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.
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Spear fishing, kayaking, and zip lining across the jungle are popular activities. At Hol Chan Marine Reserve, you can safely snorkel alongside sharks and stingrays. The Belize Barrier Reef is a favorite destination for snorkelers and scuba divers and one of the most diverse ecosystems on the planet. Experienced divers may want to plunge into the famous Great Blue Hole of Belize, designated one of the top 10 diving sites in the world by famed French explorer Jacques Cousteau. Family-friendly activities include cave tubing down the rivers of the Belizean rainforest, sailing, bird watching the over 600 species of birds, canoeing, horseback riding, or just relaxing on a beautiful sandy beach. Romantic sunset cruises are a wonderful adult option. Travelers can stay at beachfront properties like Banyan Bay Suites and Grand Colony Villas for an authentic Belize experience.
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.
Thank you so much for the kind words and I’m always happy to hear that people find this information useful. As far as Turkey in December is concerned, I wouldn’t recommend it. I actually lived in a small town near Antalya on the Mediterranean for a bit over a year and I was surprised by the fact that almost everything closed down around 1-November and didn’t start opening again until March or April. Actually, I think Istanbul would still be enjoyable in December and so would Bodrum or any of the other larger cities including Antalya. But anywhere on the coast will be a ghost town and I’m pretty sure that Cappadocia would also be mostly shut for the winter. Ephesus probably stays open, but similar to Cappadocia, the attractions are all outdoors and they can get pretty fierce rainstorms in winter.
There are not one but a cornucopia of hotspots to check out in the Aloha State come November. First, Oahu, which has, throughout the years, been transformed by Asian-Pacific locals from a holiday outpost into a globalized, cosmopolitan destination that offers all the glory of paradise in one locale. You’ve got the allure of the Island landscape, plus the buzz of modern living mixed in a relaxed, slow-paced daily lifestyle near the shores. It is (along with Honolulu) the center of the Hawaiian universe, and will no doubt sprinkle excitement into any Thanksgiving celebration. You might even want to go all out by getting a taste of authentic, fantastic Hawaiian flavor by cooking that turkey in a traditional imu (underground oven)! Those who want to work off all that feasting can hop on into the Turkey Trot 10 Mile Run on Thanksgiving morning and then spend Black Friday enjoying the annual Waikiki Holiday Parade—instead of braving those restless shopping crowds.
You still get warm ocean breezes and 70-degree temperatures, plus the Hawaiian islands go all out for the holidays. Locals host potlatch-style parties where the Christmas goose is replaced by a luau pig, and the resorts deck themselves out like tropical North Poles, including a massive tree-lighting ceremony at the Outrigger on Oahu and tree-decorating contests at Mauna Kea on the Big Island. Residents there climb to the top of the 13,000-foot-tall volcano, shovel snow into their trucks and speed back down to build snowmen in their yards before it melts.

Don’t be too shy to ask the wait staff how the food is prepared. If you suspect something might be breaded ask. Ask if any of the dressings have sugar in them. In Italy it’s not common at all for savoury food to contain any sugar, even the sauces. Most are based on olive oil or cream. If you order a steak without any sauce don’t be afraid to ask for olive oil to use on it. You might get some strange looks if you ask for butter and they might not have any available. Try to go for roasted or grilled food rather than fried as even in Italy, the spiritual home of olive oil, the food is usually fried in vegetable oils. Also don’t be afraid to ask for substitutions. I don’t like bell peppers and they always come as part of grilled vegetable sides. I simply ask them to leave them out and I’ll get more of another type of vegetable instead.
I’ll be happy to try. First off, if you are doing the actual Inca Trail hike, you’ll need 4 days for that plus another couple of days in Cusco to get acclimated. So really that whole part of your trip would be a week. Also, to get to Cusco you pretty much have to go through Lima, and it’s also an interesting city so I’d recommend probably 2 nights there. If you don’t do the Inca Trail and take the train instead, you could save 3 days in Cusco.
My other two suggestions are San Juan, Puerto Rico and Cartagena, Colombia. Both cities have really wonderful colonial districts and modern resort districts nearby. San Juan is more expensive, but still reasonable, and it has far better beaches. Both have a bit of rain in November, but it tends to come and go quickly. You’ll get similar rainstorms in most of the Caribbean in November, so it’s a bit tricky. I hope this helps. If you had something else in mind let me know and I’ll try again. -Roger
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