In the town now named Aquinnah, these cliffs are most spectacular as seen from the water. Choose a flat calm day, as the winds and waves can become quite strong (there is a reason for the name "Devil's Bridge"). Put-in at Lobsterville or Menemsha. For experienced paddlers looking for a challenging day trip, consider a circumnavigation of Aquinnah around the cliffs, Squibnocket, and back to Menemsha through Menemsha Pond.
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For many island paddlers, this is their favorite. The pond connects with both Vineyard Sound and Quitsa Pond, with many small bays and inlets to explore. Put-ins include Menemsha Harbor or the landing at Quitsa Pond. Both provide very limited parking, so arrive early in the day! Watch out for the very strong tidal currents at the entrance to Menemsha Harbor. The harbor master prefers that inexperienced paddlers stay away form the entrance altogether.
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For dramatic views, undeveloped beaches, and potentially challenging currents, the Vineyard's North Shore is the place to paddle. Be sure to check your Eldridge's for tidal information, and plan your trip carefully as there is only occasional evidence of civilization along the way. Highlights include the Menemsha Hills Reservation, Great Rock Bight Beach, Seven Gates Farm, Cedar Tree Neck, and Lambert's Cove. The only public takeouts are at the Menemsha Public Beach, the Land Bank property at Great Rock Bight (long carry), and the Public Landing on Lake Tashmoo in Vineyard Haven.
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This wind-protected area offers a quiet paddle among beautiful moored boats with views of some of the Vineyard's prettiest homes. Put-in at the town landing at the end of Lake St. and if the weather and your experience warrant, paddle through the opening out into Vineyard Sound. At the opening, the current can be strong, but the water is shallow (you can always walk your boat!).
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Thanks to the Land Bank's Sepiessa Reservation, paddlers have access to one of the island's most beautiful large ponds. Paddlers can explore the pond's long "fingers", paddle into Black Point Pond, and access the barrier beach. At times the beach is "cut" in order to bring saltwater into the pond. When open, the cut is a great place to play for experienced paddlers, but please stay away when swimmers are abundant.
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This pond is large and accessible, and though it is highly developed, it offers beautiful, quiet coves and the Felix Neck wildlife sanctuary. There are many shallow areas at low tide (even a kayak may have trouble!). Watch for swimmers, boaters and fast current at the Big and Little Bridge openings into Nantucket Sound. Windsurfers also enjoy these waters.
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This pond is as beautiful as Tisbury Great Pond, and lesser used by other boaters. However, several kayak rental operators use the only public put-in at the Edgartown town landing off of Meeting House road. Be sure to explore the magical "fingers" of this pond before future development ruins them.
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Accessed at the infamous Dike Bridge, this body of water offers miles of beach monitored by the Trustees of Reservations. You can easily find a lonely spot for lunch, as long as you stay away from the 4 wheel drive tracks! Fisherman often congregate at Wasque Point and at the cut into Nantucket Sound.
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Our favorite on or near-water accommodations:

• Pierside B&B
  Vineyard Haven, Lake Tashmoo, 508-693-5562.
• Menemsha Cottages
  Menemsha, North Shore, 508-645-2521.
• Outermost Inn
  Aquinnah, Lobsterville, 508-645-3511.
• Lambert's Cove Inn
  W.Tisbury, Lambert's Cove, 508-693-2298.
• House at New Lane
  W.Tisbury, Tisbury Great Pond, 508-693-7331.

NOAA
National Oceanic & Atmospheric Administration offers tide report for the next six months.

Maine Harbors
Tide charts for the Islands and surrounding areas (2 month prediction).

WWW Tide and Current Predictor
Current and future tide predictions.