The Chequit Inn

had a great experience here last weekend. Great room, great price. The staff were exceptional. Got me the hardest reservation on the island at VINE STREET CAFE on a saturday night on Memorial Day weekend! They were also really awesome with adjusting my room rate when I needed to leave a day early. This place is so great and I would stay here again and again.

I have backpacked across Europe during college, staying in hostels only.  I have traveled to South America on a $50/day budget.  And yet, THIS hotel was the grossest place I've ever stayed.  I only paid about $130/night which is a GREAT deal for memorial day weekend, but anything over $20/night at this place is highway robbery.   My word of advice for you all:  spend an extra $100 and stay somewhere else if you can!

We didn't arrive until 10pm on a Friday, and upon walking in, we were directed via paper directions, to go downstairs to the bar to check-in.  Fine.  We were given keys to our room on the bottom floor of the 'Summer Cottage.'  The room was about 10'x10' with one double bed taking up pretty much the whole thing.  No headboard.  Mildew on the lampshades.  Rust on the A/C.  (There IS an air conditioner though, that's where the 1 star comes in).  Walls are so thin, I heard my neighbor snoring all night.  I don't mind 'outdated,' but this place is beyond that.  I'm really not sure how they even pass inspection.  The entire place reeks of mildew.  It just all needs to be ripped up and completely re-done.

In 30 years of travel and hotels, I have never felt the need to voice a public complaint until now.  Do. not. stay. here.

I love food but I lurve atmosphere! Raving about The Chequit is easy for me because it's got both. Let's start in the obvious place, the arrival: a late-afternoon promenade through the beautiful Greenport waterfront, past the historic piers, the window shops and the antique ferris wheel. Then you hop on the Shelter Island Ferry as a foot passenger: $2 each way. Now you're literally floating as the sun begins to dip, adding pastel colors to the coastlines you are sandwiched between. After the 5 minute ferry journey you climb a short but steep hill to earn the extended decadence in which you are about to indulge and the view that the hike affords. There are multiple floors and seating areas and a bar room. I recommend sitting as high as possible and, if not outside, then at least in view of the inlet.

My family and family friends make the pilgrimage once a year for an annual celebration. I also took my ex-girlfriend here for Valentine's Day one year. The vive has never been short of elegant and the food has been consistently good. The menu may be a bit more ambitious than the result but fortunately the prices match the latter. Here's 6 words that make me happy as an East End restaurant-goer: local seafood, local produce, local wine!

I like the food but it's the experience that keeps me coming back, forever ever - until I can't climb the hill.