That Passport Life with Kevin McCullough

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THE PEARL OF THE OCEAN STATE

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Tucked along the southwestern curve of Rhode Island’s coast, where the Atlantic brushes gently against sand and storybook villages, lies Westerly—a destination that proves that not all gems need polish to shine. Known affectionately as The Pearl of the Ocean State, Westerly combines historic charm, barefoot luxury, and seaside sophistication in a way only New England can.

🏨 Where to Stay

Ocean House, Watch Hill

If you’re dreaming in soft linens, crashing waves, and butler service with a wink, then Ocean House is your address. Perched atop the bluffs of Watch Hill, this meticulously restored 1868 Victorian beachfront resort redefines “timeless.” Whether you’re sipping chilled rosé on the Verandah, indulging in a salt stone massage at the OH! Spa, or attending a sommelier-led tasting at the Center for Wine & Culinary Arts, everything here is artful, intentional, and elevated. Bonus: the views of Block Island Sound might just ruin every other coastal view for you.

πŸ₯ Brunch Goals

The Bistro at Ocean House

Brunch at The Bistro is the kind of scene That Passport Life readers expect: freshly baked croissants, poached eggs with local crab, and craft mimosas poured just-so. The sun streams in through linen-draped windows as the Atlantic winks in the distance. Pair the Belgian waffles with a latte and thank us later. Casual elegance, smooth service, and a menu that leans seasonal and seafood-centric—it’s brunch with a passport stamp of approval.

🍷 Dinner Vibe

COAST

When the sun dips and the evening breeze rolls in, it’s time to slip into something sultry and head to COAST, the resort’s fine dining jewel. With just a handful of tables and a curated tasting menu that changes nightly, COAST offers an intimate, candlelit experience that elevates every bite into a love letter to New England’s land and sea. Expect dishes like butter-poached lobster with foraged herbs, paired with sommelier-selected wines and whispered service. It’s not just sexy—it’s signature.

πŸ“ Seven Things Not to Miss

  1. Napatree Point – Hike the windswept barrier beach, spot migratory birds, and watch the sunset kiss the water.
  2. Flying Horse Carousel – A ride on America’s oldest suspended carousel is delightfully nostalgic—for all ages.
  3. St. Clair Annex – Step back into a simpler time with homemade ice cream and vintage sodas at this Watch Hill staple.
  4. Wilcox Park – A tree-lined haven for strolling, reading, or just being—right in downtown Westerly.
  5. Misquamicut State Beach – Surf, sunbathe, or catch a pop-up concert with the locals.
  6. Grey Sail Brewing – Sample crisp, coastal-crafted beers at one of the most respected microbreweries in the state.
  7. The United Theatre – A renovated downtown arts hub featuring indie films, live music, and rotating gallery shows.

Passport Life 3-Day Snapshot

Day 1

  1. Check in at Ocean House.
  2. Explore downtown Westerly’s shops.
  3. Watch the sunset with cocktails in hand.

Day 2

  1. Brunch at The Bistro.
  2. Stroll Napatree Point.
  3. Hit the carousel.
  4. Afternoon spa.
  5. Dinner at COAST.

Day 3

  1. Sip espresso at a local café.
  2. Hit Misquamicut for one last beach walk.
  3. Stop at Grey Sail for the road.

Final Boarding Call

Westerly doesn’t shout to get your attention—it whispers. It enchants with its lighthouse views, storied streets, and lobster rolls at sunset. Whether you come for romance, rest, or just to remind yourself what elegance feels like in flip-flops, The Pearl of the Ocean State will be waiting.

Location:

Westerly, Rhode Island
Westerly, RI
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