Nantucket
Nantucket is my most special place ever, as I started coming to the island when I was three months old. My family had a house on Dionis that was 12 steps to the ocean and the last property before the public beach towards the island's western tip. I first learned to sail at the Nantucket Yacht Club, so that's where my lifelong passion for sailing was born. So it was pretty magical to spend summers here from childhood to now. Of course, some of the stereotypes are true: the island is arguably the preppiest place on earth (the pink pants are called Nantucket Reds, just head to Murray's to pick up a pair), with sky-high real estate prices, where fine dining reservations are a blood-sport. Digging deeper, however, reveals the beauty of the island that is preserved by the Land Bank, its rich history as the world's whaling center in the early 1800s and a timeless summertime vibe. I spent two weeks here in August of 2020 during the pandemic, when much of the island activity was suspended, and by July of 2021, everything was back in full swing. Here are some of the highlights of my trip:
The White Elephant
The White Elephant is a classic Nantucket hotel, with pride of place along the harbor, sporting the traditional grey cedar shingles and white trim that characterize the island's architecture. There are so many great things about this hotel (food, spa and several 'on -demand' 7 Series BMWs to whisk you into town) but it really comes down to location, location, location. The view from my room offered a direct view of the steamships, sailboats and the occasional super-yacht coming into harbor. The hotel is a quick 10 minute walk to Brandt Point Lighthouse and walkable to town, for when you want to get some steps in instead of taking the courtesy BMW. This is my second stay in three years and, while it is a splurge, everything about this place is perfect.
The Endeavor
Sailing on Nantucket is a must and one of the best ways to get out on the water is to charter with the Endeavor, a sloop that Captain Jim has been sailing for almost 40 years. Capt. Jim is knowledgeable, friendly and ready to entertain with a story or two. The boat maxes out at around 12 people, so if you have a small group, it's really worth it to charter the boat for 1 1/2 hours. Just pack a cooler with some champagne and snacks and get a small taste of the seafaring history of the island.
Cisco Brewery
Cisco Brewery is a great spot on the island that features an outdoor beer garden, food trucks from some of the local restaurants and live music. Located right next to Barlett's Farm, Cisco Brewery has some great local beers (Whale's Tale is my favorite) and a chill, friendly vibe. I went withy my buddy Jon for an afternoon and had a blast. Pro tip is to go 1/2 hour before they open, park in the field just down the street and there will still be a line to get in - but we grabbed some stools in the shade and made some new friends along the way. This place did reach peak "bro" as 20 somethings swarmed patio wearing shorty bathrobes...I snapped a pic so you'd believe me.
Great Point Lighthouse
Great Point Lighthouse
With a Jeep and the oversand vehicle permit, a drive out to Great Point on the island's northern tip is a 'must do' adventure. Here the land becomes a tiny slip, with the bay on one side and the ocean on the other. This is prime location for birds and colonies of grey seals. Surfcasting fishermen line the ocean side for schools of striper and bluefish, while the calmer bayside is great for a picnic and sunbathing. The lighthouse is an iconic image of Nantucket (along with Brandt Point lighthouse), and the current structure was rebuilt in 1986 and is still a vital navigational marker for sailors and mariners. It takes a little work to get here - a permit, deflating the tires to 15 psi, bringing along food & drinks - but it's well worth it to see the unspoiled nature up-close and feel the remoteness of the island from this really unique spot.
Restaurants & Bars
The Chanticleer
The Chanticleer is about as romantic a place as imaginable. From the flower-filled garden to the wood-paneled grill room with its tiny bar, this restaurant is tops on an island that has some world-class dining. Proprietor Susan Handy is a master of understated elegance and warmth. The wine list is outstanding and edited and sommelier Rachel steered me to just the right white burgundy that was her new favorite wine this year. Tucked in the tiny town of Sconset, this feels worlds away from the business of Nantucket town. When the fog rolls in at night, this place is just magic. The Chanticleer is the best of the best. Period.
Just down the road from the Chanticleer, lies the Summer House (current under renovation) and the beachside bistro, pictured here. Down some steep steps to the pool and bar area, the beachside restaurant is under a big tent right on the sand. Even on sunny days, the fog can still roll in as the wind hits the tides and cool air of the shoreline. A great spot for a lobster roll, the Summer House is near the center of Sconset, where a shell lined path winds in between the salt box houses dating from the early 1900s. Grab an ice cream from the Sconset market and go for a walk around the town and end up on the beach, just a few steps away.
Straight Wharf Restaurant
My favorite restaurant in town is Straight Wharf - whether out on the back deck overlooking the water or in the main dining room, this place just gets it right. I always get the same thing when I'm here: Nantucket Oysters, Swordfish and Billecart-Salmon rose champagne, pictured here alongside my mother's 1970 Nantucket Basket with scrimshaw inlay (a few years pre-ban due to species protection). Reservations, as with all fine dining on island, is a blood sport but a little persistence goes a long way. After dinner, you can take a short walk out to the end of Straight Wharf to see all the mega yachts and daydream. If you want a night cap (or great drinks and food anytime), you can head to Cru for some oysters and beverages by the water. Along with Lola 41, these are my two favorite bars on the island - but, fair warning, they can tend to be quite a scene. But if you're up for mixing with the 'beautiful people' - head to both of these hotspots!
Parting Shot - My first G&T handed to me by the great Jon Greenawalt!
The White Elephant Bar - first G&T on island!