Kick Back On Nantucket Island This Summer

Update: Some offers mentioned below are no longer available. View the current offers here.

In the latest installation of our "By the Sea" summer destination series, TPG Contributor Drew Limsky holes up in serenely beautiful Nantucket, Massachusetts, just before the summer season hits.

Set 30 miles south of Cape Cod and sprawling over almost 50 square miles, Nantucket feels like it inhabits another era. Its uneven cobbled streets (leave your heels at home) and uniform gray wood shingles set a scene rooted in the early to mid-1800s. The island boasts great bike paths, walkable streets and one charming eatery after another, but most of all, Nantucket delivers a feeling; it's unspoiled New England seafront at its best.

With summer just about to hit, the weather is just balmy enough for visitors to wear shorts during the day — or even go for a swim — yet comfortable enough at night to throw open the windows and luxuriate in some of the freshest air in the Northeast.

Getting There

Nantucket Memorial Airport (ACK) welcomes JetBlue flights from New York-Kennedy (JFK), Boston's Logan International Airport (BOS) and Washington, DC's Reagan International (DCA), and Cape Air flights from BOS, Hyannis (HYA), Martha's Vineyard (MVY) and New Bedford (EWB). Nantucket (ACK) is also serviced seasonally (May-September) by Delta Connection from BOS and New York-LaGuardia (LGA), and by United Express/CommutAir from Newark (EWR). Consider taking advantage of British Airways' short-haul Avios awards — a flight from Philadelphia or Washington DC to Boston (BOS) will run you just 4,500 Avios each way, and you can book a separate reservation to cover the short hop on Cape Air.

Where to Stay

A handful of points properties (a Marriott, a Hilton, a Hyatt, etc.) can be found roughly 30-40 miles away in Cape Cod, but in Nantucket, independent hotels and inns dominate the market.

Relais & Châteaux property The Wauwinet, built in 1860, has 32 rooms and four cottages, as well as private beaches on both the Atlantic Ocean and Nantucket Bay. When this post was published, a few rooms still could be had this early in the season (grab them now if you can) for less than $400 a night, but $635 and up is more typical. Cardholders of the Amex Platinum and its Business version can book through the American Express Fine Hotels & Resorts travel portal to receive a $100 spa credit.

Daily Newsletter

Reward your inbox with the TPG Daily newsletter

Join over 700,000 readers for breaking news, in-depth guides and exclusive deals from TPG’s experts

Email address

Sign up

By signing up, you will receive newsletters and promotional content and agree to our Terms of Use and acknowledge the data practices in our Privacy Policy. You may unsubscribe at any time.

If you hold any American Express card (e.g., Platinum, Business Gold, EveryDay Preferred, etc.) you can exchange Membership Rewards or earn bonus points by booking through the American Express Travel portal. Here you'll find slightly more modest accommodations at The Beachside at Nantucket, where nightly rates start at $350.

Nantucket Island Resorts properties include The Wauwinet and the White Elephant Village. The latter offers utterly charming, shingle-style lodgings that are convenient to town. Some configurations contain two bedrooms and full kitchens. You'll find complimentary snacks such as fresh-baked cookies and cheese platters, and you can always sign out a bike or take a swim in the cabana-lined heated pool. BMW courtesy cars can drop you into town, and the staff is unfailingly gracious. Nightly rates range from $350 for a deluxe room to $3,550 for a three-bedroom residence.

Looking to spend way less? Check out the laid-back local lodgings on Airbnb, where you're more likely to spend $125 to 200 per night for private rooms in cottages, cabins, apartments and more. Entire homes range from $275 to upwards of $1,000. Check out Maximizing Points and Miles with Airbnb and VRBO, and keep in mind that Airbnb is a Membership Rewards partner, allowing you to redeem points for Airbnb gift cards in denominations of $100 or $250.

What to Do

The actual town of Nantucket is great for strolling and shopping, but not so much for biking, due to the narrow roads, one-way streets and cobblestones. But never fear: The island is crisscrossed with well-maintained paved bike paths that lead to scenic harbors, beaches (such as Surfside) and off-the-beaten-path eateries.

On my first day, the recommendation of a White Elephant Village staffer sent me straight to Sayles Seafood, located right across the street from bobbing fishing boats, for the sensational baked swordfish. The stuffed quahogs and the little neck clams are also favorites.

That was just lunch, and scarcely satisfied my need for seafood. So my friend and I booked a dinner at the Straight Wharf, which proved to be an excellent choice for its sweet-spring onion soup (served with a parmigiana gougère and local lobster salad) as an appetizer, and the oversized dayboat scallops entrée accompanied by roasted cauliflower, bacon, snap peas, smoked shiitakes and citrus relish. The atmosphere and the adorable servers made us feel as if we were in someone's especially well-appointed saltbox kitchen (with a sea view).

The following night I was in the mood for an Italian spin on New England seafood, so we met at another of Straight Wharf chef/owner Gabriel Frasca's venues, Ventuno, where we paired the line-caught halibut with a Puglia red after beginning the meal with delectable pork and beef meatballs and spicy chicken sausage topped with pecorino and broccoli rabe. The house-made gelato is crafted in a Pacojet — one of the niftiest kitchen gadgets ever created — resulting in brilliant chocolate and coffee flavors.

For a breakfast, you can have no finer meal than the buttermilk pancakes with blueberries and 100% maple syrup at the always-popular Black Eyed Susan's — it's like summer on a plate.

The walk back to the hotel was just as intoxicating; on the cusp of summer high season, we enjoyed Nantucket's chilled salt air, tinged with the toasty taste of a fireplace in someone's living room — in a hearth most likely laid in the early 19^th century.

What are your favorite things to do, see and eat on Nantucket? Please share them with us in the comments below!