Dreaming of an island getaway? We’ll let you in on a little secret … the best islands to visit are often overlooked! From snorkeling in Key Largo to glassmaking in Murano, read on to discover unique island experiences often hidden in plain sight.

Key Largo, Fla.

If you’ve ever dreamed of “sailing away to Key Largo” like Humphrey Bogart and Lauren Bacall, now is the time! One of the more underrated islands to visit in the Florida Keys, Key Largo is often dubbed the “Diving Capital of the World” because of its collection of vibrant coral reefs and mysterious shipwrecks. Key Largo’s National Marine Sanctuary protects the third-largest living coral barrier reef system in the world. Learn about coastal ecosystems and snorkel past colorful coral, swaying seagrass and schools of tropical fish as you search for aquatic treasure.

Of course, snorkeling in Key Largo is just one way to experience the natural beauty surrounding you. Join a park ranger for an expert-led walk through mangrove jungles, take a glass-bottom boat ride through shallow reefs home to hundreds of sea creatures or wade into crystal clear water and admire the sunset. You can even meet friendly dolphins at Dolphins Plus or hike through Everglades National Park while keeping an eye out for osprey, egrets and herons.

Road Scholar recommends: Snorkeling the Coral Reef in Key Largo With Your Grandchild →

Rhodes, Greek Isles

When you think of the Greek Isles, the pristine cliffside terraces of Santorini or the energetic beachside nightlife of Mykonos may come to mind. But what about the historic ports and magnificent palaces of Rhodes? One of the most underrated Greek islands, Rhodes transports its visitors to the days of civilizations past.

Discover the island’s stunning medieval city, a UNESCO World Heritage Site, as you learn about the history of Ancient Greece. Walk the corridors of the Palace of the Grand Master, where knights lived centuries ago, or explore the Port of Mandraki where the Colossus of Rhodes, one of the Seven Wonders of the World, once stood.

Rhodes is the largest of the Greek Isles and its turquoise bay, natural springs and sandy beaches provide plenty of real estate for soaking in nature. After exploring the natural beauty around you, participate in a local dance class, learn to cook authentic Greek cuisine or create your own pottery in a city where medieval traditions are still very much a part of modern life.

Road Scholar recommends: Winter in Greece: The Rhodes Less Traveled →

San Juan Islands, Wash.

Tucked away in the upper left-hand corner of the U.S., the San Juan Islands have captivated wildlife preservationists for years with their natural beauty and ecological history. Here you can do it all: unwind near scenic shorelines and hike through evergreen forests, visit a 100-year-old lighthouse and dine on freshly caught crab, or paddle alongside a pod of orcas at one of the top kayaking destinations in the Pacific Northwest. The San Juan Islands are teeming with wildlife, from harbor seals sunbathing on rocks to bald eagles soaring overhead.

Of the 170 named islands and reefs that make up the San Juan Archipelago, San Juan, Orcas and Lopez are the three best islands to visit. Stroll through San Juan Island’s Friday Harbor — bustling with galleries and museums — or embark on a whale-watching expedition off the coast of Orcas Island. Explore Lopez Island and learn about sustainable farming practices before dining on salmon raised in a local hatchery.

The San Juan Islands have adopted the seven principles of “Leave No Trace” and locals continue to prove that no act of conservation is too small. From sustainable housing and farms to beach clean-ups and marine research, the people of these hidden islands are working hard to preserve their beauty for future generations.

Road Scholar recommends: Best of Washington’s San Juan Islands: Exploring the Archipelago →


An island embroiled in complicated history but transforming rapidly in present day, Cuba lands on our list of underrated islands to visit because of its vibrant culture and stunning natural beauty. From the streets of colonial Old Havana to Hemingway’s famous haunts, the vivacious spirit of Cuba’s people can’t be ignored. Immerse yourself in Art Deco buildings, classic cars and lively music while learning how a country shaped by so many outside influences has such a strong sense of community.

Collect shells along unspoiled white-sand beaches, venture into tropical rainforests in search of exotic birds like the Cuban Grassquit or cheer on dancers and performers inside Spanish colonial plazas. In Cuba, there is much to discover.

While the U.S. government recently changed the rules around flying into Cuba, visitors can still fly into the capital city of Havana. If you have any questions about what to expect when traveling to and from Cuba, check out our Cuba Travel Guide or browse our collection of learning adventures.

Road Scholar recommends: Inside Cuba: An In-Depth Island Journey: Holguín to Havana →

Star Island, N.H.

Listed on the National Register of Historic Places, idyllic Star Island is the second-largest of the nine Isles of Shoals off the East Coast of the United States. Quaint cottages and centuries-old hotels still stand as a reminder of the Victorian-era resort communities and fishing villages that once thrived there. Today, Star Island is a hidden gem offering visitors a quiet escape filled with nature walks, kayaking excursions and leisurely swims in deep blue water.

If you’re an art lover who draws inspiration from the sea, you’re in luck! On Star Island, spend your days gazing out at the Atlantic and strolling where Impressionist painter Childe Hassam, writer Nathaniel Hawthorne and resident poet Celia Thaxter created some of their works. In the 19th century, Thaxter founded a thriving arts community on Star Island frequented by literary legends such as Harriet Beecher Stowe, John Greenleaf Whittier and Oliver Wendell Holmes. Follow in their footsteps as you participate in seaside art classes or attend a local historic play.

Road Scholar recommends: The Star Island Experience →

Spetses, Greek Isles

Another little-known island to visit off the coast of Greece, Spetses is a place of myths and magic. The serene beauty of this little island is magical enough, but its ancient history and architectural wonders will leave you breathless – if you’re willing to explore off the beaten path!

Visit Spetses’ old harbor as you learn about the island’s naval history and its role in the Greek War of Independence. Journey to the archaeological site of Mycenae, where the stories of Helen of Troy and the Trojan War come to life. You’ll gain an understanding of the power of Ancient Greek military strongholds while gazing up at the monumental Lion’s Gate and hiking to the top of the Mycenaean Acropolis.

In the town of Spetses, no privately owned vehicles are allowed within city limits, so be prepared to explore on foot or set off on a bike ride along the island’s sparkling shorelines. Charming horse-drawn carriages clip-clop through streets filled with aristocratic mansions, churches and monasteries, while boat taxis ferry visitors across the strait to explore the picturesque alleys of Nafplio.

Road Scholar recommends: Greece's Hidden Gems: Discover the Timeless Island of Spetses →

Murano, Italy

Known for its unique glass art and expert craftsmanship, Murano is a series of islands linked by bridges and canals in the Venetian Lagoon. A short vaporetto ride away from the city of Venice, crowds of visitors gather to learn about the tradition behind Murano glassmaking. Murano’s reputation for producing fine Venetian glass began in the 13th century when the Venetian Republic mandated that all its glassmakers move their furnaces there. Glassmaking remains the islands’ main industry today.

When you’re not attending a glassblowing demonstration or admiring intricately crafted pieces at Murano’s Museum of Glass, this underrated island has plenty more to offer. Stroll past Venetian Gothic architecture along the canals, visit centuries-old basilicas or board a boat to the neighboring island of Burano, known for its delicate lacework and brightly colored fishing villages.

Road Scholar recommends: The Best of Italy: Rome, Florence and Venice →

Want to learn more?

Discover more hidden islands and little-known communities near the water on an Island Learning Adventure with Road Scholar!

About the Author
JoAnn Bell, Senior Vice President of Program Development, develops and manages more than 5,500 learning adventures in 150 countries and 50 states. JoAnn's extensive experience informs her expert insight on everything from where to find the world's most charming streets to must-see hidden gems across the globe.


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