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AFAR chose a destination at random—by literally spinning a globe—and sent Chris Colin on a spontaneous journey to Iceland.

While there are a growing number of beach resorts on St. Kitts, you can still find plenty of secluded sands around the island when you want to disappear for a few hours. Visitors can also look forward to sunbathing on the black sand of Dieppe Bay, spotting dolphins on Turtle Beach, or snorkeling over shipwrecks in White House Bay.

Every once in a while, the sun shines bright in San Francisco and every city residents flocks to the nearest park or beach to soak up the sun and day drink. Baker Beach, in the confines of SF, seems worlds away from city life. The view of the Golden Gate Bridge is spectacular, and the diverse group of Baker Beach visitors is a testament to what a hodge podge San Francisco truly is. Parking can be a pain in the butt; take the 29 bus and save yourself the hassle.

This popular Mexican-food mainstay in the heart of San Francisco‘s Mission District is one of two places in the city that claim to have invented the Mission-style burrito (the other is El Faro): a hefty, elephant-leg-size wrap distinguished from other burritos by its size and the inclusion of rice and other ingredients. The restaurant was first opened as a meat market in 1967 by Mexican immigrants Raul and Michaela Duran, who are said to have served their first burrito in 1969 after noticing that local workers needed a substantial yet portable meal. The Mission Burrito was born, containing most of the food groups: protein, vegetables, dairy, and grains. The Durans converted their meat market into a full-time restaurant in 1972. Taqueria la Cumbre offers a full menu of Mexican food, all made fresh. The burritos are made assembly-line style. (Fun fact: When the Durans first came to San Francisco, they hired a high school kid to make flour tortillas before school. The kid, Jorge Santana, would go on to be a popular musician, like his brother Carlos.)

Yep, you read that right: There is a Pirate Supply Store in the heart of the Mission! In their words: “We are a ragtag group of miscreants who sell pirate supplies in order to benefit the free programming that happens at our writing-tutoring center at 826 Valencia, and in classrooms all over San Francisco.” Cofounded by author David Eggers, the non-profit organization 826 Valencia (which is their address, not coincidentally) teaches writing to teachers and students all over the Bay Area. Chapters of 826 have also been founded in seven other cities around the country. The Pirate Supply Store—if you’re still baffled by this, they do indeed sell pirate supplies like hooks and eyepatches—is just one part of the 826 network, with other chapters having similarly quirky stores, such as Brooklyn’s Superhero Supply Co., Los Angeles’ Time Travel Mart, or Washington, D.C.’s Museum of Unnatural History. The Pirate Supply Store is open every day from noon to 6 p.m.

While Heath Ceramics is over 60 years old, having been founded in 1948 in Sausalito, their colorful bud vases, dinnerware and tiles have enjoyed a boom in recent years. Straddling the line between a rough, hand-crafted aesthetic and an elegant, understated quality, their pieces are hard to miss in the pages of design magazines as well as at the homes of some of your most tasteful friends. The new retail location on 18th Street includes a workshop alongside a café serving Blue Bottle coffee. There is also a smaller location in the Ferry Building.

Jamaica is much more than just the beach. The island’s great outdoors includes thick rain forest, numerous waterfalls, rivers on which the sport of rafting was born, swimming holes, and more. Jamaica’s natural beauty has been the set for more than one Hollywood movie, and if you really can’t drag yourself away from the beach, the bioluminescent bays offer a different form of outdoor adventure.

It always feels like a different world anywhere in the beautiful Point Reyes National Seashore area, and an evening at the hidden Nick’s Cove in Marshall, will have you in love with Tomales Bay. The property was recently overhauled by a group of silent investors that purchased the cottages and the restaurant and they’ve made some phenomenal improvements. Austin Perkins is the new head chef and the genius behind the BBQ oysters. After you’ve been checked in and escorted to your cottage, a delivery of complimentary oysters arrive at your doorstep. I kept hoping the staff at reception would change so that I could check in again. The rooms are cozy and spacious and the fireplace will always be a hit on the foggy and cool evenings. Be sure to either have dinner in the restaurant/bar, or ask for take out and have the meal delivered at the end of the pier, in the famous Boathouse. I’d also recommend making arrangements to start the next morning off right, with a paddle in Tomales Bay in a kayak. Local outfitter Blue Waters Kayaking will literally meet you on the deck of your cottage (if you’re lucky enough to secure one of the rooms on the water) and show you the magic of the area, the true way it needs to be seen. You’ll need to save up (and reserve far in advance) for a room at Nick’s Cove, but the experience is worth the pretty penny.

You may know Corona, Tecate, and Modelo, but there’s much more to Mexico City’s bar scene than exported beers. Try domestic craft brews, wine from Baja California that’s rarely exported, and local spirits like tequila, mezcal, and pulque. For something less spirited, visit the many cafes where you can drink coffee or chocolate at any time of day.

Take San Francisco’s defining features—its booming tech industry, its creative heart, its killer restaurant scene—and squeeze them into a 100-year-old building in a neighborhood undergoing a sea change. That’s Hotel Zetta. The dynamic property, which re-opened as Hotel Zetta in 2013, couldn’t be more, well, San Francisco.

In the lobby, there’s a chandelier fashioned from recycled sunglass lenses, a front desk made from reclaimed wood, and a two-story Plinko board (an interactive art piece) that descends from the Playroom. About that: The Playroom caters to the work-hard, play-hard set. A shuffle board, a pool table, and video games (both current and retro) spark friendly competition. A classic London telephone booth lets guests order room service or video chat. Modern amenities continue in the rooms. Desks built from kitchen butcher blocks encourage standing while working. A G-Link docking station facilitates wireless streaming from tablets and smartphones to flat-screen Samsung Smart TVs, which come pre-loaded with complimentary Internet service, apps and HD channels.

The art? A blend of analog and digital. Art in the guestrooms include work by Nick Gentry. He made an original work as a compilation of floppy disks. Then, the work was photographed and screenprinted as a giclee on a canvas for the rooms. Downstairs, two new ventures from famed Bay Area restaurateurs Anna Weinberg, James Nicholas and Chef Jennifer Puccio (of Marlowe and Park Tavern) ensure the young and hungry are adequately fueled.

Few airports put as much thought into traveler’s well-being as San Francisco International. The Berman Reflection Room, one of many unique spaces, provides, “A center for quiet self-reflection and meditation.” Free from distractions—technology, talking and noise—here you can just take a moment to decompress. Easily accessible, pre-security in the main international hall, it can be a meaningful stop before a long journey or after saying goodbye.

A short drive from San Sebastián, the village of Getaria sits sleepily on the coast. Set between the sea and vine-covered mountains, Getaria has a privileged position that makes it a destination not to be missed if visiting nearby San Sebastián. Enjoy the local Basque wine, txakoli, in situ. Bonus points if you do so over some grilled fish, caught and brought daily to Getaria’s active port.

Make your way to Market Street and head to the Hearst Building, where downstairs you’ll find Local Edition. This cocktail bar takes its inspiration from the thriving San Francisco newspaper business of the 50s and 60s, and it shows—you’ll sip on drinks while surrounded by vintage paper presses and archival newspaper clippings. Try their updated version of a San Francisco favorite, the Bloody Mary. Local Edition is open Mondays through Fridays from 5 p.m. to 2 a.m. and Saturdays from 7 p.m. to 2 a.m.

The de Young Museum, with its perforated copper facade and spiraling tower in the center of Golden Gate Park, is as dramatic outside as it is inside. Follow the widening crack in the sidewalk into the atrium. It’s an Andy Goldsworthy–created nod to the tectonic plates that carved out California, and emblematic of the museum, too: The previous building was damaged in the 1989 Loma Prieta earthquake and rebuilt by Herzog & de Meuron, opening in 2005. Inside, Gerhard Richter’s wall-size mural, made from digitally manipulated photographs, greets visitors. The museum specializes in American art, international textile arts and costumes, and art of the ancient Americas, Oceania, and Africa. Visiting exhibitions often focus on modern works and draw massive crowds. Recent blockbusters include Georgia O’Keeffe, Richard Diebenkorn, and David Hockney. Make sure to visit the observation deck at the top of the tower. (It closes one hour before the museum.) It’s a unique view over the low-lying western end of the city.

From restaurants that lean traditionally Mexican to others that veer off into Japanese and Argentinian menus, Los Cabos delivers big flavors. Both San José del Cabo and Cabo San Lucas are as much dining destinations as they are beach spots. Yes, there are tacos. But there are also fine dining restaurants you’ll remember for their fresh local seafood and farm to table delights.