Celebrating love in alluring Martha's Vineyard

Needless to say, I was overjoyed when I received the invitation to attend my friend’s wedding in Martha’s Vineyard, Massachusetts, last year. I admit I had never heard of the island before but it’s actually quite famous. The Obamas own a very secluded, impossible to peek into, house on a 29-acre estate. And, from what I gathered, it’s also a sort of iconic holiday destination where the rich and/or famous can retreat to rewind discreetly. And now, I understand why… Throughout the island, from the streets of the towns to the beaches and natural reserves, everything is immaculate. It almost feels surreal at times.

This trip had been in the works for a long time as you can imagine. Martha’s Vineyard was the last stop on a 13-day trip, which included New York (read about it here) and Boston (read about it here). I was looking forward to this last bit obviously, and all in all, the trip went smoothly. It was a good decision not to fly between destinations since trains and buses are much more reliable than flying these days. I won’t share pictures of the wedding itself to preserve my friends and their guests privacy, and focus on what we did around the event instead.

I’m far from being a Martha’s Vineyard travel expert having been only once, so I definitely recommend pairing my suggestions with a little bit more independent research. We had a few hours here and there, between wedding-related activities, and that’s why we decided to rent a car to get a chance to explore more in the short time we had. Vineyard Haven has a few car rentals, and I definitely recommend ours. They were very flexible, the staff was friendly, and this particular one was a bit more wallet friendly than others in the area. Public transport is available but I don’t recommend it because it’s far less reliable and comfortable. Mopeds are a no-no, and I wouldn’t cycle either, given how narrow and windy the roads are.

I booked us a room in Vineyard Haven, at Vineyard Harbor Motel, for which I didn’t have high expectations to begin with. It turned out to be the loveliest stay. We were booked into the Penthouse Suite (ask for the 242 if you’d like that one), spread over two floors, with a 360° view of the marina. I loved the sea-themed decor details in the room featuring vintage maps and curated flea-market trinkets, which provided that familiar and personal touch I look for when I travel somewhere new. It was also very quiet, and had its own small roof terrace with deck chairs, a super comfortable king size bed and fully equipped kitchen. From a price perspective, it’s one of the best value for money places I found on the island and I cannot recommend it enough.

What to do in Martha’s Vineyard?

So here is our itinerary and what we did, including places we went to for the main wedding event.

While you’re on your way to Martha’s Vineyard, if you have a couple hours to spare between the bus and ferry, stop at Wood Holes Market & Provision, which is only 5 minutes away from the docks. There is a hidden terrace with sea view in the back. Order a freshly-made, mouth-watering, lobster roll and pair it with a refreshing and sugary root beer. Time will fly by!
Arriving at Vineyard Haven by sea is one of the most scenic parts of the trip. For the bulk of the first day, we lounged on the hotel’s private mini beach, which was right by the shore. Another one of the perks of booking there!
In the evening, we ventured across the island to the Aquinnah Shop restaurant, which our hosts had privatised. Admiring the sunset from the spacious terrace overlooking the rugged Gay Head Cliffs and uninterrupted sea view was spectacular. Be sure to include it on your itinerary.
The next day, we squeezed in a two-hour walking tour of Oak Bluffs. After strolling the pretty streets, marvelling at the rows of colourful gingerbread houses, and taking several million photos, we concluded that it was one of the most intriguing, quirky, and cute towns we had ever seen. It reminded me of the neighbourhood in the TV show The Good Place. If you know the reference, you’ll feel the vibe straight away.
On our way back to Vineyard Haven, we stopped at the Joseph Sylvia State Beach, which runs alongside the main road. Imagine an endless sandy carpet, azure waters, and not a soul in sight. As there is no shade on this one, make sure you bring sunscreen. I brought my trusty Hello Sunday face + body creams.
I recommend Waterside Market in Vineyard Haven, where we had brunch, for all-day breakfast and hearty, tasty food on the go. You’ll be sitting among locals who come for the coffee (said to be one of the best in this part of the island), tasty wraps and pastries.
On the last day, we drove through Felix Neck Wildlife Sanctuary and I wish we had been able to stay longer. We didn’t stop, but it looks like a great place for a leisurely hike through woodlands and meadows.

As I mentioned in my introduction, there are a lot more things to do and explore, but we were there for other reasons than just to travel, so this is just a quick look. I’d love to go back and explore more. Possibly along with a Cape Cod trip. Maybe someday!

Side note: The return trip from the island was somewhat of a nightmare, but I won’t go into all the boring/unnerving details because it’s such an insignificant part compared to the rest. All I can say is I really recommend avoiding air travel, even though there is an airport and it seems easier on paper. It’s not. The ferry and bus or train combo will take a bit longer, but the route is scenic, it’s more environmentally friendly and it will be stress free compared to flying. Trust me!

What to pack?

Especially if you’re near the sea, it can get windy and cool at night, so I recommend packing layers. By the time I arrived in Martha’s Vineyard my suitcase was a bit of a mess. Reminder to invest in packing cubes for multi-destination trips! My suitcase featured a mixed bag of second-hand finds, good basics and statement flower-power dresses from brands like Nicholas and Ghost London, which I recently discovered on The Outnet.