Amazing post! I am taking vacation the last two weeks of November. I am planning to visit Germany for the first week. I also want to soak in some sun and enjoy the beach life during the second week of my vacation . Initially I wanted to go to Spain, but after reading your post I’m a bit discouraged because is not going to be warm enough . I love to sunbathe and outdoors activities . Just as running, hiking, tennis etc . Also I love to learn new cultures and fit in with the locals. Keep it economical .I been to must of the Caribbean and wouldn’t mind revisiting . But open to new warm destinations that would make sense. I would love to hear some of your suggestions .Thank you in Advance and safe travels..

Hmmm…there may not be a Wow Factor in Puerto Rico, especially if you are that used to Caymen. I was thinking more about a really nice place that was easy and with great weather. Costa Rica could have the Wow Factor, however. The country is something like one-third national parks and it is packed with great scenery and adventure activities. It is the zip-lining and canopy tours capital of the Americas, so there are many great options along those lines. And there is the volcano and hot springs and really nice beaches. I’m not sure what you’d consider a Wow Factor, but Costa Rica is probably the most Wow destination other than Hawaii.
The only other suggestion I have, which gets almost no rain in November, is Goa, India. There are about 20 different beach areas in Goa, and some of them (Anjuna and Vagator) are famous as party beaches, while many others are more mellow and family oriented. It’s also very cheap and beach massages and that sort of thing are excellent value. Let me know if you have more questions about that. I hope one of these things works out for you. -Roger
Even cheaper than that is Cartagena, although the flight would probably be a bit more expensive. Cartagena has a gorgeous walled colonial Old City filled with cool hotels, shops, and restaurants, and it’s a 10-minute cheap taxi ride to a strip of beachfront hotels in a modern neighborhood. It helps if you know Spanish in both places, but Playa del Carmen has so many English speakers that it’s easy to get by on that alone. Those are my best picks in our region for inexpensive places that are fun with a lot to offer a solo traveler or small group. Let me know if you have any questions. -Roger
The subtropical climate of Hong Kong means that summers are particularly hot and wet, and spring is warm and humid. November is the sweet spot, with clear, sunny days and mild temperatures. During your trip, you'll want to take a traditional junk boat ride on the harbour (seen here) and check out the sweeping city views from Victoria Peak, which you can reach by tram. Another can't miss? Stockton, a hidden speakeasy-style whiskey bar in Central.
It can still be rainy in Belize in November, so it’s not an ideal time to visit. I quite like Belize and there is a lot to do there, including of course the second largest coral reef in the world. You can also head over the Guatemala border to visit Tikal and even down to Antigua for something different. You don’t get many great beaches there, but aside from that it is great.
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.

Back in 2008, we asked chef Stephanie Kimmel from Eugene's Marche restaurant to take a stab at updating Thanksgiving's well-worn green bean casserole -- you know the one we're talking about, with the canned beans and mushroom soup, topped with fried onions. Kimmel's from-scratch version features colorful fresh green beans that are baked in a homemade white sauce that tastes cleaner than the 1950s tinned three-can combo. If Thanksgiving dinner doesn't feel complete without a green bean casserole, this is the one to make!
Ethiopia is known as the Roof of Africa, and dry November, with the countryside still verdant from the recent rains, is the perfect time to plan a trek in the Simien Mountains, a dramatic plateau that’s home to endemic wildlife – from walia ibex to gelada monkeys. Equally mesmerising landscapes are on offer in Northern Thailand, where hiking trails that thread through waterlogged rice paddies to waterfalls and hilltop stilt villages are even more special without the selfie-snapping summer crowds.
Interestingly, December though February do get a bit cool in Cairo, so it's not a great winter break, but in November it's still pleasantly warm and bone-dry so you can enjoy the outdoors for long periods of time. If you don't mind staying in a locally-owned hotel you can save a lot of money and see some old-world charm at the same time. Reservations in advance aren't necessary, but it's best to book your first couple of days just to avoid all the confusion once you arrive.
The 17th-annual Hilton Head Island Motoring Festival and Concourse d’Elegance takes place Oct. 26-Nov. 4, attracting automobile enthusiasts and all who enjoy the southern charm, splendid fall weather, and extraordinary classic cars. The Hilton Head Island Oyster Festival (Nov. 9-10) is an oyster extravaganza with live music, crafts, a Kid Zone, and sports lounge. A stay at the Inn and Club at Harbour Town at the Sea Pines Resort will provide luxury and comfort in low country style. Or book a home rental through Vacation Company. 
Turkey has bars all over Istanbul and the other tourist cities, but there are also cafes and tea shops and that sort of thing that are filled with locals (and some tourists) all evening. In Dubai and Abu Dhabi, the only bars are attached to hotels (and there are a LOT of them), but almost no locals drink, so there are unlimited evening alternatives. Other nearby Muslim countries such as Oman and Bahrain are similar, except with far fewer tourists (and drinkers).
This is a tricky one. Pretty much every destination in the Tropics has its peak rates of the year during the weeks you have in mind. That said, there are still some fairly cheap destinations in the Caribbean, even at peak rates. However, since you live in South Florida and understandably don’t want to go someplace even hotter during the only semi cool time of the year, it sounds like you are ruling out most of the Tropics.

Bali, which is just south of the equator, would be a good choice in November. It does rain a bit that month, but they are summer storms that tend to only last 30 minutes or so. It’s a wonderful island with great prices on most things, including massages. The complicated thing about Bali is that the main tourist areas of Kuta, Legian, and Seminyak are now so crowded that they can be unpleasant. I spent a month there again earlier this year, and I don’t think I’ll go back to that part of the island.

Regarding Thailand, I’m not familiar with any islands that are beautiful and not touristy. Phuket has beaches all over the island and many of them are isolated so the only guests are those staying at the resort in front of them. If you search other travel sites, including travelfish.org, which I think is the best site for southeast Asia and it’s run by a friend of mine, you can find more information about more obscure Thai islands. One challenge could be that you might have to take two or three total flights and then a ferry ride to reach them.
Since flights to Mexico City from the US and Canada are usually quite cheap this time of year as well, this could be a perfect short cultural holiday. This city has great shopping, dining, and nightlife, and the central historic and tourist districts are far safer than most people would expect. There are ruins just out of town as well, so a bit of everything is available.
You might also consider Malaysia and perhaps a stop in Singapore. Malaysia is actually more modern than Thailand so everything is easy and reliable. They have cheap VIP buses that are very comfortable. Penang in the north is really nice and also interesting. Kuala Lumpur is a modern and pleasant big city. A bit south of that is the colonial town of Malacca, which is also very nice and worth a look. Going south from there you can reach Singapore in a few hours, and that is an amazing city, although accommodation there is expensive.
As you suspected, this is a tricky one. Most of the places that would work for you are having a very rainy month in November, so it’s not a good time. Thailand would actually be a good choice if you can deal with the travel time. The rainy season there ends in October and yet the crowds don’t start appearing until December, so you get low hotel prices with nearly perfect weather. As mentioned, all of the good options in Central or South America have a wet season in November. Argentina could be a good option, as November is late spring there, and it has everything you are looking for. The flights to get there are also fairly long though.
Costa Rica is kind of the Thailand of Latin America in that they have great tourist infrastructure and it’s the easiest place to get around. They also have a lot to offer with the beaches on both coasts and many natural sights and activities, plus of course the Arenal volcano, which is a really nice area. San Jose is best as a place to just pass through on your way somewhere else.

Regarding Thailand, I’m not familiar with any islands that are beautiful and not touristy. Phuket has beaches all over the island and many of them are isolated so the only guests are those staying at the resort in front of them. If you search other travel sites, including travelfish.org, which I think is the best site for southeast Asia and it’s run by a friend of mine, you can find more information about more obscure Thai islands. One challenge could be that you might have to take two or three total flights and then a ferry ride to reach them.

If you are going to that region I suggest you visit a site called travelfish.org, which is by far the best website on SE Asia and it’s run by a friend of mine who lives in Bali. They have busy forums where you can ask questions and quickly get them answered by experts on every imaginable topic there. I’m happy to help more as you are planning, so let me know if you have any other questions. -Roger
The great thing is, many hotels that have rooms with kitchenettes don’t charge more (or it’s minimally extra) than what a normal room would be. Be sure you call in advance to make sure you’re getting a full kitchen. We spent one night at a hotel that claimed they had a kitchenette, but it was really only a dorm room size refrigerator and a microwave.

It’s unfortunate and heartbreaking how many times I have recommended San Juan, Puerto Rico in the last few years. Once they get the power back on I’m sure it’ll be back to normal fairly soon after that, but I’m guessing probably March or later. And fortunately, Nate missed the Cancun area for the most part. Have you considered somewhere in the Cancun/Playa del Carmen/Cozumel area? I’m particularly fond of Playa del Carmen, and that flight to Cancun should be pretty reasonable for you.
Vietnam might be your best choice of the three. Most people (if they can) fly into Hanoi and fly out of Ho Chi Minh City (Saigon) or the other way around. Again, you can travel between them by train, although getting tickets can be a bit complicated. Hanoi is really interesting and nice (and super cheap). The best tourist city in Vietnam is Hoi An, which is between the two big cities. There’s a nice beach there and a bit farther away is Denang, which has large resorts along an excellent beach. Nha Trang is another good beach city in Vietnam, but probably not great for families. Ho Chi Minh City is bigger and more crowded than Saigon, but it’s also more modern (and hotter). You could spend two really nice weeks going north to south in Vietnam with a long stop in Hoi An.
Spend the past two days discussing your ideas. Group thoughts; Is that adventurous and cultural enough? We want a “wow” factor. We have vacationed in Cayman Islands about a dozen weeks since the kids were little (been there done that.). We have ruled out Asia only because don’t see a huge Wow factor for the amount of travel. What about African Safari? Still not ruling out your ideas, just want to know what is Wow about Puerto Rico? Costa Rica?
Really my first bit of advice is that the best place to get a really nice hotel that is on a beach or a hill and has the other nearby and also has great weather in December is Phuket, Thailand. You could go almost anywhere in southeast Asia in December and get good weather and low prices. But Phuket has over 1,000 hotels and hundreds of those are wonderful fairly luxurious hotels or villa complexes that could be perfect for a romantic honeymoon stay.
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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