As for flight connections, Barcelona and Madrid should have decent connections to Toronto and Delhi, while Casablanca (Morocco’s largest airport) probably does not. So Spain is the better choice by that standard. On the other hand, you can get to Morocco by ferry from Spain in a short time, so you could go to Spain and also visit Morocco for a day or two.
I’m not really an expert on surf destinations and even less so on skate parks, although I am aware of many places that do have good surf beaches. From Ireland I think your two best bets would be either Rincon, Puerto Rico, which has the best surfing in the Caribbean and is good for longer rentals like that. You could get a reasonably priced flight into San Juan, which is also a really nice place with some surfing and great beaches, and then hire a car for the drive to Rincon.

The article was written in 2013, but then updated and expanded every year. Since so many people visiting New Zealand do it in a rented car or camper van, all of the companies have deals that include the ferry crossing and returning the car on a different island. Just shop around online and you’ll find prices that include all of that. And also look into renting a campervan if that appeals to you at all. It’s really a wonderful way to see the country, and it’s cheaper than renting a car and staying in hotels or cabins.
I’m happy to try to help. It’s hard to say whether one 30-day trip would be better than several shorter trips. On one hand, it’s much more efficient to go for a month because it obviously saves you all the going back and forth. Also, one week is a short time to go 7 or 8 time zones away, as it takes pretty much an entire day each way, and at least a few days to adjust to the time change. Hmmm…
I have been reading the thread with great interest. I took my 2 daughters aged 11 and 18 to SE Asia in December and they loved it. Siem Reap – lovely vibe over new year and not too busy. Would stay longer than 3 days because the heat and humidity slows you down and you would rather want to cool down in the hotel pool in afternoons and try and squeeze in more than 1 wat in a day. Easy to get around and good food and vibe in Pub Street.
There are always those travelers who celebrate the end of summer and the opportunity to don a sweater and take out the wool scarves and quilted jackets. For them, Iceland would be a perfect destination, with a chance to see the Northern Lights and adorable sled dogs. Montreal is another place with a winter chill, and at the end of the month, you might even find an early Christmas market. San Antonio gets into the holiday spirit at the end of November as well. Sedona offers chilly nights and gorgeous scenery, while Hilton Head Island still enjoys autumn weather and activities.
Pay homage to the Native American heritage of the U S of A by taking in the sights and sounds of Arizona’s capital city for pure rest and relaxation before the holiday season. Phoenix anchors a sprawling, multicity metropolitan area known as the Valley of the Sun, which is highly regarded for its luxury resorts, vibrant nightclubs, designer golf courses, and long lasting sunshine and warmth—even through the winter months. Attractions include the Heard Museum and the Pueblo Grande Museum & Archaeological Park. Be sure to check them out!
Wine aficionados will enjoy sipping Argentina’s well-respected wines, Malbec, a rich red wine, and Torrontes, an aromatic white. Malbec is a perfect match for Argentina’s beef dishes, and Torrontes would make a delightful partner to Milanesa, whether veal or chicken, pounded thin, breaded, and fried. The country’s cuisine demonstrates the influence of Italy; about 3 million Italians migrated there during the late 19th and early 20th centuries. Pizza, pasta, and helado, an ice cream similar to gelato, are as much a part of the cuisine as their asados, barbecued beef grilled on a parillo. Consider a stay at the historic Savoy Hotel, WorldHotels Collection in the artsy Avenue Corrientes area with its elegant neo-baroque lobby, adorned with chandeliers and frescoes.
“Winter in Eastern Canada” might sound more like a 19th-century prison sentence than it does a pleasant vacation, but Quebec City does the cold better than anywhere in North America. Blanketed in snow, QC looks like the world’s most elaborately constructed Christmas village. The cobblestone streets in Old Quebec densely packed with storefronts beckoning you to come in for hot food and baked goods, and boisterous bars overflow with a cacophony of Quebecoise. In December the streets are draped with Christmas wreaths and populated with carolers, plus there’s an authentic German Christmas market -- a true novelty in a city so overwhelmingly French.

Pretty much everywhere is going to be at or near capacity for those dates because half the world is on Christmas break. Between Australia and New Zealand, I think New Zealand would be far more interesting for 10 to 14 days. In Australia you pretty much have to spend a few days in Sydney, a few days in Melbourne, and a few days at the Great Barrier Reef, all of which require flights and will be very crowded over those weeks.
Without knowing more about your interests, my top suggestion would be to focus on Sydney and Melbourne and the areas around both. The Blue Mountains near Sydney are also nice for a couple days or so. The main challenge you’d have in seeing a lot of Australia is that it’s all so spread out. You can hire a car for Melbourne and Sydney and that whole area, but it’s better to fly to get to Uluru (near Alice Springs) or Brisbane or Cairns/Great Barrier Reef or Perth. You’d be driving for days in between those places if you started from the southeast area where most people live.
In her dynamite cookbook “Martha Stewart’s Vegetables,” the queen of domesticity shows how acorn squash can be a canvas for a variety of flavors. Roasted with sesame seeds and cumin, the squash takes on the warmth of the Mediterranean. Tossed with bacon, maple syrup and a touch of cayenne, it echoes the comfort of the breakfast table. And paired with orange peel, sage leaves and a touch of grated Parmigiano offers the perfect balance to rich gravy and herbed stuffing.
You would probably get some rain in Cartagena in November, but mostly in the first half of the month, and even then it tends to come down in short bursts rather than all day, so it’s usually easy to avoid. I love Cartagena for trips like this because the walled historic part of the city is really lovely and fun, with plenty to see and do. The nearby beaches are big, but the sand isn’t white and fluffy, so they won’t make too many “best beaches” lists. It’s also very cheap there, and especially at the tail end of the off season like that. As long as you don’t mind the possibility of a couple of quick rain storms, it should be great.
My two years in southeast Asia was over a few trips, although I did have my own apartment in Bangkok for 3 months and in Chiang Mai for another 3 months. As an American I didn’t have a national health restriction and I didn’t even have travel insurance. I don’t recommend it for everybody, but healthcare in those areas is extremely cheap and of pretty good quality. I went to a hospital once in Chiang Mai and I saw an English-speaking doctor for about US$7, and spent another US$25 or so on a prescription. My longest total trip was 3 years and 7 months (only a few years ago), and I went in and out of Southeast Asia a few times in that period.
This sounds like a really fun trip you have in mind. I think the challenge is that most of Europe is much closer to 50F than 80F in November, and a good chunk of Europe is already colder than that. I’m running a new series highlighting the best places in Europe (and Asia) to go each month of the year, and I think that the best Europe destinations in November would be helpful to you. Another tricky thing is that you’ve been to many of the warmer places already, and I do understand your boyfriend’s desire to go someplace that neither of you have been.

If you are really only going for 4 or 5 days you only have time to visit one or maybe two cities anyway. I’d say that Lisbon would be ideal and you’d have time also for a short visit to Porto or the Algarve in the south, or at least the historic small town of Sintra, which is near Lisbon. Lisbon has fantastic weather for Europe and it’s a lovely city with plenty to see and do.
Those temples are all outdoor for the most part, so cooler and dryer conditions mean you can spend more time touring the temples and still being comfortable. Almost any other month of the year and you'll be better off going back to your hotel for a few hours in the afternoon, but in December you can carry on all day if you like. The town of Siem Reap is a delight in itself, but of course it fills up near Christmas.
I haven’t followed the Zika list, but I do understand the concern. Since you aren’t big beach people, you might just bring jackets and go to a more romantic city like Paris, and then maybe down to Nice for part of the trip and something a bit different. I’m not sure if this is helping, but if you have any questions about any of this I’m happy to keep trying. -Roger
For those from the Northern hemisphere in need of decent a blast of winter sun, the picturesque coastal town of Essaouira is the perfect place to put your feet up and relax. Fresh-caught fish sizzles on beachside grills, whitewashed houses with blue shutters lend a Mediterranean vibe, and you can lose hours wandering through the dozens of art galleries and workshops.
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