**Pilotage Plan: Oak Bluffs, MA to Chilmark, MA****Route Overview:**This cruising adventure from Oak Bluffs to Chilmark showcases the stunning natural beauty of Martha's Vineyard, making it not just a journey, but an exploration of scenic coastal waters. This route is well-suited for experienced boaters seeking a day trip or a leisurely weekend excursion. **Departure from Oak Bluffs:**Starting your journey at Oak Bluffs, the vibrant heart of Martha's Vineyard, prepare for a stunning departure from the bustling harbor. Before you leave, soak in the colorful Gingerbread Cottages and the charming beachfront. Be mindful of local boat traffic and pedestrians during the departure.**Route Path and Navigation Considerations:**1. **Setting Course:** - From Oak Bluffs, you'll head west towards Vineyard Haven, maintaining a distance off the shore to avoid shallow areas. - Your initial heading should be around 285°, navigating towards the buoy marking the entrance to Vineyard Haven Harbor.2. **Vineyard Haven Harbor:** - A noteworthy interim stop, Vineyard Haven offers opportunities for obtaining fuel, provisions, and amenities. Look for the various mooring options at the harbor. - Be sure to adhere to the harbor's local navigation rules and be cautious when passing through the narrow entrance, paying attention to the green and red buoys that guide vessels safely in.3. **Navigating to Chilmark:** - After departing Vineyard Haven, your course will direct southwest toward Chilmark. This leg of the journey allows for beautiful views of the coastline but requires attention as you approach the more complicated waters between West Chop and the red buoys marking the approach to Menemsha (buoy “M”).4. **Menemsha:** - Should the weather turn inclement, continue to Menemsha Harbor which provides excellent shelter from prevailing winds. The harbor is a picturesque fishing village with local seafood dining options and lovely beaches. Be aware of the channel markers and follow the red/green buoy system for safe passage. - If conditions allow, consider mooring here briefly to enjoy some fresh clam chowder or visit the fishing docks.5. **Final Approach to Chilmark:** - From Menemsha, the route opens to a broad stretch, but steer clear of any shallow areas near Squibnocket, utilizing local charts. Keep an eye out for local fishing boats and day trippers. - As you near Chilmark, you will appreciate the unspoiled landscapes and rocky shorelines framed by the serene blue waters.**Navigation Aids & Safety Considerations:**- Accurate charts are paramount; rely on both digital and paper charting methods. Using apps like Savvy Navvy will greatly enhance your navigation with real-time updates and community insights.- Be vigilant about tidal currents, particularly through openings and around points — these can shift dramatically. It's wise to plan your travel around the tides for a smoother experience.- Weather conditions can change rapidly in this coastal region; always check forecasts before departure and be prepared with a plan for bad weather. Ensure life jackets and safety equipment are always on board and accessible.**Points of Interest Along the Way:**- Don’t miss the iconic Gay Head Lighthouse if visibility permits. It stands as a historical beacon and offers breathtaking views of the Atlantic.- At Menemsha, indulge in fresh local fish from the market or partake in beachcombing at the sandy shores.In summary, the journey from Oak Bluffs to Chilmark is not only about reaching the destination; it’s about reveling in the untamed beauty of Martha's Vineyard, with ample opportunities to navigate safely while enjoying the unique charm of coastal New England. Happy cruising!