Top 10 Fall Travel Destinations for Stylish Getaways

Top 10 Fall Travel Destinations for Stylish Getaways

Autumn quietly transforms the world: vineyards flush with colour, palaces and riads glow in softer sunlight, and cities settle into a slower rhythm that perfectly suits a travel wardrobe built for ease and elegance. For the San Martini traveler, someone who packs light, dresses thoughtfully, and savors Martini Time at sunset, these ten destinations offer culture, food, memorable bars, and photo-ready backdrops. Below each destination you’ll find two short paragraphs on why it’s perfect in fall, a suggested local cocktail or at home barware discovery, tailored packing tips for crisp-weather style, and a San Martini closet pick to make packing simpler.

1. Loire Valley, France:

Chateau Drives, Vineyard Light, & Elegant Quiet

The Loire Valley in autumn is a study in soft light and architectural poetry. Vineyards shift from green to gold while the great châteaux, Amboise, Azay-le-Rideau, Chenonceau, take on the warm tones of harvest season. It’s an ideal time for slow drives along river bends and long lunches at auberges where local produce and Loire whites (Sancerre, Muscadet, Vouvray) dominate the table. Many smaller wineries stage harvest and tasting events in September and October, so travellers can see grape sorting and barrel tastings without the crush of summer crowds.

For cocktail hour, lean into regional wines and aperitifs, think a chilled Loire white or a sparkling Crémant-de-Loire with a lemon twist, served in elegant stemware. For barware picks on your trip, use a refined coupe or slim martini glass to enjoy terrace evenings; our Vintage martini set or Savage Coupetini work beautifully for sunset sips when at home reminiscing on your trip. Pack breathable linen layers for afternoon tours and a polished unlined blazer for château dinners. Pair with San Martini’s curated closet pieces for a relaxed, photogenic capsule that travels well.

Packing tip: lightweight trench, neutral silk scarf, a midi linen dress, low-heel ankle boot, and a compact umbrella.

2. Tuscany’s Chianti Harvest:

Sunlit Hills, Vendemmia Rituals, & Rustic Sophistication

Autumn in Chianti is harvest poetry: rows of Sangiovese ripen to deep purple and villages unfurl their agrarian festivals. Visiting during the vendemmia (grape harvest) lets you witness centuries-old ritual and family-run cellars in full swing, many farms welcome visitors for grape-picking, olive-oil tastings and communal dinners (sagre) celebrating the season. Chianti’s stone farmhouses and villas feel particularly cinematic in autumn light, making it the kind of place you’ll want to slow down in for a few days.

For cocktails, Tuscany favors wine-forward simplicity; the Negroni is a Florentine-born classic and pairs effortlessly with Tuscan bitterness and salumi. Use a robust mixing glass or opt for a coupe for spritz-like variations when you’re watching sunset over the vineyards. San Martini closet picks: neutrals, tailored linen trousers, a cashmere wrap for evening, and a pair of leather loafers, or find beautiful travel-ready sets at San Martini's curated closet collections.

Packing tip: rolled merino sweater, breathable blouse, high-waist tailored trousers, leather loafers, and a straw market tote.

3. New Hampshire’s White Mountains:

Crisp Foliage, Cozy Inns, & Outdoor Grace

The White Mountains offer one of the East Coast’s most dramatic leaf-peeping displays: winding scenic byways, covered bridges and panoramic overlooks that flash from emerald to amber into October. Hike the shorter trails for misty morning views or drive the Kancamagus Highway for one of the region’s most legendary fall experiences. Quaint towns like North Conway and Lincoln serve as home bases, with farm-to-table restaurants, local cider houses and intimate B&Bs that feel made for slow evenings with a fireside martini or hot toddy.

Local fall cocktails lean into orchard flavors, think an apple-cider martini or a maple Old Fashioned, served in sturdy rocks glassware. A quality rocks set (our Big Top Whisky DOF selection) is ideal for those dockside and fireside hours. For clothing, layer up: a brushed flannel overshirt, lightweight puffer vest, knitted scarf, and durable boots that handle leaf-strewn trails yet look polished for dinner. Link your looks to San Martini’s closet for curated, seasonal combos.

Packing tip: waterproof ankle boots, wool socks, layered knit, lightweight quilted jacket, and an on-the-go thermos for cider.

4. Bavarian Wine Route (Deutsche Weinstraße), Germany:

Vineyards, Castles, & Harvest Festivals

The German Wine Route winds through the Palatinate’s mellow hills, famed for Riesling and Spätburgunder (Pinot Noir). In autumn the route becomes a corridor of harvest markets, castle visits and food festivals celebrating new vintages and smoked sausages. Small towns such as Deidesheim and Neustadt hold Weinlese (harvest) events where local vintners pour still and sparkling wines and invite visitors to rustic tasting rooms and taverns. Driving the route rewards slow tastings, historic architecture and wide, walkable market squares.

The local sipping culture favors young Rieslings and sekt (German sparkling wine) best served in a narrow crystal flute or coupe for celebrations. For fall evenings, an aromatic Riesling with a subtle cleanness pairs well with regional cuisine; use a versatile coupe or stemmed glass to enjoy tastings at your villa. For packing, layer a tailored coat over merino knitwear, a pleated midi skirt or straight trousers, and polished ankle boots, discover matching pieces at San Martini’s Closets.

Packing tip: light trench or wool coat, silk blouse, tonal knit, comfortable loafers, and a compact cross-body bag for tastings.

5. Kyoto’s Maple Festival (Momiji):

Temple Gardens, Lantern-Lit Evenings , & Contemplative Color

Kyoto’s autumn, known as koyo or momiji, is when maple trees turn explosive crimsons and golds. Popular temple gardens, like Kiyomizu-dera, Tofuku-ji, Arashiyama, host illuminated night-viewings that feel almost reverent as lanterns and spotlights reveal layered color and architecture. For travelers interested in slow culture, autumn temple walks, seasonal kaiseki meals, and matcha ceremonies elevate every moment: Kyoto in fall is contemplative, tactile, and cinematic. Check Kyoto’s Autumn Leaves Calendar to time your trip for peak color.

Sake is the natural local accompaniment; try a warm (kanzake) or chilled seasonal sake paired with small plates in a machiya or ryokan. For barware, consider a small carafe/decanter for sake service or a coupe for modern sake cocktails that mix yuzu or plum. Pack lightweight layers and a tailored trench that can handle morning mist, plus elegant slip dresses for evening temple dinners; San Martini’s curated closet can help you assemble a respectful, beautiful capsule

Packing tip: neutral kimono-inspired wrap or silk scarf, lightweight trench, comfortable walking shoe, and a small evening clutch.

6. Napa Valley Harvest:

Pressing, Parties, & the Slow Heat of Winery Evenings

Napa Valley remains a pilgrimage for wine lovers in autumn when the valley buzzes with harvest parties, barrel tastings, and late-summer sunshine giving way to cool evenings. Vineyards stage release dinners and intimate winemaker events, and small towns from Yountville to St. Helena serve seasonal menus punctuated by locally produced cheese and farm-to-table specialties. Napa’s hospitality scene often hosts sunset concerts and festive harvest events, an ideal time to layer your outfits from warm afternoons into chillier tasting-room evenings.

Cocktail culture in wine country mixes wine-forward thinking with classic bartending: a barrel-aged negroni, a smoke-kissed Old Fashioned, or a crisp French 75 made with local sparkling. For at-home barware you bring back, a balanced decanter and a set of coupe glasses (or our Big Top coupe or Bar Giani martini set) are perfect for vineyard terraces. Pack a dressy-casual blazer, lightweight cashmere, tailored jeans and well-made boots for dinners at estate restaurants; see San Martini’s Closets to curate a harvest-friendly capsule. Note: check for any current harvest advisories, recent wildfires have affected some vineyards; plan with local winery updates.

Packing tip: layered wool sweater, lightweight blazer, travel jeans, heeled boot or loafer, and a protective tote for market finds.

7. Marrakesh Riads at Dusk:

Souks, Saffron Markets, & Rooftop Martini Light

Marrakesh in autumn is magical: riads reopen after summer closures, evenings cool into balmy nights and souks brim with saffron, dyed textiles and ceramics. Wander Jemaa el-Fna at dusk for street food and acrobatics, then slip into a rooftop riad for mint-scented cocktails or tea and lantern-lit terraces. The city’s design language, terracotta, indigo, and mosaic, creates an evocative backdrop for travel photography and leisurely evenings. Many riads host small cocktail hours that blend classic techniques with local ingredients like rosewater or orange blossom.

Local flavor experiments include saffron or rosewater-inflected cocktails and wine-forward blends that pair with tagine. For barware, use a coupe or decorative stemmed glass to highlight aromatic ingredients, and don’t forget an elegant decanter for serving friends. Pack light layers that can handle warm days and cooler rooftop evenings: a silk scarf, linen trousers, and metallic babouches (or leather sandals). Tie your looks to San Martini’s Closets for a market-to-martini wardrobe that photographs beautifully.

Packing tip: breathable linen trousers, silk blouse, headscarf, flat metallic slides and a lightweight evening wrap.

8. Québec City’s Old Town:

European Charm, Cozy Bistros, & Amber-Tinted Streets

Old Québec feels like stepping into a European postcard: cobbled streets, Château Frontenac’s silhouette and a convivial café culture that deepens in fall. The city’s gastronomy embraces maple, root vegetables and warming cocktails served in snug bistros, plus fall festivals and riverfront strolls that make the season especially romantic. Autumn light and the changing leaves on the Plains of Abraham create sublime photo opportunities; weekend festival programming often includes culinary events, concerts, and long-table dinners.

A regional specialty to try is Caribou; a spiced red-wine punch sometimes blended with maple and spirits, traditionally enjoyed at winter festivals but increasingly served in autumnal menus. For at-home entertaining, keep a small pitcher or decanter for mulled-wine or spiced-wine service. Dress in layered wool, a smart coat, insulated loafers or ankle boots, and a cashmere scarf for frost-touched mornings, San Martini’s Closets provides elegant combinations that are cozy and picture-ready.

Packing tip: insulated mid-length coat, cashmere scarf, leather ankle boots, gloves, and a cross-body for hands-free cafés.

9. Scottish Highlands:

Misty Moors & Dramatic Early-Fall Solitude

The Highlands turn deeply atmospheric in autumn, battered moorlands, lochs rimmed in burnished browns and golds, and small villages that welcome fireside evenings. This season is quieter, fewer coach tours, clearer skies for dramatic sunsets and excellent for scenic train rides and single-track drives. Hikes at Glencoe or around the Cairngorms offer a rugged, cinematic experience, and whisky distilleries across Speyside and the Highlands open their doors for off-season tastings and distillery tours.

Whisky is the native drink of the Highlands, try a dram neat, or a Rob Roy (a Scotch-based Manhattan) for a local twist on a classic. Transport your favourite cask-aged sipper to evenings by the fire in a short, sturdy tumbler (our Big Top Whisky DOF glasses are ideal). Pack rainproof outerwear, a thick knit, lined boots and a tartan or neutral scarf for warmth; reference San Martini’s Closets to pair functional layers with polish for dinners and distillery tours.

Packing tip: waterproof outer layer, heavy knit, insulated hiking shoe, wool socks, and a flask for scenic pauses.

10. Barcelona’s Fall Festivals:

La Mercè, Mild Beaches, & Catalan Evenings

Barcelona in early autumn is a feast: the crowds of summer ebb, temperatures stay warm, and the city celebrates La Mercè (late September) with parades, fireworks, human tower spectacles (castellers) and a thriving street-arts program. It’s a moment when local culture is on display everywhere, from neighborhood concerts to unexpected food-popups, making it ideal for travelers who want city energy without midsummer crush. The city’s beaches remain pleasant for daytime promenades while museums and tapas bars come alive in the cool evenings.

Catalan bar culture puts vermouth and gin & tonic high on the list, “vermut” is often enjoyed on terraces and many bars pour their own house vermouth. A sprightly vermouth with an orange slice or a Spanish-style gin & tonic in a large Copa de Balon is a Barcelona ritual best enjoyed in a comfortable terrace seat. For barware, a coupe for vermouth spritzes or a large goblet for gin & tonic pairs with city evenings. Pack lightweight cotton shirts, linen trousers, layered knit and sandals for warm daytime exploring and cooler nights, San Martini’s Closets helps you create versatile outfits for market mornings and open-air concerts.

Packing tip: linen shirt, cotton trousers, foldable sandals, light knit for evenings, and a small cross-body for festival essentials.

San Martini Picks: 

Capsule Closets & Barware for Every Destination

For each of these getaways, the easiest way to travel elegantly is a compact, mix-and-match closet. Use San Martini’s Curated Closets collection for a ready-made capsule that marries fabrics and neutrals to locale. For barware that travels well and elevates hotel or rental evenings, consider our favorites:

Pair a nimble closet with a compact bar kit (mixing glass, jigger, small strainer, and a couple of stemware options) and you’re ready to make Martini Time anywhere in the world.

Final Thoughts: 

Travel Slow, Dress with Intent, & Sip with Friends

Fall travel rewards the slow traveler. The destinations above offer the pleasures San Martini prizes most: considered rituals, seasonal harvests, tactile craftsmanship, and the kind of evenings that benefit from a well-made cocktail and even better company. Whether you’re booking a riad in Marrakech, timing Kyoto’s maples, or harvesting Chianti with winemakers, pack intentionally, choose fabrics that last, and bring one elegant glass to honor the end of the day.

References:

  • Chianti.com. “Join the Vendemmia in Tuscany: The Grape Harvest in Chianti.” Chianti.com, chianti.com/what-to-do-in-chianti/grape-harvest-with-friends.html. Accessed 16 Sept. 2025. (chianti.com)
  • Decanter. “Loire Valley travel guide.” Decanter, 2013, www.decanter.com/wine-travel/france/decanter-travel-guide-loire-valley-france-21387/. Accessed 16 Sept. 2025. (Decanter)
  • Germany Travel. “German Wine Route.” Germany.travel, germany.travel/en/nature-outdoor-activities/german-wine-route.html. Accessed 16 Sept. 2025. (Germany Travel)
  • Japan National Tourism / Kyoto Travel. “Autumn Leaves Calendar.” Kyoto.travel, kyoto.travel/en/seasonal-info/autumnleaves/. Accessed 16 Sept. 2025. (Kyoto Travel)
  • Loire Valley Wine Tour. “Grape Harvest Tour.” LoireValleyWineTour.com, loirevalleywinetour.com/harvest_tour.php. Accessed 16 Sept. 2025. (loirevalleywinetour.com)
  • Napa Valley Vintners. “2025 Harvest Parties & Celebrations.” VisitNapaValley.com, visitnapavalley.com/events/harvest/. Accessed 16 Sept. 2025. (Visit Napa Valley)
  • Quebec-City.com. “Top Things to Do in Québec City This Fall.” Québec-Cité, quebec-cite.com/en/what-to-do-quebec-city/top-things-to-do-fall. Accessed 16 Sept. 2025. (Quebec City Guide)
  • Riad Travel Guides. “Top Riads in Marrakech.” Riads-in-Marrakech.com, riads-in-marrakech.com/. Accessed 16 Sept. 2025. (Riads in Marrakech)
  • Visit White Mountains. “White Mountains Fall Foliage Tracker.” VisitWhiteMountains.com, visitwhitemountains.com/events/fall-foliage/foliage-tracker/. Accessed 16 Sept. 2025. (Visit White Mountains)
  • Visit Germany / Wikipedia. “German Wine Route.” Wikipedia, en.wikipedia.org/wiki/German_Wine_Route. Accessed 16 Sept. 2025. (Wikipedia)
  • Barcelona City Council. “La Mercè 2025.” Barcelona.cat, barcelona.cat/lamerce/en. Accessed 16 Sept. 2025. (Web de Barcelona)
  • VisitScotland. “Autumn in Scotland.” VisitScotland.com, visitscotland.com/travel-planning/when-to-visit/autumn. Accessed 16 Sept. 2025. (VisitScotland)
  • Additional sources: Tuscandream.com (Tuscany harvest overview), RoutePerfect (German Wine Route itinerary ideas), recent news coverage on Napa wildfires (The Guardian). (TuscanDream)