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 Indonesia, Spain, Italy, Alaska, Tanzania, Antigua, Portugal, Greece, Canada, the United Kingdom and Mauritius.

- Win a three-night luxury stay in Indonesia. The grand prize is a three-night stay for two at Plataran Komodo Resort & Spa, in Indonesia. The prize includes a daily signature breakfast with a Sunrise Hill Breakfast Experience one morning, an Executive Ocean Front Residence and an afternoon tea.
- Eligibility: open to all
- End date: January 31, 2025
- Enter the travel contest: click here
- Win a two-night luxury stay in Italy. The grand prize is a two-night stay for two at Villa Abbondanzi Resort, in Italy. The prize includes one of the Suites, sweet and savoury breakfast, access to the Garden SPA with sauna, Turkish bath, jacuzzi and relaxing area, 1 lunch or dinner at our Cinque Cucchiai restaurant with a 4-course culinary journey and 1 cocktail per person at the Cocktail & Wine Bar Armidà.
- Eligibility: open to all
- End date: January 31, 2025
- Enter the travel contest: click here
- Win a small ship cruise to Alaska. The grand prize is one complimentary cabin accommodating up to two guests aboard M/V Catalyst or M/V Westward for a voyage during the summer 2025 Alaska season. You’ll join a community that values sustainability, history, and exploration.
- Eligibility: open to all
- End date: January 27, 2025
- Enter the travel contest: click here
- Win a trip to Climb Mount Kilimanjaro (Tanzania). The grand prize is a once-in-a-life-time trek to the iconic Kilimanjaro summit with one of the leading adventure travel companies in the world, Kandoo Adventures.
- Eligibility: open to all
- End date: January 31, 2025
- Enter the travel contest: click here
- Win a two-night luxury stay in Spain. The grand prize is a two-night stay for two at Palacio Gran Vía, A Royal Hideaway Hotel, in Spain. The prize includes bed and breakfast for two nights and a tasting menu dinner in the restaurant “El Patio” for two people.
- Eligibility: open to all
- End date: January 31, 2025
- Enter the travel contest: click here
- Win a winter trip to Whistler. The grand prize includes round-trip flights from a major city airport to Vancouver, six nights’ accommodation in a deluxe studio suite at Westin Resort & Spa, and several winter activities as well as dining experiences.
- Eligibility: open to residents of Canada, USA, Australia and United Kingdom
- End date: May 5, 2025
- Enter the travel contest: click here
- Win a luxury stay in England. The grand prize is a two-night stay for two at Gilpin Hotel & Lake House, in England. The prize includes a stay in a Spa Suite inclusive of breakfast, a SOURCE Culinary Experience in the Michelin Star Restaurant SOURCE at Gilpin Hotel inclusive of wine pairing and In-room spa Treatment.
- Eligibility: open to all
- End date: January 31, 2024
- Enter the travel contest: click here
- Win a golf holiday to Mauritius. The grand prize is a 7-night stay at the 5-star Anahita Golf & Spa Resort on a half board basis, unlimited rounds of on-site golf on Ile aux Cerfs and Anahita Golf Club, private transfers, and return flights from the UK.
- Eligibility: open to UK residents
- End date: February 28, 2025
- Enter the travel contest: click here
- Win a luxury safari in Kenya. The grand prize includes a one-night stay Hemingways Nairobi OR Hemingways Eden Residence (on a bed & breakfast basis); a three-nigt stay at Hemingways Ol Seki Mara on a full board basis (excluding conservancy fees); and a three-night stay at Hemingways Watamu on a bed & breakfast basis.
- Eligibility: open to UK residents
- End date: January 19, 2025
- Enter the travel contest: click here
- Win a Tampa Bay holiday (Florida, USA). The grand prize includes flights and a luxurious four-night stay, where you’ll immerse yourself in Tampa Bay’s thriving art scene, savour exceptional cuisine, and explore the rich heritage that makes this destination truly unique.
- Eligibility: open to all
- End date: April 30, 2025
- Enter the travel contest: click here
- Win a romantic retreat in the Maldives. The grand prize is a romantic three-night stay to The Westin Maldives Miriandhoo Resort, inclusive of daily breakfast and dinner for two, and a complimentary shared return seaplane transfer from Velana International Airport.
- Eligibility: open to UK residents
- End date: February 28, 2025
- Enter the travel contest: click here
- Win a ski holiday for four people in Italy. The grand prize includes a 3 nights’ bed and breakfast hotel accommodation at the 4* Hotel Omama in the town of Aosta, a 2-day lift-pass covering the Pila ski resort, ski and boot hire, clothing rental, airport transfers (from Turin, Milan Malpensa or Geneva) and in-resort support and assistance from your Interski rep.
- Eligibility: open to all
- End date: February 21, 2025
- Enter the travel contest: click here
- Win a Cruise to the Azores, Portugal. The grand prize is a cruise for two to the beautiful Azores archipelago, located off the coast of Portugal. The prize draw winner will set sail from Dover on board the ship Borealis, for a 13 night adventure, staying in an Ocean View cabin. Along the way, guests will be able to experience the volcanic wonders of the Azorean Islands, from the Sete Cidades crater lakes and Furnas Valley hot springs to the ancient Algar do Carvao lava tube.
- Eligibility: open to all
- End date: January 6, 2025
- Enter the travel contest: click here
- Win an all-inclusive holiday to Antigua. The grand prize is a seven-night, all-inclusive stay for two adults in a Waterfront Suite at The Verandah Antigua. Flights and transfers are not included.
- Eligibility: open to UK residents
- End date: January 31, 2025
- Enter the travel contest: click here
- Win a Greek island cruise. The winner and guest will spend 10 days enjoying Seafarer’s Classical Greece itinerary. The prize includes two nights’ hotel accommodation in Athens and seven nights’ ship accommodation in a double or twin cabin, with buffet breakfasts and a welcome cocktail on arrival. Return flights from the UK and in-destination transfers will be provided.
- Eligibility: open to UK residents
- End date: January 31, 2024
- Enter the travel contest: click here
- Win a 3-night stay at any Small Luxury Hotels of the World (SLH) property. The grand prize is a luxurious three-night stay at any Small Luxury Hotels of the World™ (SLH) property, plus an SLH book and Swoon by SLH magazine. Small Luxury Hotels of the World is a collection of independently operated luxury hotels in the world.
- Eligibility: open to UK residents
- End date: January 6, 2025
- Enter the travel contest: click here
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