Rose O'Connor Travel
Luxury Travel Worldwide

My Travels

My Travels

Escape the Ordinary With These Unexpected Holiday Getaways

With summer winding down and fall just around the corner, it’s time to plan your holiday travels. The Festive season is one of the busiest travel times, so the sooner you start planning the more options you will have. Still unsure of where you want to go? Interested in trying something different? Here are five fresh ideas.

Yachting in the Caribbean

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Imagine escaping the cold and island hopping in the Caribbean aboard an intimate yacht. After unpacking (only once!), you will explore small ports in St. Barths, St. Lucia, and Barbados by day and enjoy top cuisine on board by night. I know what you’re thinking, and it’s not too good to be true! My partners at SeaDream Yacht Club have two holiday sailings, and when you book with me you can get $1000 off! 

Villa Rental

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If you are trying to get away during the holidays with the whole family, renting a villa is the way to go. Getting connecting rooms or even rooms on the same floor can be a battle at many hotels and resorts over the Holidays. But with your own private villa, you can all stay together while enjoying your private pool, chef, and more. 

Holiday Market River Cruise


Why fight crowds at a shopping mall or burn your retinas online shopping when you could stroll through local markets and find special gifts while sipping Gluhwein (spiced mulled wine)? A Christmas Markets cruise in Europe lets you have a unique vacation plus get your holiday shopping done – it’s a win-win!

Exotic Skiing


If a ski trip is on your holiday wish list, go somewhere different this year. How about heli-skiing in Canada, hitting the slopes in Switzerland, or snowboarding in Japan? These lesser known ski destinations are sure to please skiers and non-skiers alike.

New York


New York may not be an under-the-radar destination, but my trusted travel partners can take your long-weekend trip to a new level. From securing a private spot to watch the Macy’s Thanksgiving Day Parade to a VIP shopping experience and backstage Broadway passes, this is not your average Big Apple adventure. 

Contact me for exclusive amenities and benefits, white-glove service, and personalized itineraries that turn ordinary trips into exceptional travel experiences.

Rose O'Connor