South of the Clouds

South Street Diner offers a classic, cozy 24/7 experience in Boston, serving hearty breakfasts and nostalgic diner fare right by South Station.

At this stylish cocktail hotspot, skip the menu and indulge in inventive, customized drinks crafted to your tastes—just make sure to arrive early!

Nestled in the bustling heart of Kenmore Square, Hotel Commonwealth offers upscale accommodations with a chic New England vibe, just steps from Fenway Park and vibrant dining options.

Located in Boston's vibrant Back Bay, The Colonnade Hotel boasts stylish rooms with stunning views, a chic French restaurant, and the city's only rooftop pool perfect for soaking up the sun and sipping cocktails.

A cozy, low-key spot in Allston, Ajeen serves up customizable Middle Eastern flatbreads and delicious shawarma in a charming, newly renovated space.

Nestled in the historic Beacon Hill, the Liberty Hotel, a chic transformation of a 19th-century jail, boasts high ceilings, upscale bars, and stunning views of the Charles River—all while keeping its quirky past alive with creative design touches and a lively social scene.

This chic, pet-friendly boutique hotel at the heart of Boston delights with stylish rooms, stunning city views, and a nightly wine reception, making it an ideal urban escape.

Nestled in the Seaport, Woods Hill Pier 4 offers stunning harbor views and a vibrant farm-to-table menu, highlighted by inventive lobster popovers and craft cocktails.

Carlo's Cucina Italiana is a charming Allston gem serving hearty, classic Italian dishes in a cozy setting, perfect for a satisfying meal with big portions.

At South Boston’s Fox & the Knife, you’ll savor rustic Italian dishes crafted by chef Karen Akunowicz, paired with innovative cocktails in a vibrant atmosphere.