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8 Summer Weekend Escapes

As the long weekend approaches, discover our curated guide to summer extraordinary escapes—from secret coastal coves to mountain towns where time stands still.

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The Church of Panagia on Folegandros, Greece. Photo by Katerina Katopis-Lykiardopulo featured in Greek Islands by Assouline.

The arrival of summer sparks everyone's collective wanderlust, calling us to trade daily routines for sun-soaked adventures and new views. This season's simple pleasures calls for a new set of towns and cities around the world to visit. For those drawn to Mediterranean charm, the quieter Greek islands offer authentic experiences without the crowds. Nature enthusiasts might prefer Yellowstone's majestic spirit, where endless hiking trails and scenic bike routes are set against the spectacular backdrop of the mountains. Whether you're seeking peaceful seaside villages or thrilling wilderness encounters—our guide cuts through the tourist noise to deliver the perfect weekend  getaway.

The scenic backdrops of Big Sky, Montana. Courtesy of Lone Mountain Ranch.

Big Sky, Montana

Big Sky, Montana isn't just a destination for winter—it's also a summer haven that rivals snow season. The resort town offers adventures for every nature lover: scenic hiking and mountain biking trails through forests and meadows. The Gallatin River has premier fly fishing and exhilarating whitewater rafting. Visitors can easily spend a day exploring the nearby Yellowstone National Park's geothermal wonders, relax by the waters of Lake Levinsky, or discover Beehive Basin Trail. 

We suggest: Lone Mountain Ranch 

La Fortuna is the perfect basecamp for exploring one of Central America's most incredible landmarks: the Arenal Volcano. Courtesy of Nayara Springs.

La Fortuna, Costa Rica

Nestled in the northern lowlands of Costa Rica, La Fortuna is the perfect basecamp for exploring one of Central America's most incredible landmarks: the Arenal Volcano. With a perfectly conical volcano rising 5,437 feet above the surrounding rainforest, the park's  trails lead through fascinating lava fields from past eruptions and old-growth rainforest. Visitors can also soak in the area's natural hot springs, hike to La Fortuna Waterfall, and spend a day at Lake Arenal, the country's  largest lake, perfect for water-based activities just minutes from La Fortuna.

We suggest: Nayara Springs

Perched high above the Amalfi Coast, Ravello is a serene alternative to its more frenetic neighbors, Positano and Amalfi. Photo by GIUSEPPE GRECO/Getty Images.

Ravello, Italy

Perched high above the Amalfi Coast, Ravello is a serene alternative to its more frenetic neighbors, Positano and Amalfi. With sweeping views of the Tyrrhenian Sea and a legacy steeped in art, music, and history, Ravello offers a refined escape for travelers seeking beauty without the bustle. Lose yourself in the terraced gardens of Villa Cimbrone and Villa Rufolo, or time your visit with the Ravello Festival, a celebration of classical music held each summer. Quiet stone streets, family-run trattorias, and lemon groves cascading down cliffs make this cliffside town feel worlds away from the modern rush.

We suggest: Palazzo Avino

Folegandros remains peacefully undiscovered. Courtesy of Gundari.

Folegandros, Greece

Unlike popular Santorini and Milos, Folegandros remains peacefully undiscovered. With protected forests and no airport, the island preserves its natural beauty for visitors arriving by sea. The crown jewel of the island is undoubtedly Chora, with its stunning squares and alleys leading to the 13th-century Castle district, where cliff-edge houses dating back 500 years remain inhabited today. For breathtaking views, visit the Chapel of Chrysopigi at the island's western extremity or hike to the 1919 Lighthouse of Aspropountas. 

We suggest: Gundari

Salamanca in western Spain is the ideal destination for those who love culture, architecture, and have a passion for excellent cuisine. Photo Credit: Getty Images.

Salamanca, Spain

This UNESCO World Heritage Site in western Spain is the ideal destination for those who love culture, architecture, and have a passion for excellent cuisine. Whether you're wandering through centuries-old plazas or enjoying the lively café culture, Salamanca offers visitors an authentic Spanish experience away from the tourist paths of Barcelona and Madrid. The city's cuisine showcases the hearty flavors of Castilla y León, specializing in regional cured meats, including the famous jamón ibérico from nearby Guijuelo, paired with local cheeses like the semi-cured cheese from Hinojosa del Duero. 

We suggest: Eunice

Dorado, Puerto Rico offers discerning travelers a refined alternative to the capital's bustling energy. Courtesy of Dorado Beach, a Ritz Carlton Reserve.

Dorado, Puerto Rico

Sitting on the northern coast of Puerto Rico, Dorado is a prestigious coastal enclave offering discerning travelers a refined alternative to the capital's bustling energy. The town's compact historic district invites leisurely afternoon strolls, where colonial architecture houses charming boutiques, art galleries, and family-owned restaurants serving authentic Puerto Rican cuisine. Nature lovers should venture to nearby Ojo del Buey, where a unique rock formation resembling a bull's eye frames spectacular sunset views, or explore the ecological wonders of Hacienda La Esperanza Nature Reserve.

We suggest: Dorado Beach, a Ritz Carlton Reserve

Puebla captivates visitors with its rich colonial heritage and vibrant culture. Photo by Sergio Mendoza Hochmann/Getty Images.

Puebla, Mexico

Set between mountains and volcanoes just two hours from Mexico City, Puebla captivates visitors with its rich colonial heritage and vibrant culture. Visitors can pay a visit to  the historic center, where over 2,600 colonial buildings showcase stunning Talavera tilework and baroque architecture, most notably at the Cathedral and the gold-adorned Capilla del Rosario. For cultural immersion, explore the International Baroque Museum and Amparo Museum, before shopping for the city's famous hand-painted Talavera pottery and textiles from nearby Cholula.

We suggest: Cartesiano

One of the many white sand beaches in Amagansett. Courtesy of Roundtree Amagansett.

Amagansett, NY

With fewer than 1,000 residents, Amagansett offers a peaceful alternative to the typical Hamptons scene. Its charming Main Street features select shops and restaurants where visitors quickly feel like locals. Guests can explore Amber Waves farm and market, dine at Il Buco Al Mare, or catch live music at the iconic Stephen Talkhouse. History aficionados will appreciate Miss Amelia's Cottage, Roy Lester Carriage Museum, and East Hampton Marine Museum, which showcase Amagansett's rich past. 

We suggest: Roundtree Amagansett

The Destinations
The Classics Collection Hamptons Private
$105 USD
The Classics Collection Palm Beach
$105 USD
The Classics Collection Greek Islands
$105 USD
The Icons Collection Big Sky
$60 USD

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