Where to stay: Chatham Bars Inn. A local symbol of well-to-do elegance, it's de rigueur for wealthy Bostonians to visit on the weekend. 100 years later, a $100 million renovation has updated the hotel with 5-star service, without losing any of its traditional charm.
What to do: Hop aboard the “Bar Tender” (aka the free shuttle) to the pristine Nauset Outer Beach (seriously, it’s protected by a national park) accessible only by boat.
Where to dine: You can’t visit New England without eating a lobster roll. Insider tip: those from Lazy Lobster are the best.
Where to stay: Avoid the center of town. The tiny 5-star El Torre Del Canónigo sits within a 14th century defense tower. Getting there requires a romantic walk up a winding path, yet it’s only 15-minutes from the airport.
What to do: Party. We hear all the action goes down at Beachouse’s Sunday Party (it’s also where you’ll find the top DJs in town). Recover the next day at the hotel’s rooftop pool.
Where to dine: Ex-Noma, chef Boris Buono’s Ibiza Food Studio is the experience of a lifetime. (And you get to eat in his private residence.)
Where to stay: On a yacht, of course. But which one? Sail boats are chicer. We like the look of the 92-foot Nikola.
What to do: Greece is known for its incredible Orthodox churches. Exoghi, a quant village on the storied island of Ithaca has a hilltop monastery with a gorgeous, panoramic view. Too hot to walk it? Hire a scooter instead.
Where to dine: The island of Paxos, currently trending among creative fashion types, is home to Ermitis, a restaurant filled with local specialties (and great for people-watching).
Where to stay: Go old-school and stay at the sprawling Villa d’Este (a Lake Como classic since the 19th century)—picture uniformed valets, pastry chefs, evening pianists and giant clawfoot tubs. It's also known for its unparalleled hospitality.
What to do: Return home laden with olive oil. Stock up at Vanini Osvaldo, a 150+ year old family-run producer on Lake Como’s western shore.
Where to dine: Keep with the traditional theme. Locanda dell’Isola Comacina has been serving the same menu (an Italian 5-course feast of simple ingredients) since 1948.