If you are looking for an all-inclusive resort with reasonable airfares from Chicagoland, your best bets will be in Punta Cana, Dominican Republic, or the Cancun/Playa del Carmen area. Both have everything on your list, except perhaps wild life, depending on how you define that. You can get cheaper flights into Cancun, and there is a wide variety of offerings once you are there. If you don’t think you want to leave the hotel much, then stay in the Cancun hotel district or along the Maya Riviera nearby. But if you want to interact with a real and lovely town, then stay in Playa del Carmen or over on Cozumel. There are many nearby activities and some very interesting ruins.
If you are looking for a cheap, beautiful, and relaxing beach destination during December then Goa is ideal. This has become hugely popular with package tourists from Europe and Israel (and more recently Russia), and the facts that pretty much everyone speaks English and there aren't many cultural opportunities means that it's a perfect place to just vegetate in a beach chair for a week or two.
Santa Barbara has earned its nickname, “The American Riviera,” with its stunning coastline, lush landscapes, cafes, restaurants, and year-round Mediterranean-like weather. Sandy beaches invite sunbathers, and for those interested in more activity, there’s biking, paddle boarding, surfing, and kayaking. In the heart of Santa Barbara County wine country, the city presents more than two dozen downtown tasting rooms on its “Urban Wine Trail.” The artsy “Funk Zone,” with a variety of cleverly designed eateries and shops, is just blocks from the beach. The community is recovering from devastating fires and mudslides, and its resilience is apparent with new hotels, restaurants, and attractions. The Montecito neighborhood, particularly hard hit by the tragic events, is home to the recently renovated Montecito Inn and its new dining venues, Phillip Frankland Lee's The Monarch, and the suave Chaplin’s Martini Bar, commemorating Charlie Chaplin, one of the hotel’s original owners when it was built in 1928. The elegant oceanfront Four Seasons Resort The Biltmore Santa Barbara offers a luxurious spa and views of Butterfly Beach. Less than two hours north of Los Angeles, Santa Barbara celebrates the holiday season with colorful lights, a Holiday Parade (Dec. 7), Harbor Boat Parade with fireworks (Dec. 16), European-style Christmas market, and the traditional "Nutcracker Suite" at the Granada Theater.
The last one is a 10 day trip for spring break 2018 most likely to be from March 9th to March 18. I’m thinking Europe but I don’t want to stay only in one country. I have so many options that I need someone to shorten the list in a way that it will work out. I want to go to Amsterdam, Rome,Venice,London,Barcelona,Zurich,Madeira,Dublin, and Madrid. (Amsterdam & Barcelona are a must).
In Rome, the Coliseum and Ancient Rome are outdoors, but the city also doesn’t get as cold as the others so most likely you’ll be fine if you bundle up a bit. In Venice, they often have those floods during December, but they come and go every 6 hours so even if you get unlucky you’ll still be able to get around half the day, and it’s a small city anyway.

Cambodia could work because Siem Reap is inland and the amazing Angkor Wat temples are worth a full day or two, and the town of Siem Reap itself is quite nice. You could actually combine a couple days in Siem Reap with a few days in Bangkok, and take a (cheap) luxury bus between the two. Bangkok is a really fascinating city with a lot to see, plus it’s a great transport hub. The other main non-beach option in Thailand is the city of Chiang Mai, which is wonderfully inexpensive with quite a bit to see. It’s even a bit cool during December, so that might be a nice change of pace from India. Many people are also going to Myanmar these days, although I haven’t been yet so it’s hard for me to recommend it. I’d say if you combined 2 or even 3 of these places you could have a very interesting holiday.
Obviously you’d get a refund if an airline canceled your incoming flight, so I guess it’s more a matter of being able to book an alternative without much notice at that point, and that can be tricky. I’ll probably be coming from Hong Kong or Kuala Lumpur, and those flights are always pretty cheap. If I was coming from Europe or North America, I’d probably just wait and hope that the ash cloud starts to subside, and also get a back-up destination ready. If you mainly just want to hang out on a lovely beach and do some water activities and such, then I’d take a look at Boracay Island. However, it’s small and doesn’t come close for cultural activities or natural sights, although other parts of the Philippines are better in those regards.

The reason for the recommendation is that Bali is not only a yoga and “spiritual” hot spot, but it’s also the most popular island for solo women travelers in the region. The book and movie “Eat, Pray, Love” was inspired by this trend, and they have in turn inspired thousands of solo female visitors to go there and stay for long periods, particularly in and around the Ubud area. It’s gorgeous and quite cheap once you get there, and the locals are generally gentle and kind to all. Most other tropical hot spots in Asia have far more solo male visitors than solo females. Just avoid lingering in the Kuta Beach area, because it’s packed with bars and loud backpacker party people. Most of the rest of the island is quite mellow.

Sunny SoCal may be beautiful all year-round, but the more-than-mild temperatures of November make it an even more stellar choice for those hoping for not-too-harsh sun, sand, and sea to chase away any impending winter blues. Head on over to the world-famous Santa Monica Pier or shop till you drop at Third Street Promenade. Of course, there’s also the good old beach itself, where you’ll find surfers, beach babes, locals, and tourists alike mingling festively together at Pacific Park amusement park, the outdoor gym at Muscle Beach, or on the historic Looff Hippodrome Carousel-- there’s also Bergamot Station in the heart of the city, which houses several art galleries to check out.
In Central America you could consider Belize. It’s small, but it’s got islands and beaches (not everywhere though) and forests and other cultural sights, and English is more or less the official language. It’s not as well organized as Costa Rica, but it’s not bad and it feels safe. The other to consider there is Panama, which obviously has a lot in common with Costa Rica. It has far fewer adventure activities and the good beaches are spaced out a bit, but still it’s a relatively rich country with tens of thousands of Americans and Canadians living there as well as visiting, so they have a good tourist infrastructure and it’s safe.

The three places that jump out to me are the Playa del Carmen area just south of Cancun in Mexico, the island of Puerto Rico, or Costa Rica. All of those have endless beach activities and sights and great food and everything else, and they are all well within your budget. Puerto Rico would be easiest, and probably my first choice. Costa Rica is better known for adventure activities that might suit the younger ones. There are several good resort areas along the Pacific coast that would work.

Thank you for the kind words. I know what you mean about the image of Thailand and Bali, particularly among Australians. On one hand you could go to either of those places and easily avoid the most notorious party neighborhoods, but it’s probably easier to head somewhere else since both of those places are so crowded that time of year anyway. I do have a few suggestions, which I’ll describe briefly and then if you want more details about any that appeal to you I can do that in a follow up comment.

If a warm weather getaway sounds appealing, consider seeking the sun in Cartagena where summer is approaching. The South American city offers history, Christmas spirit, and unique gifts for holiday shopping. Sun-drenched Phuket, Thailand’s popular island, is a place to relax during the day and party at night. St. Bart's in the Caribbean is recovering nicely from hurricane damage, an ideal spot for a winter vacation. Miami’s December weather is perfect for a warm Christmas, and Art Basel, early in the month, is an exciting time for fans of contemporary art. In Santa Barbara, a few days of pampering might fit the bill, or you can join in their holiday festivities throughout the month. Death Valley, in the middle of the Mojave Desert, offers a respite from the crowds and a chance to enjoy quiet days and starry nights.

St. Bart's is a French island and a member of the European Union. First discovered by Columbus in 1493 and named after his brother Bartolomeo, St. Bart's has been populated through the years by native Arawaks, pirates, French colonists, Swedish settlers, and French citizens attracted by the island life. Owned for a time by Sweden before being returned to France, St. Bart's capital, Gustavia, was named for a Swedish king, and the language, along with French, is used for many street signs. In Gustavia, visitors interested in the island’s history can explore 17th-century forts, a lighthouse, and the small Wall House Museum. With 14 public beaches, there’s one for every taste and activity, including a swimsuit-optional spot. Boating, windsurfing, kayaking, sunbathing, shopping, people watching, and exploring the island’s shallow reefs are favorite pastimes. Last September’s Hurricane Irma caused significant damage to the island, but recovery has been swift. After closing a year for renovation, Le Barthelemy Hotel & Spa has just re-opened. Set on the Anse de Grand Cul de Sac, an ideal area for watersports, the eco-friendly hotel emphasizes wellness, with an expansive spa offering hydrotherapy, sauna, and beach yoga. This perfect December island escape is accessible by air or ferry from nearby St. Maarten.
Trekking in Nepal during peak season might not sound like the most sensible choice for penny-pinching backpackers. But you can still enjoy the ideal weather without spending a fortune on in-demand hotels and expensive permits if you're happy to swap big-name trails, like Everest Base Camp and the Annapurna Circuit, for quieter treks to Kanchenjunga Base Camp and around the Langtang Valley. Idyllic conditions (dry but not witheringly hot) are also on offer in Rajasthan, one of India’s most vibrant and varied states. Chug between notable, attraction-rich cities like Jaipur, Jodhpur and Udaipur on an atmospheric and wallet-friendly Indian train, snacking on spicy pakoras and sipping sugary chai en route.
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