Flying into St. Maarten/St. Martin, with its large cruise port and world-famous runway over Maho Beach, you’ll quickly realize that this dual-personality island bustles with two distinct vibes (quainter and French on the St. Martin side and casino-centric and Dutch on the St. Maarten side). This makes it not only unique but also a great partner island for its smaller and more tranquil neighbor, Anguilla. Book a round-trip flight to St. Martin/St. Maarten, then simply hop a 25-minute ferry from Marigot to Blowing Point on Anguilla, where the laid-back vibe is perfect for winding down. Tickets are $20 per adult, and ferries depart daily.