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Ask An Expert: Planning Your Winter Getaway

Summer may be nearing an end but that doesn't mean the best time of the year for vacationing is over. In fact, there are many places all over the world that can be that perfect, once-in-a-lifetime setting for a warm winter getaway. While some warm winter destinations may be fairly obvious, Matt Holmes of Boundless Journeys has a few other suggestions, along with some expert advice on planning your fair weather winter trip. Founded in 2003, Boundless Journey is a multi-year award winner and has been selected among the world's best tour operators, based upon readers' surveys from Travel+Leisure.

Matt Holmes (Photo courtesy of Matt Holmes)

About Matt Holmes:

Matt Holmes is the Founder and President of Boundless Journeys, an award-winning boutique, adventure tour operator based in Vermont, where he has personally hand-crafted many of the itineraries based on his own experiences. Before starting Boundless Journeys, he worked for many years as a destination manager, tour designer, travel agent and guide. He has been all over the world and continues exploring new and lesser-known destinations to introduce to travelers.

Journey Beyond Mexico

"When people think of escaping the cold, they often think Mexico, the Caribbean or Florida, which are all lovely places. However, there are so many other great places that are just as warm and wonderful in the winter months. Look a little further south, closer to the equator, and you'll find some fantastic destinations that you may not have thought about initially, some of which are serviced by nonstop flights from a few U.S. destinations. Plus, it's easy enough to stay within the U.S. time zones, so you won't be very jetlagged upon arrival. Costa Rica has a beautiful Caribbean coast and opportunities to hike and kayak through the rainforest, spot exotic birds and animals, and zipline over the jungle canopy. The Galapagos Islands during the winter are sunny and warm, with the calmest seas generally between January and March. It's quite a unique experience to enjoy your evenings on a small expedition cruise boat, much like the first explorers did (only now with better amenities)."

Related: Outdoorsman's Guide To South America

Go Where It's The Shoulder Season

"As you may know, during a destination's peak season, hotels, tours, restaurants and airlines often jack up their prices because the demand is so high — not to mention that you'll be surrounded by a lot of other people. If you're looking for better prices and fewer crowds, consider a destination during its "shoulder season," which means it's in between the high and low tourism seasons. There may be fewer scheduled flights, but if your dates are flexible at all, you may be able to score a deal. December through March is Vietnam's shoulder season and a great time to visit this amazing country. The typhoons and monsoon rains are over, and while you may get some cooler temperatures in the north (low- mid-60s), humidity is low everywhere, and southern Vietnam is sunny and warm. This intriguing country offers a captivating mix of ancient and modern history, French and Asian cultures, intoxicating markets and beautiful seascapes."

New Zealand (Photo courtesy of Matt Holmes)

Think Outside The Box

"When most of the northern hemisphere is cold and snowy, it's easy to forget that it's actually summer for the bottom half of the planet. While heading towards the equator a popular choice, if you want to really expand your options, head way down south. It's a nice change of pace from the "usual" locations we are more familiar with in our own corner of the globe. I'd recommend around two weeks for for a good introduction to a region or small country and travel time on either end. The best country to explore in that time frame is New Zealand, a truly diverse country where you can lie on the beach, hike mountains, bungee-jump, taste wine at a vineyard and visit a Maori village all in one visit. Not only will you find warm weather, but the combination of cuisine, beautiful landscapes, and friendly people make this a true paradise."

Zebras (Photo courtesy of Matt Holmes)

Experience More Than Just The Beach

If you're looking for a more rewarding and enriching vacation, there are plenty of options from hiking, to kayaking, to wildlife adventures. Leave behind the idea of an all-inclusive beach resort for a more authentic experience. It'll also give you the freedom for some spontaneity. What you may sacrifice in beach time you'll more than make up for in memorable experiences. January through March are some of the best months for spotting adorable baby animals and the migration of colorful birds while on a safari in Tanzania. The big herds of wildebeest and zebra start migrating towards the end of the winter in a spectacular display of hundreds of thousands of animals.

Make sure you go with a certified, naturalist guide, or you'll miss out on a lot of useful and interesting information about animal behavior. They'll also know where the best spots are to see specific animals. And if you're still craving some beach time, it's very easy to extend your trip to Tanzania's Zanzibar Island, where you'll find some of the most amazing beaches in the world.

Find The Hidden Gems

"For a truly exotic escape to get you out of the winter doldrums, go someplace where few people have gone. It'll be a once-in-a-lifetime experience, and you'll be rejuvenated by the feeling of "getting away from it all." It's sometimes hard to find places like that, especially before they're discovered by hordes of tourists. Find destinations that you don't know a lot about and where you might not get the best cell coverage! The South Pacific nation of Palau may well be the most stunning place you've never heard of. It's made up of about two hundred tiny islands, breathtakingly beautiful and remote, and has one of the world's most diverse marine ecosystems. You can swim among non-stinging jellyfish, kayak around uninhabited islands, see brilliant coral reefs through crystalline water, and dine on the beach with palms rustling in the gentle breeze."

Related: Best Coral Reefs To Visit In The World

Randy Yagi is an award-winning freelance writer covering national/international travel for CBS Local and all things San Francisco for CBS San Francisco. In 2012, he received a Media Fellowship from Stanford University. He may be contacted via Twitter or Linkedin .
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