A Local’s Perfect Martha’s Vineyard Weekend Itinerary
I’ve been coming to Martha’s Vineyard since I was a kid. Running, biking, driving, and boating my way around every inch of the island for decades. If you’re planning a quick two-night trip, this Martha’s Vineyard weekend itinerary is packed with everything you need: solid (affordable) places to stay, my go-to restaurants that aren’t catered for tourists, and plenty of backup ideas if the weather doesn’t play along.
Plus, I’ll share the kind of insider tips you only get from years of exploring like the best sunrise spot that’s never crowded, or the hidden shortcut that cuts 20 minutes off your drive to Menemsha for sunset.
We’ll start and end with the car ferry from Hyannis or Falmouth to either Oak Bluffs or Vineyard Haven, because getting here is part of the adventure! I’ve also included a unique list of my personal travel tips and advice for visiting the Vineyard and answered some helpful questions at the end.
👉 P.S. if you are also debating visiting Nantucket, take the quiz below to see which island may be a better choice for you!
Martha’s Vineyard Weekend Itinerary
➡️ Friday Evening: Arrival and Settling In
Your weekend on Martha’s Vineyard kicks off with the car ferry. If it’s your first time, here’s what to expect:
The main car ferry service is run by the Steamship Authority. You’ll want to book your spot a few months in advance, especially if you plan on visiting during the busy summer season or on a holiday weekend.
Ferries leave from Hyannis and Falmouth, and the ride over to the island takes about 45 minutes. You can also take a passenger-only ferry if you’re not bringing your car, but having your own wheels makes getting around much easier.
👉 Pro Tip: Dogs are allowed on both Hy-Line Cruises and the Steamship Authority cruises free of charge. They are required to be on a leash or in a carrier and are restricted to certain seating areas. They are not allowed to remain in your vehicle.
You’ll dock in either Oak Bluffs or Vineyard Haven, depending on in you departed from Hyannis or Falmouth. Oak Bluffs has more of a lively feel in the evenings, with restaurants and shops right near the harbor. Vineyard Haven is quieter, but definitely more charming and very convenient if you’re staying nearby.
Where to Stay
Here are a few good hotel options to book ahead of time:
- Summercamp Hotel (Oak Bluffs) – Fun and bright, right near the harbor.
- Mansion House Inn (Vineyard Haven) – Classic New England style and a great rooftop view.
- Harbor View Hotel (Edgartown) – If you’re up for a little splurge, the lighthouse views and classic style are hard to beat.
Dinner Plans
Once you’re settled in, head out for dinner. If you’re in Oak Bluffs, Lookout Tavern is a solid choice with their great seafood and an easygoing atmosphere (though my favorite brewpub is Offshore Ale Co. if you’re looking for something a little more laid back.)
In Edgartown, The Port Hunter is known for creative dishes and a lively vibe. If you’re in Vineyard Haven, you can’t go wrong with El Barco. They easily have some of the best tacos on the island.
I’m also a massive fan of ArtCliff Diner, but they are only open for breakfast and lunch, so stop in if you can!
Evening Strolls
After dinner, take a walk around town. Oak Bluffs has a fun energy at night with music drifting out of the bars, while Vineyard Haven and Edgartown are quieter but just as pretty for an evening stroll along the water.
Local Tips
- Parking in town can be tight, especially on weekends. Most hotels offer parking, so check ahead. Arrive mentally prepared to drive around for a bit before you find a spot!
- If you’re coming in late, grab snacks or dinner in Hyannis or Falmouth before you depart. The little cafeteria on the ferry isn’t great, but it’s handy if you’re hungry.
- Try to make the most of Friday night – you’re going to have limited time on the island, so do your best to make your way to at least a restaurant and a harbor to get some photos.
➡️ Saturday: Exploring the Island
Morning: Breakfast and Early Adventure
Start your day with breakfast at Aalia’s in Oak Bluffs – it’s a solid upscale cafe fare with hearty pastries and good coffee. If you’re in Edgartown, Blackbird Cafe has amazing breakfast sandwiches and pretty good coffee.
Next, get out and explore! If you’re up for a scenic drive, head out along State Road and South Road to Aquinnah Cliffs to see Gay Head Lighthouse. The views here of the red cliffs and contrasting deep blue ocean are unbeatable, and there’s a short trail with lookout points. Just watch out for poison ivy on the narrow trails!
If you want some beach time, Lucy Vincent is one of the nicest on the island in Chilmark, but just keep in mind that it does have a “clothing optional” section at the very far end (so don’t stroll too far if you want to stay in the “clothing required” area!)
Late Morning to Afternoon: Farmers Markets & Flea Markets
During the summer, don’t miss the island’s farmers’ markets and flea markets! They’re one of the most popular things to do on the Vineyard and many visitors miss them since they’re in the middle of the island.
- West Tisbury Farmers’ Market – Open on Wednesdays and Saturdays from 9AM to noon at the MV Agricultural Hall in West Tisbury. Fresh produce, local honey, baked goods, and homemade kombucha are always the stars here.
- Oak Bluffs Open Market – Sundays, but you might see pop-ups on Saturdays too. It’s part farmers’ market, part flea market, with art, vintage goods, and more. We always grab the angel food cakes with strawberries! Cash is helpful with the vendors.
Lunch Options
- ArtCliff Diner (Vineyard Haven) – I’ve been going to ArtCliff since I was 5 years old. It’s a beloved island institution since 1943, known for its creative, scratch-made dishes. We always went for breakfast (I’m obsessed with their housemade granola), but some lunch favorites include the fish sandwich and the Vineyard Cobb Salad.
- Among the Flowers Café (Edgartown) – Light sandwiches and fresh juices, perfect for a quick bite.
- Menemsha Fish Market – A rustic lunch spot with the best lobster bisque and clam chowder on the island.
Afternoon: Choose Your Own Adventure
In the afternoon, go for something active:
- Bike rentals are a great way to see the island. There’s a nice, mostly flat path from Oak Bluffs to Edgartown.
- Kayaking or sailing tours are another fun option if you’re up for it.
- Or, climb the Edgartown Lighthouse for a new perspective on the harbor.
- If you’re not too afraid of sharks, go jump the Jaws Bridge at Edgartown Beach!
If It Rains
If the weather turns, check out the Martha’s Vineyard Museum in Vineyard Haven for a fascinating look at local history. Or wander through the island’s art galleries like Eisenhauer Gallery, Granary Gallery, Under the Surface Gallery… there’s no shortage of creative spots to pop into.
Dinner
For dinner, try Alchemy in Edgartown if you’re in the mood for a fresh, modern menu and great cocktails. Or head to Red Cat Kitchen in Oak Bluffs for a cozy, creative meal.
Evening
End your day with a sunset drink at Nancy’s in Oak Bluffs. It’s a bit of a toursity scene, but a classic spot. Or, for a quieter evening, grab a drink at The Atlantic in Edgartown.
Local Tips
- Bring cash – some smaller vendors at the markets and farm stands don’t take cards.
- Parking can be tight in busy towns – if you’re heading to a farmers’ market or dinner, plan to arrive early.
- The vendors do sell out at the farmers markets, so get there early for the best selections.
- Menemsha for sunset is always worth the short drive – it’s a local favorite and you’ll rarely see many other visitors there.
➡️ Sunday: Brunch, Last-Minute Exploring & Ferry Home
Morning: Brunch Before You Go
Start your day with a hearty brunch to fuel up for the journey ahead. Here are a few local favorites:
- ArtCliff Diner (Vineyard Haven): I know I already mentioned this one, but it’s pretty much required for you to visit. So, if you didn’t go on Saturday, go on Sunday!
- Lucky Hank’s: A charming, chef-owned spot known for its farm-fresh menu and welcoming atmosphere. They have a huge variety of breakfast and brunch dishes, including favorites like cod cakes with eggs and sweet potato hash. It’s a local favorite for a reason!
- Biscuits (Oak Bluffs): Famous for Southern-style breakfasts, including chicken and waffles and my husband’s favorite – stuffed French toast.
Late Morning: Last-Minute Exploring
With a few hours left, consider these activities:
- Stroll through Edgartown’s Main Street: Explore local boutiques and shops for unique souvenirs.
- Visit the Martha’s Vineyard Museum (Vineyard Haven): If the weather isn’t great or you only have a little bit of time to waste, it’s a pretty cool museum to check out.
- Relax at a Beach: If the weather’s nice, spend some time at State Beach or South Beach for a final dose of sun and surf before you prepare to head to the ferry terminal.
Afternoon: Ferry Departure
Time your ferry departure to fit your schedule. Here’s what you need to know:
- Steamship Authority (Woods Hole to Vineyard Haven/Oak Bluffs): Offers year-round service with multiple daily departures and both car and passenger options available.
- Hy-Line Cruises (Hyannis to Oak Bluffs): High-speed passenger ferry with seasonal schedules (no cars).
- Island Queen (Falmouth to Oak Bluffs): Passenger-only ferry operating seasonally.
Be sure to check the latest schedules and book your tickets in advance, especially during peak seasons!
Local Tips:
- Arrive Early: Arrive at least 30 minutes before departure with your ticket in hand.
- Parking: If you’re leaving your car on the island, ensure you have a parking plan at the ferry terminal.
- Snacks: Grab a snack or drink before boarding, as options are limited and expensive on the ferry.
Unique Local Tips for Visiting Martha’s Vineyard
- Carefully time your drive to Cape Cod – Thursdays through Saturdays departures in the summer heading over the Sagamore Bridge are a curse to your vacation. You’ll need to plan to leave either very early or very late in the day to avoid the afternoon 3-hour rush from the South Shore to Falmouth on these days. If possible, plan your 2-night Martha’s Vineyard visit mid-week!
- If you’re using the Island Queen or Hy-Line ferries, remember they’re passenger-only – no cars allowed.
- If you’re bringing your car, fill up on the mainland – gas is far more expensive and sometimes scarce on the island.
- Don’t assume street parking is free – there are meters and time limits in some busy areas.
- If you want to avoid crowds, plan your trip in May, early June, or September.
- Look for pop-up events – the island hosts lots of last-minute concerts, art shows, and film nights.
- Get an early start at South Beach – preferably before 9AM, you’ll have time to get a parking spot and set up your chairs and towels before the crowds roll in.
- Grab a late afternoon ice cream at Mad Martha’s in Edgartown or Oak Bluffs – skip the main lunch-hour lines for a sweeter, more relaxed stop. They also have lobster ice cream which is worth just getting a sample of!
- Ride the 2-Car Chappy Ferry to Chappaquiddick – it’s a short, fun hop, and you can explore Mytoi Garden or East Beach on the other side.
- Take the back route to Aquinnah Cliffs (via Middle Road) instead of sticking to the main roads. It’s far more scenic and has far fewer cars.
- Skip the main streets for dinner one night – places like Chilmark General Store and State Road Restaurant in West Tisbury are favorites for a reason and feel far from the busy tourist spots.
- Pack layers – even in summer, the evenings can be cool, especially if you’re staying near the water.
- Look out for pop-up art shows and craft fairs – these aren’t always advertised widely, so ask around or check local bulletin boards.
FAQ
How many days do you need to see Martha’s Vineyard?
I’d say at least two to three days if you want to really enjoy it. One day is fine for a quick overview, maybe lunch in town, a lighthouse stop, and a bit of beach time.
But with two or three days, you can actually slow down: spend a morning at the farmers’ market, bike along the water, watch the sunset in Menemsha, and maybe even get out to some of the quieter beaches.
The island’s small, but it’s the kind of place where you’ll want to linger.
Is Cape Cod or Martha’s Vineyard better to visit?
I currently live on Cape Cod and can definitely say that they’re pretty different! Cape Cod is great if you want more of a classic road trip since it has lots of towns to hop between, easy access, and a big variety of things to do.
Martha’s Vineyard feels a little more like an escape since it takes more effort to get there, but that’s part of the fun. The Vineyard has its own pace: once you’re off the ferry, you’ll feel it immediately. If you want laid-back beaches, smaller towns, and a real “island” vibe, the Vineyard’s the better bet.
Either way, they’re both included on my list of 25 Top Summer Vacation Destinations on the East Coast!
Is it worth having a car on Martha’s Vineyard?
It’s absolutely worth having a car on the Vineyard if you really want to explore the whole island. Having a car makes it easy to reach the up-island spots like Menemsha, Aquinnah, and some of the quieter beaches that are tough to get to without one.
It’s also handy if you’re staying somewhere outside of the main towns, or if you want to bring beach gear and picnic supplies without worrying about hauling it all around.
But, parking can be a hassle in the busier towns like Oak Bluffs and Edgartown, especially in summer. So if you’re planning to mostly stick to those areas, you could get by without a car and use the VTA buses, bikes, or just walk.
Still, if you want the flexibility to check out different corners of the island and not be tied to the bus schedule, having a car is definitely worth it.
What is the best month to go to Martha’s Vineyard?
June and September are probably my favorite months thanks to the warm days, fewer crowds, and everything’s open.
July and August are busy (and lively!), but you’ll need to book ahead for hotels and the ferry. If you’re coming for beach days and sunny afternoons, summer’s great, but spring and early fall have a different feel since they’re quieter and easier to explore.
How long is the ferry to Martha’s Vineyard?
The main car ferry from Woods Hole to Vineyard Haven or Oak Bluffs takes about 45 minutes. If you’re taking a passenger-only ferry from Falmouth or Hyannis, it’s closer to an hour.
I always tell people to leave some time to get parked and loaded especially on weekends – there’s always traffic!
Is Martha’s Vineyard walkable from the ferry?
Definitely. Both Oak Bluffs and Vineyard Haven have shops, restaurants, and beaches within easy walking distance of the ferry terminals.
If you’re staying in town or just coming for the day, you can see a lot without a car. But if you’re heading up-island to Chilmark or Aquinnah, you’ll want to rent a bike or catch a bus.
Is it worth going to Martha’s Vineyard for a day?
It’s a long day if you’re coming from the mainland, but it’s definitely doable and a lot of people do this.
I suggest catching the earliest ferry over and the latest one back if you can. Even in a single day, you can have lunch by the water, walk the beach, do a little shopping, and get a feel for the island.
If you’re nearby in Falmouth or Hyannis and just want to see what the Vineyard’s about, it’s a great way to sample it.
What should I do on Martha’s Vineyard for a day?
Pick one or two towns and focus there. Oak Bluffs is fun for wandering, with the harbor, the Gingerbread Cottages, and the beaches close by.
Edgartown’s great for shopping and has that quintessential New England feel. If you have a car or are up for a longer ride, the Aquinnah Cliffs are worth it for the views.
Grab a lobster roll or some fried clams, and end the day with a walk along the harbor. It’s simple, but classic Vineyard.
No matter how you decide to spend your 2-3 days on Martha’s Vineyard whether it’s biking along the coast, poking around farmers’ markets, or just soaking up some beach time, the island has a way of making everything feel a little more relaxed.
Take it slow, leave room for those spontaneous detours, and don’t worry too much about packing every moment. That’s part of the Vineyard’s aesthetic! It’s about enjoying the in-between moments just as much as the big highlights.
I hope this Martha’s Vineyard weekend itinerary helps you get the most out of your trip and gives you a few ideas for making it feel like your own!
👉 Not sure if you want to visit Martha’s Vineyard or Nantucket? Check out my complete guide: Martha’s Vineyard vs Nantucket: Which Island Is For You?!
