Wondering where to go for your next summer vacation in New England?

Let me suggest heading east, hopping on a ferry to an island (Martha’s Vineyard — an island off Cape Cod in Massachusetts), and going on a road trip exploring Cape Cod. 

You absolutely can do this on a weekend, but ideally, you’d need a week if you want to properly relax and enjoy everything! 

In this blog post, I’m sharing with you exactly everything I did (road trip from Brooklyn to Cape Cod & Martha’s Vineyard over a weekend) and some travel recommendations for those that have to fly in and want to stay longer.

After this trip, I immediately added Nantucket (another island off Cape Cod) and Block Island (an island south of Rhode Island) to my list because I kept seeing people’s posts about them. We’ll see if we could cross them off sometimes next year!

 CAPE COD GUIDE FOR FIRST TIMERS

1. Know Before You Go – location, what to expect, and best time to go

2. Cape Cod Weekend Itinerary and Day Trip to Martha’s Vineyard

3. My thoughts on Martha’s Vineyard vs the Hamptons

1. KNOW THIS BEFORE YOU GO

Wealthy families, celebrities, and tourists flock here in the summer to enjoy its beaches, rich history, quaint towns, local seafood, and the real New England way of life. Cape Cod in particular is a popular retirement area for many residents.

Don’t miss Wellfleet oysters, cranberry bogs, Cape Cod National Seashore, Provincetown Film Festival, Sandwich Glass Museum, Pilgrim Monument, and taking the ferry out to Martha’s Vineyard or Nantucket.

BEST TIME TO GO

Oak Bluffs, Martha’s Vineyard

2. Exactly Everything I did – a Cape Cod Weekend Itinerary

I did this trip on a weekend driving from Brooklyn to Cape Cod and visited Martha’s Vineyard for one day.

If you don’t live nearby, I’d recommend flying into Boston since it’s a bigger city with lots of flight options. From here, you can rent a car and explore New England at your own pace and at any time of the year. You can even do Martha’s Vineyard ENTIRELY by BUS from Boston, BOOK IT HERE!

FRIDAY – leaving Brooklyn at 2 – 2:30 pm

1. First stop – bathroom, gas, and snack break in New Haven, Connecticut

• New Haven White Clam Pizza (if you love clams!) at Frank Pepe Pizzeria Napoletana, the original location on Wooster St. Friday wait is around 1 hour, so order online and come pick it up to eat in the car. Other times, I’d suggest dining in if the line isn’t too long. They also have an in-person take-out ordering service at the building next door, but the wait is just as long. Alternative (nearly just as good): Modern Apizza or Sally’s Apizza. I reviewed the two pizzas in my Connecticut and Rhode Island weekend post last year, HERE.

• Classic Hamburger Sandwich at Louis Lunch (known as the birthplace of the Hamburger Sandwich, est 1895, 4th gen-family run business)

2. Second stop – Providence, Rhode Island for dinner

• We sat by the bar and had a proper dinner in East Providence. With paella in mind, I picked Aguardente since it’s recommended on some food lists. We ordered lamb chop, seafood paella, fries, and sangria (they used lots of fruits!). It’s got a somewhat young crowd, and the food is 7.5/10.

• Read my Rhode Island Travel Guide blog post for more recs!

3. Check-in Inn on the Square – Falmouth, Massachusetts

• HOTEL – We paid three times the price of what this hotel/cottage of this type would normally cost, but that’s the price you’ve got to pay when traveling here during peak summer. Besides Expedia, I’d recommend checking Hoteltonight for last-minute deals and booking it as soon as you know where you want to be the day off (only if you’re traveling without a plan like us!). We booked this place on the road, just hours before checking in just because we weren’t sure whether we should get a room for 2 nights or not.

• After this trip, I do think it’s worth it to stay closer to the ferry and to pay extra. So stay in Falmouth (if possible) to avoid the hectic morning commute to the ferry. Daily parking is available at some of the ferry parking lots, but we were allowed to park our car in the hotel lot for the day.

ferry from Woods Hole to Martha’s Vineyard

SATURDAY – Martha’s Vineyard

The most popular & cost-effective commuting method on the island is by BUS!

The towns are walkable and bikeable, but you can also rent a Jeep, mopeds, taxis, and Uber. I did see tour buses. as well if you’d prefer to sit back and relax.

We have a car, but it would have cost us $250 at this time of the year to bring our own car on the ferry over to Martha’s Vineyard. Prices change depending on the seasons, HERE, so we opt for the no-car and bus routes.

1. Taking the shuttle bus to Woods Hole Ferry terminal

• Inn on the Square is just steps away from one of the Steamship Authority’s parking lots, so we left our car in the hotel parking lot and walked over to the bus station inside that parking lot. We did ask the front desk, and that was allowed plus they gave us a quick Martha’s Vineyard guide with a map.

• Be at the bus station 30 – 45 minutes before your ferry time, and the ferry ride takes about 45 minutes.

• We made it to the 9:30 am ferry from Woods Hole to Oak Bluffs with just a minute shy of having to wait another hour for the same one due to traffic at the terminal.

2. Taking the ferry from Woods Hole to Oak Bluffs

• Ferry fares – Book ferry tickets online here! $10/person one way, so round trip for each adult is $40 (and you have up to 2 years to use it. Tickets are sent to your email, and you’d need to just tap the machine to enter the ferry!)

• Martha’s Vineyard Ferry Schedules

• Woods Hole to Oak Bluffs is a more popular route because I’ve heard that there’s not much to do in Vineyard Haven, the other destination on Martha’s Vineyard that the Steamship Authority ferry goes to. Note that the ferry that goes from Vineyard Haven back to Woods Hole is the latest one (9:30 pm as of August 2023), so keep that in mind if you miss the Oak Bluffs to Woods Hole ferry at 8:30 pm when coming back.

3. Taking the shuttle bus on the island

• Yes, we did this route since we had places to go but not a lot of time. If we were to stay here for 2+ days, we’d absolutely rent a bike.

• Purchase one day pass here! – In-season $2/ride, and $8 for the whole day. We got the day pass.

• Martha’s Vineyard Bus Route Map

It’s common for public transportation to be delayed or changed, so pay attention to where you’re going. The best way to know where you’re going is to ask the bus driver for which bus to take and if you don’t know where you’re going. They’re pretty helpful here!

Things to do in Martha’s Vineyard

OAK BLUFFS

Browse the shops in downtown Oak Bluffs right when you get off the ferry. Don’t forget to grab a coffee, some donuts (at Back Door Donuts, donuts during the day and baked goods speakeasy-like at night), and snacks for your day out exploring the island at the grocery store (Reliable Self-service Market Inc). I bought some seashells at the souvenir shop here.

The ‘gingerbread cottages’ are a must-see in Oak Bluffs. You can read about the history of these tiny and colorful 19th-century houses, HERE. Give yourself 30 minutes to an hour walking and touring the area, take lots of photos, and then head to the bus stop nearby making sure it’s going to Edgartown.

Gingerbread Cottages

Ocean Park in Oak Bluffs – Martha’s Vineyard, MA

EDGARTOWN

This is the spot to be if you’re looking for the Hamptons vibe. It’s a lot better in my opinion because people are more chill. There aren’t a lot of trendy luxury boutiques, so you’re getting the real coastal New England vacation vibe here. I’d love to get a hotel for a night, rent a bike and explore this part of the island next time.

Rosewater Market is a cute cafe with great dine-in and takeout lunches. If you have time, definitely dine in at a restaurant and then browse the local shops and houses in downtown Edgartown. Nell is a popular clothing boutique that I see people mention a lot on social media, and they have a home shop across the street.

Food spots I see people recommend a lot include Behind the Bookstore (behind Edgartown Books), The Seafood Shanty (only 3-ish stars on Yelp?), 19 Raw Oyster Bar (right next to the bus station), Detente (heard the vibe is odd, but people like it for date night.)

OUTFIT: top: PARIS GEORGIA | belt: KHAITE | shorts: vintage CHIC denim | sandals: THE ROW | sunglasses: CELINE | tote: JIL SANDER

AQUINNAH

From the Aquinnah parking lot where you get dropped off by the bus, you can walk to Aquinnah Cliffs Overlook and Gay Head Light. When you’re there, don’t forget to check out the souvenir shops, and food is available there, too.

Moshup Beach is a public beach, but be warned that there are nudists, occasionally. I saw one. We got here at around 4:30 – 5 pm and spent around 2 hours on the beach. The water was incredible and warm, and the sun did come out at the end.

I’ve also heard great things about Katama Beach/South Beach in Edgartown, so I’ll for sure check it out next time as well!

Aquinnah Cliffs Overlook

Moshup Beach

swimsuit: HUNZA G

captured at sunset, post-beach swim – the most picture-perfect view of our path back to the car 

4. Taking the bus from Aquinnah back to Woods Hole or Vineyard Haven

• Make sure you pay attention to the bus schedule.

• I’d recommend being at the bus station for the second to last bus. We missed it by 5 minutes and had to wait almost an hour later for the last bus to come. According to the bus app we download and Google Maps, with one transfer, we would miss the very last ferry of the day (leaving Vineyard Haven) by 5 minutes. I knew we would be fine, but my partner was annoyed and worried. People came and went with their own cars, and hitchhiking would be the very last option if we had to come to that point. Luckily, our bus driver announced that we wouldn’t need to transfer as he would take us to Vineyard Haven. There were changes happening, and that’s why I said it’s best just to ask. We made it back to Vineyard Haven with 15 minutes to spare.

The last ferry is typically more packed, so you might have to wait around even longer for the buses to come after getting out of the ferry. Just make sure you know which parking lot you’re going back to.

5. Hotel – Sunbird Annex Resort in West Yarmouth

• I don’t recommend this spot, but it’s what’s available in the area that we wanted to stay at (plus we booked it pretty late in the day).

seashells sold at a gift shop in Aquinnah Cliffs Overlook

SUNDAY – Cape Cod: Chatham, Truro, Provincetown, Eastham, and Cape Cod National Seashore

1. Morning in Chatham

• Coffee at Snowy Owl Coffee Espresso Bar

• Browse the shops on Main St.

• Check out Chatham Lighthouse and Lighthouse Beach

• Lunch at Chatham Pier Fish Market. I’d recommend a Lobster roll with fries, a steamed Lobster with butter (1.5 lb/2 people), and Clam chowder. The food is really that good, and you can’t beat the seafood price and freshness when eating at the pier compared to any restaurants in the city. While you wait for the food, go check out the fishing pier for seals and boats unloading fish on the deck nearby.

downtown Chatham

Chatham Lighthouse and beach

2. Truro Vineyard

Great spot for day drinking! They have a food truck and tons of seating options. The vibe is pretty casual!

3. Provincetown

After a glass of wine, I got pretty sleepy during the drive from Truro. I didn’t know what to expect when arriving at Provincetown, and I’ve got to say I immediately got woken up by its liveliness. We found a free parking spot on Commercial Street and started walking along to check out the vibe. Then I quickly realized that it’s got a prominent LGBTP+ crowd, and just people-watching is a lot of fun!

Provincetown, known as P-town, is situated at the very tip of the Cape, so it does give that remote vacation feel. I bought a pearl necklace at a vintage shop, and the owner gave me a good deal. Then we got a table out on the deck looking out to the ocean at the historic Lobster Pot and stopped by Race Point Beach for an outfit picture before heading out.

• Walk Commercial Street – a colorful and lively street with a flourishing LGTBQ+ community. Get some Portuguese baked goods, explore the shops, check out some art galleries, and definitely get a table at a restaurant or bar here. Learn about the history of the town and talk to local people here.

• Dinner at The Lobster Pot – ask to sit on the deck outside! We got some drinks and a Lobster Bake meall combo to share.

• Pilgrim’s First Landing Park – read more here

• Race Point Beach – Food, restrooms, and showers. It’s free to enter past opening hours, so go for sunset if you’d like.

Commercial Street

Provincetown Wharf with lots of booths with artists selling hand-made arts

OUTFIT: top: POSSE | pants: ATTERSEE | pearl necklace: vintage, bought from a vintage store in Provincetown, Cape Cod | quilted silver earrings: AURATE NEW YORK | bag: vintage LOUIS VUITTON | flip flops: ROTHY’S (old)

4. Eastham

• Nauset Lighthouse aka the logo for Cape Cod Potato Chips

• Nauset Light Beach for sunset. There are restrooms and showers.

Nauset Lighthouse

sunset at Nauset Light Beach

5. Wellfleet & Cape Cod National Seashore

The national seashore is located in eastern Massachusetts on Cape Cod with 40 miles of pristine sandy beaches, marshes, ponds, and uplands for diverse species.

• List of beaches – entrance pass is REQUIRED ($25/vehicle – late June to Labor Day. America the Beautiful pass is accepted.) – beach and water safety

• Cape Cod tide chart

• Great White Sharks swim in the waters of Cape Cod. Learn shark safety (sharks hunt for seals in shallow water, so stay away from seals and schools of fish)

• List of walking trails – trail safety

After this trip, I immediately add Nantucket (another island off Cape Cod) and Block Island (an island south of Rhode Island) to my list, so we’ll see if we could cross that off sometime next year.

3. MARTHA’S VINEYARD VS. THE HAMPTONS

You’d often hear people compare Martha’s Vineyard in Massachusetts to the Hamptons in Long Island, New York, and after this Martha’s Vineyard trip, I cannot help but do the same.

Both places are popular summer vacation spots for many wealthy people and celebrities as they have their second houses or own rental properties here. If you’re into fashion, you’d know lots of luxury brands do their seasonal pop-ups and events in the Hamptons. In general, both places don’t have many great and affordable lodging options unless you book way ahead in advance, and many beaches are private. For example, Cooper Beach in the Hamptons is one of my favorite beaches, but I dread the commute so much for having not much to do besides the beach. Plus, beach parking costs $50. I’d rather go to Long Beach in Brooklyn as the drive is 1 hour + beach pass is only $15/person.

So far, I have done multiple day trips to go to the beach in the Hamptons and once for an event with Who What Wear, all by car. My partner and I do agree that we like Martha’s Vineyard more for its nature, beaches, activities that everyone can do, and the overall diverse and casual vibe. Although many areas and parts of the island are private, and it’s 5+ hours away from NYC. It feels more like a vacation like you’re going on an island away from the towns. Plus we were able to hit all of the spots we wanted to go to BY BUS within the day with barely any planning ahead.

• Martha’s Vineyard has a very diverse crowd. I saw families with kids, girl groups, teenagers, couples, and people from very different walks of life. Kamala Harris was there for a fundraiser event, and the secret services delayed traffic for us a couple of times.

• After reading many travel blog posts and watching hours of Tiktok videos, apparently, going to Martha’s Vineyard is very normal for many New Englanders. The ferry ride here is cheaper and shorter as compared to (let’s say) Nantucket.

• Forus from Brooklyn, it’s a 5-hour+ drive, and at least 2-night stays elsewhere if we want to do this as a day trip, arriving early in the morning and leaving on the last ferry of the day. It’s not the cheapest summer travel spot, but I do think it’s different and so worth it for the island + New England experience. I love the beach here so much!

• Bus and ferry options from Boston can save you some money, but it can get confusing if you’re trying to do this the first time. You can drive and take the car on the ferry, but I don’t think it’s worth it if you’re just going for a day. Yes, you can easily hop in and go anywhere at your own pace, but parking in popular towns like Oak Bluffs and Edgartown would be a nightmare.

• Edgartown is a really nice and cute town, and it seems like an appropriate place to put on a nice dress with a straw hat and bag (if you have a place booked here!). I didn’t spend enough time there, so I’ve got to come back.

• A lot of the beaches are private. But the public one I went to was incredibly nice. It might also be because we got lucky with the nice weather that day.

• Again, we did the entire island by BUS, and that seemed totally normal like everyone else was doing the same thing, and was so much fun!

I hope that this is helpful. Feel free to reach out if you have any specific questions, happy to help out!

Race Point Beach, Provincetown, MA

OUTFIT: sweater: BABAA | skirt: REFORMATION | claw clip: ALEXANDRE DE PARIS | flip flops: ROTHY’S

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