Sailing Events and Opportunities by Calypso Sailing Life

  • BVI Flotilla June 2026

    2026, Sun Jun 14 6:00pm - Sun Jun 21
    image of BVI Flotilla June 2026
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin Entire Boat
    Start Location
    British Virgin Islands, Road Town, Tortola
    Contacts
    Capt. Mark Noneman,
    Ph: +1-503-709-8095,
    email: info@calypsosailing.life
    Price
    $7,900 per cabin on the lead boat. Whole boat: price varies
    Explore the stunning British Virgin Islands with us on a unique and adventurous flotilla journey! This flotilla offers an incredible opportunity to discover the BVI’s hidden gems and off-the-beaten-path destinations that most charters miss. We’ll sail to picturesque anchorages, vibrant snorkeling spots, and charming islands, creating an unforgettable experience away from the more crowded locations. Our itinerary promises a rich variety of less-visited bays and coves that capture the true essence of the BVI. By the Cabin with ensuite head on the lead boat, a 50' sailing catamaran, including all onboard food and beverage, SUP, hostess, and two instructors/captains! By the Boat: charter your own yacht, bring family and friends and join in the adventure. Link to more information about this Opportunity.

  • Sporades Greece Sailing Flotilla - Catamaran by the Cabin

    2026, Sat Sep 12 5:00pm - Sat Sep 19
    image of Sporades Greece Sailing Flotilla - Catamaran by the Cabin
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Start Location
    , Skiathos
    Contacts
    Capt. Mark Noneman,
    Ph: +1-503-709-8095,
    email: info@calypsosailing.life
    Price
    €6,000 (US$ 7,000) per cabin (double occupancy). 3 cabins availa
    Join us on this NauticEd flotilla! We have chartered a boat to join this amazing Sailing vacation in Greece. Sailing through the Sporades is like stepping into a scene from a movie – because it is. This is where Mamma Mia was filmed, but beyond the Hollywood sparkle lies a Greece still rich in tradition, hidden coves, and pine-covered hills. You’ll dance barefoot in seaside villages, feast on grilled octopus and village wine, and swim in turquoise waters. This isn’t a cruise. It’s your floating home for the week. We have a local Greek flotilla leader who knows every secret anchorage and taverna worth visiting. Trip Highlights: - Explore the real-life filming locations of Mamma Mia on Skopelos - Dock in postcard villages like Skiathos, Alonissos, and Steni Vala - Swim in hidden coves only accessible by boat - Optional hikes to hilltop monasteries and breathtaking viewpoints - Sunset taverna dinners, beach bars, and evening socials - Paddleboard, snorkel, and unwind in calm Aegean waters - Nights under the stars with music, wine, and new friends Enjoy our spacious 2021 Lagoon 46, 4 cabin sailing catamaran. Each cabin includes your own head and shower. Three cabins available, two sailors per cabin. Meals include breakfast, lunches, sundowners/snacks, and some dinners on board. There will be some dinners ashore not included in the flotilla fees. Ages 18 and up. Link to more information about this Opportunity.