Offshore Sailing + Liveaboard Training Expedition - 10+ Days
Offshore Passagemaking
Step aboard SV Indie Sky for a fully offshore passage from Chesapeake Bay to Charleston, designed to immerse you in the skills and mindset needed for confident, competent liveaboard cruising.
This expedition bypasses the Intracoastal Waterway entirely — our mast is too tall for bridge clearance — so we’ll be sailing entirely in the Atlantic Ocean, navigating the shifting winds, currents, and challenges of a true coastal passage.
🧭 Who It’s For
This trip is ideal for:
- Sailors aiming to strengthen their sailing 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 eager to experience the Atlantic coastal route firsthand
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
- U.S. Coast Guard Captain-led expeditions
- Instruction provided by NauticEd Certified Instructors
- Hands-on training in all aspects of offshore sailing
- Logbook endorsements available for those building sea time or working toward certification
- Certificates, Licenses, and Endorsements awarded to crew who meet proficiency and experience requirements
🏄 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.
Crew Fees Cover
🛏️ Accomodations
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
Crew Fees Cover
🍳 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
Crew Fees Cover
⛑️ Safety Equipment
- USCG-approved inflatable life jacket- Yours to keep!
- SV Indie Sky crew T-shirts customized for the region(s) you’re sailing.
- 2 Independent Sources Satellite Tracking
- 2 EPIRBs
- 8 Person Life Raft
- Multiple Man Overboard Recovery Systems
- Multiple Subscribed Sources for trip planning and weather routing
Pricing
Port Forward Cabin:
- 10+ day expedition total: $2767.50 per person for double occupancy
- 10+ day expedition total: $5535.00 per person for single occupancy
Port Aft Cabin:
- 10+ day expedition total: $2767.50 per person for double occupancy
- 10+ day expedition total: $5535.00 per person for single occupancy
Owner's Cabin: ***WAITLIST***
- 10+ day expedition total: $3304.00 per person for double occupancy
- 10+ day expedition total: $6608.00 per person for single occupancy