Indagare Matchmaker: Anguilla

Located a short plane or boat ride from St. Maarten and only 16 miles long, Anguilla has long been a favorite of laid-back sophisticates looking for a beach escape. Boasting five-star hotels, private villas, fantastic local restaurants and more than 30 quiet stretches of talcum-powder sand beaches, the Caribbean island offers something for everyone—but choosing the right hotel can be tricky. Indagare breaks down the differences between five of the best options.

The Beachfront Classic: Belmond Cap Juluca

Since opening in 1980s, Cap Juluca has gained a steady following amongst well-heeled travelers who appreciate its authentically Anguillan feel. Situated on 179 acres of land on one of Anguilla's most beautiful beaches, the 71-room Cap Juluca was taken over by luxury brand Belmond in 2018 and fully renovated.

• Vibe: Authentic, sophisticated, barefoot luxury
• Location: The southwestern shore of Anguilla along Maundays Bay
• Best For: Those who want easy access to one of the island’s most pristine beaches, as well as families who desire a sprawling property with lots of space.
• Room to Book: The two-bedroom Jonquil suite, which boasts a beachfront private pool
• Keep in Mind: Some suites and villas come with a golf cart for guests to traverse the property. Guests in other accommodations can request carts if needed (subject to availability)

The Contemporary Hot Spot: Four Seasons Anguilla

Opened in 2009 as a Viceroy hotel, the Four Seasons offers a more contemporary aesthetic than the island’s traditional hotels. As the newest of the top luxury resorts in Anguilla, the property is more design-focused than charming, but it boasts the best amenities on island with its spacious accommodations and full-service facilities such as a large spa and gym and the island’s only kid’s club.

• Vibe: Sleek, stylish, full-service
• Location: At the western point of Meads Bay
• Best For: Those who want a grand statement and more of a Miami Beach scene. While the vibe is buzzy, the Four Seasons is also family-friendly, and parents will feel comfortable letting their children and teens roam around the kid’s club, volleyball court and rock climbing wall. Adults will enjoy the large spa and many spots to relax and enjoy a drink. Those who are looking for something quieter should consider Cap Juluca or Malliouhana.
• Room to Book: Families with young children should book the spacious, two-bedroom residences with a private plunge pool. Larger groups or families should splurge on one of the three-, four- or five-bedroom beachfront villas, some of which have direct beach access.
• Keep in Mind: The property is located on an exposed point, so the wind and waves can be strong. 

The Whimsical Boutique: Malliouhana

After an $80 million makeover, the boutique Malliouhana reopened in 2014 decked out in the chicest wardrobe it has sported since its grand premiere in 1984. The esteemed hotel’s latest incarnation resembles the home of a world traveler with eclectic tastes tied together by a mint green and soft yellow color scheme.

• Location: The eastern point of Meads Bay
• Best For: Couples or groups of adults who enjoy gorgeous views, relaxed nightlife and fantastic food. This is a boutique property, so the hotel doesn’t have tons of space or facilities; there is no kid’s club, and the spa and gym are quite basic.
• Room to Book: Any of the ocean view rooms. However, guests who are price conscious could be happy in a garden view room and spend their time in one of the many gorgeous nooks around the property.
• Keep in Mind: As the hotel is located up on a bluff (with spectacular views over the cerulean Anguillan waters), there are a lot of steps down to the beach, which might be difficult for less mobile guests. Since the property is quite small, families with teenage children may prefer Cap Juluca or the Four Seasons, both of which offer more space to run around.

The Custom Fit: Private Villas

Unlike some other Caribbean islands where guests are likely to stay on property throughout their stay, Anguilla is a safe island and there is a lot to explore plus many restaurants. There are many luxurious private villas available, where families or groups of friends can have their own pool, space to spread out and oftentimes direct beach access.

• Vibe: Large, private, fully-staffed
• Location: Sprinkled around the island, with most in Barnes Bay or Meads Bay.
• Best For: Large families or groups who would like the privacy and flexibility of having their own home, especially over the holidays when some of the hotels and beaches are at maximum occupancy.
• Keep in Mind: The villas do not have reciprocal rights to hotel facilities, so those who need the infrastructure and amenities of a hotel with a villa experience should consider the Four Seasons, Malliouhana or Cap Juluca.

The Newcomer: Zemi Beach Resort and Spa

Opened in February 2016, Zemi offers a boutique, value-oriented retreat on the removed Shoal Bay, one of Anguilla’s prime snorkeling locations. The accommodations range from standard rooms to three-bedroom suites with private plunge pools, and additional beachfront rooms will be completed in late 2016. Guests can book treatments in the original Thai House Spa or play a game of tennis on the property court while children will enjoy the kid’s club.

• Vibe: Value, remote, spa focus
• Location: On Shoal Bay, about a 30-minute drive from the West End.
• Best For: Those who are looking for a less expensive option and don’t mind being a long drive from most of the island’s restaurants.
• Keep in Mind: Since the hotel just opened, parts of the property are still under construction and the service needs some polishing.