Brotherhood of Thieves was originally opened in the 1840s as a whaling bar and much of the original setting still exists today.  

I decided on the Veggie Burger and loved every bite.  J chose the Bayou Burger and thought it was delicious – especially with the spicy red pepper remoulade.  A couple of beers from the local Cisco Brewery were the perfect partner for our burgers and provided the energy needed to continue meandering down the cobblestone streets.

We had selected our first dinner in Nantucket to be at Lola 41.  This chic global bistro had a menu that we couldn’t resist {paired with countless first hand raving recos!}, with seemingly something for everyone.  We selected a couple of random dishes, not meant to be complimentary paired, but meant to explore the menu.  We started with the Tatara, a basic starter sushi roll {J is new to sushi…we were easing into it}.  It was delicious and sizable.  We then moved on to the handmade Gnocchi Bolognese.  The buttery little pillows of potato were as light as clouds…absolutely delectable and quite possibly one of our favorite dishes of our trip!  We also shared the Pressed Sandwich – featuring thick crusty bread hugging a combination of proscuitto, arugula, asparagus, bufala mozzarella and thick, gooey aged balsamic.  We waddled home, navigating ankle-deep puddles, in a blurry haze of delicious wine and indulgent dishes.

Day two started with a delicious breakfast prepared by our innkeepers.  We had a day of exploring the island ahead of us and, therefore, I felt in necessary to have even more fuel than our abundant breakfast offered…  

A strong latte from The Bean was a good start…

But the sure way to keep me going is to have a sack full of sugar-candy!  The sweet lady at the Nantucket Candy Company viewed me as a regular by the end our our trip! 

After hours of sightseeing we were ready for a snack to sustain us until dinner and decided to pop into the Easy Street Cantina for a bite.  The location is great, on the corner of Easy and Broad Streets, right by the water and I can imagine that it is packed in the summer months.  The fish taco and chicken salad wrap were average, but did the trick.

We were seated at a cozy window table for dinner, our second night.  Black Eyed Susan’s is a teeny little BYO {cash only!} restaurant that offers breakfast and dinner.  People rave about their breakfast…but I’m only able to rave about their dinner.  I had the Salmon Tikka Masala that had a deliciously Indian flare, while J chose a safer chicken dish that the waiter offered as a special for the evening.  We so enjoyed our meal, romantic and casual…and quite bustling for off season!

The next day we embarked on an island bicycle trip and stopped at The Green, after breakfast, to pick up lunch on the go…something that would fit in the woven basket on the front of my bike {J would not hear of putting a basket on his bike!}  

Once we hit Siaconset beach {10+ miles later} and found the perfect overturned rowboat to act as our picnic respite, it was time to sample the natural/organic creations the early shift at The Green put together for us.  My multigrain wrap was stuffed with tuna, veggies, spinach and brown rice. To say it was fresh would be a massive understatement…it was the perfect fuel I needed.  J’s chicken salad wrap must have also been noteworthy because before I could ask how it was…it was gone!  

Once we got back into town, nearly 25 miles in nutty wind-gusts later, we both agreed we were owed a treat {as if the backpack full of sugar-candy wasn’t treat enough…}

Petticoat Row is a darling bakery bursting with even more darling treats.  In the 1800s, many of the island men were away on whaling voyages for months, if not years, on end.  The wives at home were forced to step up and fill in with the labor shortage and started running businesses and shops.  The lady-run shops on Centre Street started being referred to as Petticoat Row.

The macarons were massive, the cookies were trouble with their gooey centers and crispy edges and the misc goodies left us wanting more {while also feeling sickly full}…  

After a bit of relaxation, it was time to gear up for yet another meal!  After a menu change at our originally planned restaurant, Toppers, we selected Dune for our final dinner.    

The almost urban setting was bustling with an interesting mix of chic, glossy patrons and with a few casual hoodie-clad locals, all simply awaiting a delish dinner with drinks.

I convinced The Man to start with Oysters on the half shell.  We shared the pepper pappardelle with black truffle and risotto.  The dinner was delicious and we were so glad to have shared our last dinner there.

The morning of our departure, we realized we had yet to make a visit to a local favorite…Downyflake Donuts.  

We decided to walk, even though it’s location was described as middle island.  The donuts were surprisingly small…allowing us the further indulgence of a sampling of a few of their flavors:  regular, chocolate, and pumpkin spice.  The walk was way more manageable than expected, therefore not easing my conscious…perhaps I worked off the free sample bite left on the counter?

Before the weekend came to an end, we needed snacks for the flight and treats for friends at home and made a final stop at Sweet Inspirations, where chocolate covered gummy bears {surprisingly delicious} and chocolate covered cranberries {local and seasonal} came home with us by the boatload.

I haven’t yet stopped my two-a-day workouts and am pretty sure I shouldn’t for months to make up for the few fabulous days of dining we experienced on Nantucket.