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Shoulder season is one of travel’s best kept secrets. These weeks just before and after peak season offer warm weather, open reservations, lighter crowds, and dramatically lower prices. For travelers who want luxury without the splurge, May and October unlock some of the world’s most beautiful destinations at a fraction of the usual cost.
The Amalfi Coast, Italy (May)
Peak season: June to September
Why May works:
Ideal hiking temperatures around the mid 60s to mid 70s
Coastal towns covered in spring blooms
Hotels offering early season rates
Restaurants reopening with fresh seasonal menus
Insider tip: Staying in Praiano often delivers the same sweeping views at a lower price than Positano.
Santorini, Greece (October)
Peak season: July to September
Why October works:
Sea temperatures still warm enough for swimming
Comfortable evenings for sunset views
Easier reservations at popular restaurants
Caldera scenery without crowded pathways
Insider tip: Luxury hotels frequently offer complimentary upgrades during this period.
Maldives (May)
Peak season: December to April
Why May works:
Short rain showers mixed with plenty of sunshine
Strong underwater visibility for divers
Resorts running seasonal promotions
Better access to overwater villas
Insider tip: Half board options often pair well with restaurant promos offered in May.
Maui, Hawaii (Early October)
Peak season: June to August, December to March
Why early October works:
Pleasant weather between stormy and rainy periods
Whale watching season begins
Fewer families traveling
Relaxed resort pool areas
Insider tip: Car rental prices typically dip, perfect for exploring the Road to Hana.
Swiss Alps (May)
Peak season: December to March for skiing, July to August for hiking
Why May works:
Alpine flowers in bloom
Early hiking trails opening
Cable cars running without crowds
Luxury hotels offering soft opening rates
Insider tip: Early season packages often include spa credits.
Cabo San Lucas, Mexico (October)
Peak season: December to April
Why October works:
End of hurricane season
Ideal beach weather
Prime time for fishing
Perfectly warm resort pools
Insider tip: All inclusive resorts frequently enhance meal plans during October.
Bali, Indonesia (May)
Peak season: July to August
Why May works:
Light rainfall with lush scenery
Rice terraces at peak greenery
Smoother service at luxury resorts
Easier reservations across top restaurants
Insider tip: Many villas offer free night promotions this month.
French Riviera (October)
Peak season: June to September
Why October works:
Mediterranean waters still warm
Comfortable sightseeing weather
Local life returning after summer tourism
More flexibility at high end restaurants
Insider tip: Yacht tours often drop to half price.
Dubai, UAE (May)
Peak season: November to April
Why May works:
Pleasant mornings and evenings
Relaxed luxury shopping
Cooler desert safari outings at sunset
Hotel pool days well below peak season prices
Insider tip: Many hotels offer promotional brunches.
Queenstown, New Zealand (May)
Peak season: December to February
Why May works:
Brilliant fall foliage
Lower pre winter pricing
Wine harvest season
Clear skies for photography
Insider tip: Luxury lodges sometimes include bonus activities.
How to Maximize Shoulder Season Savings
Ideal booking windows
Hotels: 2 to 3 months before travel
Flights: 3 to 4 months out
Activities: Often best booked after arrival
Weather preparation
Pack layers
Bring a light rain jacket
Review historical weather trends
Extra ways to enhance the experience
Email hotels directly to ask about unlisted offers
Join loyalty programs before booking
Ask about upgrade availability at check in
Choose flexible rates to account for unpredictable weather
Mistakes to avoid
Forgetting to check whether attractions are open
Assuming shoulder season conditions are identical everywhere
Skipping a backup plan for rainy days
Missing local festivals that can influence prices and crowds
Shoulder season travel blends value, comfort, and authenticity in a way peak season rarely can. Travelers enjoy easier access to iconic landmarks, more relaxed service, and scenery that feels entirely their own.
Talk soon,
Your Maestro Concierge
Editors Note: Opinions expressed here are only the author’s and have not been reviewed, approved, or endorsed by any bank, credit card issuer, hotel, airline, or other entity.
