Registration will close approx 90 days before the trip (June15, 2026), however, most of my trips sell out in less than a WEEK. If you are interested in going, I encourage you to sign up as soon as possible versus later. You can always pay a deposit and get a full refund within the first 30 days of registration.

Please note that I only have 8 couple spots available.

I require an initial deposit of $500 per person ($1000 per couple) to hold your spot and then I offer payment plan options of either 3 payments of $1208/person or 5 payments of $725/person. 

If you choose to pay the remaining balance before those deadlines you can contact me at [email protected]

International flights to and from Athens, Greece are NOT included in your trip fee. In addition, alcoholic beverages and snacks, tips for guides, incidentals, and travel fees are not included.

Keep in mind that travel insurance is not included, but HIGHLY recommended to cover you in case of any incidents or medical care, trip cancellation and even lost or stolen baggage.

To get a free quote to cover your trip, go here (it's fairly inexpensive!).

Also, coasteering on Kefalonia (approx $100/person USD) is an optional and an extra fee, if you decide to participate. There is also an option of a wine tasting tour (approx $100/person USD), if you choose not to do the coasteering tour, or you can do neither.

Lastly, if you add the 2 day Zakynthos extension, there is an optional private boat tour to Turtle Island, the Keri Caves, and Mizithres Beach—one of the most striking viewpoints in the Ionian Sea. This costs $100 per person.

Your trip fee covers all accommodations in 3 and 4-star hotels, all fees associated with the catamaran (including the skipper/captain, fuel, mooring fees, taxes, etc), domestic flights from Kefalonia or Zakynthos to Athens, ground transportation, all meals, guides, excursions, entrance fees, mindfulness practices, as well as a gallery of professional photos of your trip.

Mid-September is truly one of the best times to experience Greece. The peak summer crowds have thinned, the intense August heat has softened, and the Ionian Sea is at its warmest after months of sunshine. Expect long, golden days with temperatures typically in the high 70s to mid-80s°F (25–30°C), and plenty of bright, sunny skies—ideal for sailing, swimming, and enjoying Greece’s famous beaches without the peak-season rush.

Evenings tend to be comfortable and pleasantly cool, especially once the sun dips behind the cliffs and harbors. Light layers are perfect for sunset dinners by the water or strolling through charming villages.

Wind conditions are generally calm and reliable at this time of year, making it an excellent season for smooth sailing and spending full days out on the water. Overall, mid-September offers that perfect blend of warm weather, vibrant landscapes, and relaxed Mediterranean energy—an ideal backdrop for your Greek Isles adventure.

When you arrange your flights to Greece you will need to book roundtrip tickets to Athens (ATH) airport arriving no later than 3PM on Sept 11th (local time). 

If your flight comes in anytime that day, we will arrange transportation to pick you up. If you arrive the day before, you will need to arrange your own hotel for the night, along with transportation to and from the hotel.

As for return flights, please arrange your departure from Athens anytime after 3PM on Sept 19th, or if you opt for the 2 day add-on to Zakynthos, arrange your departure for Sept 21st after 3PM.

Most guests do not experience significant motion sickness on this trip, as we’ll be sailing in the Ionian Sea, which is known for its generally calm, protected waters—especially in September. Our route stays close to shore and between islands, which helps minimize swells and keeps the sailing smooth and comfortable.

That said, everyone’s sensitivity is different. If you’re prone to motion sickness, we recommend bringing remedies like Dramamine, Bonine, SeaBands, or my personal favorite—scopolamine patches, just in case. The good news is that catamarans are typically more stable than monohull sailboats, and you can always move to the deck for fresh air and steady horizon views if you start to feel off.

Most guests are pleasantly surprised by how good they feel on the water, even if they’ve struggled with seasickness in the past. And of course, if you have any concerns at all, feel free to reach out—we’re here to help you feel comfortable and prepared.

You’ll be staying in comfortable double cabins aboard a spacious, modern 55 ft luxury catamaran. Each cabin sleeps two adults and includes its own private ensuite bathroom, ensuring plenty of privacy and convenience throughout the trip. Cabins are thoughtfully designed with air conditioning, a window or porthole for natural light and fresh air, and space to store your luggage and personal items.

While catamaran cabins are cozy by nature, they’re well-appointed, clean, and designed to maximize comfort at sea. You’ll have access to shared indoor and outdoor lounge areas, a fully equipped kitchen, and plenty of deck space for relaxing, reading, or enjoying the views as we sail from island to island.

If this is your first time sleeping on a boat, don’t worry—most guests are surprised by how comfortable and peaceful the experience is. It’s a unique and unforgettable part of the adventure! If you have questions about cabin layout or space, feel free to reach out.

If you have food allergies, we will accommodate you food needs and preferences. I always send out a survey prior to the trip for this reason, so we can plan our meals at restaurants that accommodate different food allergies and preferences (such as gluten-free, vegetarian, dairy-free).

*Please note that alcoholic beverages or specialty drinks (such as mocktails) and snacks are not included in your trip fee. Also, keep in mind that there is a meal budget, so if you want to order more than that, you will just pay me the difference at the end of the trip.

This trip is designed to be active but accessible—you don’t need to be an experienced hiker or athlete to enjoy it. Most of our hikes are in the 3–5 mile range with moderate elevation gain, and we move at a relaxed pace with plenty of breaks for photos, swimming, and taking in the views. In Paxos, you’ll hike to the dramatic Tripitos Arch and along coastal paths with beautiful sea views. On Kefalonia, we’ll do a scenic hike up to Assos Castle and walk to viewpoints overlooking the famous Myrtos Beach and other stunning stretches of coastline.

Beyond hiking, many of our activities center around the water and exploring the islands in fun, memorable ways. You’ll have opportunities to kayak or paddleboard through the sea caves, swim and snorkel in turquoise bays, and join an e-bike tour through olive groves and coastal villages on Paxos. There will also be options for a wine-tasting experience or a more adventurous coasteering activity on Kefalonia, plus epic boat tours if you join the Zakynthos extension (Shipwreck Beach, Blue Caves, Turtle Island, etc).

Everything is thoughtfully paced with a balance of adventure and downtime—there’s always space to rest, read, or simply enjoy being on the water. And of course, all activities are optional. If you’d prefer to sit one out, relax on the boat, or enjoy extra free time in a village, that’s completely up to you. If you have any questions or concerns about the hikes or activities, feel free to email me at: [email protected].

Absolutely. While all activities are thoughtfully curated to give you the best experience possible, everything on this trip is optional. If you ever need some downtime or prefer to explore on your own, you’re welcome to do so.

Just keep in mind that the itinerary is designed as a group experience, so transportation and logistics are arranged around scheduled activities. If you choose to skip something, any additional costs for separate transport or meals would be your responsibility.

This is your adventure—you get to make it what you need it to be.

If you choose not to participate in the mindfulness practices exercises such as guided meditations or journaling, that is completely up to you.

I offer "transformational" mindfulness practices on my group trips because they are a powerful way to reconnect more deeply with yourself, especially in the midst of such awe-inspiring places.

If you're seeking to build more confidence, gain clarity, release what’s no longer serving you, or simply feel more grounded and present in your life—these practices will fill your soul in ways you didn't expect.

Many of my past trip guests say these meditations were some of the most unexpected and life-changing parts of their journey. They came for the adventure…but left with something so much deeper.