As a somewhat scruffy guy who’s been sailing yachts to Bermuda (between New England and the Caribbean) since 1993, I’ve always had a special spot in my heart for this island’s timeless elegance. 

And as a somewhat scruffy preppie guy who’s also spent a fair amount of time onboard superyachts in some of the most “exclusively hip” destinations in the world, I can also say that not too many members of the superyacht set would ever accuse Bermuda of being “hip.”

Until now.

The easy reason for this is the America’s Cup and all the excitement that comes with yacht racing’s premier event presented by Louis Vuitton has come to town and many of the world’s most luxurious superyachts have arrived so owners and guests can watch the racing up close and personal. And there are more private planes arriving daily.

But there’s way more to Bermuda than just the America’s Cup. In fact, some of the island’s oldest hotels and resorts like these here are becoming downright “hip.” And others, like The Loren – a brand-new boutique hotel that’s profiled on page 78 – are “hip” right out of the gate. Here’s just a taste.


Photo courtesy of Hamilton Princess & Beach Club


The high-profile people watching in the lobby of this grand hotel that has played host to countless shipping magnates, businessmen and famous visitors since it opened in 1885 has always been spectacular. But even the America’s Cup A-listers who are in residence will probably agree that the modern art on display throughout the hotel, which recently completed a $100 million renovation, is the real star of the show. The “hip” factor only increases when you combine its private beach club, pool, full-service marina and multiple restaurants with the buzz of downtown Hamilton.


Photo courtesy of Fairmont Southampton


The large “Pink Lady” perched atop the highest point in Bermuda truly has something for everyone. All of its 593 guest rooms and suites have private balconies and fantastic views. Golf, tennis and a myriad of water sports can be easily arranged when you want some action. Its private beach club is just a short walk (or shuttle ride) down the hill. Spa treatments, dinner reservations or simply lounging by the pool all contribute to the goal of deep relaxation. The hotel’s relative close proximity to all the action in the America’s Cup village makes this an ideal spot to stay if you want to watch the racing up close. The Fairmont’s location on highest point in Bermuda means you can also easily watch the racing—on Great Sound—off to the north west from comfortable chairs on the hotel lawn too.


If you’ve come to watch the America’s Cup, Cambridge Beaches Resort & Spa is the closest resort to the America’s Cup Village in the historic Royal Naval Dockyard. And if you are just looking to relax, it’s hard to compete with the soothing pool area that looks towards Great Sound or the full-service spa that can sweep away stress with everything from facials to deep tissue massage.


When it comes choosing the best place to experience all the excitement of the America’s Cup any of the resorts profiled above have pulled out all the stops to ensure their guests can get as close to the action as possible. But none of these resorts can get you closer to the America’s Cup action than a catamaran yacht charter from The Moorings. So, in addition to having access to watch the racing form the special on-the-water spectator area during the Cup, up to 10 charter guests are enjoying spacious accommodations aboard an air-conditioned catamaran, personalized service from a professional captain and chef, a full selection of water toys too. 


Image Credits: Photo courtesy of Cambridge Beaches Resort & Spa.