Saint Barthélemy vs Anguilla

St. Barts packs an extraordinary amount of beauty into fewer than ten square miles. Start in Gustavia, the pocket-sized capital that wraps around one of the prettiest natural harbors in the Caribbean - during high season the megayachts anchored here rival anything you would see in Monaco.

Walk along Rue de la République past Swedish-era stone warehouses that now house Cartier and Hermès boutiques, then climb to the ruins of Fort Karl for a sunset view over the harbor that costs nothing except the short uphill effort. Shell Beach, just around the corner from the harbor, is a small crescent of crushed shells where you can swim and then dry off over cocktails at Shellona, one of several beach restaurants right on the sand. The real star beaches are elsewhere on the island.

Colombier Beach, on the northwest tip, is reachable only by a 25-minute hike from the trailhead at the end of the road past Flamands, or by boat - the trail drops through dry scrub with views of neighboring islands before revealing a protected cove with gin-clear water and excellent snorkeling along the rocky edges. Gouverneur Beach, on the south coast, is framed by steep green hills and has no commercial development at all - bring your own water and shade, and arrive by mid-morning for parking. Saline Beach, the favorite of longtime visitors, requires a short walk through salt ponds and sea grape trees before opening onto a wide stretch of golden sand with reliable waves for bodysurfing.

For a different perspective on the island, rent a car and drive the vertiginous roads that connect the hilltop neighborhoods - the descent into St. Jean from the airport side is legendary, passing directly over the tiny runway where small planes seem close enough to touch. The Tuesday and Friday morning market at Marigot in nearby St. Martin (reachable by ferry from Gustavia) is worth a half-day trip for spices, tropical produce, and Creole prepared foods, but on St. Barts itself the shopping leans decidedly upscale, with Ligne St. Barth producing island-made skincare products using local ingredients like roucou oil and green papaya.

Anguilla is a place where doing less feels like the whole point, but that does not mean there is nothing to do - it means everything worth doing happens at a slower, more intentional pace. Start at Shoal Bay East, consistently ranked among the best beaches in the Caribbean, where the sand is so fine and white it squeaks underfoot and the water transitions from pale aquamarine to deep sapphire in clean, visible bands. Rent a chair from Uncle Ernie's Beach Bar, order a rum punch, and let the morning disappear.

When you are ready to move, walk the full mile of shoreline to the eastern rocks where the snorkeling is surprisingly good over patch reef just a few yards offshore. Meads Bay, on the northwest coast, is the luxury beach - lined by Belmond Cap Juluca and Four Seasons Resort, it has a more manicured feel but the swimming is excellent and the sunset views across to St. Martin are hard to beat.

For something more secluded, drive to Little Bay, accessible only by a short scramble down a cliff with a rope (or by boat from Crocus Bay). The effort is worth it: a tiny cove with calm, snorkel-worthy water and virtually no one else around. Sandy Ground Village is the closest Anguilla gets to a scene.

This narrow sand spit between the sea and Road Bay salt pond has a string of restaurants and bars - Elvis' Beach Bar is the local institution, serving cold Heinekens and grilled crayfish with your feet in the sand while live music drifts across the water on weekend nights. For history, visit the Heritage Collection Museum in East End, a small but genuinely informative collection documenting Anguillian life from the Arawak period through the 1967 Revolution, when Anguilla broke away from the St. Kitts-Nevis federation in what may be the most polite revolution in Caribbean history. A day trip to Prickly Pear Cays by boat from Sandy Ground is essential - the two small uninhabited islands sit inside a reef and the snorkeling over elkhorn coral and sea fans is the best in Anguillian waters. Boats typically include lunch and rum punch for around $80 per person. Dog Island, farther out, rewards adventurous snorkelers and divers with pristine reef and solitude that feels genuinely remote.

St. Barts does not do budget accommodation. The island's limited size and zoning restrictions mean there are no high-rise resorts and no all-inclusives - instead, you choose between boutique hotels and private villa rentals.

Eden Rock, perched on a rocky promontory that divides St. Jean Beach, is the island's most iconic property, with rates starting around $1,200 a night in high season and climbing steeply for its signature suites carved into the rock itself. Le Barthélemy Hotel & Spa in Grand Cul-de-Sac offers waterfront luxury with a Michelin-affiliated restaurant from around $900.

Chéval Blanc St-Barth Île de France, the LVMH property on Flamands Beach, is the choice for guests who want a large, swimmable beach with five-star service - expect $1,500 and up. For something more personal, Hôtel Le Toiny in the hills above the southeast coast has just 22 private villa suites, each with a plunge pool, starting around $800. Villa rentals are the preferred option for groups and families, and they can actually represent better value than hotels.

A well-located two-bedroom villa in Lurin or St. Jean runs $500 to $1,000 a night in season, while larger properties in Gouverneur or Pointe Milou with infinity pools and ocean views command $2,000 to $5,000 per night. Agencies like St. Barth Properties and Wimco Villas have the deepest inventories. Low season (mid-August through October) brings discounts of 30 to 50 percent, but some restaurants and hotels close during September. Book December through March at least six months ahead, especially over New Year's when the island hits full capacity.

Anguilla positions itself firmly in the luxury bracket, and accommodation prices reflect that. The two flagship resorts are Belmond Cap Juluca on Meads Bay and Four Seasons Resort on Barnes Bay, both offering the kind of white-on-white, feet-in-the-sand elegance the island is known for, with rates starting around $800 per night in high season and climbing well past $2,000 for premium suites.

Aurora Anguilla, formerly CuisinArt, reopened after a major renovation and sits on Rendezvous Bay with its own hydroponic farm supplying the restaurants - rates start around $600. Malliouhana, perched on a cliff between Meads Bay and Turtle Cove, is another classic that balances luxury with genuine character, starting around $700.

For mid-range options, Shoal Bay Villas and Serenity Cottages on Shoal Bay East offer well-kept beachfront units from around $250 to $400 per night, putting you steps from the best beach on the island without the resort markup. Villa rentals are popular on Anguilla and often provide better value for groups - expect to pay $300 to $600 per night for a two-bedroom villa with a pool, with high-end properties reaching $2,000 or more.

Budget accommodation is genuinely scarce. A few guesthouses in The Valley and South Hill offer rooms from $120 to $180, but they lack beach access and the kind of setting most visitors come to Anguilla for. The most cost-effective strategy is a shoulder-season visit in May or November, when even the top resorts drop rates by 30 to 40 percent.

Dining on St. Barts operates at a level unmatched anywhere else in the Caribbean. The French culinary DNA is everywhere, but the island has developed its own identity that folds in Caribbean ingredients and beachside informality. For a signature lunch, L'Isoletta at the western end of St.

Jean Beach serves thin-crust pizza and Italian seafood dishes with your feet in the sand - arrive by noon for a table. Maya's, tucked beside the harbor in Gustavia, has been the island's go-to for Creole-Caribbean cooking for decades: grilled mahi-mahi with plantains, accras de morue (salt cod fritters), and rum punch served on a waterfront terrace. Bonito, overlooking Gustavia harbor, does inventive French-Asian-Latin fusion with ceviches, tartares, and wagyu tataki - it draws a lively crowd from 7 p.m. onward. For a blowout dinner, La Case de l'Île at Chéval Blanc on Flamands Beach delivers refined French cuisine in a candlelit setting right on the sand.

Expect to spend $150 to $250 per person at these top-tier spots. On the more casual end, Orega in St. Jean turns out excellent poke bowls and acai for $15 to $25, and the Rôtisserie at the JoJo Burger counter in Lorient serves loaded burgers and rotisserie chicken that locals swear by. For breakfast pastries, stop at Boulangerie Choisy in St.

Jean for croissants and pain au chocolat that rival anything in Paris. Grocery shopping at Marché U in St. Jean is essential for villa stays - the cheese, wine, and charcuterie selection reflects that this is, after all, France. Budget around $80 to $100 per person per day for eating out, or half that if you mix in some villa cooking.

Anguilla punches far above its weight in dining for an island of 15,000 people. The cuisine blends Caribbean flavors with French, Italian, and Asian influences, driven by a handful of chefs who have made the island their home.

Blanchards, on Meads Bay, is the island's most celebrated restaurant - a white-tablecloth beachfront spot serving dishes like sesame-crusted tuna and Angus beef tenderloin in an open-air setting that has drawn loyal return visitors for over 25 years. Reservations are essential in high season, and dinner for two runs around $200 to $300 with wine.

Their more casual sibling, Blanchards Beach Shack next door, serves excellent fish tacos, jerk chicken, and burgers for $12 to $20 at picnic tables on the sand - the best lunch value on the beach. Veya, in Sandy Ground, is chef Carrie Bogar's creative fusion spot where Thai curry meets Caribbean lobster in a garden setting.

Straw Hat on Meads Bay offers a more relaxed fine-dining experience with an approachable menu and reliable quality. For local Anguillian food, Tasty's in South Hill serves classic dishes like crayfish with rice and peas, salt fish, and johnnycakes in a no-frills setting that draws locals and visitors alike - lunch plates run $15 to $25. Ken's BBQ in The Valley does spit-roasted chicken and ribs with side dishes that taste like someone's grandmother made them. On the beach bar circuit, Elvis' Beach Bar on Sandy Ground is the essential sunset spot, while Scilly Cay, a tiny private island just off Island Harbour reachable by a two-minute boat shuttle, serves grilled crayfish and lobster in one of the most atmospheric settings in the Caribbean - open Wednesdays and Sundays only.