Upcoming Passages.

Explore Greece: Ionian Sea, Greek Islands & Corinth Canal. April - May 2026


Discover the beauty of the Ionian Sea, Greece’s stunning islands, and the historic Corinth Canal on a fully customizable sailing adventure tailored to your pace and interests.

Trip Highlights

  • Sail iconic Greek islands, mainland coastlines, and transit the Corinth Canal
  • Swim, snorkel, kayak, and relax in secluded bays
  • Explore charming villages, historic sites, and picturesque harbours
  • Savor authentic Greek cuisine at local tavernas
  • Enjoy onboard amenities including kayak, WiFi, and floating water toys
  • Day Sailing adventure, Perfect for novices.
  • Availability / Schedule
Dates Route / Departure Notes / Highlights Berths Available
15–30 April Preveza → Preveza Cruise the region and return to Lefkas 4 Berths Available
1–5 May Kefalonia → Kefalonia Fully Booked Fully Booked
5–13 May Kefalonia → Kefalonia Fiscardo, cruise the region, return to Fiscardo 4 Berths Available
14–18 May Kefalonia → Kefalonia Fully Booked Fully Booked
18–21 May Kefalonia → Kefalonia Cruise the region, return to Kefalonia Marina 4 Berths Available
26 May – 2 June Kefalonia Marina → Corinth Canal Traverse the Corinth Canal 4 Berths Available

Cabin Options

  • 2 Single Berths in Shared Bunk Cabin – 7 Nights
  • 2 Berths in Shared Queen Cabin – 7 Nights
  • Minimum stay 7 nights, 10 – 14 nights recomended. Shorter trips by negotiation.

*Footnote: All dates are indicative and may be adjusted based on weather, route preferences, and operational considerations.

Explore Greece: Corinth Canal, Peloponnese, Saronic & Cyclades, Crete - June 2026


Sail from Isthmia (East end of the Corinth Canal) south through the Greek islands, enjoying day sailing, charming anchorages, and authentic Greek culture, finishing your journey at Crete.

Trip Highlights

  • Depart from Isthmia (Corinth Canal) and explore the Saronic Islands (Agistri, Methana,Poros, Hydra)
  • Continue through the Cyclades (Kynthos Syros, Serifos, Naxos, Paros, Fira)
  • Cruise along southern Greek coastlines, anchoring in scenic bays and harbours
  • Swim, snorkel, kayak, and paddle in secluded coves
  • Explore charming villages, harbours, and historic sites
  • Enjoy authentic Greek cuisine at local tavernas
  • Flexible day sailing routes based on your interests and weather
  • Use of kayak, WiFi, and floating water toys included
  • Availability / Schedule
Dates Route / Departure Notes / Highlights Berths Available
2–9 June Isthmia → Saronic Islands (Agistri, Methana,Poros, Hydra) Day sailing 4 berths Available
9–16 June Saronic Islands → Cyclades  Poros  to Naxos (Kynthos Syros, Serifos,  Fira) Day sailing 2 berths available
16–23 June Cyclades → Crete Day sailing 4 berths Available

Cabin Options

  • 2 Single Berths in Shared Bunk Cabin – 7 Nights
  • 2 Berths in Shared Queen Cabin – 7 Nights
  • Minimum stay 7 nights, 10 – 14 nights recomended. Shorter trips by negotiation.

*Footnote: All dates are indicative and may be adjusted based on weather, route preferences, and operational considerations.

Crete to Malta & Tunisia – Offshore Passage, Malta. June- July 2026


Sail from Crete to Malta and onward to Tunisia, with two weeks of day sailing around Malta—perfect for experienced offshore sailors and those wanting to prepare for longer passages, including the Atlantic.

Trip Highlights

  • Depart Crete around 23 June, sailing west across the southern Mediterranean toward Malta
  • 560 NM overnight offshore passage to Malta (3–4 nights) – experience required
  • Ideal for sailors wanting to gain confidence for longer ocean passages such as the Atlantic
  • Explore Malta and Gozo with day sailing, visiting hidden bays, anchorages, and charming harbours
  • Swim, snorkel, kayak, and paddle in secluded coves
  • Sample authentic Maltese and Mediterranean cuisine ashore
  • Continue to Tunisia after the Malta leg (day sailing or overnight passage)
  • Flexible, fully customizable routes depending on interests and weather
  • Use of kayak, WiFi, and floating water toys included

Availability / Schedule

Dates Route / Departure Notes / Highlights Berths Available
23–27 June Crete → Malta 560 NM offshore passage, 3–4 nights – experience required Available
28 June – 11 July Malta 2 weeks day sailing around Malta & Gozo Available
12–15 July Malta → Tunisia Offshore / day sailing combination Available

Cabin Options

  • 2 Single Berths in Shared Bunk Cabin – 7 Nights
  • 2 Berths in Shared Queen Cabin – 7 Nights
  • Minimum stay 7 nights, 10 – 14 nights recomended. Shorter trips by negotiation.

*Footnote: All dates are indicative and may be adjusted based on weather, route preferences, and operational considerations.

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Late Season Mediterranean Cruising – August to November 2026


As the summer months fade, the second half of the season is still wide open, offering full options and possibilities. Osprey has carried us safely through the Mediterranean, and now the choices ahead will shape the final cruising weeks before winter and our trip to the Caribean.

Options include lingering in Malta, enjoying familiar anchorages, quieter bays, and extra days of swimming, walking, or relaxed day sails. Alternatively, we can head north toward Sicily or west through Sardinia, Corsica, and Minorca, combining scenic day sails, overnight passages, and quiet anchorages:

  • Sardinia: Calm southern bays ideal for swimming, snorkeling, and relaxing on quiet beaches.
  • Corsica: Sheltered anchorages with dramatic cliffs and turquoise waters, with charming towns to explore ashore.
  • Minorca: Secure harbours and anchorages like Cala Macarella and Cala Galdana, perfect for day sails and swimming.
  • Malta: Charming harbours and secluded bays around Valletta, Gozo, and Comino, with opportunities to explore historic fortifications and enjoy local cuisine.
  • Sicily (Southern Coast): Explore secluded bays and harbours along Trapani, Marsala, and the Egadi Islands, ideal for swimming, kayaking, and tasting authentic Sicilian cuisine.

Whichever route is chosen, the focus is on exploration, leisure sailing, and safe cruising, with flexibility for day sails, overnight passages, or extended anchorages. The ultimate goal is to arrive in Gran Canaria by 15 Novemberto prepare the yacht for the upcoming Atlantic season.

Dates Route / Departure Notes / Highlights Berths Available
Flexible August–September Malta & surrounding Mediterranean Day sailing / overnight passages optional 4 Berths Available
Flexible October–15 November Western Mediterranean / Canary Islands Scenic coastal and overnight passages, arriving Gran Canaria 15 Nov 4 Berths Available

Cabin Options

  • 2 Single Berths in Shared Bunk Cabin – 7 Nights
  • 2 Berths in Shared Queen Cabin – 7 Nights
  • Minimum stay 7 nights, 10 – 14 nights recomended. Shorter trips by negotiation.

*Footnote: All dates are indicative and may be adjusted based on weather, route preferences, and operational conside

ATLANTIC CROSSING|ARC RALLY 2026| 30 DAY PROGRAM


15 November  2026 to 15 December 2026 – 30 Nights

Let us help you create unforgettable memories sailing from the Canary Islands, across the Atlantic, and arriving in the Caribbean. Back in time to celebrate Christmas 2026.

Join us for a true bluewater adventure that combines preparation, ocean passage, and island celebration. This is a serious offshore voyage designed for experienced sailors who want real sea miles, challenge, and reward — all in company with the ARC Rally fleet.


Trip Highlights

Departure Date:
Arrive Gran Canaria 15 November 2026, 7 DAY Pre rally Seminars and shore based training mixed with Provisioning, Safety Checks, repairs and preparation.
ARC Rally start: 22 November 2026

Crossing expected between 15-18 Days

Upto 7 days post race celebration and recovery.

Destination:
Rodney Bay, St Lucia, Caribbean

Duration:
30 days total

Experience:
A structured ocean passage with time for preparation, training, and celebration.
Prepare the boat in the Canaries, sail the trade winds west, and make landfall in St Lucia with a crew you’ll trust and rely on.


  • 🌊 ATLANTIC CROSSING – 30 DAY ADVENTURE 🌊
    Mid November to Mid December 2026
  • Includes:
  • ✅ Approx. 30 days total experience
    ✅ 7 days pre-departure preparation, refit & briefings in the Canary Islands
    ✅ 16–21 days ocean crossing (ARC Rally fleet)
    ✅ Up to 7 days upon arrival in St Lucia to relax, explore & celebrate
    ✅ Rally entry fees, Food, Fuel, Marina Fees and all onboard expenses.

  • Who This Is For
  • Experienced sailors only

  • Priority given to those who have sailed with us before

  • Adventurers ready for watch rotations, shared cooking & life at sea

  • Sailing couples welcome

  • Maximum crew onboard: 7, including
    Sally (Captain), Tony (Deckhand), and  Oliver (29, strongman).
     4 berths available. 

  • Available Cabin Options
  • 2 x Single Berths in Shared Bunk Cabin 

  • 2 Berths in Shared Queen Cabin


 

Check back regularly for new dates, updated information, and upcoming opportunities. The 2027 season will take us to the Caribbean.

Contact Us

If you are ready for adventure, teamwork, and unforgettable experiences on the sea, get in touch! Let us know a bit about your sailing background, interests, and availability — and let’s plan an incredible voyage together
Disclaimer: Osprey Sailing Adventures is a private sailing activity operated on a cost-sharing basis only. Participants share actual expenses and are active crew, not passengers. No commercial transport or passenger fares are offered.