are due before we begin crafting your itinerary. Booking payments follow the timelines set by each hotel, experience provider, or partner.

After You Submit

  • We personally review your submission and respond within 48 hours to confirm next steps, timeline, and availability.

  • Yes. If you would prefer to connect before or during the design process, we are happy to arrange a call.

  • If you enjoy planning independently, our Italy Guides are a beautiful place to begin. Each guide is thoughtfully curated with local recommendations and suggested pacing, offering structure and inspiration while allowing you full flexibility.