St. Martin and St. Maarten boast warm temperatures year-round. The summer and early fall months tend to be the warmest, with highs in the upper 80s. From the late fall through the early spring, temperatures dip down to the low 80s, making St. Martin and St. Maarten an ideal destination for warm weather lovers. January through April is the dry season and also the busiest season for tourism on the island. Though it's a pleasant time to visit, you might encounter large crowds and inflated prices. May and June typically bring much lower prices but also the beginning of hurricane season. July through October is the peak of hurricane season in the Caribbean, and also off-season in St. Martin and St. Maarten, which means some attractions may be closed.

Access the island by flying into Princess Juliana International Airport in St. Maarten. If you plan to focus on relaxing and casual exploration, consider taking the island buses or spend a little more to take a taxi. For more freedom to travel between St. Maarten-St. Martin villas and the island's many attractions, rent a car once you land.

In St. Martin, hit the beach at Orient Bay, a popular spot for parasailing, people watching, and partying. On the southern end of St. Maarten, Cupecoy Beach includes three swimming areas bordered by dramatic cliffs. Don't miss the sunset from the sand or one of the nearby beach bars. Also in St Maarten, Mullet Bay Beach offers great surfing and relative quiet compared to other stretches of sand. Take a stroll along St. Maarten's Front Street, where you'll find the area's best shopping. Try your luck at the Casino Royale or one of St. Maarten's other casinos, where you can play the slots, partake in table games, and soak up the glitzy atmosphere.

St. Martin and St. Maarten have no shortage of events to entertain locals and visitors. Carnival celebrations capture the island spirit for multiple weeks in the late winter and early spring. French St. Martin celebrates Carnival in February, while Dutch St. Maarten resumes the festivities in April. In March, the Heineken Regatta welcomes sailors from almost 40 countries to participate in races along the coast. Here you'll also find great food and live music all over the island. In May, Fish Day focuses on appreciation for the island's fishermen with a three-day festival that includes live entertainment and plenty of local food. In November,  St. Maarten-St. Martin Day commemorates the island's discovery by Christopher Columbus and highlights the unique culture of this island.