Bermuda is the easiest, most beautiful getaway from NYC - a two-hour flight and you're there. I loved walking off the plane and seeing a giant painting of Queen Elizabeth II. It has this distinct Britain meets island paradise vibe and it's so unique. As of 2017, rental cars are banned on the island (even if you live there, you can have only one car per family!), so it's best to hire a driver for the days where you will be doing a lot of sightseeing, and take taxis the rest of the time. It will be one of your biggest expenses while on the island. We had a terrible driver the first couple of days, and found an AMAZING ONE for the last two days. We will always remember our time with Samuel!
Everything depends on what part of the island you're staying in - we managed to drive and bike a good portion of the entire 20-mile island. Study the map before you go and map out your dining/sightseeing excursions. I'd probably do one day of solid sightseeing with a driver, and then plan 2-4 lunches/dinners out. The rest of the time, I'd stay at a great hotel. Samuel was so wonderful because he also doubled as a great tour guide.
The parish of St. George's is close to the airport, and Wahoo's Bistro is a great place to stop for lunch when you first land. Try the enormous fish tacos and Bermuda Fish Chowder. Owned by Austrian expat Alfred Konrad, everything is super fresh and comes with a great patio view.
In St. George's, I would also stop by Lili Bermuda to shop for local perfumes, go into the adorable tiny St. Peter's Church in the center of town (which seems ready for destination weddings), and if you have time, walk up to the Unfinished Church behind the town and wander through the colorful houses on the way down.
Our driver took us for a quick photo stop at Fort St. Catherine - worth it for beautiful blazing blue views. If you're into forts (like my father), you may want to spend more time here.
Crystal Caves - They really push the Crystal Caves as one of the top attractions in Bermuda. It is pretty cool, but it's a required guided tour and not cheap. I've done it once, but won't go back on my next trip to Bermuda.
Climb to the top of Gibbs Hill Lighthouse - I loved doing this 185-step climb in Southampton Parish for a panoramic view of the entire island. Queen Elizabeth II visited the lighthouse shortly after her coronation on June 2, 1953 – one of four trips she has made to Bermuda.
Hamilton is Bermuda's largest town. It is a great place to spend time shopping and dining. If you're staying at the Hamilton Princess Bermuda, they have a beach club you can visit (but know that you aren't right on the beach). I highly recommend eating at Marcus Samuelsson's restaurant overlooking the harbor at the hotel - everything is delicious, like Obama's Short Rib and the Jerk Cauliflower dish. The hotel also has one of the most incredible art collections I've seen on my travels.
Have lunch at the famous Ascots, a beautiful space at the Royal Palms Hotel.
And have tea or just pop into the Rosedon Hotel behind the Hamilton Princess - it is so lovely!
Shopping in Hamilton: Don't miss Della Valle Sandals. Italian Vincenzo Della Valle has made shoes since he was a child living in Capri. In 2016, he opened a shop on Hamilton’s Queen Street, a must-stop for well-priced, custom women’s sandals. Go on your first day in Bermuda so Valle has time to finish them before you leave – he doesn’t ship (depending on your order, turnaround time is a couple of days). I wish I had bought more than one pair.
For colorful Bermuda shorts and polos, look no further than TABS Bermuda, owned by a wonderful woman named Rebecca Singleton (we happened to meet her husband while on the island, and ran into them our last night at dinner).
Visit the Masterworks Museum of Bermuda Art which showcases only pieces inspired by Bermuda (and some by Winslow Homer and Georgia O'Keeffe). If you're not into art, I'd skip it, but I loved spending an hour here at this small museum (where Prince Charles is a patron). I toured with curator Elise Outerbridge, whose passion for this space is contagious - you can also ask her about her David Bowie encounters - he had a home on Bermuda. Stroll through the small Bermuda Botanical Gardens surrounding the museum after your visit (183 South Road, Paget).
Our favorite dinner was at Rustico, in Flatts Village. Order pizzas to share and sit on the patio on a beautiful night. You'll be surrounded by locals (or those with second homes on the island, so they feel local).