WHERE TO GO IN SEPTEMBER | THE BEST PLACES TO TRAVEL THIS MONTH
September might be the best travel month of the year. Kids are back in school, prices drop after Labor Day and the weather in a lot of places is still beautiful.
Here are my top picks for September, plus a splurge and a save hotel for each one so you can choose what fits your budget.
1. Napa & Sonoma
Harvest season! The vineyards are buzzing, the weather is warm and dry and it's the most exciting time to visit wine country. Book tastings and dinners ahead, and plan at least one lazy afternoon among the vines. Sonoma is a little more laid-back if you want to avoid the crowds.
Splurge: Auberge du Soleil — Hillside views over the valley during harvest, with Michelin-starred dining and a gorgeous spa.
Save: Carneros Resort and Spa — Cottages surrounded by vineyards, right between Napa and Sonoma, so you can easily explore both.
2. The North Fork
After Labor Day the crowds clear out, but the water is still warm and the wineries and farm stands are in full harvest mode. Go apple picking, grab pies from the farm stands and spend afternoons on vineyard patios. It's a beautiful, relaxed time of year out east.
Splurge: Sound View Greenport — Where I stayed: retro-modern rooms right on the Long Island Sound with a private beach and the Halyard restaurant on site.
Save: Silver Sands Motel — A retro waterfront motel in Greenport with its own beach, cozy and nostalgic at a more relaxed price.
Read more: Where to stay in Greenport
3. Santorini & the Greek Islands
The sea is at its warmest, the summer crowds thin out and the sunsets are just as good. September is perfect for island-hopping, with calmer ferries and better hotel rates. Add a quieter island like Naxos or Milos for beaches and local tavernas.
Splurge: Katikies Santorini — Cliffside infinity pools in Oia with some of the most iconic views in the Cyclades.
Save: Astra Suites — Caldera views in quieter Imerovigli with a beautiful pool, a little away from the Oia crowds.
4. Kauai, Hawaii
Fall is a quieter time on the island, with warm water, fewer visitors and great value compared to the holidays. Take a Nā Pali boat tour, hike Waimea Canyon and spend lazy afternoons on Poipu Beach. It's a great time for a relaxed honeymoon.
Splurge: 1 Hotel Hanalei Bay — Stunning North Shore views and a beautiful, nature-inspired design.
Save: Kauai Shores Hotel — Casual, colorful and right on the beach, with an easy central location for exploring.
Read more: Top 5 things to do in Kauai
5. Tuscany & Florence
Grape harvest season in the countryside, warm days and fewer crowds in Florence than in the peak summer months. Spend a few days in Florence for art and food, then rent a car and drive through Chianti and the Val d'Orcia. Long lunches at the wineries are a must.
Splurge: Rosewood Castiglion del Bosco — A Montalcino estate with its own winery, golf and incredible views over the Val d'Orcia.
Save: Hotel L'Orologio — A stylish stay on Piazza Santa Maria Novella, walkable to all of Florence's highlights.
Not sure where to go?
Take my Trip Finder quiz. Answer a few quick questions about when you're traveling, your travel style and your budget, and I'll match you with a destination plus three places to stay.
Or skip the research entirely. I plan trips for readers, from long weekends to honeymoons, and I'll build an itinerary around your dates, budget and style. Here's how planning a trip with me works.
Every trip is different, and weather, events and hotel availability can change from year to year, so double-check dates before you book.
More months: Where to go in August · Where to go in October
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