Sailing Events and Opportunities by SV Indie Sky

  • Dominican Republic to Turks & Caicos Training Expedition

    2026, Sun Jun 14 9:00am - Fri Jun 19
    image of Dominican Republic to Turks & Caicos Training Expedition
    Category Type
    Practical Training/Assessment Event,
    Specialized Endorsement Training,
    SLC/ICC Training and Licensing Assessments,
    Catamaran Endorsement,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Start Location
    , Providenciales
    Contacts
    Gabriel Burgess,
    Ph: 5093103017,
    email: gabriel@svindiesky.com
    Price
    5+ Days starting at $1406.08
    This training expedition takes you from Luperón, Dominican Republic, to South Bank Marina in Providenciales, Turks & Caicos. Offered on a by-the-cabin basis, this is a hands-on sailing and seamanship experience with provisioning included. Crew members actively participate in all aspects of the passage, including navigation, watchstanding, weather routing, sail handling, boat systems, and passage planning. This voyage is Leg 1 of a multi-leg expedition from the Caribbean to the Mediterranean, providing an opportunity to join the beginning of an ambitious offshore adventure. Whether you're building sea time, working toward certifications, or looking to gain real-world passagemaking experience, this leg offers a practical introduction to offshore cruising in the Caribbean. The passage concludes at South Bank Marina in Providenciales, Turks & Caicos, positioning the vessel for the next stage of the journey north toward Bermuda and eventually across the Atlantic to the Azores and the Mediterranean. Link to more information about this Opportunity.

  • Turks & Caicos to Bermuda Training Expedition

    2026, Sat Jun 20 12:00am - Mon Jun 29
    image of Turks & Caicos to Bermuda Training Expedition
    Category Type
    Practical Training/Assessment Event,
    Specialized Endorsement Training,
    Skippered/Crewed Charter Vacation,
    SLC/ICC Training and Licensing Assessments,
    Catamaran Endorsement,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Start Location
    , Providenciales
    Contacts
    Gabriel L Burgess,
    Ph: 5093103017,
    email: gabriel@svindiesky.com
    Price
    From $2812 per person
    This training expedition takes you from South Bank Marina in Providenciales, Turks & Caicos, to St. George's, Bermuda, on a challenging offshore passage of approximately 10+ days. Offered on a by-the-cabin basis, this is an immersive sailing and seamanship experience with provisioning included. Crew members participate in every aspect of offshore passagemaking, including watchstanding, navigation, weather analysis, sail handling, vessel systems management, passage planning, and offshore safety procedures. This leg marks the transition from Caribbean cruising to true bluewater sailing. Once clear of the islands, the crew will settle into a round-the-clock watch schedule and experience the rhythm of ocean passagemaking as SV Indie Sky heads north through the Atlantic. Weather routing, Gulf Stream considerations, and offshore decision-making become key elements of the training. This voyage is Leg #2 of a multi-leg expedition from the Caribbean to the Mediterranean. Bermuda serves as both a rewarding destination and a staging point for the Atlantic Crossing to the Azores. For sailors seeking meaningful offshore miles, overnight passages, and real-world ocean sailing experience, this passage provides an outstanding opportunity to build confidence and skills in an open-ocean environment. The expedition concludes in the historic harbor of St. George's, Bermuda, one of the Atlantic's classic landfalls and a memorable stop on the route to Europe. Link to more information about this Opportunity.

  • Ponta Delgada, The Azores to Portimao, Portugal Training Expedition

    2026, Tue Jun 30 12:00am - Mon Jul 20
    image of Ponta Delgada, The Azores to Portimao, Portugal Training Expedition
    Category Type
    Practical Training/Assessment Event,
    Specialized Endorsement Training,
    Skippered/Crewed Charter Vacation,
    SLC/ICC Training and Licensing Assessments,
    Catamaran Endorsement,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Start Location
    , Ponta Delgada
    Contacts
    Gabriel L Burgess,
    Ph: 5093103017,
    email: gabriel@svindiesky.com
    Price
    From $2812 per person.
    This training expedition takes you from Ponta Delgada, Azores, to Portimão, Portugal, on a rewarding offshore passage that connects the mid-Atlantic islands with mainland Europe. Offered on a by-the-cabin basis, this hands-on training experience includes provisioning and provides crew members with the opportunity to participate fully in navigation, watchstanding, weather routing, sail handling, vessel systems management, passage planning, and offshore seamanship. After exploring the volcanic landscapes and maritime culture of the Azores, SV Indie Sky departs for continental Europe, following one of the classic routes used by cruising sailors for generations. Depending on weather and routing, the voyage typically includes a mix of open-ocean sailing, shifting weather patterns, and the increasing excitement of approaching the European mainland. This passage offers an excellent balance between offshore sailing and destination cruising. Crew members continue to build confidence and experience while refining the skills developed during the earlier legs of the expedition. Long ocean swells, changing sea states, and strategic weather decisions provide valuable real-world training in offshore passagemaking. As Portugal draws closer, anticipation builds for landfall on the European continent. Arriving in the Algarve after days at sea is a memorable experience, with dramatic coastal scenery, welcoming marinas, and centuries of maritime history awaiting just beyond the breakwater. This voyage is the final offshore leg of SV Indie Sky's Caribbean-to-Mediterranean expedition and provides the opportunity to complete an extraordinary journey spanning thousands of miles across the Atlantic Ocean. The expedition concludes in Portimão, Portugal, a vibrant sailing destination on the Algarve coast and an ideal gateway to further cruising adventures throughout Europe and the Mediterranean. Link to more information about this Opportunity.

  • Atlantic Crossing- Bermuda to the Azores

    2026, Tue Jun 30 9:00am - Mon Jul 20
    image of Atlantic Crossing- Bermuda to the Azores
    Category Type
    Practical Training/Assessment Event,
    Specialized Endorsement Training,
    Skippered/Crewed Charter Vacation,
    SLC/ICC Training and Licensing Assessments,
    Catamaran Endorsement,
    Sailing Training Adventure,
    Mile/Resume Building Adventure
    By the Cabin
    Start Location
    , St. Georges
    Contacts
    Gabriel L Burgess,
    Ph: 5093103017,
    email: gabriel@svindiesky.com
    Price
    From $5905.52 for 21+ Days
    This expedition takes you from St. George's, Bermuda, to Ponta Delgada, Azores, on one of the world's classic offshore sailing passages: a true Atlantic Ocean crossing. Offered on a by-the-cabin basis, this hands-on training expedition includes provisioning and places crew members at the center of every aspect of offshore passagemaking. Crew stand watches, assist with navigation and weather routing, manage vessel systems, handle sails, and gain firsthand experience with the rhythms of life at sea. For many sailors, an Atlantic crossing sits at the very top of their bucket list. There is something fundamentally different about leaving sight of land behind and setting a course for another continent. Days blend together under a canopy of stars. Weather systems become your landmarks. The crew settles into the timeless routine of watch rotations, sail trim, meals underway, and the simple satisfaction of making miles toward a distant horizon. This is not a delivery trip where passengers sit back and watch. It is an immersive training experience designed to develop confidence, seamanship, and offshore decision-making in one of the most rewarding sailing environments on earth. The voyage follows favorable North Atlantic summer weather patterns toward the Azores, a remote volcanic archipelago that has welcomed ocean sailors for centuries. After roughly two weeks at sea, making landfall in the Azores is an unforgettable moment—green mountains emerging from the horizon after more than a thousand miles of open ocean. This passage is the centerpiece of SV Indie Sky's multi-leg expedition from the Caribbean to the Mediterranean and offers the opportunity to earn meaningful offshore sea time while accomplishing something few sailors ever experience: crossing an ocean under sail. The expedition concludes in Ponta Delgada, Azores, one of the most celebrated landfalls in offshore cruising and the gateway to Europe. Link to more information about this Opportunity.