Arrive in Antigua and transfer 40 minutes to the dramatic southwest coast of the island, marked by a ridge of rain forest-covered hills rising abruptly from a patchwork of farmland. Take the rest of the day to settle into your resort, perhaps indulging in a spa treatment to refresh yourself after your flight.
Explore Nelson's Dockyard, a fascinating restored British naval station with an array of elegant 18th-century colonial buildings. In the afternoon, relax at your resort's white-sand beach, wander a hiking trail, kayak through the mangroves or head out for some deep-sea fishing.
Visit the weekly market in St. John's, where vendors sell colorful produce and local handicrafts. You can also see a local independent farm and sample tropical delights such as custard apples, West Indian cherries and up to 14 varieties of mangoes (depending on the season).
Tour a sugar plantation dating from 1674, complete with a restored windmill. A bit farther on is Indian Town, a national park noted for its dramatic natural bridge. The surf spouts through numerous blowholes, making for excellent photo opportunities.
Spend today doing whatever you wish. Beachcomb, sail, snorkel, scuba dive, have a massage, unwind with a good book—the Harper Alliance resorts present numerous tempting options. Make the evening particularly romantic with a private dinner on the jetty.
Take an unforgettable helicopter flight to nearby Montserrat, where you can view the remains of its ruined capital city, charred by flows of lava and ash.
After a leisurely morning, return to Antigua's airport and board a nonstop 45-minute flight to tranquil Anguilla. This tiny island (just 16 miles long and three miles wide) boasts luminously turquoise seas and some of the best beaches in the Caribbean. Take the remainder of the afternoon to unpack and relax.
Use these days to leisurely explore Anguilla. Enjoy some sailing or snorkeling, pamper yourself in the resort's spa, shop for beautiful local handicrafts, make a day trip to a deserted cay, head out for some fishing or just do nothing. On Friday night, enjoy a festive beach buffet complete with live music.
Finish your last full day with an unforgettable private beach dinner, surrounded by glowing torches.
Transfer to the airport and take your flight home.