5 Shoulder Season Destinations You’ll Fall in Love With in 2026
- Ellie Friese
- 21 hours ago
- 4 min read
If you’ve ever traveled during peak months like July or December, you know the drill: higher prices, bigger crowds, and a pace that doesn’t always feel like a true vacation. But here’s the secret seasoned travelers - and us travel advisors ;) - swear by: shoulder season.
Those beautiful in-between months — spring and fall — where destinations breathe, the weather softens, and you get a more authentic version of the place you're visiting.
Shoulder season is where travel magic happens. It’s also one of the smartest ways to travel more intentionally in 2026, without battling peak-season chaos.
Below are five destinations that shine brightest during shoulder season — a blend of coastal charm, wine country calm, dramatic landscapes, and soul-filling escapes.
🇵🇹 1. Portugal’s Douro Valley
Best: April–May & September–October
There’s something undeniably romantic about the Douro Valley in shoulder season. The vineyards glow in soft golden light, river villages feel slow and inviting, and temperatures are perfect for exploring.
Why it’s perfect in shoulder season:
The summer heat hasn’t arrived yet, and autumn harvest season is vibrant but less crowded. Wineries offer more attentive, intimate experiences, and river cruises feel peaceful and restorative.
If you want a deeper look at Portugal’s magic, don’t miss our recent women’s group trip — it captures the warmth, culture, and connection that make this destination unforgettable.
👉 Read it here.
Advisor Tip:
Book winery lunches early — river-view spots fill quickly during spring bloom and autumn harvest.
Best For:
Wine lovers, couples, photographers, and anyone craving slow, sensory-rich travel.
🇪🇸 2. Basque Country, Spain (Hondarribia & Getaria)
Best: May–June & September
Basque Country is one of Europe’s most underrated coastal gems. Shoulder season unlocks its charm: sunlit seaside towns, relaxed beach days, and long afternoons spent pintxos hopping between bars.
Why it’s perfect in shoulder season:
Restaurants are easier to book, beaches feel serene, and the weather is ideal for walking tours, coastal trails, and exploring the region’s incredible culinary scene.
Advisor Tip:
Book Michelin-starred restaurants months ahead — but keep a few meals open for spontaneous pintxos stops and local recommendations.
Best For:
Food lovers, culture seekers, coastal explorers, and anyone who wants Europe without the overwhelm.
🇮🇹 3. Tuscany & Umbria, Italy
Best: April–June & September–October
Tuscany and Umbria were practically made for shoulder season. Rolling hills turn bright green in spring and warm gold in fall, while towns like Siena, Cortona, and Montepulciano feel pleasantly unhurried.
Why it’s perfect in shoulder season:
Mild weather makes exploring easy, landscapes are at their most photogenic, and hotels, villas, and agriturismos offer better availability and pricing than during peak summer.
Advisor Tip:
Consider a countryside villa stay — in shoulder season, you often get more space, better amenities, and gorgeous views for a fraction of summer rates.
Best For:
Couples, families, first-time Europe travelers, and anyone who craves food, wine, and timeless scenery.
🇿🇦 4. South Africa
Best: March–May & September–November
South Africa is a shoulder-season powerhouse. Cape Town enjoys mild temperatures, the Winelands shine with color, and safari experiences often come with clearer visibility and better rates.
Why it’s perfect in shoulder season:
You get an incredible blend of value, weather, and wildlife. Flights and hotels are easier to secure, and itineraries feel smoother without peak-season crowds.
Advisor Tip:
Combine Cape Town + the Winelands + Safari for the perfect 7–10 day itinerary — shoulder season makes this more affordable and easier to book.
Best For:
Bucket-list travelers, wine lovers, adventurers, and honeymooners seeking a “trip of a lifetime.”
🇺🇸 5. Hawaii (Maui, Kauai, or Oahu)
Best: April–June & September–October
Hawaii in shoulder season is dreamy. The islands feel calmer, the beaches less crowded, the ocean warm and inviting, and the weather is consistently perfect — sunny days, breezy evenings, and that relaxed island pace that instantly resets your system.
Why it’s perfect in shoulder season:
Summer prices haven’t kicked in yet (or have just tapered off), whale-watching and sea life encounters are at their best in early spring, and hotel availability is noticeably better than peak months
Advisor Tip:
Interisland hopping is easier and more affordable in shoulder season — consider pairing two islands (like Maui + Kauai) if you want a mix of adventure and pure relaxation.
Best For:
Beach lovers, honeymooners, families, hikers, and anyone craving a warm, rejuvenating getaway with breathtaking natural beauty.
Why Shoulder Season Works (and Why 2026 Is the Year to Try It)
If you want meaningful travel — not rushed itineraries and crowded streets — shoulder season is your secret ally.
You’ll enjoy:
Better weather
Better prices
Better hotel availability
Better restaurant reservations
Better photos (yes, it matters!)
And most importantly… a better experience
If you want to pair these getaways with PTO, check out our guide on maximizing your 2026 time off — it’s full of ways to turn a single PTO day into a 4–9 day vacation.
Read it here.
2026 is expected to be a busy travel year. Shoulder season is one of the smartest ways to enjoy the world at its most beautiful — without the peak-season bustle.
Ready to Plan Your Shoulder-Season Escape for 2026?
Whether you’re dreaming of quiet wine country mornings, European coastal charm, a bucket-list safari, or a restorative desert escape, let’s design a trip that fits your pace, your schedule, and your travel style.