A Weekend on Martha’s Vineyard

4th September 2009

Our President just vacationed on Martha’s Vineyard – what can I say? Clearly, it’s a fabulous place.

I was brought to the island five years ago for work. As I learned early on, you’re either an Nantucketer or a Vineyarder, and I’m a Nantucker. Most people don’t venture to both islands. But I have to admit, I’ve found a special place in my heart for the Vineyard. I never imagined it could happen, but it did. These days I happily return (just don’t tell my Nantucketer friends that!).


People always ask me, what’s the difference between the Vineyard and Nantucket? Where do I begin? First, how are they similar? They are both islands off the coast of Massachusetts and they both have fabulous beaches. That’s about it for similarities. How are they different? For starters, the Vineyard is about five times as big as Nantucket, and it’s only five miles off the coast of Cape Cod, not thirty miles like Nantucket, making it much easier to get to. The Vineyard also has three large towns and a handful of smaller communities (with shops, restaurants, etc.). Each town is very different and special in its own right. Between the size and diversity, you’re bound to find you’re own special spot.

So, here is a list of all the things I’ve fallen in love with:


Kelley House – this hotel is in a great location just off Memorial Wharf in Edgartown. The rooms are nice and large, not fabulous. However, two factors make it my favorite place to stay: there is a huge parking lot for guests in town (clearly parking is an issue!) and a pool. You can’t ask for much more than that!

Harborview – the hotel sits on a bluff overlooking the Edgartown lighthouse, probably one of the most spectacular views on the east end of the island. It was completely renovated in 2008; I’ve not stayed there since but hear it’s lovely. Expensive, but well worth it.


Colonial Inn – a basic, comfortable hotel in the heart of Edgartown. I’m particularly fond of the rocking chairs on the front porch – a great place to sit with a glass of wine and people watch. If you have a family or larger group, I would also suggest the residences attached to the Colonial Inn. They’re expensive, but beautifully remodeled with lovely decks overlooking Edgartown harbor.

The Hob Knob – expensive, but fabulously country-chic. Breakfast is included in your stay, and it’s the best free breakfast I’ve had in my entire life.


Chesca’s – my favorite restaurant in Edgartown. Honestly, you can’t go wrong with anything on the menu.

The Homeport – this is my personal favorite – I make a pilgrimage there every year. The restaurant is located in Menemsha, a small fishing village on the west end of the island (also a favorite spot to the watch the sunset). From your chair inside the restaurant you can watch the sky turn beautiful shades of pink and purple as you stuff yourself with steamed lobster. Its so amazing it makes me hungry just thinking about it.


Sharky’s – an island favorite with locals and tourists alike. There are now two outposts, one in Oak Bluffs and one in Edgartown (with great parking!). They serve the best mexican food you’ll find north of the border. I highly recommend the watermelon margaritas.

The Seafood Shanty – grab a seat on the deck upstairs and watch the boats go by ALL day long. I highly recommend the lobster quesadilla.

The Atlantic – this place was just remodeled last year and it’s fabulous. The food and drinks are very expensive, but the restaurant and bar have a great atmosphere and a wonderful view of Edgartown harbor.

Dock Street Coffee Shop – a day on the Vineyard cannot begin without breakfast at Dock Street. Enough said.

See and Do

For starters, you’ve got to go the beach. Wasque and South Beach are favorites, but there are amazing spots all over the island.

If you have the time and a car (ferry reservations for cars are hard to get – plan ahead!), spend a day driving around the island and check out all the different communities. The cliffs and lighthouse in Aquinnah are amazing, and you’ve got to make a trip to Menemsha for dinner at the Homeport.

If you’re like me and want to be out on the water, call Leigh and Todd who own the Magic Carpet and go for a sail. The boat is moored in front of the Edgartown harbor – it’s absolutely spectacular.

Photos by:  Brian Powers, The Harborview,  Professor Bop.

Leave a Reply