Friday newsletters always feature luxury travel contests, tips, or news.
Today: Travel contests & sweepstakes: win luxury holidays!
Every month, you can win exclusive holidays in my pick of the best luxury travel contests & sweepstakes on the internet. These contests are weekly updated on my travel blog here, so check back regularly.
In this issue: win holidays to Scotland, Sri Lanka, Thailand, Nepal, New Zealand, Australia, Vietnam, Dominican Republic, Lapland, South Africa, Kenya, Switzerland, Morocco, and Japan.
- Win a seven-night cruise in the Scottish Highlands. The grand prize is an all-inclusive 7-night cruise through the spectacular Scottish Highlands with Lord of the Highlands, Hebridean Island Cruises. As a 4-star+ vessel accommodating just 38 guests, Lord of the Highlands promises an intimate and refined cruising experience. All meals, drinks and snacks, gratuities, taxes, onshore visits and excursions are included – so you can simply relax and immerse yourself in the very best of Scotland.
- Eligibility: open to all
- End date: May 31, 2025
- Enter the travel contest: click here
- Win a three-night luxury stay in Thailand. The grand prize is a three-night stay for two at Samujana, Thailand. The prize includes daily breakfast for two and a Thai Discovery arrival dinner.
- Eligibility: open to all
- End date: May 31, 2025
- Enter the travel contest: click here
- Win a(nother) five-night luxury stay in Thailand. The grand prize is a five-night stay for two at the Four Seasons Bangkok at Chao Phraya Hotel. Note: flights and dining are not included.
- Eligibility: open to USA residents
- End date: May 19, 2025
- Enter the travel contest: click here
- Win a three-night luxury stay in Sri Lanka. The grand prize is a three-night stay for two at Ravana Garden, in Sri Lanka. This exceptional prize includes full access to Ravana Garden’s transformative wellness experiences, daily Ayurvedic therapies, nourishing dosha-specific meals, and a thoughtfully curated programme of cultural and spiritual activities — all designed to restore balance and promote deep wellbeing. it’s important to note, the wellness programs at Ravana Garden are a unique blend of Ayurvedic treatments and sacred ancestral rituals that date back thousands of years.
- Eligibility: open to all
- End date: May 31, 2025
- Enter the travel contest: click here
- Win a vacation in Finnish Lapland. The grand prize is a two- to four-night holiday package for two guests offered by Apukka Resort in Finnish Lapland. All holiday packages include high-quality glass igloo accommodation at Apukka Resort, daily breakfast, 2–3 tours/experiences, and airport transfers. Flight or train tickets are not included in the prize, as they need to be organized and paid for by the winner. The nearest airport and train station are located in Rovaniemi, Finland, with transfers from either managed by Apukka Resort.
- Eligibility: open to all
- End date: May 23, 2025
- Enter the travel contest: click here
- Win a two-night luxury stay in Auckland, New Zealand. The grand prize is a two-night stay for two in an Oasis room at Naumi Auckland Airport Hotel, including breakfast for two people
- Eligibility: open to all
- End date: June 30, 2025
- Enter the travel contest: click here
- Win a trek to Everest Base Camp, Nepal. The grand prize is an 15-day Everest Base Camp Trek. Note: flights and insurance are not included.
- Eligibility: open to all
- End date: May 16, 2025
- Enter the travel contest: click here
- Win a trip to Vietnam. The prize is an 11-day Vietnam adventure for two: explore bustling Ho Chi Minh City; cruise the Mekong Delta and visit local orchards; cycle through Hoi An’s countryside and riverside; and experience Halong Bay on an unforgettable cruise. Note: flights are not included.
- Eligibility: open to all (except residents of India, Belgium, Sweden, Quebec, Florida, Rhodes Island and New York)
- End date: May 31, 2025
- Enter the travel contest: click here
- Win a safari in South Africa. The grand prize includes return Economy flights for two to Cape Town; 3 nights in the Marriott Hotel, Crystal Towers; choice of Stellenbosch Wineries or Table Mountain tour; a 2-day safari including 2 nights at Inverdoorn Private Safari Lodge; a Cheetah Educational Tour & Cheetah run experience; and a VIP travel management.
- Eligibility: open to residents of Europe, United Kingdom, Australia, New Zealand, USA, Canada, South America, and South Africa
- End date: September 30, 2025
- Enter the travel contest: click here
- Win a VIP trip to the formula E in Berlin or London. The grand prize is six VIP family trips to Berlin or London, each package featuring four VIP tickets, Formula E Electric Lounge access, flights from any European country, and two nights in a premium hotel. And that’s not all – you could also win a set of iON tyres, featuring the same cutting-edge technology used in Formula E.
- Eligibility: open to residents of Europe
- End date: May 15, 2025
- Enter the travel contest: click here
- Win a trip to Tokyo, Japan. The prize for the winner and companion consists of return flights to Tokyo from Europe, a 6-night (13 to 19 September 2025) 4* hotel stay in Tokyo, and stadium event tickets for the World Athletics Championships.
- Eligibility: open to residents of Netherlands, Spain, Belgium, Norway, Sweden, Denmark, Finland, France, Germany, United Kingdom, Ireland, and Austria
- End date: June 15, 2025
- Enter the travel contest: click here
- Win a free flights to your dream destination. Simply search, share, and submit your flights on the Kayak website to be in with a chance of winning.
- Eligibility: open to residents of France and the United Kingdom
- End date: May 19, 2025
- Enter the travel contest: click here
- Win a five-night golf holiday in the Dominican Republic. The grand prize is five nights of All Inclusive Caribbean luxury at the legendary Casa de Campo Resort and Villas. The prize includes five nights for two in an Elite Patio Room at the 5-star Casa de Campo Resort and Villas, on an all-inclusive basis – enjoy gourmet meals, drinks, and luxury service, three rounds of golf, including a tee time at the world-famous Teeth of the Dog course*, transfers and return flights to the UK from the Dominican Republic
- Eligibility: open to UK residents
- End date: May 31, 2025
- Enter the travel contest: click here
- Win a trip to Australia. The grand prize is includes an all-expenses-paid trip for you and a guardian to Sydney, three nights’ accommodation in Sydney, all flights, and premium rugby tickets.
- Eligibility: open to UK residents
- End date: May 31, 2025
- Enter the travel contest: click here
- Win a five-night escape in Morocco. The grand prize includes two nights in Marrakech, two nights in Essaouira, and one night in the Agafay Desert. All flights, transfers as well as daily breakfast and dinner are included.
- Eligibility: open to UK residents
- End date: October 31, 2025
- Enter the travel contest: click here
- Win a luxury safari in Kenya. The grand prize is a luxury 5-night all-inclusive safari for two in Asilia’s premier safari lodges across Kenya; $5,000 USD travel credit that can be applied towards flights, transfers, or additional luxury accommodations; and unforgettable wildlife encounters with the Big 5 and the last two remaining Northern White Rhinos.
- Eligibility: open to USA and UK residents
- End date: June 21, 2025
- Enter the travel contest: click here
- Win a ski trip to Aspen, United States. The grand prize includes seven nights accommodation for two at Frias Properties of Aspen Snowmass, six days of skiing, lift tickets and ski/snowboard hire, one day of instructor for two for a 5-hour period, and a flight voucher worth £500.
- Eligibility: open to residents of the UK, Norway, Sweden, Denmark and Finland
- End date: June 30, 2025
- Enter the travel contest: click here
- Win a ski trip to Davos Klosters, Switzerland. The grand prize includes return economy flights with Swiss International Air Lines to Zurich; first-class rail transfers to Davos; a three-night, half-board, Superior-room stay at Hotel Grischa; and passes for Landwasser World. The prize is valid to 31 October 2025. It must be booked at least three weeks in advance, and at least two travel dates must be supplied.
- Eligibility: open to residents of the UK
- End date: May 31, 2025
- Enter the travel contest: click here
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What an incredible roundup of dream-worthy travel opportunities! The diversity of these contests is astounding—from the serene wellness retreat in Sri Lanka to the adrenaline-pumping Everest Base Camp trek. As someone who’s always hunting for ways to experience luxury without the hefty price tag, this list is pure gold.
One question: For contests like the Four Seasons Bangkok stay (which I’d love to win!), do you recommend any strategies to increase odds? I’ve heard entering early/late or via multiple platforms can sometimes help.
DH