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Styling Harvard Travels: Spring in Nantucket

We fell in love with Nantucket last year and looked forward to the first opportunity we would get to visit again. We have a new addition to our family and with our 9 year wedding anniversary in May, we thought it was be a nice little getaway for the 3 of us.

Nantucket is a pretty dog friendly place. Most stores allow them in and lots of the restaurants allow them to dine with you outdoors. We spent a little over 24 hours there and packed in a lot. Here’s my recap on our trip and what to do during Spring in Nantucket


The first order of business was to find a pet friendly place to stay. We loved our last hotel but they don’t allow pets so we had to rule them out. I quickly found a great alternative – The Cottages at Nantucket Boat Basin. They have adorable cottages on the wharf including some for your furry friends called The Woof Cottages.

When we got off the ferry, a staff member from The Cottages was waiting for us with a golf cart to take our bags and drive us over to check in. Since it was only 10 am, our cottage wasn’t ready so they held our bags for us and brought them to the cottage once it was ready.

Alfie got the royal treatment there! When we got to our cottage, not only did they have a chilled bottle of wine, some chocolates and a card wishing us a happy anniversary, but Alfie had a whole bag of goodies waiting for him!

Inside the bag was a collapsible pet bowl, a giant bone, a tennis ball, a stuffed toy and a poop bag holder. It was such a nice and thoughtful surprise. They also provided a super comfy pet bed and food and water bowls so we didn’t have to worry about traveling with ours.

Our cottage, Rambler, had a little patio area at the front that overlooked the wharf. It was such beautiful weather so we sat outside later in the day after we settled in and had some drinks. There’s a Stop & Shop a minute’s walk from there so I ran over to get some charcuterie foods to snack on. We sat outside for a couple of hours just relaxing, meeting people and their dogs who passed by and soaking up the sun.

By the time we were done, we (especially Alfie) were tired from our day so we ordered takeout from B-Ack Yard BBQ (just past the S&S at the end of the road) and cozied up at the table for 2 for some yummy food.

We loved this location so much that we can’t imagine not staying there again next time we visit (even if we came without Alfie)!

Exploring the Island

One thing we did this time around was rent a car during our stay. With May weather being somewhat unpredictable, I rolled the dice and booked a convertible Mini Cooper. Best decision ever. The weather was beyond great and we spent 2 days zipping around the island with the top down. Alfie loves the outdoors and he loves the wind blowing through his hair. He was in his glories!

Having a car at our disposal was perfect for exploring more of the island without having to find a taxi or wait for the bus. We took a trip to Jettie’s Beach after we picked up the Mini for our first beach visit. Alfie loves the beach and this was no exception. We took a little walk before heading to our next destination.

We decided to just drive around aimlessly as we explored more of the island. We found our way to Madaket and quickly voted it our new favorite beach. We went for a long walk and spotted a seal close to shore. We couldn’t get enough of the gorgeous weather.

As we were wrapping up, I got a call from The Cottages desk to let me know our cottage was ready. We zipped back downtown, found a parking spot (parking was a little tough around this time – around 1:30 pm on a Sunday) but we managed to get a decent spot about a block away from the wharf.

After we did a quick change, we headed back out in the Mini over to Cisco Brewers. We didn’t get a chance to make it last time we were there so we really wanted to check it out this time. Again, most of Nantucket is dog friendly and Cisco was no exception. There were tons of dogs there relaxing in the sun while their owners did the same. We tried some great new (to us) drinks and split a little pizza.

The next day, we wanted to make the most of our morning so we got up early to head to Brant Point Lighthouse to take some family pictures. Alfie was exhausted from his busy day on Sunday so it was tough getting him to try and cooperate but we managed to get a few good shots in.

Next, we stopped to get some coffee and a light breakfast at Island Coffee and then we were off to Sconset. What a beautiful beach! Parking is extremely limited but since we were there early on a Monday in the middle of May, it was easy to get a spot. We spent a bit of time there playing fetch and snapping more pictures.

We needed to check out of the cottage and return the car so we headed back toward downtown to wrap things up. After we checked out, we drove the car back to the rental company. A one minute walk and we were right back in the heart of all the downtown shops. I did a little bit of retail therapy and we grabbed a sandwich to split from Provisions. There’s a great courtyard there full of shade so we had a nice rest while we waited for our ferry.

A quick hour ride ferry back to Hyannis with my little love snuggled on my lap wrapped up the end of another great adventure. We can’t wait to be back on Nantucket again!


P.S. Alfie’s travel bag came in so handy! We brought it with us everywhere we went. Get your customized tote here.

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