
Last year,2016, me and my s.o. (who is now my fiance) and I decided to do something fun for the both of us. We invented something we called the ‘$5 fun-jar’ — that every time we got a $5 bill as change we’d put into our jars and then we will count it. At the end of the year we would use our jar-money for a fancy dinner, short trip or something else fun.
All year long we both kept adding more and more $5 to the jar and became increasingly excited to count them all at the end of the year to see how much we had and what we could do with it. Since we both have crazy schedules it was almost impossible for us to do more than a 5 days vacation unless we book 6–7 months in advance. And at the same time, we were trying to save up for basically being a real ‘adult’ life this coming year.
At the end our $5 bills totalled of $640 !!! — that’s worth a short trip somewhere !! Our original choices were, Maine, Boston, Upstate New York and Florida but with our timing and workloads, we decided to pick somewhere local, somewhere we’ve never been and can drive to easily.
Shelter Island- New York came to mind.
My fiance is a Long Island native but had not gotten a chance to visit Shelter Island. The island is situated between the north and south fork of Long Island and is reached by taking a ferry from Greenport. And after only a 15 minutes boat ride and we were here !

The Chequit boutique inn is a 140 years-old building, but it is fully renovated with a restored hardwood floor. It is literally a 2 minutes drive from the ferry, located in Shelter Heights, that means you can overlook the harbor when you wake up in the morning through your window. Since it was the low season, there were not many guests. The hotel provided a you wine bar right next to the fireplace in their gorgeous lobby. This provided a certain vibe that we loved.
Since we got there a little late it was pretty dark (of course) cold outside. We decided to have dinner at the hotel’s own restaurant — and it was phenomenon !! We treated ourselves to beets salad to start along with my cocktail and his beer. I ordered pork tenderloin with chorizo, mashed purple sweet potato, haricots verts and tamarind sauce. My fiance got braised beef brisket accompanied by roasted garlic mashed potatoes, sautéed apple, red cabbage and a whole grain mustard demi glace. We were so full that we didn’t even have any room for desserts.

The next day we took it slow and easy. We had a breakfast at the hotel and drove around the island, visited a bunch of sites and took the ferry to Greenport to explore antique stores, walked along to the shore and visited a winery.


Shelter Island has its own brewery run by a really nice family called “Shelter Island Crafted Brewery” on N Ferry Rd. A good tip we got was to order a Mexican food from the bodega next door and bring it over to the brewery. We were surprised that you could find such an authentic and delicious Mexican food right on Shelter Island. We took the ferry back to Greenport to walk around the neighbourhood and rode on an empty carousel by the bay, after that we visited Kontakosta Winery ( http://kontokostawinery.com/ ) and enjoyed sunset along with their Cabernet Franc.
That was it !! our 2 day vacation- if you want a short getaway to a place that would be otherwise packed in summer time, Shelter Island in the winter can give you a whole different experience. Just remember to pack yourself a nice and warm sweater and a cozy beanie and you’ll be all set !
As for our money, we spent almost all of the money in the jar. This included gas, ferry, food and hotel. We are continuing our $5 jar this year, and I’ll talk about where are we going next year. Feel free to take this idea and do it yourself. Make sure you let me know where did you decided to take your journey to !!
ps. Food photos are from http://www.thechequit.com
Original post : https://www.kritchaya.com/summer-space-studio/2017/2/3/hello-test
