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Off the coast of Port Antonio is a small, uninhabited plot called “Pellew Island,” otherwise known as “Monkey Island"--there used to be a colony of imported monkeys here. To get here, you could first head to San San Beach, a beautiful and private stretch open daily (10 a.m.4 p.m daily, US$5). Rent a kayak and snorkel gear and make your way over to the small plot, within clear view ahead. The island is completely covered in vegetation, there’s a small white sand beach, and the waters are shallow. Rest your kayak on shore and snorkel around the island for as long as you please. Visibility is incredible and this is one of the best snorkeling spots in the area. Just watch your step if you’re barefoot, as there can be sea urchins on the seabed.

Why we love it: A Mission Revival property that blends Hollywood history with hang-ten culture

The Highlights:
- A location just minutes from the secluded Cress Street Beach
- A rooftop lounge with sweeping ocean views
- Guest rooms designed by iconic surf brands

The Review:
Once the haunt of writers, filmmakers, and Hollywood celebrities, this historic hotel on the Pacific Coast Highway famously hosted a lobby backgammon game between J. Paul Getty and Howard Hughes in the 1930s. Today, the pet-friendly property maintains its original grace with Spanish-style stucco and domed arches, but 10 of its 41 suites have moved on to a decidedly different sort of California cool. Created in collaboration with iconic skate and surf brands like Etnies, Roxy, and Billabong, the Casa Surf rooms feature hand-painted surfboards, underwater photo murals, and George Nelson furniture, fully immersing guests in Laguna surf culture. For something more traditional, book one of the Spanish rooms, which include wrought-iron accents and ornately carved dark-wood furnishings.

La Casa sits just a stone’s throw from Cress Street Beach, where hotel guests enjoy access to chairs, umbrellas, and beach towels as part of their resort fee. Also included in the fee is daily breakfast, access to the nearby Art of Fitness gym and its juice bar, and reservations at the on-site Rooftop Lounge, where you can sip mojitos while watching the sun set over the Pacific. When you’re in the mood for something more substantial, head downstairs to K’ya Bistro, with offers small plates full of Mediterranean flavor.

Home of the Venice Film Festival, the Lido is also where you’ll find Venice‘s beaches—Shelley and Byron went horseback riding here back in the day—as well as the Grand Excelsior Hotel, whose bar is often crowded with celebrities during the festival (and other times of the year, as well). If you’re a classic film fan, the hotel might look familiar: Luchino Visconti’s Death in Venice was shot here. The island has a decidedly lively feel compared with Venice itself, less a museum piece and more a buzzing destination, popular with Venetians and visitors looking to spend a day by the sea.

I love staying in a private villa home over a hotel when traveling with a small group, and Breezy Villa by Island Escapes is both affordable and impressively chic. In a secluded hillside location, complete with multiple, swaying palms for privacy and glassy sea-foam green lagoon views that are just a shade lighter than the infinity pool melting into them, it’s easy to check skinny-dipping in paradise off the bucket list when sleeping here. If naked swimming isn’t your thing, no worries, the pool is also perfect for nighttime stargazing floats. And then there is the leeward lagoon location itself -- it is super calm and you can wade for ages through calm and crystalline water here without gaining much depth. There is no direct beach access, but a series of steps wind their way down from the travertine-tiled pool terrace to a small pier where a ladder offers direct sea access. Breezy Villa’s stylish interior is equally appealing. From the arched doorways and pitched roof in the open living room and modern L-shaped kitchen to the square-shaped original ocean-hued paintings hung on either side of the front door to the Grecian-Roman columns on terrace, I love the Zen beach house meets Italian palazzo vibe. Similar-sized sleeping quarters, each featuring a unique wooden bed frame and French doors opening directly to pool terrace, make this three-bedroom home equally perfect for families, especially those traveling with a nanny. It also works well for multiple couples.

Why we love it: A historic property teeming with rich, Moorish style

The Highlights:
- Iconic architecture and bold interior design
- A serene pool area surrounded by lush greenery
- A focus on sustainability, with low-energy lighting and water-efficient landscaping

The Review:
Built by Frank Miller and Arthur Benton in the early 1900s, this regal stone building presides over Laguna Beach, echoing the area’s Spanish Mission roots with white stucco, red terra-cotta roof tiles, secret turrets, and spacious patios. Inside, renowned interior designer Martyn Lawrence Bullard enhanced the castle-like structure with hand-painted furniture, Moorish tiles and lanterns, and wainscoting worthy of a Marrakech palace, giving the hotel a bohemian vibe. He also added softer notes like oxblood-leather armchairs and cerulean velvet couches that echo the blue of the Pacific below. Despite being a registered historic structure, Casa Laguna became the area’s first hotel to receive the Green Eco-Leaf rating from iStayGreen.org. Its sustainable initiatives range from bulk amenities and soaps to low-energy lighting and water-efficient landscaping.

The 23 suites all feature custom marble vanities, handcrafted natural fiber mattresses, and Martyn Lawrence Bullard fabrics and wallpapers. Expect beautiful attention to detail at every turn, from Dean & DeLuca snacks to Cowshed amenities made famous by the spa in Somerset, England. If you’re visiting for a special occasion, book the Bungalow, a freestanding, 600-square-foot sanctuary that offers ocean views from the living room and jetted clawfoot tub. It also has a large private balcony with a hammock for two. When not relaxing in their rooms, guests can enjoy a complimentary European-style breakfast as well as Mediterranean small plates throughout the day, all of which are available in the lobby, by the pool, or packed up for a picnic on the beach. There’s also an intimate spa with an outdoor area, where you can enjoy ocean views from the soaking tub before indulging in a hot stone massage.

A short boat ride north from San Pedro will deposit you onto a portion of Ambergris Caye that feels worlds away from any town or city. Once ensconced in a private bungalow on a private beach, there isn’t much to distract the guest from complete enjoyment of the charms of Caribbean water, sunshine, and the slower pace that characterizes day-to-day life in the North Islands. Massage therapists are available, as are spa services, and a full range of excursions and activities can be arranged via the concierge. Thirteen exclusive villas are available, one of which includes a steam room and private infinity pool, while other villas either feature beach access, jacuzzi tubs, private outdoor showers, or decks that stretch over a saltwater lake. El Secreto’s full-service restaurant serves breakfast, lunch, and dinner, and a bar is poolside in the main lodge. Rates begin around $3,000 for a three-night stay, and more information is available at www.elsecretobelize.com.

We hiked along a rocky trail starting at Playa La Ropa to get to Playa Las Gatas. You can make it in sandals although it’s not a walk in the park. Once we arrived we were met with a crowd of locals enjoying their weekend. As you stroll the beach you’ll be greeted by many who want you to sit at their tables. If you can resist the cold beer and fun atmosphere at first try to make it to the end of the beach where there is an old hostel and a small grove of mangroves. You’ll know you’ve arrived when you see the sign: “Leave nothing but footprints. Take nothing but pictures. Kill nothing but time.” A wonderful daily reminder. Now you can have that icy cold beer and ponder why you don’t come to Mexico more often.

Malapascua, a tiny island in the Visayan Sea north of Cebu, is well-known for its thresher-shark cleaning station, where divers gather daily to see these beautiful creatures ascend from below to be cleaned by fish before returning to deeper waters. Reef sharks can be seen here, too. What fewer visitors know, however, is that behind the strip of resorts that line Bounty Beach is a traditional village. There are quaint shops and restaurants as well as a large church, and the people are wonderfully friendly and inviting. It’s a great peek into real Filipino island life, meaning Malapascua is a worthwhile stop even if you aren’t interested in the sharks.

You won’t find a better pool than the one that awaits at this 357-room family-friendly resort situated on the powdery sands of Palm Beach. With cascading waterfalls, a swim-up bar and grill, two outdoor Jacuzzis, and a two-story waterslide, the 8,000-square-foot stunner is every kid’s dream. If more adult-centric diversions are on your wish list, the concierge can arrange catamaran-sailing excursions, deep-sea fishing trips, and snorkeling and scuba-diving expeditions off nearby shores, as well as spa treatments that utilize local ingredients like red mud, seaweed, and aloe vera. The resort’s 10 dining options provide plenty of atmosphere for winding down after a jam-packed day: sample seafood specialties like scallops a la plancha in a setting inspired by the island’s plantation ruins, or watch the sun set over the water, rum punch in hand, from your perfect perch at the pier bar.

Known as one of the best casinos in Florida, Isle of Capri Casino in Pompano Park is a popular attraction for locals. The 157,000-square foot Las Vegas-style casino include over 1,500 slot machines and a super fun harness racing track. There’s a buffet restaurant and a deli. The second floor has two restaurants and grandstand seats for fans to watch harness racing. The facility is smoke-free and includes live entertainment on weekends. Gaming includes digital poker and slots. Participate in one of the many tournaments and promotions scheduled throughout the month.

Established in 1993, Dawson Cole Fine Art is one of Laguna’s top galleries, with works by such big names as Picasso, Matisse, Chuck Close, Wayne Thiebaud, and more. Here, the focus is on contemporary and modern art, with everything from sculpture to drawings to prints on display. When you’re done browsing the showroom, head out back to the stunning sculpture garden, where you can check out even more art while soaking up the California sunshine.

Situated in three high-rise towers on the Golden Mile along Eagle Beach, the Blue Aruba complex is home to luxury condominiums as well as a full-service resort. Expect enormous windows with stunning ocean views and modern furnishings in apartment-style configurations that top out at more than 2,000 square feet; most come with fully equipped kitchens, and ground-floor residences have private patios and Jacuzzis. All the resort touches are here, including private beach facilities, two infinity pools, a spa and fitness center, and even a high-end restaurant that offers eight-course dinners. But golf lovers have an excellent reason to venture off-resort: The nearby Tierra del Sol Resort combines tee times on an 18-hole championship golf course designed by Robert Trent Jones II with sublime seaside panoramas.

Near the northern end of Eleuthera, Coral Sands is one of the few hotels fortunate enough to sit directly on Harbour Island’s famous Pink Sands Beach, declared one of the world’s prettiest shorelines. Opened in 1968, the hotel has recently been updated in typical Bahamian style with bright colors and crisp whites, plus plantation shutters, soaring ceilings, and inlaid-wood furnishings with seaside themes. Public spaces follow suit: classic black-and-white tiles anchor the restaurant, where continental specialties are served beneath elegant plaster arches, and an open-air bar is backed by the island’s turquoise waters. Because the beach is protected by a barrier reef, its surf is hardly ever more than ankle-high, but swimmers find comfort in the heated freshwater pool.

Sugar Ridge is much about the view. One of those rare Caribbean hotels that doesn’t sit at the edge of the sand, this boutique luxury resort, ranging up a hillside on Antigua’s west coast, not only overlooks palm-lined beaches and the marina at Jolly Harbour but also looks out across the greens and blues of the Caribbean toward St. Kitts, Nevis, and Redonda. The rooms, in clusters of four, two upstairs, two down, are Caribbean modern, with a focus on the four-poster, netting-draped, king-size beds. There are two restaurants, two pools, an Aveda Spa, and a fitness center so large it’s almost as if they were expecting a sports team to show up. And beach lovers fear not. A complimentary shuttle will have you down to the shore in minutes.

Once summer has arrived in all her glory, city folk yearn to escape the concrete jungle. The cheap and chic solution for locals is to pack a picnic and head for a beach day on the Toronto Islands, just a short ferry ride away. Of the three primary islands, all of which are connected by paths and bridges, Centre Island boasts the highest number of visitors; people head straight to its main strip to get to the beach and the amusement park. Ward’s Island offers more charm: In addition to the sandy shore, there are small summer cottages and gardens. Those intent on exercise can rent bicycles or paddleboats.