Hey there, fellow travelers! As the leaves start to change and the temperatures begin to drop, it’s natural to start dreaming of cozy sweaters, hot cocoa, and all things fall. But who says you have to endure the chilly weather? Why not escape to a warm and sunny destination this autumn? There are plenty of places to soak up the sun and explore this fall. Here are some of my faves!

Autumn in Algarve is a fantastic season for a visit, as the summer crowds start to dissipate while the weather stays warm and enjoyable. The temperatures usually range from the mid-70s to low 80s Fahrenheit (around 24-28°C), making it perfect for soaking up the stunning beaches and coastal views. The region’s picturesque coastline, adorned with striking cliffs, golden beaches, and secluded coves, is especially appealing. Well-known beaches such as Praia da Marinha and Praia da Rocha are renowned as some of the most exquisite in the world. Are you up for an adventure? Reserve a boat tour to the Benagil Caves to enjoy the crystal-clear water. Keep in mind: Access is limited for environmental conservation as of August 2024. Portugal is famous for its ceramic tiles. Be sure to stop at one of the numerous azulejos shops for a lovely keepsake. Lastly, Ponta da Piedade is a group of rock formations that tower up to 20 meters above the Atlantic Ocean. The rock formations provide stunning coastal views that are a must-see during sunset in the fall. Ponta da Piedade is only a 15-minute drive from Lagos and offers free parking.

October is a fantastic time to explore Sicily, with mild weather and temperatures ranging from the mid-60s to low 70s Fahrenheit. Fall foliage brings a touch of autumn colors to the Madonie and Nebrodi mountains. The summer crowds have returned home, creating a more relaxed atmosphere to discover all the island has to offer. Wine festivals are held to celebrate the harvest season with famous Sicilian wines. Visiting archaeological sites like the Valley of the Temples and Taormina’s ancient theater is also less crowded, allowing for a deeper appreciation of their historical significance. If you’re looking for breathtaking sea views, be sure to visit coastal towns like Cefalù and San Vito Lo Capo.

Negril, Jamaica is a breathtaking destination during the autumn months, offering warm temperatures, beautiful beaches, and a relaxed vibe. In the fall, temperatures typically range from the low to mid-80s Fahrenheit. Although fall is part of the Caribbean hurricane season, Negril generally experiences mostly short rain showers. Visitors can indulge in the soft sands of Seven Mile Beach with activities like stand-up paddle boarding, snorkeling, or simply relaxing in the crystal-clear waters. This season is less crowded compared to winter, providing a more peaceful experience for travelers. However, this also means that nightlife may be quieter starting in November. Don’t miss out on exploring local attractions like the breathtaking cliffs at Rick’s Cafe, where you can enjoy a cold Red Stripe beer, witness the sunset, and even try cliff diving. I highly recommend sampling some beef patties from Hammond’s Bakery, indulging in curried goat, and savoring local fruits like starapple or my favorite, breadfruit.

In October, San Juan, Puerto Rico is a lively and bustling destination with warm temperatures ranging from the mid-70s to mid-80s Fahrenheit. Due to this time being hurricane season, airfare prices are generally lower. Fewer visitors allow for a more laid-back experience at popular attractions like Old San Juan. Here, you can marvel at the vibrant colonial architecture, explore historical forts like El Morro, and wander around charming plazas. There are nightly festivities to immerse yourself in the local cuisine, music, and traditions. Some popular dishes include mofongo, tostones, pasteles, tembleque, and coquito. You can travel to this Caribbean island without a passport if you’re a US citizen. Additionally, many locals are fluent in English.

Temperatures are pleasantly warm from September to November, remaining in the 80s. The beaches are still a popular destination for sunbathing, swimming, and water activities without the large summer crowds. South Beach is full of activity with its lively nightlife, including bars, clubs, and restaurants offering a variety of cuisine and entertainment. Miami’s fall events showcase the city’s diverse population and offer a range of cultural experiences. The South Beach Seafood Festival in October features snow crab dishes created by local chefs. Celebrate Orgullo, a festival celebrating Hispanic & Indigenous LGBTQ+ culture, through art, music, and outdoor activities. The Caribbean Carnival, also in October, features a parade with over 30,000 masqueraders in colorful costumes and a variety of international artists from Trinidad & Tobago, Antigua, Haiti, St. Lucia, and South Africa. Enjoy traditional mojitos, empanadas, Cuban sandwiches, and live music at Old’s Havana Cuban Bar & Cocina in Little Havana. For a special occasion, consider treating yourself to a luxurious day cruise on a private yacht.