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A belle epoque grande dame presiding over San Sebastián’s iconic La Concha Beach, the Hotel de Londres y de Inglaterra has been a palace, casino, hospital, and of course hotel since its construction in 1865. Before and after World War I, it was the kind of place where well-to-do Europeans went on seaside holidays for months at a time, enjoying direct beach access, the city’s renowned seafood, and the hotel’s elegant design. Nowadays, the society consists of a somewhat less star-studded lineup—once Toulouse-Lautrec, Archduchess Elizabeth of Austria, and Mata Hari were all guests—but the unobstructed Bahía de la Concha views, lovely rooms (all with private balconies), and pride of place at the heart of the city remain. The window-lined brasserie takes its cue from classic French bistros—it’s not hard to imagine that the well-dressed gentlemen at the next table are French aristocrats-in-exile—and its tables along the beachfront promenade are the perfect place to while away a few hours over pintxos, txakoli (a sparkling white wine from Basque Country), and people watching. If you were to spend a few months in a seaside town, this would be the way to do it.

Inaugurated in 1912 by its namesake, the Spanish regent Maria Cristina, this belle epoque landmark has welcomed international elite to its gilded halls from day one. Designed by the same architect behind the Ritz in Paris, the hotel has long been a favorite of celebrities during the San Sebastián Film Festival (Bette Davis was, notably, a fan). A $25 million renovation in 2012 only cemented its status as the city’s most luxurious hotel. With three of the city’s most elegant eateries (including a favorite see-and-be-seen bar), panoramic views of iconic belle epoque buildings and the Urumea River from the many terraces, and signature Luxury Collection concierge service, the Maria Cristina still feels fit for the aristocracy who frequented it in the city’s beach-destination heyday. Spacious and decadent rooms with an updated belle epoque style, as well as a central location within walking distance of many of San Sebastián’s Michelin-starred restaurants, only sweeten the deal.

The Beatles stayed here. Cary Grant stayed here. The Spanish royal family has even stayed here, in their own home city. Can there be any better endorsement?

A grande dame in a city known for drama and extravagance, the Gran Meliá Fénix is exactly the kind of traditionally luxe hotel every European capital needs. An imposing structure presiding over one of Madrid’s main avenues, the hotel’s first impression is topped only by its second: a columned marble lobby worthy of a palace, filled with elegant Louis XVII chairs and crowned with a stained-glass dome. Rooms exude Old World splendor, while Red Level suites take the royal residence atmosphere to the next level, with over-the-top service that includes a private lounge with an open bar, free breakfast, and a private balcony overlooking the city—even though many of the top suites also have scenic private terraces with hot tubs.

As with all opulent institutions, even nonresidents participate in the hotel’s ritzy society scene, courtesy of its acclaimed, art deco–styled brasserie and sultry cocktail bar where, if you order a martini, you’ll receive a numbered certificate in accordance with the automated martini counter over the bar. But, with a scene like this, most guests here don’t worry about counting their martinis.

What is more romantic than an intricate and well-used Spanish fan? Fans are a highly personal item, and like perfume, one should only use the best they can find (or so my mother always said). For the royal minded there is only one choice, Casa de Diego. Founded in 1858, this a business steeped in international approval, and the generations have been privileged to create masterpiece shawls, umbrellas, and of course fans for royal families all over the world. Proudly facing the Puerta del Sol is the window display of fans, giving only a glimmer into the magic on the other side of the doors. Right outside is the hustle and bustle of city center, but inside the shop you are transported to a haven of beauty. Take home a piece of Spanish tradition with you, and smile every time you fan yourself, remembering Madrid.

Madrid’s largest park, named after King Juan Carlos I, is a short metro ride from downtown, but from the moment you leave the station you feel as though you’ve been transported to a faraway land of fairy tales. Giant sculptures decorate the massive grounds, with dedications to Galileo, victims of the Holocaust, and world peace, respectively. If the weather is fair, there is a free train which offers rides every hour on the hour around the entire park—the only way you can see the whole place in a day!

The Catalan capital has plenty of places to cozy up with your loved one and enjoy your drink of choice, be it a meaty Tarragona red or a café carajillo—the Spanish spin on Irish coffee. Lean your elbows on the marble tables of Casa Almirall, located in Barcelona’s gritty Raval neighborhood and founded in 1860, while nibbling olives and sipping the house vermouth on the rocks. Alternatively, share a bottle of cava at El Bosc de les Fades, a fairytale forest-themed café inside Barcelona’s Wax Museum off La Rambla. With its soft lighting and bohemian ambiance, Andú (c/Correu Vell, 3) is the perfect place to share cava and light tapas in a homely and intimate setting.

It was raining when we arrived in Donostia-San Sebastian, but the skies cleared on our second day, and we rode the funicular railway up Mount Igueldo to take in the view back on the city, La Concha Bay, and the empty beach. The “low” travel season had just begun, and the strange little children’s amusement park on the mountaintop had shuttered up for the fall and winter, adding just the right disorienting touch of weird desolation to the Basque country panorama.

Over the last several years, Madrid‘s river redevelopment has really come together. What used to be sludgy is now sparkling, with walkways and bridges intertwined along the river, with kids playing, people jogging and chatting. A great place to get away from the crowds, even in the winter. Tourists don’t really know about it, which makes it even better. Go at sunset so you can watch the lights of the city come on and the moon rise. Start on the south side, by the new Matedero arts center and move your way up north to the Royal Palace. Delightful way to spend an early evening.

Michelin-star chef, and virtually self-taught man, Francesc Rovira’s cafe and restaurant in sleepy Gombrèn is not centrally located for gastronomy enthusiasts to find. Far from Barcelona, but not too far to drive for a day, nestled in the Pyrenees - it is worth its own adventure. Rovira is one of many chefs who cooks with local ingredients and because mushrooms are so important to the region he cooks, mushrooms are one of his most well used ingredients. From the nearby forest at Montgrony he sources fungi in varying colors, shapes and sizes - only purchasing what he cannot pick himself because he is now known for the way he uses this ingredient. If mushrooms aren’t your thing, venture to Fonda Xesc anyway. The pumpkin soup with elderberry ice cream was a revelation in my mouth and the wine pairings were some of the best I’ve ever experienced. There’s no pretention in Rovira’s restaurant, only very good gastronomy.

Anyone with an iota of interest in art will certainly visit the Prado while in Madrid. But be sure to save some time to visit another nearby museum, where there’s something wonderful to see before you even get inside. Just a 5-minute walk down Paseo del Prado you’ll find the CaixaForum Madrid, with its awe-inspiring vertical garden. From a distance, you might even think you’re looking at a mural there on the wall, but as you approach, the lush greens and earth tones come to life with varying textures that are luscious and welcoming. A masterpiece where nature is the medium!

Even now I’m craving their guilt-free collection of tapas-style breakfast miniatures. You can expect to find little croissants stuffed with jamon, light pastries topped with berries, and fresh squeezed orange juice. It’s simple, inexpensive, and quick—nothing fancy but perfect for a snack. I should note it’s a chain but it’s where the locals go, so don’t write it off and pop in when you see one. Tip: Grab a little tile to your right when you walk in, order at the counter and they’ll write on it. If you’re like me, you’ll go back for more so bring it up with you for round two. Then pay when you’ve finished.

Eat dinner like a conquistador at Restaurante Sobrino de Botin. The combination of its central location off Plaza Mayor and its claim to be the “Oldest Restaurant in the World” makes it charming and fun for family and friends. Make sure to put in a reservation in advance and order a traditional dish. I particularly enjoyed the incredibly thin jamon because it was light and not oversalted.

Vinos Ezeiza is a store of a dying breed. A knowledgeable owner stands among dusty wine bottles, able to answer any question you might have about his collection. Headed out to a fiesta? Bring your wineskin and fill it by volume. Buying Rioja wine in bulk is the ultimate Basque shopping experience.

One of Mallorca’s oldest converted fincas (rural farmhouse estates), Es Castell epitomizes the eco-conscious boutique hotels that are subverting the island’s conventional tourist image. From $175. C/Binibona s/n, 34/971-875-154 This appeared in the October 2014 issue. Tom Downey explored Mallorca beyond the beach and found...shoes? Read the full story here

“A poorly grilled turbot is a turbot that has died in vain.” This is the motto that hangs in Kai Kaipe, one of the two stars in a village that really shouldn’t have any. They specialize, like Elkano, in grilled fish. Locals who prefer Kai Kaipe do so for the wine list and the ambience.