Best Fishing Charter: Skipper/Vineyard Sound Charters Inc.
Berth 74 near the Island Queen, Oak Bluffs, 508-693-1238, mvskipper.com
Runner-up: Coop’s Bait & Tackle Charters
147 Edgartown–West Tisbury Road, Edgartown, 508-627-3909, coopsbaitandtackle.com
What do you get when you sign up for an outing with Vineyard Sound Charters? Well, you get a rod and a reel, and you get the Skipper himself, John Potter, whose tales of the sea are sure to keep your group entertained. Since the Skipper can take up to forty people out, you can bring the extended family along. Cooper Gilkes of Coop’s Bait & Tackle is a wealth of marine knowledge and fishing know-how – just ask the awards committee of the annual Striped Bass and Bluefish Derby.
Best Nature Walk: Cedar Tree Neck Sanctuary
Obed Daggett Road off Indian Hill Road, West Tisbury, sheriffsmeadow.org
Runner-up: Menemsha Hills Reservation
North Road, Chilmark, 508-693-3678, thetrustees.org
Choose any or all of the four different trails in the lush 400-acre Cedar Tree Neck Sanctuary and find something new every time. Just watch out for piping plover nests on the shore. Menemsha Hills is home to the second highest point on the Island, Prospect Hill. Three miles of trails take hikers through a varied landscape from woods to rocky shore. A section of the trail was recently cleared to provide even better views of the Vineyard Sound.
Best Beach: South Beach
Atlantic Drive, Edgartown
Runner-up: State Beach
Beach Road, Edgartown and Oak Bluffs
Miles of sand, miles of crashing surf: South Beach has it all. Bring your shades and sunscreen – South Beach is perfect for soaking up the sun, too. Parking is plentiful at this Katama beach, but you can still find a spot away from the crowds. Lifeguards are on duty, with the daily water conditions posted at entrances. State Beach is perfect for a calmer day, with placid waves and a beach that’s great for finding shells.
Best Place to Kayak: Sengekontacket Pond
Runner-up (tie): Chilmark Pond and Edgartown Great Pond
Whether it’s a midday paddle from Little Bridge or a moonlight tour from Felix Neck Wildlife Sanctuary, Sengekontacket provides calm waters and unique views. Bring your binoculars, because with plenty of coves to explore the pond is a haven for birdwatchers. And how can you choose between the Great Ponds? Both Chilmark and Edgartown offer public access to drop in for an afternoon trip.
Best Summer Camp: Camp Jabberwocky
200 Greenwood Avenue Extension, Vineyard Haven, 508-693-2339, campjabberwocky.org
Runner-up: Fern & Feather Natural History Day Camp at Felix Neck Wildlife Sanctuary
100 Felix Neck Drive, Edgartown, 508-627-4850, massaudubon.org
Camp Jabberwocky is about tradition: even the campers’ walk from the Vineyard Haven ferry to the idyllic cabins outside of town is a big deal. The red camp buses are everywhere throughout the summer, but be sure to check out the campers and counselors in their midsummer play and the Fourth of July parade. Felix Neck’s Fern & Feather camp turned fifty last year, celebrating its birthday with – what else? – even more great nature programs.
Best Fishing Spot: Wasque
Currents swirl and schools of fish swarm at Wasque on Chappaquiddick, where seasoned shore fishermen take up spots alongside newcomers. The shoreline of this favorite spot has been changed by erosion, but the fishing still remains as good as it gets. In Menemsha, watch the commercial fishermen come into the harbor to unload their daily catches, then get inspired to go nab your own dinner off the jetty.
Best Bike Rental: Edgartown Bicycles
212 Upper Main Street, Edgartown, 508-627-9008, edgartownbicycles.com
Runner-up: Wheel Happy
18 North Summer Street, Edgartown, 508-627-7210
8 South Water Street, Edgartown, 508-627-5928
204 Upper Main Street, Edgartown, 508-627-5881, wheelhappybicycles.com
More than just a rental shop, Edgartown Bicycles is the place to go for two-wheel expertise. The staff can send you on your way for a day trip or help you pick out a brand-new bike. And if things need fixing, well, they can help with that, too. Family-owned Wheel Happy offers everything from tandems to cargo bikes, and has three different Edgartown locations.
Best Sailing Charter: The Black Dog Tall Ships
Vineyard Haven harbor, Vineyard Haven, 508-693-1699, theblackdogtallships.com
Runner-up: Mad Max Sailing Adventures
25 Dock Street, Edgartown, 508-627-7500, madmaxmarina.com
When Captain Robert Douglas’s schooners aren’t greeting ferry passengers in Vineyard Haven harbor, they’re out cruising the Sounds. A sunset sail on the tall ships is a must; the only tough decision to make is whether to book your trip on the Shenandoah or the Alabama. What’s better than cruising the blue-green waters off of Edgartown? Cruising them in a catamaran. Mad Max’s double hull plies the seas with ease.