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One of the island’s best lookouts, Drake’s Seat offers a panoramic view of Magens Bay and the U.S. and British Virgin Islands to the east. The site is named for Sir Francis Drake, who is said to have kept watch over the harbor from this vantage point. (Was Drake benevolently watching over his own fleet or looking for ships to plunder? The answer will depend on whether you subscribe to the British’s regard of him as a celebrated explorer or to others’ belief that he was a brutal privateer.)

Situated off the eastern shore of Long Island, The Chequit is old school in an elegant way. The hotel occupies a big white building, surrounded by grassy lawns, impeccably maintained hedgerows, and towering deciduous trees, and features bright, homey rooms, complete with large windows that let in plenty of natural light. While all the rooms have been refurbished, those in the main house retain much of their original architecture, lending them a certain vintage charm. The Chequit operates on a bed-and-breakfast model, and guests can either take their morning meal in the lobby or opt to have a lighter option sent straight to their room. While the target audience here is weekenders seeking an escape from New York City, the hotel is also a popular spot for weddings and retreats, with two meeting rooms and full catering services available from on-site Red Maple Restaurant.

Served with Hawaii’s familiar aloha, the Puka Puka Kitchen cooks up delicious Island food including ahi don, garlic curry, and chicken katsu. It seems like there is a Greek and Indian influence to the Hawaiian flavors which makes Puka Puka unique and worth a visit!

I’m not sure exactly how Rainbow Beach got its name, though I wouldn’t be surprised if it actually had a lot to do with rain. The island’s most popular beach bar, especially on Sundays, is centrally located on St. Croix’s West Coast, some of the island’s tallest peaks and dense rainforest just a few miles behind it. Prevailing weather patterns, particularly during the summer months, make brief afternoon showers a fairly regular occurrence here. That doesn’t stop the party, though. Live bands play on and everyone keeps dancing. When you’re already wet from the sea and feeling the vibes, a little rain doesn’t hurt one bit.

A trip on Oahu’s windward side to the North Shore is not complete without a stop at the yellow Shrimp Shack. Two wonderful women operate this truck and serve up locally sourced fresh shrimp and other delicious food. As a warning, the meals are usually loaded with garlic and spice, but oh so wonderful. Instruction are painted on every yellow table top: “Suck, peel, dip, and EAT.” Drinks (and other convenience-store items) are available at Ching’s Store next door. The truck is bright yellow and impossible to miss on the North Shore. Be sure to stop in and say hi and indulge in some amazing spicy shrimp!

The summit of Monte Solarno, the highest point in Capri is almost 2,000 feet high! You can choose to climb it or opt for the considerably easier chairlift. Along the ride and at the top, you will enjoy an incredible 360-degree view over the island and sea. There is a small café for a cold drink. Make the short hike down to the sweet, tiny 15th-century Hermitage of Cetrella, a chapel where local sailors used to visit and pray for protection before setting out to sea.

Every Saturday from 7 a.m. to 1 p.m., the island’s largest open-air market sprawls across the University of Hawai‘i Maui College campus, creating a lively scene with more than 200 vendors. Many of Maui’s best boutiques sell their wares here, but for much cheaper prices than at their brick-and-mortar locations. Browse for muumuus, wood carvings, and other handmade crafts like bone and shell jewelry, or treat yourself to a shave ice while perusing piles of leis, local fruit, and homemade baked goods. The market is especially strong when it comes to street food—don’t miss the spam kebabs, banana bread, and goji kombucha.

Expect the unexpected at Ka‘ana Kitchen, set within the funky yet sophisticated Andaz Maui. Here, executive chef Isaac Bancaco draws from the best of the island’s bounty, using local ingredients in a mix of Filipino, Chinese, Japanese, French, and Native Hawaiian cuisine. Think breadfruit hush puppies, Kona clams with savory malasadas (Portuguese doughnuts), and ahi tataki with burrata and lilikoi (passion fruit), enhanced only by the restaurant’s sweeping coastal views. You don’t need to change out of casualwear to dine here, but Bancaco has a knack for turning meals into events, inspiring diners to dress up a little.

Coney Island’s history dates back to the 1800’s, when it was envisioned as a working man’s paradise. For pocket change, you could enjoy rides and hot dogs. While you’ll need a little more than pocket change now, this venture outside Manhattan has a true charm, and can connect with most anyone’s inner child. Over the summer you’ll find packed beaches, Friday night fireworks, and the famous Nathan’s hot dog eating contest on July 4. But if you’re coming from Midtown or the Upper East/West Sides, be sure to take an express train or you’ll be in for a ride not quite as amusing as the Cyclone.

This is it. The moment you arrive on-island, do not pass go, do not collect $200 — just get yourself to the La Reine Chicken Shack to immediately immerse yourself in the uniquely local St. Croix vibe. No, this is not haute cuisine, this isn’t even a nice looking place, but what it is is an institution sporting the best BBQ chicken on island. Everyone eats here from senators to sanitation workers and all walks of life in between. On Sunday’s you can even expect some roast pork added to the menu. Whatever you order, you won’t go wrong pairing your styrofoam wrapped meal with a nice rum & Coke!

Fete Paradiso, the much buzzed about traveling vintage French carnival that has taken over Governor’s Island for the summer, features an incredible collection of extremely rare artisan-crafted carousels, rides and games. Families and Francophiles have been lining up for the 5-minute ferry from downtown Manhattan since opening weekend, which coincided with Bastille Day, to check out this whimsical weekend fair. A few of Fete’s highlights include the late 19th century bicycle carousel (one of only 2 bicycle carousels left in the world — the other, featured in Woody Allen’s Midnight in Paris, is in France), a Chinese Dragon Carousel with a misleading name (though our daredevil 2 year old didn’t mind being whipped around fast and then backwards) and a ball-toss game with life-size caricatures of Charlie Chaplin and Edith Piaf called the Music Hall Ball Guzzler. Set to run from now until September 29th, 2013

Housed in a 17th-century town house at the heart of L’Isle-sur-la-Sorgue, this boutique hotel offers superior service, luxurious rooms, a secret garden with a swimming pool, and an art gallery, where pieces by local artists and designers hang alongside souvenirs from the owners’ extensive travels. Past the hotel’s monumental entrance with its 300-year-old locks, a staircase lined with 17th-century stained glass leads to four spacious rooms, each uniquely decorated with fine furniture, carefully selected fabrics, and objects from around the world. Guests can also look forward to a cozy lounge with a fireplace, and a bright kitchen, where cool-as-can-be owners Frédéric and Marie-Claude serve a mind-blowing breakfast spread each morning.

Yes, Hauz Khas Village is perhaps most known for its artsy vibe, boutique shops, and trendy restaurants. But before it became a lively commercial district, Hauz Kaus was (and remains) a 13th-century historical complex with a mosque, tombs, and an Islamic seminary. Take a break from the bustle of shopping and dining to explore the sites from Muslim royalty, then spend some time at the charming lake with its swans, ducks, and other wildlife.

One of Dallas’s earliest neighborhoods, this formerly industrial area just east of downtown has a long history as an entertainment hub, from its days as a hotbed of blues and jazz clubs in the 1920s, to the 1980s, when local bands like the New Bohemians, Butthole Surfers, and Old 97’s were launched from its clubs. Today, the area is not quite as counterculture as in the past, but it’s still got an indie steak, with vibrant street murals and public art providing the backdrop for a host of independent galleries, shops, bars, breweries, cafés, tattoo studios, and over 60 restaurants and 30 live music venues. Among the most iconic music spots are Club Dada and Trees, both of which have been revamped in recent years, as well as The Door, the Prophet Bar, jazz/blues favorite the Free Man, and the century-old Sons of Hermann Hall. As it has grown, the area has also become more family friendly, particularly during events like the annual Deep Ellum Arts Festival, which features stalls from around 200 juried visual artists, and five stages hosting 100 musical acts.

Sonny’s has been open since 1944, making it the second oldest continuously operating eatery on Galveston Island. Hit it on a Friday gumbo night if you can, which comes in your choice of shrimp, crawfish, or both. Sonny’s may seem like a hole-in-the-wall, but don’t let that scare you off. It’s just old school and really friendly seafood place. Photo via galveston.com