Singaporeans are known to be savvy travelers, and with the 2026 public holiday calendar offering numerous long weekends, now is the time to begin planning the perfect luxury vacation. Whether the goal is indulging in a solitary island retreat, restoring one’s senses at an alpine sanctuary, or discovering ancient UNESCO World Heritage cities in style, early bookings ensure special access to some of the world’s luxury retreats from Singapore 2026
Tailwinds Travels, a Singapore-based luxury travel company, offers a carefully curated selection of high-end holiday experiences that require prior reservation.
1. Soneva Fushi, Maldives
Experience barefoot luxury at Soneva Fushi, Maldives, with overwater retreats, private beaches, and gourmet dining. One of the top resorts for long weekends from Singapore.
Ideal For: Families, honeymooners, and wellness seekers
Why Book Early: These iconic villas are often fully booked up to a year in advance of long weekends.
Key Features:
Private overwater and beachfront villas
Outdoor theaters, astronomical observatories, and upscale restaurants
Green luxury maximalism
Tailwinds Travels, one of Singapore’s most reputable travel agencies, specializes in customized holiday packages for the Maldives, including VIP transport, spa treatments, and expertly planned water activities.
2. Six Senses Bhutan
Ideal For: Cultural explorers, wellness travelers
Why Book Early: Bhutan has annual limits for visitor arrivals; long weekends fill up quickly.
Key Features:
Five lodges across Bhutan’s valleys, each with local character
Personalized wellness programs and transformative experiences
Perfect for couples or solo travelers seeking meaningful escapes
Explore Bhutan with Singapore’s top travel company, known for personalized itineraries to monasteries, private yoga sessions, and luxury transport to hillside cottages.
3. Aman Kyoto, Japan
Ideal For: Design aficionados, history buffs, couples
Why Book Early: Limited villa availability and strong domestic demand
Highlights:
Minimalist architecture, geothermal springs, and Zen gardens
Personalized tea ceremonies and private temple access
Enhanced cultural connectivity within Kyoto
Tailwinds’ Japan portfolio includes Aman Kyoto as a premium upgrade, with first-class train travel and dedicated local interpreters.
4. The Datai, Langkawi – Malaysia
Ideal For: Nature lovers, spa enthusiasts, families
Why Book Early: School holidays and long weekends drive demand
Key Features:
Ancient rainforest setting with rich biodiversity
Award-winning spa and sustainable nature tours
Michelin-level dining experiences by the beach
Tailwinds Travels, one of Singapore’s top travel companies, offers custom vacations to Langkawi with nature safaris, yacht charters, and high-end beachside cuisine.
5. COMO Uma Paro, Bhutan
Ideal For: Solo travelers, wellness seekers, photographers
Why Book Early: Bhutan enforces strict tourism limits; holiday periods are especially restricted
Highlights:
Himalayan views and tranquil rooms
Holistic wellness and guided excursions
Cultural immersion in surrounding monasteries and villages
Tailwinds includes COMO Uma Paro in its Central Asia Tour Packages, with experienced guides and optional meditation retreats.
6. Capella Ubud, Bali
Ideal For: Couples, creatives, wellness travelers
Why Book Early: Only 22 uniquely themed luxury tents
Highlights:
Tented jungle accommodations with artisan craftsmanship
Personal butlers and deep wellness immersions
Curated Ubud explorations
Tailwinds, Singapore’s best travel agency, offers privileged rates and tailor-made itineraries to Capella Ubud, delivering the most refined experiences Bali has to offer.
Strategies for Securing Your Luxurious Retreat in 2026
Use the Long Weekend Calendar Wisely:
Plan trips around Hari Raya, National Day, Deepavali, and Christmas for the perfect blend of relaxation and adventure.
Tailwinds Travels, a Singapore-based luxury travel company, ensures flawless coordination of your holiday, including room upgrades and airport transfers.
Maximize Value through Packages:
Choose travel packages from Tailwinds that combine flights, transfers, and accommodations to simplify your plans and unlock savings.
Go Beyond Standard Promotions:
Tailwinds specializes in elevated travel — from bespoke yacht charters to personalized safari tours and private VIP guides.
Final Thoughts: Embrace the Opportunity
The most sought-after retreats fill quickly, particularly around Singapore’s public holidays. Booking early is essential to secure access to top villas, suites, and unique cultural events.
Tailwinds Travels, the best travel agency in Singapore, crafts exclusive luxury vacations tailored to your preferences. Let our experts help you transform your long weekend into something unforgettable.
✨ Ready to Start Planning?
Explore Tailwinds Travels packages today and begin your journey toward a luxurious 2026 retreat.