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Skippered/Crewed charter vacations

View the Skippered opportunities below or click here to charter an entire boat, skippered and/or crewed, in your desired location.
  • Croatia Flotilla 2025 June 14-21

    2025, Sat Jun 14 5:00pm - Sat Jun 21
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla
    By the Cabin Entire Boat
    Operated by Start Location
    Croatia (Hrvatska), Trogir/Split, Split-Dalmacija
    Contacts
    Emily Leach,
    Ph: 512-696-1070,
    email: flotillas@nauticed.org
    Price
    Varies per cabin and boat
    Embark on an unforgettable sailing adventure along Croatia’s stunning Dalmatian Coast with NauticEd’s 2025 flotilla. This time, we’re turning up the excitement and allure, inviting you to explore the ancient cities, pristine beaches, and secluded bays of the Central Dalmatian Coast. Learn more
  • Greece Ionians Friendly Flotilla

    2025, Sat Jun 21 5:00pm - Sat Jun 28
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla
    By the Cabin Entire Boat
    Operated by Start Location
    Greece, Lefkada, Ioannina
    Contacts
    Emily Leach,
    Ph: 5126961070,
    email: flotillas@nauticed.org
    Price
    See website link for the various options
    JOIN NAUTICED ON A GREECE FLOTILLA SAILING VACATION. The Ionian Islands on the western side of Greece are some of the most beautiful islands in Greece. Sailing the southern Ionian from a Lefkas home-base makes for an exciting, serene, and varied Greek island adventure. Learn more
  • Scotland: Sail Oban to Stornoway

    2025, Sat Aug 02 10:00am - Mon Aug 11
    Category Type
    Skippered/Crewed Charter Vacation
    By the Cabin
    Operated by Start Location
    United Kingdom, Oban, Argyll
    Embark on an unforgettable adventure as we reimagine Scotland’s iconic North Coast 500 - this time, under sail aboard Big Blue, our stunning expedition yacht. Your journey begins in the coastal town of Oban, famed for its historic whisky distillery... Learn more
  • Scotland: Sail Stornoway to Kirkwall

    2025, Thu Aug 14 10:00am - Sat Aug 23
    Category Type
    Skippered/Crewed Charter Vacation
    By the Cabin
    Operated by Start Location
    United Kingdom, Stornoway, Roos-shire
    Set sail on a breathtaking twist of Scotland’s legendary North Coast 500 - aboard Big Blue, our beautifully equipped expedition yacht. Join one leg, combine it with a scenic drive, or experience the full sailing journey along this epic coastal route. Le... Learn more
  • Category Type
    Skippered/Crewed Charter Vacation
    By the Cabin
    Operated by Start Location
    United Kingdom, Kirkwall
    Join the final leg of our extraordinary sailing journey along Scotland’s iconic North Coast 500 - reimagined by sea aboard Big Blue, our elegant expedition yacht. Whether you’ve joined earlier legs or are stepping aboard for the first time, this i... Learn more
  • Athens Greece Sailing Flotilla September 2025

    2025, Sat Sep 13 5:00pm - Sat Sep 20
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla
    By the Cabin Entire Boat
    Operated by Start Location
    Greece, Athens, Attika
    Contacts
    Emily Leach,
    Ph: 5126961070,
    email: flotillas@nauticed.org
    Price
    Varies by the cabin and boat
    Set sail with us on a journey through the enchanting waters of Greece’s Argo-Saronic islands in 2025. Picture yourself aboard our fleet, navigating ancient sea routes once traveled by Odysseus himself. From the vibrant shores of Athens to the secluded tranquility of Hydra and the charming allure of Poros, every day promises a new discovery and a fresh vista to captivate your senses. Learn more
  • Ibiza Regatta

    2025, Sat Sep 20 5:00pm - Sat Sep 27
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla,
    SLC/ICC Training and Licensing Assessments,
    Sailing Training Adventure,
    Mile/Resume Building Adventure,
    International Regatta
    By the Cabin
    Operated by Start Location
    Spain, Ibiza, Balears
    Contacts
    Grant Headifen,
    Ph: 512-696-1070,
    email: info@nauticed.org
    Price
    €3600 per person sgl occupancy or €4600 for double occ.
    SOLD OUT: Ibiza Race Days are Sep 22-25. About 3-4 hours racing per day. Then back to the marina for hour hours, events, and dinners. We sleep onboard. We will also get some mile building in by first sailing the boat from Mallorca to Ibiza on Sunday 21st and delivery back to Mallorca on Friday 26th. The International Ibiza Regatta has been running for 12 years and is renown for the good times. Come join NauticEd CEO and Global Director of Education as Skipper on a fast Jeanneau 490. Learn more
  • The Seychelles for Young Adults

    2025, Sun Sep 28 5:00pm - Sun Oct 12
    Category Type
    Practical Training/Assessment Event,
    Skippered/Crewed Charter Vacation,
    Catamaran Endorsement,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Operated by Start Location
    Seychelles, Victoria, Victoria
    Contacts
    Holger Heye,
    Ph: +27828591609,
    email: holger@heye.co.za
    Price
    €910 per person plus shared costs for food and other operating e
    Adventure, sailing, and training trip for 18 to 29-year-olds in the Seychelles • 28th September – 12th October 2025 (14 days) • 6 guests in 3 double cabins (each cabin has its own bathroom with an electric toilet and hand shower) on a 40ft catamaran • Includes skipper and sailing instructor • The program is based on 3 principles: Sail training with certification – Life skills – Unforgettable experiences • Internationally recognized sailing qualification by NauticEd • Development of important life skills: Control and responsibility, team spirit, handling sails and ropes, navigation, organizing provisions, cooking, etc • No previous sailing experience is required • Island hopping, snorkeling, free diving, and exploring the wonderful island and underwater world • Skippers are qualified freedivers with special local knowledge, enthusiasm for the environment (aquatic and terrestrial) and choose a cost-conscious lifestyle (e.g. anchoring off the islands, cooking together on board) Learn more
  • South Atlantic Expedition: Cape Town to St Helena

    2025, Mon Oct 27 10:00am - Sat Dec 13
    Category Type
    Skippered/Crewed Charter Vacation
    By the Cabin
    Operated by Start Location
    South Africa, Cape Town, Western Cape
    Embark on a truly extraordinary sailing expedition across the South Atlantic - designed not just to challenge and inspire, but to teach you exactly what it takes to plan and complete a major ocean crossing. Led by a highly experienced skipper and firs... Learn more
  • Sailing Flotilla in the Seychelles SOLD OUT

    2025, Sat Nov 01 3:00pm - Sat Nov 08
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla
    By the Cabin Entire Boat
    Operated by Start Location
    Seychelles, Victoria, Victoria
    Contacts
    Emily Leach,
    Ph: 512-696-1070,
    email: flotillas@nauticed.org
    Price
    Varies by cabin and boat. See webpost
    SOLD OUT - sorry! The Seychelles is an enchanting archipelago of 115 islands in the Indian Ocean, located off the coast of East Africa. Known for its stunning beaches, vibrant coral reefs, and lush nature reserves, the Seychelles is also home to rare wildlife, including the giant Aldabra tortoises. Come join NauticEd for an epic adventure. Learn more
  • Thailand Mini Flotilla

    2025, Sat Nov 01 5:00pm - Sat Nov 08
    Category Type
    Skippered/Crewed Charter Vacation,
    Sailing Flotilla,
    SLC/ICC Training and Licensing Assessments
    By the Cabin Entire Boat
    Operated by Start Location
    Thailand, Phuket, Phuket
    Contacts
    NauticEd,
    Ph: 512-696-1070,
    email: flotillas@nauticed.org
    Price
    $3000 per cabin Monohull or $4500 per cabin for the Catamaran
    This is a mini NauticEd-sponsored flotilla with 2-3 boats. Join by the cabin or charter the whole boat (we can provide a skipper if needed). You will be sailing the east coast of Phuket and the surrounding islands. See this guide https://charter-yacht.com/wp-content/uploads/2023/12/IS-PHUKET-CRUISING-GUIDE-2023.pdf. Available are a Monohull 46 ft Bavaria or a 45 ft Lagoon Catamaran. We have not build a specific webage for this event. email us if interested. Learn more