Where to Travel in September & October
As the summer crowds thin and the air turns crisp, September and October are some of the best months to travel. From wine harvests and fall foliage to shoulder-season perks like fewer crowds and better hotel availability, this is the golden window to explore. Here are some of my favorite destinations to consider:
Turkey – Cappadocia & Istanbul
September and October bring cooler, more comfortable weather to Turkey. Float over Cappadocia’s surreal landscape in a hot air balloon at sunrise, sip wine in local vineyards, and explore the rich history of Istanbul without the sweltering heat. With fewer crowds at landmarks like the Hagia Sophia or Topkapi Palace, it’s an ideal time to experience Turkey’s cultural heart.
Portugal – Douro Valley, Porto & Lisbon
Autumn is harvest season in Portugal, making it perfect for wine lovers. Head to the Douro Valley to join grape-stomping festivals, enjoy scenic river cruises, and savor port straight from the source. In Lisbon, the golden light of early fall pairs beautifully with wandering Alfama’s cobblestone streets and soaking in those miradouro (lookout) views.
Check out my recent itinerary, and where to stay.
Croatia – Dalmatian Coast & Dubrovnik
The Adriatic is still warm in early fall, but the cruise ships have sailed away, leaving Croatia calmer and more relaxed. Stroll Dubrovnik’s Old Town walls without the high-season crowds, sail between the islands of Hvar and Korčula, or head inland for truffle hunting in Istria. September and October balance sunshine, sea, and serenity. It also happens to be unanimous favorite destination in Travel+Leisure by myself and six other travel experts.
Why Croatia is better when a travel agent plans it for you? Check out the multi-destination trip by land & sea here.
New England – Vermont, Maine & Massachusetts
Leaf-peeping season is legendary here. Drive through Vermont’s scenic byways ablaze with red, orange, and gold; hike Acadia National Park in Maine with ocean views framed by foliage; or cozy up in a historic inn in Massachusetts. Fall festivals, apple cider donuts, and pumpkin patches make it the quintessential autumn getaway.
Great ideas for East Coast Road Trips straight ahead for more ideas.
Nova Scotia – Coastal Beauty & Seafood
Just across the border, Nova Scotia is equally stunning in fall. The Cabot Trail bursts into color, offering some of the most dramatic coastal drives in North America. Don’t miss fresh lobster shacks and the Celtic Colours International Festival in October, a celebration of music and culture.
Train Across Canada – A Scenic Epic
For a truly bucket-list experience, board The Canadian, the iconic train journey from Toronto to Vancouver. In September and October, the landscapes transform into a painter’s palette of autumn colors—rolling prairies, the Rockies dusted with early snow, and endless stretches of golden forest. It’s slow travel at its finest, with observation cars perfect for leaf-peeping.
More Ideas for Fall Travel
Scotland – Whisky trails, castle stays, and cozy evenings by the fire.
Italy (Piedmont & Tuscany) – White truffle season and vineyard tours.
Japan – Crisp autumn days, colorful temples, and seasonal koyo (fall leaves).
Spain (Andalusia) – Pleasant weather for tapas hopping and exploring Moorish palaces.
Why Travel in September & October?
Shoulder season savings: Better availability and often better rates.
Mild weather: Ideal for sightseeing, hiking, and outdoor dining.
Festivals & harvests: Wine, truffles, cultural events, and local traditions in full swing.
Whether you’re drawn to vibrant cities, quiet coastlines, or colorful countryside, these months are the sweet spot for experiencing destinations at their best.
