After a decade of sending clients to Martha's Vineyard, I've noticed the same questions come up over and over. Here are the honest answers I give people who are planning their first trip to the island.
A: The Steamship Authority ferry from Woods Hole, Massachusetts is how most people arrive. The ride takes 45 minutes and costs about $9.50 one-way for walk-on passengers (2026 rates). If you're bringing a car, you'll need a reservation months in advance for summer — it's $85-95 one-way for a standard vehicle plus driver, and summer slots sell out in March.
Alternatively, seasonal flights operate from Boston (BOS), JFK, and Newark to Martha's Vineyard Airport (MVY). Cape Air runs year-round turboprops from Boston for about $150-250 one-way.
A: Honestly, no — not for a short trip. The three "down-island" towns (Vineyard Haven, Oak Bluffs, Edgartown) are connected by bike paths and the island bus system (VTA, $1.25 per ride or $8 day pass). Bikes are the preferred way to get around — $25-40/day from shops near the ferry terminals.
You'll want a car only if you're going "up-island" to Aquinnah, Menemsha, or Chilmark, which are more spread out. Rent on-island or bring your car on the ferry (book early).
A: June through September for full services and beach weather. July-August is peak season with everything open but maximum crowds and prices. My favorite window is mid-September through mid-October — the ocean is still warm enough for swimming, the summer crowds have left, fall foliage starts, and many businesses are still open.
Note: many restaurants, shops, and attractions close entirely from November through April. The island is very quiet in winter.
A: The Oak Bluffs Gingerbread Cottages. Over 300 colorful Victorian cottages with ornate trim, surrounding a central tabernacle that's a National Historic Landmark. Free to walk through. The Cottage Museum ($2) shows an original furnished interior. If you visit in late August, Grand Illumination Night — when hundreds of Chinese lanterns light up the cottages — has been a tradition since 1869.
A: Depends what you want. South Beach (Katama) has the best surf and is popular with young crowds. State Beach on the Oak Bluffs-Edgartown road is calm, family-friendly, and right on the bike path. Menemsha Beach faces west for the best sunset. Aquinnah Beach at the base of the Gay Head Cliffs is the most dramatic setting (with a clothing-optional section).
All public beaches are free. Parking ranges from free to $20 in summer.
A: The island's most elegant town. White clapboard whaling captains' homes, upscale boutiques, the 1672 Vincent House (oldest on the island), and the Edgartown Lighthouse with a free harbor walk. North Water Street has the best architecture. It's quieter and more refined than Oak Bluffs. Good for a half-day of walking and lunch.
A: Yes, especially at sunset. These 46-meter clay cliffs in red, orange, and white are sacred to the Wampanoag tribe. Free viewpoint from the parking area ($20 parking in summer). The Gay Head Lighthouse ($5 entry) offers panoramic views. Allow 1-2 hours. It's a 45-minute drive from the down-island towns.
A: It's not cheap, but it's manageable. A lobster roll at Larsen's Fish Market in Menemsha runs $28-35 — expensive but you're eating at a working fishing dock with a sunset view. A casual seafood dinner is $25-45 per person. The Bite in Menemsha does famous fried clams for $15-22.
Budget tips: bike instead of renting a car (saves $100+/day), eat lobster rolls at lunch instead of dinner, buy supplies at Reliable Market or the farmers market for picnic meals.
A: Three contenders. Larsen's Fish Market in Menemsha for the classic — cold lobster with mayo on a roll, waterfront setting. The Bite for the fried clam plate alongside it. Net Result in Vineyard Haven for a more casual, less crowded experience.
The real debate is cold (New England style with mayo) vs. warm (Connecticut style with butter). Larsen's does cold. You'll develop an opinion.
A: Summer rates: $200-400/night for a B&B, $300-600+ for a hotel, $150-250/night for an Airbnb. Off-season (September-October) drops 30-40%. Booking 3-6 months ahead for summer is standard.
The most affordable option is camping at Martha's Vineyard Family Campground in Vineyard Haven — tent sites from $60/night in summer.
A: The paved bike path network covers the three down-island towns beautifully. The Oak Bluffs to Edgartown Beach Road path (10 km) is flat, scenic, and hugs the coastline. But up-island (West Tisbury, Chilmark, Aquinnah) doesn't have dedicated bike paths, and the roads are hilly with narrow shoulders. Doable for experienced cyclists, stressful for casual riders.
A: Menemsha, no contest. The tiny fishing village faces due west. Arrive an hour early for parking. Watch the sun drop while eating a lobster roll. This is the most quintessential Vineyard experience. Bring a blanket for the beach.
A: If you want a peaceful escape from beach crowds, absolutely. This 350-acre Mass Audubon sanctuary has 6.4 km of trails through salt marshes and woodland. Entry $6. Excellent birding — osprey, barn owls, piping plovers. Allow 1.5-2 hours.
A: Don't try to see the whole island in one day. People do this on day trips from the ferry and it's exhausting. The island has six distinct towns, each with a different personality. Pick two or three for a day trip, or better yet, stay overnight.
Also, skip the overpriced tourist shops on Circuit Avenue in Oak Bluffs. The good shopping is in Edgartown and Vineyard Haven.
| Need | Answer |
|---|---|
| Ferry time | 45 min from Woods Hole |
| Bike rental | $25-40/day |
| Bus pass | $8/day |
| Best beach (families) | State Beach |
| Best beach (sunset) | Menemsha |
| Lobster roll | $28-35 |
| Casual dinner | $25-45/person |
| Peak season | July-August |
| Sweet spot | September |
If you're exploring the northeastern US coast, Key West offers a similarly island-paced lifestyle with a completely different vibe. For our seasonal guide, check out Martha's Vineyard in autumn.
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