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Upcoming trip

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New York City, New...
posts: 1,289
reviews: 211
Upcoming trip

We are coming to Oak Bluffs by boat in August with our Yachting Club. We will be on the island for 2 days. Please help me plan an itineray that will cover everything we want to experience. Restaurants, bars, beaches, etc.

9 replies to this topic
Boston, MA
Destination Expert
for Cape Cod, Massachusetts, Martha's Vineyard
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1. Re: Upcoming trip

You'll need transportation to experience the whole island, so you may want to look into renting a car while you are there. In no particular order here are some things you might like to see:

In Oak Bluffs: the Gingerbread Cottages;lots of small shops & plenty of places to eat, a few to recommend: Sweet Life Cafe & the Red Kat Kitchen.

Definitely visit Edgartown, a beautiful old whaling community with upscale shops & restaurants. Some well reviewed restaurants: L'etoile; Detente; Atria. Go for drinks on the porch at the Atlantic, right on the water, Visit the lighthouse, maybe take the On Time ferry over to Chappaquiddick & take a tour with the Trustees of the Reservations, you can also visit the Mytoi gardens.

The Outermost Inn in Aquinnah has a very good restaurant restaurant with an incredible view. We also like the Beach Plum in Menemsha, both are up island and you would need a car (or take a very expensive cab ride)

For beaches: South Beach is a big ocean beach with great waves, in Edgartown. State Beach is on the road in between OB & Edgartown, calm and warm. Menemsha Beach is a great place for a sunset.

Martha's Vineyard
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for Martha's Vineyard
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2. Re: Upcoming trip

Is this for adults only or families with children? It will make a difference in what I suggest.

New York City, New...
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3. Re: Upcoming trip

Thanks Kendrick.

Knows it is adults only. Recommend away---

Martha's Vineyard
Destination Expert
for Martha's Vineyard
posts: 721
reviews: 96
4. Re: Upcoming trip

'Restaurants, bars, beaches, etc.'...

Ideally, renting a car for one of the days is the way to go. If you want to visit a great beach, Moshup beach in Aquinnah can't be beat. It's at the other end of the island, requires packing all food/drink, arriving around 11am to get a good parking space in the lot owned by the town $15/day. You can drop everyone off with the supplies and then park and walk the wooden foot trail. Go to the right on the beach, the closer you get to the cliffs, the less clothing you will see, but this is optional. Keep it all on, take it all off, whatever. At least take a walk around the cliffs. Gorgeous. Take out at the back door of the Home Port has become quite popular again, as the restaurant has new management and chef. Fish tacos I am told, are great, and dining on the outdoor patio. Call to ask about alcohol policy. Not sure if you can still byob anything or what is available. Sunset in Menemsha is nice, can be crowded.

The bus is a great way to get around the 'down-island' towns of Vineyard Haven, Oak Bluffs and Edgartown. You didn't say which town you're coming in to... In Edgartown, visit the museum for island history, stop by the Luce House for a look at one of the oldest houses on the island. Walk down N. Water St to marvel at the old whaling captains homes and end at the Lighthouse looking across to Chappaquiddick. Lunch on the harbor at Atlantic is great. Dinner in Edgartown at L'Etoile (for expensive lovely dining experience), Alchemy or Atria is nice.

If you are in Oak Bluffs, I second kendrick's recommendations, with Sweet Life Cafe as a fine dining experience (outdoor reservations recommended) and Red Cat as a more funky, fun, high end food experience (reservations needed,as well) Drinks on the harbor either at Coop de Ville (very casual) or up on the top deck at Nancy's. Nice sunset view from here. Lunch at the Lookout is good too, right across from the Steamship dock. When you walk through the MV Camp Meeting Association's gingerbread cottages, make sure to stop by the small museum that is one of the houses on the main circle, set up as they originally appeared inside.

Vineyard Haven is more known for shopping than architecture or history. Great independent shops and lovely colonial and greek revival style homes off the main street. Lunch choice here is either the Black Dog on the water, or Waterside Market on Main St.

Loads of hiking trails on the island, if that interests you, I can go into more detail. The Trustees of Reservations over the sand and lighthouse tour or kayak tour out on Cape Poge, located on chappaquiddick is fun for a group and reservations are needed thetrustees.org/places-to-visit/cape-cod-isl…

Anything else?

New York City, New...
posts: 1,289
reviews: 211
5. Re: Upcoming trip

Thanks...sounds good. I am thinking of renting a jeep to tour the island for one day. I would love to finish the tour on the beach with a sunset picnic. We are docking in Oak Bluffs so the day without a car, we want to stay close..what can we walk to and where would you recommend for dinner--night life--drinks on foot or close cab?

Edited: 5:14 pm, June 25, 2014
Sarnia, Canada
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reviews: 1
6. Re: Upcoming trip

Hello. Thank you for the info on Martha's Vineyard. I was wondering what the best area is to stay. I am taking my mom. 75 years. Pretty good shape but can only walk so far. There will be 4 ladies total. Looking for a nice clean inexpensive place to stay. Maybe $150 to $200 a night.

Any suggestions would be appreciated.

Dena

Boston, MA
Destination Expert
for Cape Cod, Massachusetts, Martha's Vineyard
posts: 4,823
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7. Re: Upcoming trip

Dena - you might want to start your own thread to get the best responses, rather than adding on to this one. Include the dates you plan to come.

Lollygal - check out the Sweet Life Cafe for dinner in Oak Bluffs - it is about a mile from the docks.

http://sweetlifemv.com/

The Red Cat Kitchen is even closer

http://www.redcatkitchen.com/

Martha's Vineyard
Destination Expert
for Martha's Vineyard
posts: 721
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8. Re: Upcoming trip

For your day/eve in Oak Bluffs, dinner recommendations have been noted three times above, same two places. Where to have drinks on the harbor is also abpve. Nightlife can be found on Circuit Ave. Hard to miss. Bands play at Park Corner, Offshore Ale, the Ritz (just sold and should reopen soon) and Lamppost. Best bet is to check the local paper that comes out every Thursday, or read on-line mvtimes.com. Check the Calendar section. You'll def see more info in the print version. In Oak Bluffs, and all the down-island towns, everything is walkable, quite close actually.

Northampton, MA
posts: 2,702
reviews: 29
9. Re: Upcoming trip

Coop de Ville and the Lookout for casual outdoor dining on the water in OB. Sweet Life for fine dining.

In Edgartown the best upscale gourmet menu is at Detente. You will not have a waterview. Restaurants with a waterview have mediocre food but great views. The best bars are in Oak Bluffs. Edgartown is more of a yacht club crowd, oh I forgot you're in a yacht club!

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