After a few days in Edgartown, driving “up island” towards Chilmark, I finally understood all the fuss about Martha’s Vineyard. The southwestern half of the island is less populated, more rural with rolling hills, stonewalls, farms and general stores.  Turn a corner and you’d swear you’re in the English countryside. And the beaches - the reason that brought me to the Vineyard in the first place - are wilder with dramatic cliffs, rock outcroppings and fewer crowds: absolutely beautiful. Edgartown was a lovely first date, but the villages of West Tisbury, Chilmark and Aquinnah…well they were keepers.

Tripper Tips:

It’s B.Y.O.B. in Chilmark as it’s a dry town… stock up on wine for your stay at MV Wine and Spirits by the airport. The staff is super friendly, knowledgeable and they have a large selection.

When renting a house…visit Beetlebung Farm for fresh produce, eggs and meats. It’s charmingly unmanned, pick what you want, write it down on the yellow pad and leave your money in the tin box.

Everyone claps when the sun goes down in Menemsha. An alternative to dinner is to head down to the beach, bring a bottle of Rose, get some lobsters and watch the sunset on the beach. (Or head to a late dinner after) Don’t think of driving as parking is impossible, instead take the path from the Beach Plum.

Way to go…book a ticket on the frequent ferries from Hyannis, (car reservations must be made well in advance) or avoid the summer traffic to the Cape and head to Quonset Point in Rhode Island to board the boat to Oaks Bluffs, an hour and a half fast ferry.

Stay: The Beach Plum Inn is sweet with just 5 rooms in the main house and 5 cottages scattered over its seven acres. It’s all lush gardens and ocean views of Menemsha Harbor with comfortable, beachy décor and a well-regarded farm to table restaurant that draws crowds for sunset dinners. The biggest bonus: the inn provides parking and walk on passes to both Lucy Vincent and Squibnocket beaches, two of the island's best beaches, private for residents of Chilmark. (Next door, Beach Plum’s sister property, the Menemsha Inn, is larger, more rustic and works well for families with larger cottages.)

On the Way: Driving from the ferry, the airport, or Edgartown, stop for breakfast in West Tisbury at 7a Foods.  Order one of their tasty egg sandwiches on a homemade biscuit to eat on the porch with the morning bikers. Get a hippie cookie to enjoy later in the day and their iced coffee, made with a blend of Cocoa Hazelnut from Java Tree. Starting at 11:15 am, 7a starts selling their gourmet sandwiches and salads, perfect for a picnic hamper at the beach. (Vegetarians will be happy ordering the Shitake Umami Tsunami.)

Don’t Miss: Right next door to 7a, Alleys’ General Store has been serving the Vineyard since 1858; browse the aisles for a hit of nostalgia. 

Farmers Market: On Wednesdays and Saturdays don’t miss the Farmers Market, held from 9-12, showcasing the goods from more than 40 farmers and purveyors from across the island.

Lunch: After checking into Beach Plum, it’s just a scenic, short walk down a woody path to the beach at Menemsha, a public beach known as the premier spot for sunset on the island. Wander around the working fishing harbor, the colorful fishing boats and shacks present endless photo ops. There is nothing more quintessential New England than eating a lobster on the docks at Larsen’s Fish Market or a basket of fried clams or shrimps at The Bite. Don’t forget to get extra napkins!

Beach:  Load up on beach chairs and umbrellas at the inn and spend the rest of the afternoon at Lucy Vincent Beach--it doesn’t get much better. Take a walk down the beach and don’t be surprised when you get to the stretch of beach that’s clothing optional. Walk back along the clay bluffs admiring the rock formations below. 

Dinner: State Road is one of those restaurants that you want to order everything on the menu—and you can’t go wrong—it is a delicious meal, from start to finish, right down to the excellent wines served by the glass. 

Day Two: 

Provisions: Have breakfast at Beach Plum or head to the Chilmark General Store and eat on the porch. Get some sandwiches and snacks to take to the beach. Buy a few of the 1 lb. bags of Chilmark Coffee Company, made on the island, to bring home.

To the Lighthouse: It’s a beautiful drive to Aquinnah, formerly called Gay Head, to visit the historic lighthouse and the Gay Head Cliffs on the westernmost point of the island. The light was dark for the last few months, as the lighthouse was carefully moved back 120 feet due to eroding cliffs. Climb the small hill past the shops of the Wampanoag Indians for incredible views of the cliffs and ocean below.

Back to the Beach: Another day, another unique beach—that’s what makes Martha’s Vineyard special. Go early to get a spot at the small parking lot of Moshup Beach. It’s a nice 10-minute walk down to the beach. This was my favorite beach; the multi colored cliffs a stunning backdrop, changing colors with the light. It’s also beautiful in the late afternoon. If you want to visit another beach venture to Squibnocket where the surfers hang out.

Dinner: It’s Chef Chris Fischers’ second season at the helm of the restaurant at the Beach Plum, with much of the produce coming from his nearby family’s Beetlebung Farm. At dusk the lawn starts filling with couples sipping wine, children playing ball or chasing the roaming chickens and wild turkeys; all getting ready to watch the day fade away and dine on the seasonal farm to table menu.  Or head to Chilmark Tavern, Jenna’s Sprafkin’s casual American bistro, featuring a seasonal, creative menu using mostly local products. Highly recommended!

Don’t Miss: Before returning home, have breakfast at the Art Cliff Diner. Go early to avoid a long wait, it’s popular for a reason—you’ll understand after your meal of spicy chicken hash and eggs, breakfast tacos or delicious fresh made scones or waffles.

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Mount Desert Island, Maine (MDI) is a small gem of an island combining lakes, mountains, ocean, and the East Coast’s oldest national park, Acadia, into a single destination.  Our good friend, Jon, travels to MDI every summer and knows all the best spots. Jon recommends you allot several days to fully explore the island, but offers these suggestions for what a perfect day might look like.

Tripper Tips:

Book well in advance… Acadia attracts tons of visitors in the summer months. Many families choose to stay at the Bar Harbor Inn or at the Harborside Hotel, Spa and Marina. For a quieter stay,  try the Ullikana, a B&B overlooking Frenchman Bay or The Asticou Inn, located in Northeast Harbor.

When to Go…The peak summer season runs late June through Labor Day. Fall brings spectacular foliage and winter’s the time for excellent cross-country skiing.

Early Morning: You’ll thank yourself later for getting up at dawn to catch the sunrise on Cadillac Mountain, the highest peak on the East Coast at 1,532 feet. Enter the park near Bar Harbor, drive up the winding road, and join the blanket-wrapped masses to see the sunrise before anyone else in the United States. It’s a sight you’ll long remember. Make sure to check the exact time before you go, and give yourself an extra 20 minutes for the drive up the mountain.

Morning Meal: Once the sun is up, head into Bar Harbor for breakfast. Jordan’s Restaurant opens at 5am, and will welcome you (and local lobsterman) with friendly service and quality diner fare. If you can wait until 7am to eat, other more upscale options are Café This Way and Two Cats. Blueberry pancakes are a tradition for breakfast in MDI, but lobster eggs Benedict is quickly becoming another favorite. Eat well — you’re going to need the fuel. 

Hit the Trails: One of Acadia National Park’s most beloved features is the 40+ miles of carriage roads. John D. Rockefeller spent thirty years supervising and financing the creation of a network of broken-stone roads free of motorized vehicles that make the park one of the most beautiful and bike-friendly destinations in the US. You can rent bikes at the Bar Harbor Bicycle Shop, then either drive or hop on the free Island Shuttle busses to Eagle Lake parking lot. You could bike around Eagle Lake (a 6 mile loop), or if you’re feeling adventurous, continue further to Jordan Pond House, which is famous for popovers and jam.

Scenic Road: Another option is to get back in your car after biking, re-enter the park near Bar Harbor, and drive the Park Loop Road — 27 miles of postcard-worthy Maine scenery. A park pass is needed, but the funds are an important part of maintaining Acadia’s beauty. You’ll want to pull over often to take pictures and explore some of the footpaths along the coast. Keep an eye out for Sand Beach (a rarity along a rocky Maine coastline), and Thunder Hole, where waves collide loudly with land. 

Lunch: Next, head to the western half of the island, known as the “quiet side.” If you’re hungry, pull over at Mother’s Kitchen in Town Hill. It’s a small stand-alone building next to a hardware store, and serves popular gourmet sandwiches made with local, organic ingredients. Another option is to drive into Southwest Harbor and stop at either Eat-a-Pita (which has much more than pita, and offers outdoor seating) or Little Notch Café, which features artisanal breads, pastries, and pizza, all made expertly in their own bakery. (There is also a Little Notch Bakery outpost in Bar Harbor.)

Get moving: Next, it’s time to work off lunch with a hike and a swim. There are many great hikes in Acadia, from easy strolls along the shore to iron-rung trails like the Precipice and Beehive trails. (Not for the faint of heart)  A good guidebook with maps and descriptions is essential. On your way out of Southwest Harbor, you could explore a good moderate trail by parking at the Echo Lake parking lot and hiking up the Acadia Mountain or St. Sauveur trails. These are loops that have the advantage of ending at Echo Lake so you can swim afterwards.

Stay Moving: Another option on the quiet side is to drive to the end of Beech Hill Road and hike the Beech Mountain Trail up to the fire tower, which is a good workout and offers summit views of the surrounding islands, or the Canada Cliffs trail, which has spectacular views of the Cranberry Islands and Echo Lake. Stay on the lookout for blueberries as you hike — in late July and early August, they are all along the trails.

Farm Market: Once you’re back in the car, you’ll pass Beech Hill Farm, a sustainable 73-acre farm run by the College of the Atlantic and offering great local vegetables, flowers, dairy, other organic goodies. You could then take a quick swim at nearby Long Pond (which also rents kayaks and canoes), or the smaller Somes Pond favored by locals.

Dinner: After a well-deserved nap, it’s time for dinner, and nothing says mid-coastal Maine like fresh lobster. There are many options for great lobster on the island. Two favorites are Beal’s in Southwest Harbor, which has a fun, family-friendly vibe overlooking the harbor, and Thurston’s in Bass Harbor, which added a full bar two years ago. Thurston’s serves IslandBound Treats’ excellent berry pies for dessert. You can’t go wrong with either, but be patient because the lines can be long and cooking lobster takes time.

After-Dinner Fun: Assuming you left room for ice cream (come on, you’re on vacation), swing by Mount Desert Island Ice Cream back in Bar Harbor. Their Maine Sea Salt Caramel ice cream is amazing, but they make many unusual gourmet flavors and gladly let you try samples. Then while exploring the town’s many shops, you could check out the newly restored Criterion Theater, built in 1932, which features movies, music, and more in a 1932 Art Deco setting, or play Bocce at the Lompoc Café and grab a local craft beer while you share highlights of your day on MDI.

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Montauk: Local Take

*Photographs by Car Pelleteri

*Photographs by Car Pelleteri

Located on the eastern end of Long Island, at the tip of the South Fork, Montauk is home to beautiful beaches, world-class sport fishing and excellent surfing. No longer sleepy, Montauk has changed a lot in the last few years with the opening of new hotels, restaurants and late night hot spots. Yet, it still remains more authentic than the rest of the Hamptons. Our friends, Jamie and Steven, have been spending summer weekends together in Montauk for years, and here Jamie shares her favorite spots with DT365 for a perfect summer day.

Tripper Tips:

More tips from Jamie…

There's a SoulCycle in the old movie theatre if you're feeling sporty. Want to go paddle boarding?  Head to Fort Pond by The Puff and Putt miniature golf. You can rent paddle boards, kayaks and sail boats there.  Another good place to rent longboards, paddle-boards and bicycles is at Air and Speed Surf Shop. They also offer surfing lessons.

Have a house and want to stay in? Stock up at the butcher section at Herb’s, a Montauk classic that’s been around forever—or forget cooking and get their fried chicken and a bunch of homemade sides to go with it!

Night Drive: Night Drive: If you get out late, Jamie recommends heading to The Inlet on East Lake drive, just past the airport.  “They have fresh sushi, an amazing artichoke appetizer and some of the best-grilled fish tacos outside of LA.  If you can make it for sunset, it’s one of the few west-facing restaurants. The view is spectacular overlooking the inlet between Gosman's and Gin beach.” 

Morning: Start your day in the sand at Ditch Plains Beach. Grab a coffee from the Ditch Witch and watch the morning surfers. After, try a class at Love, my favorite yoga studio or just head to Naturally Good for their scrambled tofu wrap. Make sure to get extra fresh salsa.  (They also have great juices and smoothies.) Sit in the back garden at the picnic tables and chill. Next-door to Love Yoga is a new micro brew coffee shop called Left Hand if you need another morning fix. 

Other Spots: We also like Goldberg's for amazing bagels and lox, and Joni’s for healthy breakfast wraps and smoothies. (Cash only.) Happy Bowl's on 27 has delicious Acai bowls, or pick up some cold pressed, organic juice at Montauk Juice Factory.  Be prepared to wait on line everywhere you go.

Town: Not much to do in town except walk around and look at the local T-shirt stores. My favorite is called Local Knit.  Nate is the sales guy there and he's sweet and chill. (If you want to really shop, brave the traffic on 27 and head to Amagansett, East Hampton, or Sag Harbor.) There's a great small spa called Deborah Thompson Day Spa in the middle of town.  Don’t miss the grape stem facial with either Deborah or Amy; it may be the best I've ever had.

Sun and Sand: The beach at Kirk Beach by the IGA supermarket is really nice.  You can park almost anywhere and there's no hassle. Or head back to Ditch Plains, my favorite beach. Ditch reminds me so much of my life in Manhattan Beach, all the people have known each other forever and chat like family.

Seafood Lunch:  Both the Topside or Inlet Cafe at Gosman's Dock are phenomenal.  The raw bar is maybe the best around. Look for Little Linda who is sometimes the bartender and sometimes the waitress.  Grab a bloody Mary and hang out for a while and watch the boats come in and out.  Even if you're not cooking dinner at home, treat yourself to a walk through Gosman's market--all the pies are fresh baked, the produce is locally grown and the fish is right off the boat! And the lobster salad is the best ever! Buy a pound and some hot dog buns and you’ve got DIY lobster rolls.

Hopping Lunch: Then there's Navy Beach, if you’re looking for more of a scene.  Martine is the Maître d’, he's a cute roly- poly guy with a tiny little curly ponytail.  Sit in the back on the beanbags and listen to the live music.  

Sunset Aperitifs: For drinks before dinner head to the Crow's Nest.  It's right off 27 on the way to the lighthouse.  There's a boat in front and it's right on Old West Lake Drive. Go down past the restaurant to the small beach, sprawl on a lounge and have some rosé. It’s one of my favorite summer places! Other sunset spots are: The Inlet, The Montauket, Navy Beach, and Duryea's Lobster Deck. 

Dinner: New this season, we’re digging the small plates and delicious cocktails at Flagship, from father-and-son team Eric and Adam Miller. One of my favorite restaurants is South Edison right in town. They have some of the best food in Montauk, everything from seafood to steak. It’s low key and delicious. For those who just love eating with an ocean view check out Scarpetta or Tillie’s at Gurneys. On our list to try is Arbor and Grey Lady.

Late Night: If you're up for some nightlife, there are plenty of choices.  The Surf Lodge attracts a great looking, young crowd and has live music concerts every weekend. Ruschmeyer's is another extremely popular spot; have a drink on the lawn under the lights and you’ll be transported back to summer days at camp.  

Sweets: For a late night treat stop by Buddha Berry for frozen yogurt.  The flavors are crazy and they offer more toppings than you could ever imagine.  They also have a small sitting area out back, kick back and look up at the stars.

Stay: The big news has been the remodeling of Gurneys.  It’s the most resort like hotel in the Hamptons, on a beautiful stretch of beach. Make sure to book one of the renovated rooms, as not all have been redone.  The Montauk Yacht Club was also recently renovated, with many different room options. I’d suggest one of the bungalows, with decks overlooking the marina.  The Montauk House is a boutique hotel right in town, a block from the ocean. Halfway between Amagansett and Montauk, White Sands, right off route 27 is simple, laid back, clean and quiet. And it’s right on the ocean—location, location, location.

Plus More:  Our friend Amanda Russo Rubman just got back from a few days of Montauk R and R and shared these highlights from her stay. “We hiked at Camp Hero. There are multiple hiking trails, with picnic benches along the way, why not pack a picnic lunch? If you’re looking for a real journey, you can continue hiking to the Montauk Lighthouse.  Fashionistas will enjoy the Leiber Museum, located on Judith Leiber’s property. (Check ahead as it’s only open a few days a week for a couple of hours.) You enter into a whimsical garden filled with bold sculptures, think Storm King on a much smaller scale. Inside the structure are thousands of Judith Leiber handbags and accessories, curated from her collection and private collectors. Post beach or for pre-dinner cocktails check out Lynn's Hula Hut.  You may even find Lynn behind the bar. 

* Special thanks to Car Pelleteri for her beautiful photographs. 

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