Known as the Grey Lady, Nantucket is frequently foggy: this means to relax on a short trip, you should budget a little extra time on both ends because flights can often be delayed. That being said, we traveled in mid-June and enjoyed three perfectly sunny days. Get your bearings when you arrive by wandering through the town - grab an ice cream or lemonade from the Juice Bar - enjoy the cobblestone streets, take in the Harbour and exhale before a seaside dinner at the beloved Galley Beach. If you get a clear warm evening, make sure to reserve a table on the sand and watch the sunset over a cocktail and a classic dish - crab cake or clam chowder are a perfect start.

Grab a java from Island Coffee, and a quick bite from Nativ or Corner Table before renting bikes to explore the island. For a more leisurely breakfast, head to Lemon Press. Bike out to Siasconset, taking in some fresh air and vaca vibes. The ride will take about 40 minutes. As you come into this quaint, elegant town, take in the charming houses and stop for sandwiches at the town general store Sconset Market. Don’t leave without indulging in a piece of their homemade carrot cake. Bike out to see the famed historic Sankaty Headlight (Lighthouse) and then hit the beach. If it’s warm, pack a towel and your swimsuit and plan to have a swim. Take your time before biking back to town. Wander through town to take in a few boutique shops (we loved Nantucket Looms, For Now, Stoke ACK and Wheat) or pop in to the Whaling Museum for a dose of mariner history.

Have a cocktail at one of Nantucket’s hip spots - we loved the gorgeous patio at Sister Ship and the newly opened Life House. Dinner at Sister Ship or Via Mare both have inviting porches where the evening slips away. Be sure to wander the streets after dark - the street lights evoke the feeling of time before electricity, set against the cobblestone streets that are sure to transport your spirit.

Wander out past the Harbour to see the town waking up and enjoy a coffee on the water down by Brant Point. Consider a morning swim on Jetties Beach, one of the calmest on the island, perfectly framed by dunes and sea oats. For an elegant lunch, make a reso at Cru Oyster Bar. This swanky ‘it spot’ is on the harbour and offers a delicious spread: oysters, shrimp cocktail, spaghettini with clams and a chilled glass of white wine are a must. If you’re up for another bike ride, we recommend heading west towards Madaket. The peaceful and scenic ride is an easy way (shorter than Sconset) to reach Madaket beach for a sunset picnic. Pack a blanket and stop by local favourite Millie’s (the only stop in Madaket). At Millie's, pick up a couple lobster rolls or quesadillas, and the tuna tacos are also delicious. Watch the sun go down for your last night on this special island. Cycle back to town, or hop on the WAVE with your bikes (make sure you check the times back). If a beach picnic isn’t your thing, Lola 41 is a perfectly lit, vibey sushi spot with the best cocktails we had on the island.