“It was so special to experience the world from the unique perspective of living on the water with the sea as our home. And it’s an unbelievably gorgeous place to explore! Sailing in Italy is utterly glamorous; the food is fresh, simple, and so delicious; each island feels like a treasure; and you’re with a group of incredible people who share a spirit for adventure. What a perfectly wonderful trip!” ~ Sara B, Boulder, CO
As seen in Yolo Journal, November 2024
On this six-day sailing retreat through the Tyrrhenian Sea off the coast of Naples, we hold space for a particular kind of traveler: the woman standing at a threshold. Maybe a chapter has just closed. Maybe the next one hasn’t yet opened. Maybe you simply know, in your body, that something is ready to move, and you’re looking for the right conditions, to let that movement happen.
Timed to the summer solstice, we’ll sail into the longest, sun-drenched daylight of the year together. In Italian folklore, the solstice is itself a threshold, a portal connecting two worlds. It’s a fitting, almost magical moment to honor what is ending and tune into what wants to emerge.
You’ll step outside your comfort zone into an environment built for genuine adventure, going with the captain’s wishes, the wind’s wishes, the sea’s wishes. Anything can happen, anytime, and there’s real delight in that. That unpredictability isn’t a flaw in the trip; it’s the whole point. The nature of sailing itself asks you to surrender, and there’s a surprising amount of laughter in learning how.
This isn’t a vacation from your life. It’s a refuge within it: six deliberately spacious, sun-warmed days where the sea does some of the work that willpower usually tries to do alone.
We’ll meander from cove to harbor aboard a 60-foot private sailboat, letting the wind, weather, and wisdom of our captain help set the pace. Mornings might begin with a plunge into cool blue water to wake the body before that first cappuccino; nothing clears the head quite like salt water at dawn. Lemon groves flourish above sun-bleached villages, and simple, joyful dishes are shaped by what the land and water provide, with cones of white peach gelato passed hand to hand to cool the long, golden afternoons.
We’ll cook together, read poetry aloud, watercolor, hike to thermal waters, dive into grottoes, and dance beneath the stars.
What you tend to love most is what you didn’t plan for: dolphins escorting you into port, a particular sunset, a burst of laughter over a shared meal, a revealing conversation you didn’t see coming, the exact conditions lining up so the trip becomes, without your engineering it, the one you needed. And beneath it all, we’ll practice something as rewarding as it is hard: paying attention.
Aboard a boat, there’s nowhere to rush to. A stretch of afternoon with nothing scheduled, or the pause between one cove and the next, stops feeling like a gap and begins to feel like the point. Not everything that surfaces in that space will be comfortable. A feeling you’ve been outrunning on land has a way of catching up with you on water, and we won’t rush you past it. Staying with the discomfort of what is true, rather than immediately trying to fix it, is where real movement, and eventually, real lightness, begins.
There is also room for what you don’t see coming: a conversation that answers a question you haven’t said aloud, a line from someone else’s story that illuminates your own, or a book that finds its way into your hands at exactly the right moment. Our approach is informed by Buddhist principles of impermanence, non-attachment, and compassion, held lightly as ways of meeting what is actually happening with greater openness and ease.
Each day follows a rhythm of group coaching, guided introspection, and somatic practice, balancing reflection with body-based awareness. Sailing becomes part of the inquiry: the wind you cannot control, the course you adjust to meet it, and the crew you learn to depend on. These are the real conditions through which we’ll explore the questions that often accompany a transition:
The work begins with the understanding that beneath the roles, habits, and protective patterns we accumulate, there is an essential self we already know, even when we have lost touch with her. Together, we’ll notice the unconscious patterns shaping how you meet your life and practice choosing your response with greater awareness and intention.
Once the lines are cast off, you’ll be invited to meet the untethered experience of life on the water without needing any moment to be different. As plans shift, feelings surface, and the elements set the pace, you’ll have the opportunity to notice what you resist and how much ease and joy there is, when you soften and yield.
Beauty, rest, love, nourishing food, and the intimacy of life at sea create an opening to see yourself more clearly and feel more fully. Rather than forcing an answer about what comes next, we’ll create the conditions for your inner knowing, to become easier to hear.
You’ll travel through new waters while moving through an inner passage of your own, returning with a deeper connection to yourself, a lighter heart, and a clearer sense of what deserves to be carried forward.
This Is for You If You Are:
No prior sailing experience is necessary.
This Is Not for You If You Are:
We are calling all spirited, curious women to join us in the radiant energy of the summer as we explore outer and inner landscapes, the beauty of the Med, her foods and her sea. If you long for transformative, off-the-beaten path travel, take your place at our floating table.

Ashley Wick is an insatiably curious and creative connector of people, ideas, and opportunities. In 2015, she left a career in New York fashion public relations to become a Professional Certified Coach (PCC) based in Boulder, Colorado. Since then, she has supported high-performing women, creative entrepreneurs and leaders, in developing the self-awareness and leadership needed to build deeper meaning in their personal lives and greater impact in their professional ones. She is the founder of WICK AND Co. and co-creator of the Take The Leap and The INGENIUS Life workshop series. As a transformational coach, Ashley provokes her clients to explore and release old patterns while strengthening their connection to inner wisdom, values, and innate talent, helping them take exciting, joyful leaps toward their callings.
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Peggy Markel is a writer, photographer, illustrator, Southern storyteller, and seeker. She left home young to explore the world, and for over 32 years has designed and directed far-flung food and culture trips for small groups built on long-term relationships, handpicked properties, and carefully crafted itineraries. Each trip is a deep dive into the most delicious culinary happenings of a place, with a hands-on approach: guests learn how food is made, or learn to make it themselves. Peggy offers an insider’s look into influential kitchens and tasting rooms from Morocco to India. She plays curator, translator, educator, and poet, providing the context for guests to experience a perfect alchemy of place, people, and food, because for Peggy, food has always been a pathway to deeper learning, self-nourishment, openness, and connection. When not traveling, she lives on the fourth floor of a 16th-century palazzo in the center of Florence, and keeps a pied-à-terre in Boulder, Colorado to be near family.
June 19 – 25, 2027
Double: $7,800 per person
All creative souls, fit and adventurous, spiritual seekers, entrepreneurs, writers, culinistas, and dreamers are welcome as we travel on a 60ft sailboat from island to island, learning about regional specialties, tasting local fare, diving off the boat into azure seas and deepening your connection to yourself. We’ll eat everything lemony; pasta, dolce, and sip famed Limoncello from the sfuso amalfitano lemons of Amalfi. Our meals will consist of local fish, fruitti di mare with tasty pomodorini tomatoes and fresh herbs, local cheeses and plenty of vegetables, fruits and other local specialties.
Let us send you a detailed itinerary.