Back when I was a barefooted, dirty kid running rampant on the streets of Siasconset in search of a snickers bar before 9 a.m. there were rules about who came to Nantucket. Namely - you came with your family. End of rules. But recently the rules have been changed. I think because I'm getting to the age where I should be bringing the next generation of the family line buuuuut, instead I'm bringing my 20-something friends.
It's cool, Granny would much rather have drunken young professionals than great-grandchildren sleeping in her house. Everyone knows that.
Not everyone recognizes the five day rule, so I've managed to come up with the perfect 24 hours in Nantucket. When I am talking perfect, I am talking both controlable and non-controlable elements. Sometimes it rains. You will not have the perfect day - but you also probably won't get sand in your bathing suit. There is always a silver lining.
Here's how you do it right.
Get off the boat. Make sure your dumb friends who are meeting you don't drink too much the night before and forget how time works because the best thing about arriving on Nantucket is being waved at when the ferry is docking.
Eat some breakfast. I recommend Black-Eyed Susan's. If your human form does not allow for 45 minute waits for breakfast, I recommend Queequegs. If you're one of those "I'll just have coffee," people, head to The Bean.
Look at things in town. Some things you can look at include: stores, people, restaurant menus, fancy boats, water, bicyclists failing at cobblestones, fancy houses, the Brant Point light house, rich kids trying to sell you lemonade, aaaand all the crap in the Hospital Thrift Shop.
Get your Provisions sandwich. I don't recommend getting anything that is going to be made gross by spending a few hours in your backpack. Don't get the lobster roll. You will be the saddest.
Be up at the Visitor Center by 11:30 am so you can get that first shuttle to the brewery. If island boozing is not your thing than you can hike to Alter Rock with the rest of the 9 year olds. The Brewery is a great place to get boozy but its also just an awesme place to sit and eat a sandwich. I'm sure they have juice. Rainy day alternatives: read a book, the Whaling Museum, ice skating, taking an all-day nap.
Cisco Brewers has gotten a little high falutin' recently. But if you get there around noon, you should miss most of that. Enjoy as much brewery as you like and then take the most BOGUS EXPENSIVE CAB RIDE OF ALL TIME from the brewery to Cisco Beach. Cabs on Nantucket are proof that nothing can ever really be perfect.
$20 of bullshit later, sit on the beach, play in the ocean, take the always delightful beach nap. Maybe you brought yourself a six pack, because you're a genius planner. Maybe you're trying to sober up a little bit because you're not 22 anymore. Whatever it is - have some perfect beach time.
Also, get in the Atlantic. It's cold, but so is your mom. Do it.
Then, get yourself back to 'Sconset. If you're super lucky, you have an amazing family who will drop everything to squire your friends around the island. If you don't have this, take anothe bogus cab ride. Sit in the back of that cab and think about capitalism.
If you're feeling like you need a Nantucket history lesson, take Polpis Road and peep Sankety light house. Make sure someone tells you about it.
Change yo' clothes (a day on Nantucket requires three outfits or you're not doing it right). Get boozy on the porch. Peep the ocean. Feel real rich. Ignore the mold. Tolerate Granecdotes* because they are the reason for the season.
Head back into town for dinner. The options change from year to year, but you cannot go wrong with Slip 14, 12 degrees East, Straight Wharf, or Cru. If you're a baller shotcaller - head to Boarding House, The Lobster Trap, or Company of the Caldron. And if you're on a budget - The Tavern, Sea Dog Brew Pub, or The Brotherhood of Thieves will feed you.
And now its time to wander around the town of Nantucket at night, stopping in bars (I'm not going to list them all, throw a stone and you'll eventually run into somewhere to serve you booze), stumbling over cobblestones, taking a trek down to Children's Beach to put your drunk toes in the water.
When you've had quite enough to drink, you finish the night with ice cream (from the Juice Bar - get a waffle cone, or you're a terrorist, btw) or pizza (from Steamboat Wharf Pizza) or both (if you're awesome). Get in one more dumb cab and stumble up the step stairs of your fishing shack. Pass out.
Wake up for a stroll to the 'Sconset Market for a pastry and a cup of coffee. Make sure you bring extra pastries for your hostess and whomever has been helping you out. No one doesn't like a 'Sconset Market blueberry muffin.
Eat breakfast on the porch. Enjoy all the people walking by who are jealous, both of your house and your pastry. Instruct them that the beach is to the right and the bluff walk is to the left.
Head back into town one last time. If you have some free minutes, you can spend them climbing the stairs of the First Congregational Church, picking up some Portugese bread from The Nantucket Bake Shop (I've already discussed my stance on this matter), get a Henry Jr's sandwich for the ride home (get it on the homemade roll, vacation is not the time or the place for whole wheat bread).
Get on the boat. Realize that you should have spent way more time on Nantucket because there was so much you didn't do! You didn't go see the airport from Wings, or rent bikes, or go to Madaket Millies for scallop quesadillas. LUCKILY, you're with a seasoned veteran, who will hand you a penny and instruct you to throw it into the harbor, just as the ferry rounds the Brant Point Lighthouse - and then you'll get to come back.