Painted nebula sky in rose and emerald with shooting stars

Your holiday,
planned in minutes
booked your way.

“A quote that matched the final bill to the rupee.” — The Pathak family, Bali, 6N

Sky — Holidaywins Travel Planner

Online: Ready to plan your trip.

Hi! I'm Sky. Tell me about your dream trip — where, when, who with, and your budget — and I'll build your full itinerary in seconds.

Best for November 2026

In season next month

These trips are genuinely good in November 2026 — right weather window, roads and ferries open, nothing we'd have to talk you out of.

See all packages

Where Indians are flying in 2026

Destinations we know street by street

Each page carries real content, honest seasonality advice, FAQs on visas and food, and the packages we actually sell — not a stock-photo brochure.

Andaman Islands
India

Andaman Islands

Radhanagar's white sand, Elephanta reefs and glass-bottom lagoons

from ₹38,500/ person

Bali
International

Bali

Emerald rice terraces, cliff-top temples and private pool villas

from ₹52,500/ person

Italy
International

Italy

Rome's ruins, Florence's Renaissance and a Venice gondola at dusk

from ₹1,52,000/ person

Northeast India
India

Northeast India

Meghalaya's root bridges, Dawki's glass river and Kaziranga rhinos

from ₹32,500/ person

Rajasthan
India

Rajasthan

Lake palaces in Udaipur, Jaipur's forts and Jodhpur's blue city

from ₹36,500/ person

Uttarakhand
India

Uttarakhand

Rishikesh rapids, Nainital's lake and the Jim Corbett jungle

from ₹22,500/ person

Vietnam
International

Vietnam

Golden Bridges, Ha Long Bay junks and street-food evenings

from ₹49,900/ person

Goa
India

Goa

North Goa's beach clubs, South Goa's quiet sand and Portuguese Panjim

from ₹28,500/ person

Himachal Pradesh
India

Himachal Pradesh

Shimla's colonial ridge, Manali's snow lines and the Solang valley

from ₹24,500/ person

Maldives
International

Maldives

Overwater villas, glass-clear lagoons and the world's slowest sunsets

from ₹58,000/ person

Switzerland
International

Switzerland

Jungfrau snow, lakeside Lucerne and the Glacier Express window seat

from ₹1,89,000/ person

Kashmir
India

Kashmir

Houseboats on Dal Lake, Gulmarg gondolas and saffron fields

from ₹48,000/ person

Kerala
India

Kerala

Backwater houseboats, Munnar tea hills and Ayurveda slow-downs

from ₹49,500/ person

Dubai & Abu Dhabi
International

Dubai & Abu Dhabi

Sky-high suppers, desert dunes and the world's biggest playground

from ₹56,000/ person

Thailand
International

Thailand

Krabi cliffs, Phuket beach clubs and Bangkok street energy

from ₹54,000/ person

Most-booked right now

Featured packages, indicative INR estimates

Every price is an indicative estimate, per person on twin sharing. Final pricing depends on travel dates, supplier rates, availability and selected inclusions — our team will confirm the final quotation.

Why Holidaywins

Built for travellers who hate being sold to

We're a small team of travel planners, not a call centre. That means fewer, better trips — and enough honesty to tell you when a destination isn't worth your dates.

Enquire any time. Our team replies Mon-Sat, 9 AM - 9 PM IST — typically within 12 minutes during business hours.

01

Real prices, dated

Every package shows an indicative INR estimate plus the date we last reviewed it. No bait pricing, no surprise surcharges — our team confirms the final quotation.

02

Private, not herded

No 45-seat coaches. Private vehicles, your pace, and itineraries we rewrite around your dates, kids' ages and parents' knees.

03

One human, one thread

You get a named travel expert on WhatsApp — the same person from first enquiry to the ride home from the airport.

Why Holidaywins

Three promises we keep on every trip

Instant Magic

Dream to Itinerary in Minutes

Tell Sky where you want to go — she builds a personalized day-by-day itinerary instantly. No forms, no waiting.

  • AI-powered personalized planning
  • Transparent INR pricing always
  • Co-create your journey your way

The Human Touch

Expert Travel Concierge on Standby

Our travel experts verify every itinerary. Get the speed of AI with the wisdom of someone who has been there.

  • Every itinerary reviewed by our experts
  • On-demand changes — swap hotels, add experiences
  • Hybrid planning — AI speed meets human care

The Zero-Surprise Promise

From Booking to Destination

We handle everything so you only show up and enjoy.

  • Visa, insurance and paperwork handled
  • On-ground support throughout your trip
  • 24/7 WhatsApp support before, during and after travel

4.9 average · 600+ trips planned

What travellers tell us afterwards

They talked us out of the villa we'd picked online and into a better one for less. The sandbank dinner was the best night of our lives.
Shruti & KaranMaldives honeymoon, 4N
Jain food arranged in every city, a driver who adored the kids, and a quote that matched the final bill to the rupee.
The Pathak familyBali, 6N with two kids
Booked eight days before flying. Houseboat, Gulmarg gondola, Pahalgam — everything held together in peak season.
Rajiv NairKashmir, 5N
HOLIDAYWINS

Handcrafted private holidays for Indian travellers. Transparent indicative INR estimates, and a human on WhatsApp from first enquiry to touchdown back home.

Mon-Sat, 9 AM - 9 PM IST · Typical reply in 12 minutes

Talk to us

Company

© 2026 Holidaywins. All prices shown are indicative estimates per person on twin sharing, in INR. Final pricing depends on travel dates, supplier rates, availability and selected inclusions. Our team will confirm the final quotation.