A Blue Water Sailing Club Offshore & Caribbean Cruising Experience
November 2026 – April 2027
The Caribbean Challenge Cruise (CCC) is a unique, multi-phase sailing adventure that combines offshore passage-making, Caribbean island cruising, and optional charter participation—all within the camaraderie and shared experience of the Blue Water Sailing Club.
Designed for flexibility, the CCC allows sailors to participate fully or selectively, making it accessible to couples, families, and individuals with varying schedules, boats, and ambitions.
What Makes the Caribbean Challenge Cruise Different
- Offshore sailing without a race environment
- Multiple entry and exit points
- Integrated charter opportunities for non-owners or time-limited participants
- A proven Blue Water Sailing Club cruising model
- Shared leadership, seamanship, and social connection
This is serious cruising—structured, supportive, and flexible by design.
At-a-Glance Schedule
CCC Part One – Southbound
November 1 – December 13, 2026
- Depart New England (Boothbay or Newport)
- Sail to Bermuda, then onward to the Eastern Caribbean
- Cruise south through the Leeward and Windward Islands
- Conclude in Martinique
Leeward Islands Charter (Optional)
November 23 – 29, 2026
- Based out of St Martin
- Includes Anguilla, Prickly Pear, Tintamere, and St Barts
- Ideal Thanksgiving-week option for family and friends
- Charter boats sail alongside BWSC boats before returning to St Martin
Winter Recess & Haul-Out
December 13, 2026 – March 8, 2027
- Optional haul-out in Le Marin, Martinique
- Lower costs than New England
- Time for maintenance, upgrades, or travel home
- Protects holidays and winter commitments
CCC Part Two – Northbound
March 8 – April 18–24, 2027
- Resume cruising in Martinique
- Sail through St Lucia, St Vincent, and the Grenadines
- Offshore passages north via St Martin and Bermuda
- Return to New England homeports
Windward Islands / Grenadines Charter (Optional)
March 15 – 29, 2027
- Two-week charter through the Grenadines
- Includes Bequia, Mustique, Tobago Cays, Mayreau, Union Island, and Grenada
- Aligns with some school vacation schedules
- Joins BWSC boats already cruising in the region
Who Should Consider This Cruise
- Owners of offshore-capable cruising sailboats
- Sailors who want to build offshore experience without racing
- Couples or families with different time availability
- Sailors interested in chartering but within a club framework
- Members seeking meaningful, long-distance cruising with peers
Participation requires Blue Water Sailing Club membership, except for charter guests sailing under a BWSC member.
How the Cruise Works
Independent Boats, Shared Experience
- Each boat is responsible for its own decisions
- No fixed departures or flotilla sailing
- Weather windows govern offshore passages
- Boats may join or leave the cruise at multiple points
Captain of the Day (C.O.D.) System
- Skippers rotate leadership for specific legs
- Responsibilities include navigation notes, local knowledge, and coordination
- Daily 8:00 AM group VHF call
- Encourages engagement, learning, and shared ownership of the experience
Seamanship & Safety Philosophy
- Emphasis on judgment, preparation, and conservative decision-making
- Offshore passages require appropriate boats, crew, and equipment
- Captains must provide leader a sailing resume showing a minimum 2 consecutive overnight sail on the same boat doing any passage on this cruise.
- Crew sourcing supported through BWSC networks and Offshore Passage Opportunities
- No race pressure, no artificial schedules, no “follow-the-leader” mentality
This cruise places responsibility where it belongs—with each skipper—while benefiting from collective experience.
Flexibility Is Built In
- Sail your own boat the entire route—or just part of it
- Join via charter for one or two segments
- Pause for winter, then rejoin in spring
- Extend your cruising beyond the planned itinerary if desired
The CCC is intentionally modular. Participation adapts to your life—not the other way around.
Why Sail the Caribbean Challenge Cruise?
- Offshore passages with purpose
- Some of the best trade-wind sailing in the North Atlantic
- A rare blend of independence and community
- Access to destinations from Bermuda to the Grenadines
- A continuation of the Blue Water Sailing Club’s long-distance cruising tradition
This cruise builds experience, confidence, and connection—on the water and ashore.
Registration & Next Steps
- If you are NOT a Blue Water Sailing Club Member you are encouraged to apply for membership. Please email John Slingerland for non-member participation.
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If joining any of the offshore passages, membership (which includes a release) is required of the captain.
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If joining as a guest on a charter boat, a release is required.
- You may join all or specific segments of the cruise
- Charter participants arrange their own boats (group discounts may apply)
- Detailed logistics, captain assignments, and communications will follow closer to departure
Ready to Sail Farther?
The Caribbean Challenge Cruise 2026–2027 offers a rare opportunity to combine offshore sailing, Caribbean cruising, and club camaraderie into one cohesive experience.
Whether you sail your own boat across oceans or join for a week among turquoise anchorages, the CCC delivers great sailing in remarkable places—with great people.