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Perched high above the Bay of Positano, Il San Pietro is the epitome of Italian seaside glamour—the hotel has attracted a coterie of international VIPs since its opening in 1970, including Gregory Peck, George Clooney, and Julia Roberts—but retains the charm of a family-run inn. Michelin-starred Zass restaurant culls ingredients from the property’s organic gardens, which spill down to the sea across 10 terraces teeming with local produce, and rooms feature custom ceramic tiles made in local factories using traditional techniques. If the 400 steps down to Positano’s only private beach sound daunting, an elevator cuts through the rock to water level, where tangerine loungers on the stone sundeck give way to a cove with sandy shores. Here, breezy Carlino restaurant serves up lemon spaghetti beneath a cheerful thatched roof. Prefer more active endeavors? Hugging the cliff face above, seaside tennis courts serve up sets with a dazzling view.

Original Joe’s has the same birth year as another pretty famous San Francisco landmark: the Golden Gate Bridge. Both are definitely worth checking out, but only Original Joe’s will serve you a hearty Italian meal in a red leather booth. Back in 1937, the restaurant was a 14-stool counter on Taylor Street where immigrant and family patriarch Tony Rodin served Croatian-Italian-American comfort food. Original Joe’s is run by the third generation of the family. A fire destroyed the first location in 2007, but the corner spot in North Beach that opened five years later can’t be beat. Inside, the family’s San Francisco history is revealed by walls hung with black-and-white photos, letters, and other ephemera. The menu showcases some of Tony’s recipes, such as eggplant parmigiana, Joe’s meatballs, and veal parmigiana. Those counter stools are there, too, saved from the fire and brought over to the new Original Joe’s.

Renowned Costa Rican architect Ronald Zürcher looked to his country’s colonial past when designing this hacienda-style property—witness its central courtyard, arched doorways, and terra-cotta roofs. Set amid a 30-acre coffee plantation just outside the capital city of San Jose, the hotel’s 308 traditional accommodations follow suit with dark wood furnishings, but a modern aesthetic pervades renovated guest rooms with streamlined furniture, intricately patterned bathroom tiles, and expansive views that extend from green lawns to forested mountains and urban skyline; some include small balconies that overlook the hotel’s two pools. On-site dining options include gourmet takes on Costa Rican fare at Hacienda Kitchen, Peruvian specialties at La Isabela, and fresh-made sushi at La Castilla, as well as a sports bar and café. The open-air great room invites reading and quiet conversations, but if you’re up for something a little more energetic, there are tennis courts, a driving range, a fitness center, and invigorating coffee scrubs at the spa.

Snorkel, fish, relax and recover while you’re in Panama on Contador Island, in the Pearl Islands Archipelago. These beautiful boats are ready for hire (in hugely affordable fashion) once you’ve left Panama City and landed on this enchanting island. With Air Panama there appear to be two or three short (45 minutes) flights a day that will get you there from Panama City. Be sure to pack your swimsuit, a good book and some sunscreen. This is a very small island and you can explore land on foot or by a rental scooter to see it all. In Spanish, Contador means ‘the one that counts’, and it’s easy to make your day on the island count with a local rental boat. Your captain (that will inevitably also be fishing while you’re moving) are a reliable way to go and find nearby remote snorkel locations. Be sure to agree on the price before you head out for your big day on the water.

Just a five-minute boat ride from St. Vincent, Young Island is both a private resort and the first in the Grenadine islands chain. Here, you’ll find a small, white-sand beach facing the channel that separates the island from the mainland. It’s technically for hotel guests only, but go for lunch at the very good beachside restaurant and bring your bathing suit—the resort won’t mind if you take a quick dip after your meal.

Occupying three whitewashed colonial buildings sheltered from the bustling streets of Old Town Cartagena, Casa San Agustín sits on the site of a former aqueduct and channels its heritage with a swimming pool that tunnels through its stately remnants. Inside, common spaces feature a mix of Colombian art and artifacts with contemporary wicker furnishings and marble floors. The 20 rooms and 10 suites are cozy and a bit more polished than those found at other historic properties nearby: Units feature 200-year-old wood-beamed ceilings and iron canopy beds topped with Frette linens; some have patios with hot tubs or brick terraces with views of surrounding buildings. But there’s plenty of space to unwind throughout the property, namely a library with original frescoes and a lounge with a long wooden bar and ceiling-high wine cabinet. It’s a good idea to make reservations in advance for dinner at Alma, considered among the city’s best restaurants, where the upscale international cuisine includes fresh ceviche and dry-aged beef cured on-site.

Founded in 1971 as the first women-owned and operated community center in the country, the San Francisco Women’s Centers has been working to guarantee a safe space and reliable social services for women and girls in the city. And since 1979, they’ve done it from the Women’s Building—or El Edificio de Mujeres—in the Mission, a women-led community space advocating self-determination, gender equality and social justice. Through education, cultural arts activities, and economic services (all available in both English and Spanish), the Women’s Building helps more than 20,000 low-income women and their families every year. Looking to take part? Visit the website to see their list of events, rental spaces and equipment, and volunteer opportunities.

If you want to vacation like British royalty, visit the mosquito-shaped island of Mustique, which Naomi Campbell, Mick Jagger, and Princess Margaret have all called their home away from home. Once on land, there’s no better place to stay than the Cotton House, a private retreat that feels like the lap of luxury. Set on 13 acres of cerulean beachfront and gardens thick with jasmine and frangipani, the 20 rooms and suites are awash in neutral hues inspired by their surroundings, with wicker pendant lighting, ikat throw pillows, and breezy mosquito nets over the beds. Explore the coral reefs near the shoreline in a glass-bottom kayak, or improve your backhand with help from the resident tennis pro. After a day of sun-soaked adventure, dine on fresh-caught specialties (pan-seared barracuda, Caribbean-style sushi) at Veranda restaurant, then retire to the Great Room, a colonial-inspired lounge offering rare and local rums.

Scrub Island is one place where being shipwrecked might actually be a good thing—pity that dockside boat slips abound. Located on a volcanic speck just 75 miles east of Puerto Rico, Scrub Island Resort is the ultimate tropical idyll, with a spa, marina, and three restaurants. Its 52 suites and villas sit on 230 pristine acres, complete with neutral, colonial–style interiors (think four-poster beds, marble baths with soaking tubs, and floral curtains) that intensify the ocean views. Charter a boat to explore hidden coves or test your nautical skills at the resort’s sailing school. You can always forget what you know once the time comes to lift anchor and head for the mainland.

The Mafia Archipelago (its name is said to come from the Arabic word morfiyeh, which means “archipelago”) consists of several islands and atolls, the largest of which is Mafia Island itself. Mafia Island is a nearly undiscovered alternative to Zanzibar, with similar picture-perfect beaches and diverse marine life, but without the crowds of tourists. Its history can be traced back to the 8th century, when boats would stop to refuel and repair along the lucrative coastal trade route. This legacy is evident in the crumbling ruins of a former town called Kua, which include a mosque and unexcavated Chinese and Persian pottery. South of the island is the submerged town of Kisimani Mafia, which was destroyed and submerged by an 1872 cyclone and has yet to be fully excavated. A protected marine preserve encompasses the islands and reefs, making this region is a diver’s paradise. Mafia Island Lodge offers makuti (similar to thatch-roofed) rooms with sea views, plus fishing, biking, walking, diving, and snorkeling, as well as historical and cultural tours.

There’s a little slice of New Brunswick, Canada, off the coast of Maine, and it’s well worth a visit. Grand Manan Island is accessed by ferry from Black’s Harbour NB. The island is only 34km long and 18km wide, so it doesn’t take long to explore by car. Another popular option is to walk onto the ferry and rent bikes on the island. The main sights on Grand Manan are the beaches, rocky cliffs, and lighthouses. It’s a haven for artists, bird-watchers, and hikers. It’s also a great spot to enjoy fresh seafood. The journey to the island is one of the best parts as you often see whales, seals and other sea life from the ferry decks.

Once a separate municipality, San Ángel—in the city’s south, nestled into its western foothills—is a leafy, genteel enclave whose relative isolation adds a soigné feel (for better or worse) you won’t find in neighboring Coyoacán. Ground zero for promenading is quaint Plaza San Jacinto, whose cute parish church (and beautiful cloister garden) is a sort of spiritual last stand amid the surrounding area’s high-toned consumerism. That said, the plaza’s true spirit comes alive Saturdays, at the so-called Bazar Sábado, an artisanal market that fills the area with stall after stall of handmade jewelry, textiles, crafts, and accessories, plus a great deal of art—some finer, some less so—in styles that go from hippie to haute. Strolling musicians and performers add to the carnival atmosphere.

For panoramic views of the entire city—for the price of a subway ride—take the Roosevelt Island Tram. As the suspended car runs parallel to the bridge, spanning the gap between Manhattan and Roosevelt Island, you’ll have unparalleled vistas of the New York syline and the East River below. There are few experiences as memorable or accessible, so be sure to ride the tram there and back—it’s particularly dramatic in the morning and evening.

Montage is a hip, and highly curated collection of vintage men’s and women’s clothing, jewelry, and accessories, focused on the 1940’s through the 1990’s. The jewelry is particularly worthy of note, as much of their collection is made from broken or scrap pieces that have been reinvented and revitalized.

You haven’t truly seen The Bahamas if you haven’t done a day trip to one of their many unspoiled islands. When in Exuma, a short water taxi ride, which will cost you only $12, will bring you to an island off the port of Georgetown. It’s pristine waters and beaches will surely spoil you- the Exuma Cays has one of the clearest waters I’ve seen in the world! Be sure to be on the lookout for Stingrays next to the Chat ‘N’ Chill Bar. Feeling adventurous? Walk across waist-deep water to bring you to the other side of the island, where the waves crash over the coral. Go beyond that and take one of the the hidden walking trails that will lead you to the end of the island. Just make sure to not get lost on your own, some of the paths do seem endless like it will lead to nowhere. However far you get, remember to go back as the island tends to elude your sense of time. Your water taxi awaits!