Dreamy Island Getaways: Our Favorites from Panama to Greece

Cold dark days got you feeling down? These eight island escapes are sure to lift the spirits and  tempt with a warm-weather getaway. From an adults-only Caribbean Sea paradise with soaring treehouses to a “secret” Greek isle that’s about to make a splash on the jetsetters’ map (featured in our “Mini Insider Guide: Best of the Cyclades” below), these escapes offer the perfect antidote to the winter blues.

Where to Stay: Nayara Bocas del Toro

Set on a private island off Panama’s Caribbean coast, the all-inclusive, adults-only Nayara Bocas del Toro is an off-the-grid haven spanning nine acres of dry land, more than 80 acres of mangrove, and 3.1 miles of pristine shoreline. The property’s 16 overwater bungalows seem to float above crystal-clear waters, offering direct access to the sea—just slip on a snorkeling mask and dive in. Unwind with a tropical cocktail at the property’s show-stopping overwater beach (the world’s first) that is perched on stilts and stretches 90 feet long and 20 feet wide. A set of stairs leads directly into the sea, a seamless transition between sunbathing and snorkeling. Off property, guests can take a seaplane to Isla Escudo de Veraguas, a remote island home to three-toed pygmy sloths known for their unusual habit of swimming in the surrounding waters. Other excursions include scuba diving, fishing, touring local chocolate farms, and visiting a secluded wildlife haven for rescued and orphaned monkeys.

Cool Factor: At Nayara Bocas del Toro, guests can fulfill Robinson Crusoe fantasies in solar-paneled treehouses, some soaring 50 feet above the ground. Designed by Bali’s Elora Hardy, each treehouse was crafted from locally sourced bamboo and reclaimed hardwood that came from beneath the Panama Canal. Outdoor jungle showers and deep soaking tubs invite al fresco bathing, while a pulley system ensures unobtrusive room service.

Where to Stay: andBeyond Mnemba Island

A private paradise off the coast of Zanzibar, andBeyond Mnemba Island epitomizes easy-breezy barefoot romance (in fact, many guests remove their shoes the minute they arrive and don’t put them back on until they leave). The intimate property recently emerged from a complete rebuild by longtime andBeyond collaborators Fox Browne Creative and Nicholas Plewman Architects. Capitalizing on the Indian Ocean scenery, the 13 beachside bandas open to the island’s warm, tropical air, with palm roofs, coral brick walls, and coconut fiber furnishings providing a sense of place. Spend lazy afternoons strolling along the property’s mile-long stretch of powdery sand, or pick up the pace with stand-up paddleboarding, paddle boarding, or an exhilarating ride in a clear-bottom kayak. A private marine reserve encircles the island, ensuring no other boats can venture within 400 meters of its shores.

Cool Factor: New island experiences include a full-day private excursion on the lodge’s dhow boat and an island conservation tour highlighting the efforts to preserve the delicate Mnemba Atoll aquatic ecosystem (think: turtle hatching and coral restoration).

Where to Stay: White Elephant Resorts

Nantucket is the ultimate New England getaway, located some 30 miles off the coast of Cape Cod, Massachusetts. For many return visitors, the island is synonymous with the iconic properties that make up the White Elephant Resorts collection. The centerpiece is the White Elephant Nantucket, a meandering landscaped sea- and harborside property that comprises a hotel, an inn, garden cottages, residences and downtown lofts — with an unbeatable location in the center of the action. Down the street right in town, the Jared Coffin House is one of New England’s oldest and most atmospheric hotels, housed in a three-story former captain’s mansion. And the secluded Wauwinet, a Relais & Châteaux property, is the portfolio’s romantic sibling, located in the midst of some of Nantucket’s most glorious landscapes on the eastern end of the island with expansive views of the sea and bay.

Cool Factor: The Cottages and Lofts at the Boat Basin (in Nantucket’s picturesque marina) recently debuted a multi-million-dollar renovation led by local designer Audrey Sterk. The 29 individually designed cottages are primed for summer entertaining with full kitchens, and many also have private outdoor decks overlooking the Nantucket Boat Basin. Pet lovers should book ahead to snag one of the dedicated “Woof Cottages,” outfitted with special doggie amenities.

Where to Stay: Island Outpost

With its rich culture and sublime scenery, Jamaica has inspired countless artists and creatives — from Bob Marley to James Bond creator Ian Fleming. The nation’s unique character has also fueled the vision of music industry legend Chris Blackwell, the Rock and Roll Hall of Famer who launched the careers of Bob Marley and U2. Beyond music, Blackwell is just as well-known for his collection of celebrity-favorite boutique hotels as part of the Island Outpost portfolio. These include the legendary GoldenEye, previously owned by Bond creator Ian Fleming, who penned his best-selling spy series from the property’s famed waterfront villa; the Strawberry Hill mountain estate (where he grew up having Sunday tea); and the honeymoon-favorite The Caves. Each property feels like a private home, with an intimate scale, stylish design, and an emphasis on community. In 1995, Blackwell founded the GoldenEye Foundation to drive sustainable development across the island. Over the years, the foundation has spearheaded numerous initiatives in Oracabessa, from creating a fish sanctuary and rehabilitating coral reefs to launching public health programs and leadership opportunities for local youth.

Cool Factor: This year marks the 30th anniversary of GoldenEye, the James Bond film starring Pierce Brosnan that is said to have resurrected the franchise. At GoldenEye—the hotel—guests stay in the very villa where Ian Fleming penned the series (his original writing desk still stands!).

Once home to one of Europe’s earliest civilizations, Greece’s Cycladic Islands now lure a diverse mix of history buffs, adventure seekers, and sun worshippers, all drawn to the iconic blue-and-white architecture, azure waters and volcanic landscapes. With more than 200 Cycladic islands to choose from, here’s where you should go:

Where to Stay: Gundari

Want bragging rights for staying on a gorgeous, lesser-known island in the Cyclades? Look no further than Folegandros, where Gundari, the destination’s first luxury boutique hotel, completes the second phase of its official opening with the unveiling of three exclusive villas — clifftop havens perfect for privacy-seekers—and a wine bar housed inside an original farmhouse. Set amid a wildlife reserve on Folegandros’ rocky southeastern coast, the property takes its aesthetic cues from the wild and wind-carved landscapes. It comprises just 30 bioclimatic, Cycladic-style suites and villas set on a 100-acre property framed by dramatic limestone cliffs. Each suite features a private solar-powered heated infinity pool that appears to drop into the Aegean Sea below.

Cool Factor: The EarthCheck-certified hotel boasts a fleet of eco-friendly toys, including 12 electric bikes and Fiat 500e Cabrios for exploring the island’s pebbly coves and time-preserved traditional villages, including whitewashed Chora, considered one of the jewels of the Cyclades.  Gundari is also dedicated to the protection of the threatened Eleonora’s Falcon, one of the island’s rare native species.

Where to Stay: Kalesma Mykonos (with new rooms and suites!)

Since being launched by an all-Greek team in 2021, Kalesma Mykonos has been a magnet for discerning travelers seeking to discover the other (some might argue more authentic) side of the popular Greek island: hidden coves, family-owned farms, rugged horseback trails. This summer, the boutique hideaway will nearly double in size, with an additional 19 new accommodations, including sea view deluxe rooms and junior suites, bringing the total count to 44 rooms and two villas. Also new: another gorgeous pool, as well as a traditional all-day Greek taverna offering such classic Greek mezedes as dolmades, saganaki, and dakos salad, with a side of panoramic views, natch. Off-property, guests can embark on a guided tour of Delos (home to a newly reopened archeological museum) or visit a local farm to learn Greek recipes, before ending the day with a hammam experience and brightening facial at the on-site Dr. Barbara Sturm spa.

Cool Factor: Style file alert — Kalesma Mykonos celebrates a new partnership with expert weaver Faye Chatzi who creates shawls, caftans, bags, scarves, and hats on her traditional, 300-year-old loom using Myconian lambswool, Greek cotton, and silk.

Where to Stay: NOŪS Santorini

Located in the charming town of Mesaria on the edge of the Santorini caldera, NOŪS is a rare sanctuary of sophistication and tranquility less than 10 minutes from the island’s capital, Fira. It’s also a hub for Greek art and design, owned, as it were, by world-renowned art collector Dakis Joannou. The property features more than 160 site-specific artwork by Greek artists and international heavyweights alike (don’t miss the volcanic-inspired light fixtures designed by designer Eleftheria Deko, who has also created award-winning light displays for the Acropolis and the 2004 Olympics opening ceremony). During the day, the center of the action is the showpiece pool, Santorini’s largest, and the full-service spa that was inspired by the ancient Greek principles of wellbeing and self-care. Come night (read: atmospheric, alluring, buzzy), the resort is famous for its panoramic sunset views and home-style Italian cooking at a lively outpost of the iconic Elio’s New York chophouse.

Cool Factor: The concierge can arrange top experiences that take guests off the beaten path, including touring an art gallery set within a subterranean wine cave in Exo Gonia; visiting the village of Imerovigli, which is rightfully known as “the balcony to the Aegean” (it’s built into the highest point of the caldera cliffs); and exploring the well-preserved ruins of the city of Akrotiri.