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Affectionately called the First Lady of Waikiki, this grande dame opened in 1901. Its gracious architecture harks back to the sugar-plantation era and wraps around a courtyard anchored by a massive banyan. Pull up a chair under its spreading branches—or else a seat overlooking the ocean—and enjoy island-inspired fine dining. East meets West here with appetizers like Kona abalone bourguignon, tempura asparagus with Parmesan custards, and twice-cooked octopus with macadamia romesco. Entrée standouts include the miso salmon and Korean-fusion Beach Bim Bop starring fiddlehead ferns, kimchi Brussels sprouts, and Ali’i mushrooms from Hawaiian grower Hamakua. Save room for its tour-de-force finale: A “dessert tree” with small bites of everything from macarons to red-velvet cheesecake.

Music producer turned hotelier Chris Blackwell has made a name for himself converting Caribbean properties (Pink Sands on Harbour Island, GoldenEye in Jamaica) into jetset destinations with studios where his rock-and-roll friends can kick back while recording their next album, but it all began at Compass Point. Bob Marley, the Rolling Stones, and Eric Clapton have all stayed in some of the resort’s 18 rainbow-hued stand-alone huts, which are inspired by the colors of Bahama’s Junkanoo carnival and are simply furnished to encourage engagement with the outdoors; though the interiors are air-conditioned, most have sea-view balconies that are sighted to catch ocean breezes. In keeping with the theme, each comes with a surround-sound system and a library of CDs by artists who have recorded at Compass Point, but you’re just as likely to keep them off, preferring instead to listen to the waves that crash on the hotel’s small beach.

A visit to John Watling’s Distillery offers both a tour of a historic estate in downtown Nassau and the opportunity to sample locally made John Watling’s rum. The distillery, the only locally owned one on the island, is housed in the Buena Vista Estate, which began construction in 1789. The estate grounds encompass tropical gardens and a 200-year-old water well. Visitors can also take a free tour of the museum and distillery, where you can see the aged white oak barrels filled with rum. Finish the tour with a cocktail from the on-site Red Turtle Tavern, or pick a bottle of John Watling’s rum from the store.

The 1905 Cadillac sparkling under the bright lights really commands the attention of the room. This hot ride, in the center of the Cayman Motor Museum, is the exact model of the first car ever driven on the island. Browse through more than 55 classic and exotic vehicles as well as 18 various vintage motorcycles. This museum displays rare and one of a kind automobiles and isn’t just for motor enthusiasts. Cars like the original Batmobile used in the 1960’s television series of Batman as well as Elton John’s Rolls Royce make this museum a must-see.

My sister freaked out when she heard that Kenny Chesney would be playing a special concert at the Atlantis Resort on Memorial Day weekend last year. She begged me to go, and with neither of us having been to the Bahamas, it was an absolutely fabulous experience. We shopped and laid out by the pool during the days, while experiencing all the nightlife and restaurants that the resort has to offer. We had a great weekend, and Kenny was the topping on the cake!

Travelers hoping to find the lap of luxury need look no further than the Ritz-Carlton. Backed by the aquamarine waters of Palm Beach, the resort’s 320 rooms are generously sized, with cheery turquoise-and-yellow color schemes and balconies overlooking the ocean. Leisure pursuits can be as easy as a daytime doze in a poolside cabana or as strenuous as a catamaran sailing trip complete with diving lesson. Need a break from all that sun? Indoor facilities include a spa that specializes in island-inspired treatments (think full-body massages with local aloe and divi-divi tree oil) and a state-of-the-art gym that’s open 24 hours so guests can sneak in early-morning workouts. Before you roll your eyes, consider the four on-site restaurants (BLT Steak, from noted chef Laurent Tourondel, is a favorite). For an even more memorable experience, staff can arrange a private sunset dinner on the beach to the tune of a serenading violinist.

Graceful palms and lush gardens greet guests at Grotto Bay Beach Resort. Situated on 21 acres, this peaceful colony of cottage-style rooms overlooks the beautiful blue water of Bailey’s Bay in the Parish of Hamilton. Tangerine salt body scrubs, sweet milk and lavender facials, and hot stone massage will melt away all of the exertion of snorkeling excursions, golfing, exploring the resort’s on-site cave, or bicycling around the island. On the other hand, why not take it easy and lounge by the pool, which features a swim-up bar, or on one of the resorts private beaches. Dine among the island ambience of palms, rattan furnishings, and ceiling fans in the Hibiscus Room or Palm Court Dining Room. Afterwards, you can enjoy drinks and tropical breezes on the terrace before retreating to guest rooms outfitted in bright prints and tropical tones.

One of the best strolls through Venice begins in the neighborhood of Arsenale and finishes on the Island of Sant’Elena. Walk along the main drag of Via Giuseppe Garibaldi, a street full of shops and colourful local life until it dead ends. Make a right on to Viale Giuseppe Garibaldi where a monument to the streets namesake stands. From here the streets become very quiet. Follow Viale Giuseppe Garibaldi to the end and turn left onto the Fondamenta San Giuseppe. This is a mostly residential area where you see laundry hanging from pastel painted houses and hear small fishing boats tapping against the sides of the canal. Make the first right off the Fondamenta and get lost in the twist of back streets here until you come upon the Via XXIV Maggio. From here, look for signs pointing to the Church of Sant’Elena, a beautiful 12th-century monastery on the island.

Much more than just a restaurant or smoothie stop, Choice Health Bar is a culinary fusion of food, lifestyle, and positivity. This small restaurant in the Lahaina industrial park serves fresh kale salads and heaping acai bowls. The place is a favorite hangout for island locals from surfers and paddlers to vegans. Just because it’s healthy, don’t think the food will taste like cardboard. Creative concoctions pepper a menu that is constantly being reinvented, and you’d never expect that a quinoa quiche could possibly taste so good. Locals also love Choice for the laid-back atmosphere and powerful, positive vibes. A sign on the door informs all patrons that this is officially a “bummer free zone,” and instead of simply “super-sizing” your meal, you can “make it epic” with ‘superfoods’ like kale and cacao. Consistently voted as the island’s top pick for healthy, vegan cuisine, Choice is the absolute best spot on the West Side for infusing your body with nutrients.

You are lucky the sun only rises and sets once a day on Hawaii—otherwise, you’d spend all of your time transfixed by the horizon. Hike to the leeward (eastern) side of any island on a clear evening and train your eye over the ocean in search of the “green flash,” an optic phenomenon in which a green sliver of light hovers in the wake of the setting sun. (On Oahu, the remote Kaena Point is a good spot to see the flash.) Sunsets on Kauai, “The Garden Island,” make the beauty of the coastal surroundings even more poignant. If you rise early and tackle the Lanikai Pillboxes trail on Oahu or summit the volcano at Haleakala National Park on Maui, you’ll experience an unforgettable morning as the sun rises over the ocean for a new day.

La Isla de Guilligan (Gilligan’s Island, though not the one from the television show) is a popular hangout for Puerto Rican locals. I myself am only home for several weeks a year and I still go once or twice every year. The island is sometimes isolated and sometimes crowded. It boasts snorkeling (I’ve spotted many anemones, fish, crabs, starfish, and barracudas), calm water perfect for floating and swimming, and several trees from which you can jump into the water. It’s off the coast of Guanica, and there are two ways to get there. Either take a ferry (call 787-821-5706 for more information) or rent a kayak from Mary Lee’s by the Sea. If you choose to do the latter, you might want to take your kayak to Isla Ballena (see my highlight “Kayaking and Snorkeling and Hoping for Whales”). This tends to be a day trip, so I suggest you have some food. You can either pack up your own or, if you take the ferry, place an order before embarking and tell them when you’d like to have it delivered. There are picnic pavilions that you can claim if it’s a calm day or you get there early.

Many Caribbean islands (Anguilla included) are made primarily of limestone. Over many thousands of years, caves often form in this type of rock speckling the islands with tons of little caves to explore. On Anguilla there are plenty to explore, but the hike to the Iguana Cave is particularly pleasant. It starts on the quiet and isolated sands of Katouche Bay Beach just past the Masara Resort. It’s pretty much due West of the capital of The Valley and very easy to find. The only awkward part is the very steep road that descends the last mile toward the shore. There you should find a gap in the sea grape trees. Staying on this path will take you past a salt pond, through a forest crawling with hermit crabs, up an old stone staircase, through a grove of cactus, past the occasional red-footed tortoise, and finally to the cave. Going at an easy pace, the hike clocks in at around 45 minutes up and 45 minutes back. For the most part, it’s pleasant and I highly recommend it as a way to break up a bounty of beautiful beach days.

One of the more relaxing evenings away from home was spent at the Outrigger Hotel in Kailua-Kona on the Big Island of Hawaii. I checked in with no problems and was even upgraded to a partial ocean view room! I had enough time to mosey on through town to grab some dinner and watch the sun sink to the ocean (complete with a green flash). The hotel was comfortable and situated next to a beach filled with a all sorts of fish and sea turtles. Snorkeling at Kahaluu Bay Beach Park, right next door to the hotel in the morning was one of the best snorkeling experiences I have had in Hawaii. The water was clear and the marine life was over-abundant! Sitting at the beach bar in the evening with live music and the sound of the surf was enough to relax the body and soothe the soul for a great night of sleep! If you are local, make sure to book their Kamaaina rate. **Unfortunately, the Keauhou property has closed. However, the Outrigger has several other properties on the Big Island.

For a reasonably priced Island eatery, Kona Canoe Club has pupus (appetizers), salads, sandwiches, burgers, fish & chips, and several local entrees. The location is phenomenal for sunset and every dish is served with aloha!

Designed by Fuster + Architects, an award winning firm located in San Juan, Puerto Rico, El Blok takes its visual cues from the surrounding light, land and sea. In addition to being a playful structure, it is highly functional and built to withstand storms and hurricanes (a big plus anywhere in the caribbean!). It is located at the beach, at the start of Esperanza’s sleepy malecon, with its low-key seaside huddle of restaurants, bars, and stores, most of them back open after hurricane Maria’s devastating sweep of the island.

I loved my room, one of the spacious corner suites. The way the space captured the light was uncanny, every time I got back to my room, a new play of light beams and shadows was waiting for me. The restaurant downstairs serves up amazing food, hands down the best I had on island. Executive Chef, Carlos Perez. brings to the table a delicious, fresh take on Puerto Rican cuisine, centered around their bayahonda mesquite fired grill and Rotisol rotisserie. Just don’t expect much of a breakfast at the hotel. I took a short walk each morning to some cafés nearby, to grab a coffee and omelet. El Blok’s rooftop bar was ‘the’ place to hang in the evenings with locals and travelers alike, while listening to amazing music. When we were there, the duo Más Que Dos was playing and it made for an all around perfect sunset.

El Blok currently has 22 rooms and is adding another 11, slated to open in summer 2019. We were warned about construction noise between 8am and 2pm, but I can honestly say it didn’t interfere at all with my stay. It’s of course when you’re supposed to be out and about anyways, exploring the island!

Rates start at $140 per night plus tax.

A heartfelt thank you to Discover Puerto Rico (@DiscoverPuertoRico) for 3 days in beautiful Vieques and a fun stop-over in San Juan, Puerto Rico.