There's plenty to explore and savor in this vibrant paradise on the Caribbean Sea, including numerous beaches, an assortment of water sports, and plenty of delicious eats and cocktails.

San Gimignano, a stunning medieval hilltop town in Tuscany, Italy, is often called the "Medieval Manhattan" due to its remarkable skyline of ancient towers. Encircled by 13th-century walls, the town is a UNESCO World Heritage site that offers a mesmerizing journey back in time. As you stroll along the cobbled streets of the historic center, you'll be enchanted by the preserved Romanesque and Gothic architecture, from charming piazzas to grand churches.

Toiny is a quiet, scenic village located on the eastern coast of Saint Barthélemy (St. Barts), known for its unspoiled natural surroundings and authentic Caribbean charm. Unlike the more developed west coast beaches, Toiny offers a serene retreat where rolling hills meet the Atlantic Ocean, and dramatic cliffs frame the coastline.

Nuevo Vallarta, located along the Bahía de Banderas in the state of Nayarit, is a coastal destination known for its wide, sandy beaches and marina-lined canals. Originally developed as a tourism project in the late 20th century, it has grown into a well-organized resort area with luxury hotels, golf courses, and waterfront condos. Unlike older beach towns with colonial roots, Nuevo Vallarta was designed from the start to offer modern comfort while being surrounded by natural landscapes.

Santa Monica, California, a gem on the Pacific coast, offers a quintessential Southern California experience. The city is renowned for its iconic Santa Monica Pier, which features an amusement park, aquarium, and family-friendly dining. A ride on the historic Ferris wheel provides stunning ocean views and a sense of nostalgia.