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How to Plan the Perfect Southeastern New England Getaway

Featured image: Samantha Labrecque Semle

There’s a particular kind of nostalgia that settles over New England in the summertime—a golden, ocean-salted warmth that feels both timeless and fleeting. 

The saltbox houses, with their peeling white paint and hydrangeas in full bloom, the sound of Red Sox games wafting over the radio. The days stretch long on Cape Cod and in Rhode Island, where summer isn’t just a season, it’s a return—year after year—to something familiar and quietly enduring. But the summer season around these coastal towns folds into the next quickly and—if you’re lucky—with late-afternoon swims, sticky fingers from melted ice cream, and buttery lobster rolls on the back porch. 

Sun-soaked days, the smell of the salty ocean air, and clam shacks by the shore bring me back to me childhood days. Life was simple then. And when I return home again, it’s as if time pauses—the same gulls cry overhead and the same breeze rustles through the dune grass. New England remains a constant, but the fleeting summer days pass like the tide, steady and always too soon. 

We’re sharing a guide from the perspective of someone born and raised in the Ocean State, on how to make the most of your days where the summer is short and every moment counts, covering Block Island, Newport, and Cape Cod. 

Block Island 

Block Island is a charming escape just off the coast of Rhode Island, known for its rugged beauty and laid-back vibe. With its windswept bluffs and quaint downtown, the island offers a peaceful retreat where visitors can unwind, explore scenic trails, and soak in ocean views. 

How to get there: 

There are several convenient ways to reach the island, though most people arrive by ferry. The Block Island Ferry offers year-round service from Point Judith (Galilee) with both low-speed and high-speed options. For an extra fee, you can bring aboard your car, bicycle, and whatever else you might need. If you prefer to fly, there’s a small airstrip located on the island, too.  

The Barrington Inn | Image: Samantha Labrecque Semle

Where to Stay:

The Barrington Inn

The Barrington Inn is a charming, family-run retreat nestled atop a hill overlooking New Harbor and Great Salt Pond. Built in 1884, the Victorian farmhouse blends historic character with modern comforts and design, and is a charming bed and breakfast-style retreat for visitors. The inn offers six guest rooms and two longer stay apartments, which all have their own private bathroom and ocean views. Each room is also equipped with air conditioning, a tv, and in-room refrigerators. While the views from the inn are stellar, the made-to-order breakfast, afternoon wine and cheese, and complimentary beach gear really take your stay up a notch. 

Ballard’s | Image: Samantha Labrecque Semle

Where to Eat/Drink: 

The Oar

The Oar is a popular waterfront restaurant and bar located at the Block Island Boat Basin in New Harbor. Known for its laid-back atmosphere and iconic collection of signed oars decorating the walls, it’s a favorite spot for both locals and tourists alike. The menu features fresh seafood, classic American fare, and sushi rolls, all of which are best enjoyed during sunset hour. 

The Surf

The Surf at Block Island Beach House is a stylish beachfront spot perched above Crescent Beach in New Shoreham. It’s got everything you could need for the perfect al fresco spot: sweeping ocean views, yummy cocktails, and a menu of fresh seafood, beach BBQ classics, poke bowls, and more. 

Ballard’s

Just off the ferry docks is arguably Block Island’s most well-known beach bar. Listen to live tunes, rent a cabana on the beach, or dine at one of several spots around Ballard’s—from your toes in the sand to hiding indoors from the sun—dining here is a full beachside experience. Their menu consists of seafood, classic American fare, and lobster served several different ways, but no matter which you choose, pair your meal with a frozen cocktail from their daiquiri bar for complete island vibes.   

Spring House Hotel 

Perched atop a sweeping lawn, take a seat at the restaurant’s wrap-around veranda for stunning views of the Atlantic. Whether you’re slurping back briny bivalves, digging into a lobster roll, or savoring clam chowder, dining here at one of Block Island’s most iconic settings is truly a quintessential Island experience.

Dead Eye Dicks

Nestled in New Harbor, Dead Eye Dick’s is a longtime Block Island institution. First opened in the 1940s, the restaurant slings out fresh seafood including their signature swordfish and lobster dishes. Diners can also enjoy homemade soups, an extensive raw bar, and creative cocktails, in the casual dining room or outside on the deck overlooking New Harbor.

Block Island Beaches | Image: Samantha Labrecque Semle

Things to Do: 

Captain Nick’s Rock-n-Roll Bar 

A weathered watering hole and the heart of Block Island’s nightlife scene, Captain Nick’s is the ultimate dive‑bar but in the best way: there’s beer, cocktails, and live music. Whether you’re turning up for classic rock, country night, or just people watching, the bar delivers an energetic and unpretentious pulse of Block Island’s summer spirit. 

Yellow Kittens Tavern

Established in 1876, this popular bar is Block Island’s oldest tavern and is a well-loved destination for both locals and visitors. The tavern comes alive with live entertainment and vibrant nightlife all summer long, and if you’re hungry, their deck restaurant—Los Gatitos—serves up tacos and nachos. 

Shop or Walk around Town

Directly off the ferry docks, island-goers are dropped off on Water Street and Dodge Street where shopping and dining are plenty. From antiques and galleries to Block Island-themed souvenir shops, there’s several different stores where you can purchase keepsakes (a Block Island sweatshirt is always my go-to!) to remind you of your time on the island. 

Mohegan Bluffs 

Arguably Block Island’s most photographed spot is Mohegan Bluffs. An iconic natural landmark that rises about 150 feet above the Atlantic Ocean, the dramatic clay cliffs can be accessed at the top overlook, located near the Southeast Lighthouse. From there, a staircase with more than 140 steps descends to the beach below. I have never personally been to the beach at the bottom of the stairs, but if you choose to go down, you’ll be rewarded with spectacular views on your way back up (just don’t forget to look over your shoulder!).

Bike or Moped

From personal experience, I don’t recommend biking around the island (there’s a lot of killer hills), but biking around town or to the beach is a pleasant experience. Most people on the island rent mopeds, which is a fun way to explore. There’s several moped and bike rental companies right in town, so scooping up your ride is an easy experience.  

Rodman’s Hollow Nature Preserve

This pristine 230-acre conservation area is a glacial outwash basin featuring winding trails that take you through meadowlands, shrub thickets, and along bluffs overlooking the Atlantic. The most popular route is the Rodman’s Hollow Trail, a roughly 0.9‑mile loop that offers coast-to-coast vistas. Whether you’re hiking, birdwatching, or grounding yourself in nature, the preserve is a peaceful sanctuary on the island. 

The Beach

Of course you can’t go to an island without spending some time on the beach! While the island is home to some of the most beautiful and unspoiled coastlines in New England, each beach varies and depending on the vibe you are looking for. For me, it’s Mansion Beach due to it’s quiet and natural scenery, but if you’re short on time, Crescent Beach is walkable from town and is a good option for families. 

Newport, Rhode Island

Rhode Island might be the smallest state, but it’s packed with coastline for miles, fresh seafood, and spectacular ocean views. While the Ocean State is home to many coastal towns, Newport is one of my favorite well-known and loved seaside cities. Peppered with Gilded Age mansions, historic cobblestone streets, and sailboats in the harbor, there’s really no better way to spend a day (or a few!) here than by diving right in. 

Where to Stay: 

There’s a wide range of hotel options in Newport that are perfect for a weekend getaway or seaside escape. From grand, Gilded Age mansions turned boutique hotels to waterfront resorts with sweeping views of Narragansett Bay, there’s something to suit every traveler’s budget. Iconic spots like Hotel Viking, Castle Hill Inn, and The Chanler at Cliff Walk are always at the top of my list, but newer locations like Hammetts Hotel and Newport Harbor Island Resort are great options, too. Whether you’re staying downtown near the yacht-filled harbor or tucked away on Ocean Drive, these hotels are a great home base for exploring the coastal city’s mansions, beaches, and seafood scene.

Clarke Cooke House | Image: Samantha Labrecque Semle

Where to Eat/Drink: 

There’s no shortage when it comes to delicious dining in the sailing capitol of the world. Here’s some of my go-to’s. 

Castle Hill Inn 

For the most dramatic views of Narragansett Bay, a visit to Castle Hill Inn is a must. Adirondack chairs scattered across the lawn invite leisurely afternoons, while the outdoor patio creates a picture-perfect setting for sunset dinners. Adirondack seats are first come, first served.   

The Mooring Seafood Kitchen & Bar 

This moodyNewport jaunt offers upscale waterfront dining with stunning views of the harbor. Known for its locally-sourced seafood and coastal classics like lobster rolls and clam chowder, guests can dine indoors in nautically inspired rooms or outside on the harbor-facing patio.

Bar ‘Cino

A neighborhood‑style Italian restaurant nestled the historic Washington Square, Bar ‘Cino’s menu features house-made pasta, antipasti, and seasonal mains. The restaurant gets quite busy, so making a reservation is high recommended.

The Black Pearl 

A Newport institution on Bannister’s Wharf, The Black Pearl is famous for its clam chowder and classic New England seafood. With harbor views, a cozy tavern, and elegant Commodore’s Room, the mainstay offers a range of dining experiences in a prime waterfront setting.

The Landing Restaurant

Perched right on Bowen’s Wharf, this lively restaurant is full of fresh seafood, raw bar selections, and live music. It turns into a bar scene at night throughout the summer. 

Clarke Cooke House 

Also located on Bannister’s Wharf, Clarke Cooke House is a historic 18th-century building that is well traversed by both locals and tourists. With multiple dining spaces—my favorite is the lower bar because you feel like you’re inside a ship—enjoying bites or drinks at the restaurant is a quintessential Newport experience. 

Midtown Oyster Bar 

A hop, skip, and a jump from the main wharf, Midtown Oyster Bar, is another well-known restaurant that specializes in oysters and other raw bar selections. The restaurant features multiple dining areas, including a lively tavern on the first floor, a cozy upstairs Burgee Bar, and two outdoor decks.

Other notable spots:

A large sailing ship with white sails glides through calm waters, with numerous passengers on board and an American flag flying from the stern.
Newport Classic Cruises Sailboat Ride | Image: Samantha Labrecque Semle

Things to Do:

Sailboat Ride

There is really no better way to explore Newport Harbor than on a sailboat ride. Cruise past mega yachts and other vessels while the crew does the hard work for you. Sit back, relax, and learn about the surrounding area while sipping a glass of vino. My favorite company to sail with is Newport Classic Cruises—they have several different sails to choose from, most notably the sunset sail. 

Shopping

There’s a plethora of charming shops, from boutiques and art galleries to specialty stores, nestled throughout Newport’s historic downtown and waterfront areas. Whether you’re looking for a Newport-themed tchotchke, a preppy sweater, or nautical map, Newport’s shopping scene truly has it all.  

Cape Cod 

Cape Cod, Massachusetts is a classic New England destination known for its charming seaside towns and sandy beaches. Stretching into the Atlantic like a crooked arm, the Cape offers everything from upscale boutiques and art galleries, to seaside shacks, scenic bike trails, whale watching, and wide-open beaches. Whether you’re exploring dunes in the National Seashore or slurping up clam chowder in a cozy harbor town, Cape Cod is the ultimate place to be for coastal summer living. 

Where to Stay: 

There’s plenty of high-end resorts dotted along the Cape, including Chatham Bars Inn, Wequassett Resort and Golf Club, Ocean Edge Resort, and Wychmere Beach Club. But, a stay on the Cape is really about renting a cottage in a quiet neighborhood, often with weathered shingles, screened-in porches, and cozy, lived-in interiors. Cottages are the best way to bottle up Cape Cod’s nostalgic summer charm.

A close-up of a lobster roll held in a hand, featuring fresh lobster meat on a toasted bun, with a scenic waterfront background.
Lobster Trap | Image: Samantha Labrecque Semle

Where to Eat/Drink:

Sundae School Ice Cream 

When it comes to ice cream on Cape Cod, everyone has their favorite. For me? It’s undoubtedly Sundae School. Pick your favorite flavor—mine is Oreo—and ask for the works: fluffy homemade whipped cream, rich chocolate sauce, and a fresh cherry on top! Sundae School has been making homemade ice cream since 1976, and while the line can get long… trust me, it’s worth the wait! 

Sesuit Harbor Cafe

The salted shingled café in Dennis is a popular waterfront spot known for its fresh seafood, especially its hefty lobster rolls. With outdoor picnic seating and a casual BYOB policy, Sesuit Harbor offers a classic Cape Cod dining experience by the water. Just note, the café is cash only! 

Seafood Sam’s 

Seafood Sam’s is a beloved Cape institution, serving fresh, local seafood since 1974. With locations in Sandwich and Falmouth, the fast casual spot offers a diverse menu featuring fried seafood and more. For the land lubbers, the fried chicken platter is—in my humble opinion—one of the most underrated items on the menu. 

Sand Bar

There’s not many places where you can dine closer to the water than at the Sand Bar. A West Dennis watering hole and seashell padded patio, the Sand Bar is one of my go-to spots after the beach for fresh seafood, live music, and frozen mudslides.   

Lobster Trap 

One of my most visited restaurants on the Cape, Lobster Trap is a seafood restaurant and fish market situated along the Back River. With it’s rustic elements and design, the inside feels like you’re dining at a Lowcountry joint right on the water, while the outside patio provides uninterrupted views of the saltwater marshes. And while Lobster Trap is known for their hearty seafood fare, the restaurant also incorporates Asian-inspired flavors into its menu. One of my go-to orders is actually the panko chicken, which is covered in a ginger garlic sauce that’s irresistible to lap up. 

Landfall Restaurant 

A Woods Hole staple since 1946, Landfall Restaurant serves classic New England dishes like lobster and swordfish with views of Great Harbor and the Martha’s Vineyard ferry. If it feels like you’re dining in the hull of a ship, that’s because you sort of are—the restaurant was built from reclaimed ship wood.

Lighthouse Keeper’s Pantry 

The Cape’s most charming coffee shop can be found in Yarmouthport on Route 6A. The Lighthouse Keeper’s Pantry, a café and gourmet retail shop inspired by the recipes of a lighthouse keeper on Sandy Neck Beach, is a sweet little spot slinging out pastries, lattes, ice cream sandwiches, and more. If you only order one thing, let it be the viral Fluffy Seagull coffee paired with a homemade pop tart. 

Other notable spots:

A vibrant street scene in Chatham, Cape Cod, showcasing charming shops with colorful awnings and patrons enjoying the summer day.
Chatham | Image: Samantha Labrecque Semle

Things to Do:

Beach 

I wouldn’t be much of a New Englander if I told you my favorite Cape Cod beach to park it (if you know you know), but really, you can’t go wrong with whatever stretch of sand you choose. While the Outer Cape beaches are great for surfing, be aware that this is where most sharks are spotted (and it is where the seals primarily hang out!), plus the current can be strong. There’s plenty of beaches on the South side of the Cape facing Nantucket Sound, but my favorite beaches are on the Bay side. Many tourists flock to Mayflower Beach, Coast Guard Beach, and Race Point Beach, just to name a few.  

Shining Sea Bikeway 

The Shining Sea Bikeway is a scenic 10.7-mile paved trail stretching from North Falmouth to Woods Hole. As the only bike path on the Cape that runs alongside the sea, it offers picturesque views of Vineyard Sound, salt marshes, and cranberry bogs. The trail is suitable for cyclists, walkers, and joggers.

Explore the Villages 

Each town on the Cape offers a unique vibe and downtown village scene. A few must-visit spots include: 

  • Sandwich Village is historic and primarily home to year rounders
  • Chatham has a bustling main street full of shops and restaurants
  • Wood’s Hole is primarily where island-goers hop aboard the ferry, but there’s waterfront dining, too 
  • Provincetown is the Cape’s LGBTQ Mecca and is a hopping spot for nightlife, dining, and art galleries

The Beachcomber 

The Beachcomber in Wellfleet is a lively oceanfront restaurant and bar perched atop Cahoon Hollow Beach, known for its stunning views and fresh local seafood. A Cape favorite since 1978, it offers a raw bar, signature cocktails like the Goombay Smash, and live music throughout the summer season. 

Play Mini Golf 

There are several mini golf spots that are dotted along Route 28, but Pirate’s Cove Adventure Golf is a fan favorite. Putt your way through mountain caves, across a full-scale pirate ship, over footbridges, and under cascading waterfalls. 

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