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About Up In the Air

Up in the Air Travels is a travel planning service that takes your pre-departure experience to the next level by providing unique experiences, a sense of anticipation, and above all personalization. When you book with UP, a mystery trip will be planned on your behalf. Full of surprises, but none of the stress, a customized trip based on your preferences will be planned for you and your travel group.


After you complete the initial survey, we can put together your perfect package. Leading up to your departure you’ll receive personalized letters and gifts in the mail, along with a weather appropriate packing list. But don’t worry – we’re careful not to give away the surprise too soon!


Through our partnership with CARE Travel, the personal connections we’ve curated in destination, and our team’s combined expertise – we are ready to provide you with your next holiday. Whether it’s a weekend in Chicago or your dream trip to the Maldives.


Our collaborative approach to itinerary design ensures your receive above and beyond attention, exclusive access, and insider tips to make your trip unforgettable.


“CARE Travel has been my personal travel agency for over 7 years now and the attention to detail is as great today as it has ever been. They have tremendous knowledge on the Caribbean and a ton of its’ hidden treasures. Me and my WHOLE FAMILY would never take a trip (personal or business) without having them manage it from our front door to our vacation door and back. If there is better out there, then I’d be hard pressed to find one. I travel extensively and the CARE Travel team is THE BEST!!!

~ Joel T