Future Liveaboard / Bare boat Skipper Training
San Juan, Puerto Rico to TBD
TBD
. 🌊🏝️
⛵ Who It’s For
This trip is ideal for:
- Sailors aiming to strengthen their resume to meet bareboat charter or insurance requirements
- Sailors looking to gain the experience required to earn certifications, licenses, or endorsements
- Aspiring cruisers looking to build confidence in offshore conditions and/or transition to full-time liveaboard life
- Crew looking for the unique experience of crossing the Gulfstream
- Crew looking for an introduction to international operations and the realities of checking in and out of foreign countries
Whether you're preparing for your own bluewater journey or simply curious about the realities of life aboard, this offshore adventure offers hands-on training and real-world experience along one of the most iconic stretches of the U.S. coastline.
🌊 What You’ll Learn
This journey is more than just sea miles — it’s a hands-on, real-world training program covering:
- Passage planning & navigation
- Weather routing & offshore decision-making
- Sail handling & trimming for ocean conditions
- Watch rotation & night sailing
- Anchoring techniques & safe harbor selection
- Liveaboard routines: systems, provisioning, and vessel care
You won’t just observe — you’ll be part of the crew, participating in all aspects of the voyage.
⛵what you can earn
All SV Indie Sky expeditions are led by a U.S. Coast Guard Licensed Captain and NauticEd Certified Instructor to ensure safety and top-tier instruction.
Crew Members Receive:
- Hands-on training in all aspects of offshore sailing — navigation, sail handling, anchoring, docking, weather routing, and more
- Logbook endorsements for those building sea time or working toward NauticEd or other sailing certifications
- Certificates, licenses, and endorsements awarded to crew who meet proficiency and experience requirements during the expedition
🏄 Adventure Support
- 🛶 Ashore Access: Flexible shore transfers via chase boat for beach exploration, hikes, provisioning runs, or local cultural stops—even in remote anchorages.
- 🚤 Chase Boat Support: On-the-water assistance for surfing, freediving, foiling, and other water sports—launch, recovery, and safety coverage included.
- 🐟 Spearfishing & Lobstering: Dive in for sustainable seafood—where legally permitted and in season, we provide the tools, guidance, and safety protocols to do it right.
- 🎯 Condition-Driven Flexibility: We adjust daily plans based on weather and crew goals to maximize time on the water, whether that’s riding swell or chasing dinner.
- 🤝 Crew-Led Adventure: No hand-holding here—you’ll be actively involved in planning, prepping, and executing your next mission.
What's Included
🛏️ Accommodations
Your accomodations are included in your crew fees. You can choose to have your own cabin or share one (they are all double occupancy).
- Port Forward & Port Aft Cabins
Features a queen bed, chest of drawers, closet, and an en suite (private) bath with a full-sized sink, shower, and head.
- Owner’s Suite – Entire Starboard Hull
Features a queen bed, two dressers, two closets, an office, extra sofa, and a private library. It also has:- A private head with a full-sized sink
- A separate private bath with a walk-in shower
- Additional Comforts
- Bedding, bath towels, soaps, and shampoos provide
- Cleaning supplies included
- Cabins are intended for rest and downtime during training and expedition activities
- Connectivity & Entertainment
- Unlimited Starlink high-speed internet (available at anchor, moored, or in marinas)
- 50" TV in Salon for streaming NauticEd training materials or entertainment
- NAS server with 2,000+ movies, TV shows, and Brazilian Jiu-Jitsu videos
- Library stocked with sailing books
What's Included
🍳 Provisioned Galley & Communal Meals
- Galley stocked with fresh, local ingredients
- All onboard meals and snacks included (except for offshore food and drinks)
- LPG Range & Oven, Full-Size Microwave, 3 Large refrigerators, 1 Large Freezer, Ice Maker
- Meal prep is a shared experience — crew members collaborate on cooking
- No alcohol provided
What's Included
⛑️ Safety Equipment
- USCG-approved inflatable life jacket for you to use; or we can order you inflateable life jackets for a significant Crew Discount.
- SV Indie Sky crew T-shirts — customized for the region you’re sailing (looking cool adds to safety)
- 2 independent satellite tracking systems
- 2 EPIRBs (Emergency Position Indicating Radio Beacons)
- 8-person life raft
- Multiple man overboard recovery systems
- Multiple subscribed sources for trip planning and weather routing
💵 What's it cost?
Port Forward Cabin: ⚠️ Join Waitlist ⚠️
- 8 day expedition total: $2656.00 per person for double occupancy
- 8 day expedition total: $5312.00 per person for single occupancy
Port Aft Cabin: 🟢 Available 🟢
- 8 day expedition total: $2656.00 per person for double occupancy
- 8 day expedition total: $5312.00 per person for single occupancy
Owner's Cabin: ⚠️ Join Waitlist ⚠️
- 8 day expedition total: $3256.00 per person for double occupancy
- 8 day expedition total: $6512.00 per person for single occupancy