As the long, sunny days of summer 2025 wind down, many travelers are already starting to plan their next escape. Just because the season of beach umbrellas and poolside cocktails is ending doesn’t mean your adventures have to! In fact, late summer and early fall are some of the best times to travel—think smaller crowds, lower prices, and milder weather in many destinations.

Whether you want to savor those last golden rays, chase colorful autumn leaves, or enjoy a cooler escape, here are my top recommendations for your post-summer getaway.

By the time September rolls around, the Mediterranean has just the right balance of warm weather and peace. Greece, Italy, and Spain are still sunny, but most of the peak-season crowds have gone home. Imagine wandering through Santorini’s blue-domed streets or enjoying fresh seafood along the Amalfi Coast without bumping into dozens of tour groups.

Travel Tip: This is also prime time for Mediterranean cruises—you’ll often find better deals, plus smoother seas and cooler temperatures for sightseeing.

If you’re not ready to give up your flip-flops just yet, the Caribbean is still calling. Early fall is shoulder season for many islands, meaning fewer travelers and better resort rates. Places like Aruba, Curaçao, and the Bahamas are perfect for relaxing beach days with turquoise waters as far as the eye can see.

Travel Tip: While September is part of hurricane season, many southern Caribbean islands lie outside the main storm belt—ask me about safe and sunny options.

From Vermont’s maple-covered mountains to Nova Scotia’s colorful coastal drives, late September through October is prime leaf-peeping season. This is also a fantastic time for cozy small-town stays, wine tours, and autumn festivals.

Travel Tip: For an unforgettable trip, consider a New England to Canada fall foliage cruise—you’ll get a blend of charming ports, scenic views, and crisp autumn air.

If you want luxury and seclusion, head straight for an overwater bungalow in the Maldives or Bora Bora. These destinations offer crystal-clear lagoons, white-sand beaches, and the ultimate “I’m on vacation” feeling.

Travel Tip: Fall is a great time for special offers at luxury resorts. I can help you find packages that include meals, activities, and transfers so you can relax from the moment you land.

Europe in September and October is pure magic—milder temperatures, shorter lines at major attractions, and local events like wine harvest festivals in France and Germany. Cities like Paris, Rome, and Barcelona feel more relaxed and authentic compared to peak season.

Travel Tip: Fall is also ideal for river cruises along the Danube or Rhine, where you can see multiple countries in one trip without the summer heat.

 Better Deals – Many destinations drop their prices after August.
Cruise Discounts – End-of-season offers make luxury sailings more affordable.
Perfect Weather – Warm but comfortable in many regions.
Unique Experiences – Seasonal festivals, harvest events, and local traditions you can’t see in summer.

Whether you’re craving one last taste of summer or ready to embrace fall’s cozy charm, I can help you plan a trip that’s perfectly timed and tailored to you. From finding hidden deals to creating personalized itineraries, all you have to do is pack your bags—I’ll handle the rest.

📧 Let’s start planning your end-of-summer 2025 adventure today!
Carmen Rosario | Rosario’s Travel Company