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Posted by Leah Klein, guest blogger of Leah's Life: Pearls & Oysters

This weekend, I saw some of the happiest couples strolling down Tremont Street in Boston’s South End. The couples looked into each other’s eyes as they meandered through a stream of people on Newbury Street. The pairs basked in the sun together amid the pink petals swirling down from the trees in the Boston Garden. These couples were six-legged couples; they were dogs and their owners glad to be outside together. As the sun heats up even more, the ocean beckons and you don’t have to leave your four-legged BFF at home. Here are some great places to Sit (and enjoy a bite to eat or a great view), Stay (pet-friendly lodging) and Play (hikes, beaches, and more play spaces) with your dog on Nantucket and Martha’s Vineyard.
bikes cottages at the boat basin (1)
Sit: Grab a Bite, Eat, Relax
On Nantucket, get up early and head just off the busy main street to Black-Eyed Susan’s for a quick breakfast. There is a bench out front and tables by the window.  If the sun is still low, and your pup is patient you can leave your dog out front by the bench away from the busy street while you enjoy your cup of coffee and heuvos rancheros with black-eyed peas. Cisco Brewery is a party that you’re invited to crash. With a nice cold beer, some bites from the food trucks, a little live music, and plenty of space to hang out with your dog by your side it is a true pet-friendly gem. For lunch or dinner you can grab a pizza, a sub or some pasta at Pi Pizzeria, and enjoy it on the deck.  Next door, is The Green with their own little patio to enjoy a fresh juice or signature smoothie, and some gluten-free (or gluten-full) goodies for breakfast or a Plant Eater wrap or Mother Clucker sandwich for lunch.
Martha’s Vineyard’s Black Sheep is a little store with a luncheonette. The perfect place to buy a picnic to go or to stop for a bite to eat with your dog by your side.  Black Sheep has cute little patio spaces where you can sit and enjoy your Croque Monsieur and a smoky tomato soup or your fresh breakfast scone. Nat’s Nook in Tisbury has a perfectly pet-friendly patio on which to enjoy your breakfast bagel or delectable sweet or savory crêpes (regular or gluten free). In Vineyard Haven, grab a seat under the umbrella at one of Little House Cafés picnic tables. Your pooch can take a breather on the grass while you enjoy a roasted turkey sandwich with cheddar, cranberry relish, pickled red onion and arugula on a multigrain ciabatta roll or a crispy fish taco with salsa fresca, avocado and shaved cabbage with lime.
Stay: Curl up, Relax, Stretch Out
Take the ferry over to Martha’s Vineyard and stay a while at Summercamp Hotel in Oak Bluffs.  Their dog-friendly king rooms are located on the ground floor and welcome up to two dogs per night. Summercamp is playful and stylish. It is like that dream summer house from a magazine with all the amenities and none of the work. After a day out at the beach, relax on the porch with your dog by your side and a cold drink in your hand.
On the Steamship Authority ferry to Nantucket, you can sometimes find more dogs than people out on the deck relaxing. It seems like a majority of Nantucket locals and visitors alike are dog-lovers to the core. Staying at the The Cottages and Lofts at the Boat Basin is an ocean lovers dream as they are located right out on the pier and surrounded by water. The Woof Cottages are exceptional and your puppy will be treated like a VIP with a welcome bag of treats and toys at check in, and doggie turn down service. There is no need to bring a dog bed or food and water bowls, as they will all be waiting for you when you get to your cottage. Each cottage is unique and beautifully designed. The Cottages and Lofts at the Boat Basin are perfect Nantucket Island dream homes away from homes. While everyone is taking a nap after the day at the beach, you can take one of the dedicated cottage bikes for a ride around town.
trail dog
Play: Run, Walk, and Fetch
On Nantucket, rent a jeep or take advantage of your stay at the Woof Cottages at the Cottages and Lofts at the Boat Basin and take the dog-friendly beach shuttle out to the beach, but don’t forget your leash. Nantucket’s beaches that have lifeguards are all dog-friendly before 9 a.m. and after 5 p.m., which is perfect for that early morning stroll before the sun is too strong or for that evening picnic on the beach. Head out to Smith’s Point for a beautiful stroll along a parcel of land that juts out into the channel between Madaket Harbor and Tuckernuck Island. If you want to walk a few short loops by the ocean, through grassy paths and over cute little footbridges, head over to Nantucket Land Bank’s Holly Farm.
Sunset on Martha’s Vineyard with your dog by your side sitting at Menemsha Public Beach is a postcard perfect (or rather Instagram-worthy) experience.  Take the ferry over to Cape Poge Wildlife Refuge on Chappaquiddick Island for a day of exploring.  At Cape Poge Wildlife Refuge there are 14 miles of trails, a beach for swimming, a picnic table for your dining, and the historic Cape Poge Lighthouse. Fresh water for you and your pup are available by hand pump at Wasque and Mytoi parking areas.
stroll through town nantucket
If you need any toys or supplies there are plenty of great local shops on Martha’s Vineyard and Nantucket including Good Dog Goods on Martha’s Vineyard & Cold Noses on Nantucket.
*All photos courtesy of Leah Klein.