[dropcap size=big]I[/dropcap]f you’re based in the northern hemisphere, you’ve no doubt noticed the recent shift in climate as summer bids farewell and autumn settles in. Gone are the lazy, sunny evenings that seem to last forever. Now there’s a chill in the air and the leaves are starting to turn brown. win a $5000 5-night luxury stay

So, if you’re anything like me, you’ve already started daydreaming about booking a winter escape…but wouldn’t it be awesome if you could win one? win a $5000 5-night luxury stay

Fancy $5000 to help make your dream a reality?

Enter the Choose Your Travel Adventure trip sweepstakes from Tokio Marine HCC – MIS Group to win a $5000, five-night stay at one of three incredible destinations! The prize package includes lodging and airfare to the selected location and the remaining funds will be given to the winner for meals and activities on the trip.



A luxurious 5-star hotel in the heart of Sydney’s central business district, choose to stay at Swissotel Sydney and you’ll be within walking distance of some of the city’s most notable landmarks and cultural attractions, including the Sydney Harbour Bridge, Sydney Opera House, and the beautiful Royal Botanic Garden.

Plan your stay with the help of this city guide from my friends Caz & Craig over at Y Travel Blog.



A fabulous 4-star hotel located in Greater Reykjavík, the Hilton Reykjavik Nordica is spacious, easy-going, and oozes Scandinavian chic, making this Hilton perfect for a lavish Icelandic stay. Upper floors have sea views and amenities include 24-hour room service, gym, spa and gourmet restaurant Vox.

Looking for some Icelandic travel fodder to whet your appetite? Check out my guide to the most picture perfect places in Iceland.



Few places within Tuscany boast such a unique history. Steeped in culture, mystery, trade and religion, a stay at the Hotel Brunelleschi is enriched by its fascinating past. Situated in the heart of Florence close to the Dome, the Piazza della Signoria, and the Uffizi, the hotel boasts a Florentine interior of oak floors, tall ceilings, and beds with high velvet headboards.

Check out this guide to Florence by Tokio Marine HCC – MIS Group.

For full terms and conditions click here.


  1. Entrants must answer a series of questions about Atlas Travel insurance. Entrants must answer 3 of the 5 questions correctly to be eligible for the grand prize.
  2. Provide name, email address, and future travel plans (i.e. “are you planning to travel in the next 3-6 months?”). The person must also provide their Twitter handle if they wish to earn the additional entries outlined below.
  3. Entrants may gain additional sweepstakes entries for sharing on social media according to the following guidelines.
  • One additional entry for a social share on Twitter that includes the contest hashtag (#5kTripSweepstakes), mentioning the MIS Group Twitter handle (@hccmis), and linking to the sweepstakes homepage at Tweet must be published within the contest timeframe of Oct. 3-16.
  • One additional sweepstakes entry for following the TM HCC – MIS Group profile on Twitter, located at Those who were already following the MIS Group twitter profile at the onset of the contest will be awarded this extra entry, providing they give their Twitter handle when registering for the contest.

The Grand Prize winner will be randomly selected from those entrants who meet entry conditions.

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Best of luck, and if you win … take me with you!

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