Chosen By: Amie O’Shaughnessy, founder and CEO of Ciao Bambino. After having her son, Amie searched extensively for credible resources to provide family-focused advice, direction and useful accommodation information. She quickly realized that there were no relevant resources available, particularly for a discerning traveler, so she decided to help solve this problem and started Ciao Bambino.
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Why: While the devastating hurricanes of 2017 impacted just a portion of the Caribbean region, it damaged some of its more cruise-popular spots, like Tortola in the British Virgin Islands, St. Martin, Puerto Rico, St. Bart's, and the U.S.V.I.’s St. Thomas, St. Croix and St. John. While all are under significant rehab and rebuilding — and most are actually now open to cruise ships and tourists, this could be a perfect year to explore more exotic islands. That’s because lines like Windstar, which had, pre-hurricanes, planned to offer BVI-centric trips, relocated ships to other parts of the Caribbean. The winning trip? We love Wind Surf, one of the line’s sailing vessels, with its trip out of Barbados; ports include Martinique, Guadeloupe, and Montserrat — all islands that heretofore have often been bypassed by established cruise lines. And get this: There’s plenty of cruise capacity in this region, particularly when it comes to small ship sailings. In part, excess cabins are available because many skittish travelers canceled their bookings. As well, they can typically be more expensive (look for $300 per person, per day) than big ship vessels. But do the math: Windstar, and other small ship lines like Crystal, Regent Seven Seas, Seabourn, Azamara, Oceania and Viking Oceans, can actually be quite a good value when compared to land-based properties because they’re more price inclusive. Look for deals that include cocktails, gratuities and shore excursions not to mention pre- and post-cruise hotel stays and, in some cases, airfare to the ships’ port of embarkation.

Why: Oaxaca de Juarez is one of the most beautiful destinations to travel to in Mexico. Colorful markets, charming architecture, cobblestone streets, fun festivals and delicious food are just part of the attraction. Stroll through Oaxaca’s main square, the Zócalo, and relax at a café, people watch and be entertained by dancers and singers in the evenings. Just a few minutes walk from the square is the Mercado Benito Juárez, where you’ll find embroidered goods and straw baskets. Continue walking the pedestrian street called Calle Macedonio, where you’ll find art galleries, cafes, shops and boutique hotels. Visit the Santo Domingo de Guzmán church and monastery that dates back to 1555. Don’t Miss the Museum of Oaxacan Cultures, where you can see the treasures found on Mont Alban — the skull covered in turquoise, carved jaguar bones, gold jewelry and ornaments for a nominal fee. Hungry? Stop by at the food market 20 de Noviembre, where you’ll find piles of fried grasshoppers (chapulines) and Oaxaca cheeses, tamales, meat-filled tortillas, tlayudas, chocolates, coffees and seven types of mole. Get a taste of local dishes at food stalls for under $5 or free Mezcal tastings at Mezcaloteca. It’s easy to find your way around this town, but if you prefer to join a guided walking tour, contact Enjoy Oaxaca — they offer several tours from city tours to day trips to see Mont Alban, Mitla Ruins, Hierve el Agua bubbling springs and the petrified waterfall, as well as cooking classes and many festival tours including the Day of the Dead. Where to Stay? There are several boutique hotels and quaint B&B’s in town. You can reserve a room at Parador San Miguel Oaxaca for as low as $86 per night.
Why: It might be expensive to get to the Northern Territory of Australia, but the investment of money and time is worth it to experience this once-in-a-lifetime destination. The Northern Territory of Australia is best known for Australia’s most famous natural landscape, the dual World Heritage listed, Uluru-Kata Tjuta National Park, which spans 311,000 acres of wilderness. Australia’s spiritual center, Ayer’s Rock, is all lit up by internationally acclaimed artist Bruce Munro’s immersive installation, “Field of Light Uluru.” The exhibition has been so popular since it launched in April 2016 that the artist has agreed to keep the installation open until December 31, 2020. Voyages Indigenous Tourism Australia sustainably manages Ayers Rock Resort on behalf of the Indigenous Land Corporation, and all profits from the business go toward supporting indigenous training and employment across Australia. Safari in Australia? What's that you say, mate? The diverse geographic terrain of the Northern Territory allows for travelers to go from the Outback to the tropical Top End, which experiences some of the dramatic climatic extremes of any region in Australia. The coastal floodplains are Australia’s answer to the Okavango Delta and the Kakadu and Arnhem Land are the heartland of indigenous culture. Stay at Kakadu Lodge and Caravan Park for as little as $78 a night, where you can save your money for the ultimate treat: a stay at the bucket list-worthy Bamurru Plains, a bush camp on the edge of the Kakadu National Park.

* All airline related taxes and fuel surcharges are included. Prices are per person, based on double occupancy, and are subject to change prior to purchase. Some foreign authorities require fees at arrival or departure that must be collected directly from the passengers at the airport. Airline-imposed baggage fees may apply and be due at the airport; please consult your airline prior to departure for the latest fees.
Travel Auctions. There are two kinds of travel auction sites. One allows you to enter your preferred travel dates, destination, and class of service (such as economy or business class), and travel companies compete to offer the lowest-priced trip that meets your criteria. Flightfox is one site that operates this way: It charges a per-trip fee, and while the exact price depends on the trip itself, you can expect to shell out around $30. The other type of travel auction operates the opposite way: Companies offer flights, hotels, or packages, and users can bid on the trips. When the auction closes, the top bid wins. SkyAuction.com operates using this model. It’s free to bid – though you should be aware that additional taxes and fees are unlikely to be included in your bid price, so you will end up paying more than your bid if you win.
Northern California also has many riches and wonders to offer. Nothing beats the morning mist swathing the Golden Gate Bridge during a San Francisco vacation. Be sure to hike at Batteries to Bluffs Trail and take in the expansive ocean views. If you’re craving sparkling pools, shimmering night skies, and majestic mountain scenery, instead of bay views, spending your vacations in Palm Springs is the way to go. Hollywood’s Waiting Room for Heaven is the ultimate desert playground for people-watching and wandering through art galleries.

Package vacations are a great choice for effortless traveling, as they are quick and easy to book and ensure that everything will be taken care of for you. For example, if your flight is canceled, it’s the travel provider’s job to find a new flight for you. You can rest easy knowing that your vacation will be stress-free and you are protected in case of changes to your itinerary.

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