Eight trips to Martha's Vineyard. Some lessons took embarrassingly long to learn. Here's the condensed version.
Ferry & Transport
1. Walk On the Ferry, Don't Drive On
The Steamship Authority car ferry sells out months in advance for summer. Walk-on tickets ($9.50) rarely sell out. Once on the island, rent a bike ($25-40/day) or use the bus system (VTA, $8 day pass). You'll see more, spend less, and avoid the parking nightmare in Edgartown and Oak Bluffs.
2. The Hy-Line Ferry Is Faster But More Expensive
The Hy-Line high-speed ferry from Hyannis takes an hour and costs about $40 one-way. The Steamship Authority from Woods Hole is 45 minutes and $9.50. Hy-Line is convenient if you're coming from Boston, but Woods Hole is the better deal if you're on Cape Cod.
3. Rent Bikes Near the Ferry, Not in Town
The bike shops at the Vineyard Haven and Oak Bluffs ferry terminals rent bikes by the hour or day. Grab one as you walk off the boat. Trying to rent later in the day means longer waits and limited selection.
Food
4. Eat at Larsen's, Not the Galley
In Menemsha, two seafood spots compete for attention. Larsen's Fish Market has the better lobster roll ($28-35). The Bite has the better fried clams ($15-22). The Galley is fine but overpriced for what you get. Get one item from Larsen's and one from The Bite and eat on the beach. That's the move.
5. Back Door Donuts Is Worth the Hype
The back door of the Martha's Vineyard Bakery in Oak Bluffs sells fresh apple fritters after 7:30 PM. The line can be long in summer, but the warm, sugar-coated fritters are genuinely excellent. $4-5 each. Cash preferred.
6. Picnic Supplies Save a Fortune
Breakfast and lunch on the Vineyard can drain your wallet fast. Morning Glory Farm Stand sells sandwiches, salads, and produce. Reliable Market in Oak Bluffs has deli options. Pack a cooler, hit a farm stand, and eat on the beach. You'll save $30-50 per person per day.
7. The Portuguese Bakeries Are Underrated
The Vineyard has a strong Portuguese heritage from its whaling days. The Portuguese bread at Vineyard Haven bakeries is extraordinary — soft, slightly sweet, perfect for sandwiches. Ask for linguica (Portuguese sausage) at any diner that has it.
Beaches & Activities
8. State Beach Is the Best All-Rounder
Calm water (it's on the Nantucket Sound side), right on the bike path between Oak Bluffs and Edgartown, and free. It's not the most dramatic beach on the island, but it's the easiest to enjoy without any hassle. Good for families, good for solo swimmers, good for a quick stop during a bike ride.
9. The Chappy Ferry Is 2 Minutes and $5
The tiny On Time ferry from Edgartown to Chappaquiddick Island takes 2 minutes. On the other side, Cape Poge Wildlife Refuge has miles of empty beach and the Cape Poge Lighthouse. Rent a bike on the Edgartown side and pedal over. Most tourists don't bother crossing. That's exactly why you should.
10. Grand Illumination Night Is Magical
In late August, the Oak Bluffs Camp Meeting Association holds Grand Illumination Night. Hundreds of Chinese and Japanese lanterns are lit on the Gingerbread Cottages. It's been happening since 1869. The date varies — check mvcma.org. Arrive early. It's free and it's the most photographed night on the island.
11. Felix Neck Is a Crowd Escape Valve
When the beaches feel too packed (this happens every August Saturday), Felix Neck Wildlife Sanctuary is a 350-acre exhale. Trails through salt marshes and woodland, osprey nesting platforms, and absolute quiet. $6 entry. Open dawn to dusk.
Up-Island
12. Don't Skip Aquinnah
Most day-trippers stick to the three down-island towns. They're missing the island's most dramatic landscape. The Aquinnah Cliffs — 46 meters of red, orange, and white clay — are sacred Wampanoag land and genuinely stunning. The drive is 45 minutes from Oak Bluffs. The Gay Head Lighthouse ($5) gives panoramic views.
13. West Tisbury Is the Artsy Town
The Granary Gallery shows excellent local art. Alley's General Store has been operating since 1858 and sells everything from nails to penny candy. The West Tisbury Farmers Market (Saturdays in summer) is smaller and more local than the Vineyard Haven version.
Practical
14. Cash Is Still King in Menemsha
Most Menemsha fish shacks and smaller establishments prefer cash. ATMs on the island charge $3-5 fees. Withdraw cash on the mainland before you cross.
15. Book Accommodation by March for Summer
This isn't an exaggeration. The island's bed capacity is limited and demand is enormous. Hotels and popular B&Bs sell out for July-August by spring. Airbnb has more last-minute availability but prices spike.
16. Bug Spray After Sunset
The salt marshes breed mosquitoes. They come out at dusk. If you're watching sunset at Menemsha or walking the Felix Neck trails in the evening, bring DEET. The no-see-ums in August are particularly vicious.
17. The Island Has Six Towns, Each Different
Vineyard Haven is the working town with the best year-round services. Oak Bluffs is the fun, colorful one with the Gingerbread Cottages and nightlife. Edgartown is elegant and historic. West Tisbury is artsy and rural. Chilmark is quiet and upscale. Aquinnah is remote and dramatic. Knowing this helps you pick where to stay and what to prioritize.
