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Martha’s Vineyard is one of the popular islands off of Cape Cod, while technically not the Cape — locals will tell you so, loudly lol — but it’s a 45 minute ferry from Woods Hole or Falmouth, and it’s absolutely worth building into a Cape trip or as its own long weekend trip. Three days is the sweet spot: enough to do both main towns properly, get up-island to the cliffs and the fishing village, and still have a couple of long lazy beach afternoons.
The island splits into two personalities. Oak Bluffs is the fun & eclectic — brightly painted gingerbread cottages, a colorful harbor lined with bars, and the best nightlife on the island. Edgartown is a bit more preppy & upscale — white clapboard, manicured hedges, luxury boutiques, and a bit quieter. Then there’s up-island, which is farmland, clay cliffs and a working fishing harbor, and feels like a completely different place away from the touristy vibe of the other two.
Here’s how I’d spend three days doing all of it.
Jump To:
- Getting to Martha’s Vineyard
- Getting Around the Island
- Where to Stay
- Day 1: Oak Bluffs
- Day 2: Up-Island, Aquinnah & Menemsha
- Day 3: Edgartown & the Beaches
- Best Bars & Restaurants
- Best Beaches on Martha’s Vineyard
- Martha’s Vineyard Map
Disclaimer: This article contains some links where I earn commission through booking. There is no extra cost to you, and I only recommend things I’ve used and love or places I’ve stayed and enjoyed!
Getting to Martha’s Vineyard
There are two options from this stretch of the Cape, and which one you want depends on whether you’re bringing a car.
From Woods Hole — the Steamship Authority
The Steamship Authority runs from Woods Hole, just past Falmouth, and the crossing takes about 45 minutes. You can land at Vineyard Haven year-round, or Oak Bluffs seasonally from around May through October — and if you’re following this itinerary, Oak Bluffs is the one you want. This is the only ferry that takes cars.
Bringing a car requires an advance reservation and costs well over $100 each way in summer, which is why I don’t bother. Walk on as a foot passenger — it’s around $11 each way — and sort out wheels once you’re on the island.
From Falmouth — the Island Queen
If you’re staying in Falmouth or driving from Boston, the Island Queen leaves right from Falmouth Harbour and goes straight into Oak Bluffs in about 35 minutes — faster than the Steamship route and it drops you exactly where you want to be. It’s passenger-only, so no cars, but for a trip where you’re renting a Jeep on the island anyway that’s not a drawback.
It runs seasonally, roughly late May to mid-October, with seven to nine sailings a day in peak summer. Tickets are in the $12–24 range and reservations are recommended.
One thing to plan for: parking at Falmouth Harbour is about 200 yards from the dock, runs around $20 a day, and is cash only — so bring bills or you’ll be hunting for an ATM with a ferry to catch.
Getting Around the Island
Rent a Jeep. This is my recommendation and it’s not just for the photo (although that is fun too!) — the island is bigger than people expect, some of the best beaches are a real drive from Oak Bluffs or Edgartown, and having your own car is the difference between seeing two towns and relying on Ubers (which is hit or miss) and seeing the whole island. Book ahead in summer, they sell out.
If you’d rather not drive, you have options: the VTA buses connect all the main towns and are cheap and reliable, and the island has excellent bike paths — including one that runs from Oak Bluffs to Edgartown right along Joseph Sylvia State Beach, with the sound on one side and the Atlantic on the other. That ride alone is worth doing.
Where to Stay
Stay in Oak Bluffs. It’s my pick over Edgartown — it’s got the bars, the harbor, the gingerbread cottages and the best nightlife on the island, and it’s where the ferries from both Falmouth and Woods Hole come in, so you can arrive without needing a car. Edgartown works perfectly well for this itinerary too if you’d rather have the quieter, more classic Cape Cod looking version, and the two are only about 15 minutes apart, so you’re never far from either.
Book a house, not a hotel. Martha’s Vineyard runs much more on rentals than on hotels — there simply aren’t that many hotels on the island, and the ones that exist get expensive fast in peak season. An Airbnb or house rental is usually the way to go, especially if there are a few of you, and it’s how most people do the island. If you are splitting the trip and want a base on the Cape itself, that is covered in my where to stay in Cape Cod guide.
Book early. Summer rentals on the Vineyard go months ahead, and lots of them run Saturday to Saturday in July and August rather than letting you pick any three nights. If you’re planning a peak-season trip, start looking in the winter.
Day 1: Oak Bluffs
Day 1 at a glance: Ferry into Oak Bluffs → gingerbread cottages & Flying Horses → lunch on the harbor → beach afternoon → sunset drinks → dinner and a night out on Circuit Ave.
Morning — Arrive & Explore
Get an early ferry so you’ve got the whole day. Oak Bluffs harbor is right there when you step off, and the town is small enough that you can drop your bags and start walking.
Head straight for the gingerbread cottages — the Martha’s Vineyard Campground, a tight cluster of tiny Victorian houses painted in sherbet colours with elaborate scrollwork trim. It started as a Methodist camp meeting in the 1800s and the cottages are still privately owned, so you’re wandering through someone’s neighbourhood. It is genuinely unlike anywhere else in New England.
Right next to it is the Flying Horses Carousel, the oldest continuously operating platform carousel in the country, running since 1876. It’s a few dollars a ride and absolutely worth it.
Lunch — On the Harbor
Oak Bluffs harbor is lined with places to eat and most of them have a deck over the water. Coop de Ville for wings and a raw bar, The Lookout for lobster rolls with a view, or Nancy’s if you want the family-run spot that’s been on the harbor since 1960 with the best frozen drinks in town.
If you want the full toes-in-the-sand version, go to the Sand Bar & Grille — it has an actual sand floor, so you kick your shoes off and eat with your feet in it. It’s right on the harbor steps from the ferry, which makes it a very easy first stop off the boat.
Save room, or don’t — Mad Martha’s ice cream is an island institution and you’ll walk past it approximately six times today.
Afternoon — Beach
Joseph Sylvia State Beach runs along the road between Oak Bluffs and Edgartown and is the easiest beach afternoon on the island — calm, warm, shallow water on the sound side. If you’ve got bikes, ride there along the path rather than driving.
Evening — Sunset Drinks & Dinner
This is where Oak Bluffs earns its reputation. Fishbones faces west over the harbor, which makes it one of the better sunset spots on the island. Samewith Jetty Beach House, the newest of the bunch, all frozen drinks and seafood towers. And the Sand Bar & Grille is the one with the actual sand floor — shoes off, toes in, cocktail in hand, right on the harbor. Noman’s is the island’s beer-garden-style hangout with lawn games and live music — and a free shuttle from the ferry terminal, which is very useful.
After dinner, Circuit Avenue is where the night happens. It’s compact, it’s walkable, and it’s the only real nightlife on the island if that’s what you’re after
Day 2: Up-Island, Aquinnah & Menemsha
Day 2 at a glance: Drive up-island → Aquinnah clay cliffs & Gay Head Lighthouse → beach or lunch at Lobsterville → Menemsha for oysters and the best sunset on the island.
Morning — Drive Up-Island
This is the day you’ll be glad you have wheels. Up-island — Chilmark, Aquinnah, Menemsha — is about 45 minutes from Oak Bluffs and feels like a different world: stone walls, farmland, almost no development, and far fewer people.
Late Morning — Aquinnah Cliffs
The Aquinnah Cliffs (also called the Gay Head Cliffs) are the single most dramatic thing on the island — striped red, orange and grey clay dropping straight into the Atlantic. There’s an overlook at the top with the Gay Head Lighthouse beside it, and a public beach below if you want to walk along the base of them.
The cliffs are a National Landmark owned and protected by the Wampanoag Tribe of Aquinnah. Climbing on them or taking the clay is not allowed and genuinely damages them — admire from the overlook and the beach.
Which beach to go to: this is the bit that catches people out, because there are two beaches below the cliffs and only one of them you can use. Moshup Beach is the public one — it runs from the cliffs along the shore and it’s the one you want. Philbin Beach, just beyond it, is restricted to Aquinnah residents and renters with a sticker in summer, for parking and for walking on, so don’t just wander down the sand assuming it’s all open.
Parking for Moshup is in the public lot on Moshup Trail and it’s a walk of about ten minutes down to the sand — factor that in, and wear something you don’t mind walking in.
Afternoon — Lobsterville & the Beaches
Just around from the cliffs is Lobsterville, a quiet stretch of beach on the Vineyard Sound side that’s about as far from the Oak Bluffs crowds as you can get. Good for a long, empty afternoon. Pack a lunch
Evening — Menemsha for Sunset
Menemsha is a working fishing village, and it has the best sunset on Martha’s Vineyard — it faces west across the sound, which on an island where most of the good beaches face south or east makes it the spot.
The move is to buy seafood straight from one of the fish markets on the dock — oysters, lobster, chowder — grab a blanket and some drinks, and eat it on the beach while the sun goes down. Everyone on the beach is doing the same thing. Get there a good hour before sunset for parking.
Day 3: Edgartown & the Beaches
Day 3 at a glance: Wander Edgartown → South Beach for the afternoon → sunset drinks at the Pelican Club → dinner at the Seafood Shanty before the ferry home.
Morning — Edgartown
Edgartown has a typical Cape Town aesthetic — white clapboard captain’s houses, boxwood hedges, and a harbor full of very nice boats. It’s lovely to wander with no particular agenda: the shops are good, the streets are photogenic, and it’s all walkable.
Afternoon — South Beach
South Beach (Katama) is the island’s big Atlantic surf beach, just south of Edgartown. Proper waves, wide open sand, and a completely different feel from the calm sound-side beaches. If you’d rather stay flat and warm, Norton Point nearby is long, wild and undeveloped.
Evening — Drinks & Dinner in Edgartown
The Pelican Club is the chicest spot on the island — an outdoor patio bar at Faraway with sushi, small plates and very good cocktails under fringed umbrellas. Book ahead. For dinner, Seafood Shanty sits dockside over Edgartown harbor and has been doing seafood and sushi there for over fifty years, with live music later on & a deck overloooking the harbor.
Then it’s the ferry home — or one more night, which is what usually happens.
Best Bars & Restaurants on Martha’s Vineyard
These are all on the island. If you are drinking your way around the Cape too, I have a separate roundup of the 15 best bars in Cape Cod.
- The Lookout, Oak Bluffs — perched over the harbor with big views, known for its lobster rolls and sushi. Works for lunch, dinner or just a sunset drink. My overall favorite.
- Nancy’s, Oak Bluffs — family run since 1960 and right on the harbor. Classic seafood plus a surprising amount of Middle Eastern food, and the dirty bananas (frozen drinks) are a must try Vineyard favorite.
- Coop de Ville, Oak Bluffs — casual waterfront spot for wings, a raw bar and a cold beer. Very low key, very good.
- The Sand Bar & Grille, Oak Bluffs — the one with the actual sand floor. Kick your shoes off, dig your toes in and have a cocktail. Right on the harbor, steps from the ferry.
- Fishbones, Oak Bluffs — right on the harbor facing west, one of the better sunset spots on the island. Oysters and cocktails.
- Jetty Beach House, Oak Bluffs — the newest of the bunch, a raw bar and cocktail lounge with harbor views. Seafood towers and extremely photogenic spritzes.
- Noman’s, Oak Bluffs — the island’s beer-garden-style hangout. Outdoor tables, lawn games, live music and a free shuttle from the ferry.
- Seafood Shanty, Edgartown — dockside over Edgartown harbor and has been for over fifty years. Seafood, sushi, and live music later on.
- Pelican Club, Edgartown — the chicest of the list, an outdoor patio bar with sushi, small plates and good cocktails. Book ahead.
Best Beaches on Martha’s Vineyard
These are the island ones. For the Cape side of the water, see my guide to the 7 best beaches in Cape Cod.
- Aquinnah Public Beach — for the clay cliffs, unlike anything else in New England
- South Beach — the island’s big Atlantic surf beach, near Edgartown
- Norton Point — long, wild and undeveloped, connecting Katama to Chappaquiddick
- Joseph Sylvia State Beach — calm, warm and easy, right between Oak Bluffs and Edgartown
- Menemsha — not really a swimming beach, but the place everyone gathers for sunset
Martha’s Vineyard Map
Everything from this itinerary is pinned on my Cape Cod & Islands map below.
More Cape Cod & Islands Guides
- Cape Cod Travel Guide: Beach Towns, Fried Seafood & Painkillers with a View
- Where to Stay in Cape Cod: Best Towns, Hotels & Classic Beach Motels
- 7 Best Beaches in Cape Cod | Best Beach for Every Vibe
- Provincetown Day Trip from Boston: The Perfect Summer Escape
- 15 Best Bars in Cape Cod: Best Spots in Every Town
- Best New England Summer Getaways
- Massachusetts Travel Guide
