Anastasia Island

St. Augustine and St. Augustine Beach

Anastasia Island is where beach life meets deep historical context. Sitting just east of St. Augustine, this barrier island offers something many Florida beach destinations do not: a layered sense of place that stretches beyond the shoreline.

A close-up view of the St. Augustine Lighthouse & Maritime Museum at night. Photo by Roberto Gonzalez.

Anastasia Island runs roughly 14 miles along the coast, from Anastasia State Park to the Matanzas Inlet area. The island is bordered by the Atlantic Ocean on one side and the Matanzas River on the other, creating a narrow strip where water is always close. That geography matters. It shapes the island’s breezy feel and also gives it multiple modes of outdoor recreation. You can spend a day on the beach and still find kayaking and calmer water experiences nearby.

How it feels: Beach-town ease with cultural weight.

Who it’s for: Travelers who want variety and a sense of story.

What to do: Beach days, seashore stretches, casual dining, water time.

Anastasia State Park anchors the island’s preservation story. It is the kind of park that makes you grateful Florida still sets land aside and then resists the temptation to “improve” it. Trails, dunes, camping and natural shorelines give the island an outdoors-forward identity.

Then there is the historical layer: the Spanish Coquina Quarries within the park. Coquina, a stone formed from compacted shells and sand, was used to build iconic structures in St. Augustine, including the Castillo de San Marcos. This is not a detail that feels like trivia once you see it. The story ties the island’s physical material directly to the mainland city’s history.

Outside the park, Anastasia Island offers the everyday pleasures of a beach town: breezy sand, less crowd density than more commercial Atlantic areas, and accessible attractions. Even mini golf fits here in a way that feels charming rather than loud, with places like Fiesta Falls offering a classic vacation diversion.

“Anastasia Island doesn’t rely solely on its beach or its history. It lets each deepen the other.”

Anastasia Island’s greatest strength is balance. You do not have to choose between history and beach. You can do both without making either feel like a side trip.

Jupiter Island

Palm Beach County

Blowing Rocks Nature Preserve sanctuary on the barrier island of Jupiter. COURTESY THE PALM BEACHES

Jupiter Island, nestled between the Indian River Lagoon and the Atlantic Ocean, carries a reputation for lush landscape, privacy and careful stewardship. Conservation areas and protected natural spaces matter here. The Hobe Sound National Wildlife Refuge offers a reminder that barrier islands can serve as essential habitat, particularly for species like sea turtles and manatees.

Blowing Rocks Preserve, known for dramatic sea spray when waves collide with rocky shoreline, adds geological personality to a coastline often associated with sand. The Jupiter Inlet Lighthouse area deepens the sense of history and navigation. It is the kind of landmark that makes you imagine the coastline as it once was: darker at night, quieter, and more mysterious.

How it feels: Quiet and residential.

Who it’s for: Those looking for a relaxed beach getaway.

What to do: Enjoy a great round, or two, of mini golf at Lighthouse Cove Adventure Golf.

The food scene in the broader Jupiter area reflects South Florida’s coastal culture. Guanabanas stands out for its open-air tropical atmosphere, live music and a menu that fits the island vibe.

“Opened by Jupiter surfers as a sandwich shop in 2004, Guanabanas has grown to become an institution in northern Palm Beach County.”

Opened by Jupiter surfers as a sandwich shop in 2004, Guanabanas has grown to become an institution in northern Palm Beach County for three reasons: The lush, tropical setting; great cuisine and cocktails, and live music from both national acts and the hottest names in South Florida.

Singer Beach

Palm Beach County

Singer Island offers a more family-friendly barrier island experience, with snorkeling trails, parks and easy water access. John D. MacArthur Beach State Park is a highlight, offering a stretch of pristine coastline plus nature trails and paddling options. It is also the kind of park that helps define the region’s best version of itself: natural, accessible and still textured with wildlife.

How it feels: Tropical and accessible.

Who it’s for: Day-trip explorers.

What to do: Snorkel Ocean Reef Park, visit Peanut Island, and explore John D. MacArthur Beach State Park.

Nearby, Phil Foster Park’s snorkel trail and the ability to hop to Peanut Island for boating and paddling adds variety. These are the islands where your “beach day” can become a water day, a snorkel day, and a paddling day without much effort.

Palm Beach

Palm Beach County

Think you have to travel to the Caribbean for reefs? On Singer Island, the reef at Ocean Reef Park is shallow and close to shore. COURTESY THE PALM BEACHES.

Palm Beach itself is a barrier island with a polished identity shaped by history. It carries the legacy of Henry Flagler and the era when Florida’s coastal destinations were marketed as winter retreats for the elite. Even if you do not step into a luxury hotel, the built environment tells the story: architecture, landscaping, and a certain sense of curated calm.

How it feels: Elevated, carefully maintained, coastal with polish.

Who it’s for: Travelers who enjoy mixing nature, refinement and day trips.

What to do: State parks, snorkeling trails, lighthouse history, breezy dining.

If you are looking for a luxury stay, White Elephant is quite popular, a sister property to the incredibly in-demand and equally posh White Elephant in Nantucket. The Breakers offers a more historic stay, steeped in old-world glamour and sumptuous brunches.

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