The kid-free Nantucket Itinerary Part 1

Apr 19

I’ll preface this post by saying, I love when a friend or a friend of a friend reaches out about “what to do on Nantucket” and I get the chance to share all my ideas (opinions) and help plan their trip. I decided it was time to write it all down to make it easy to share. I hope this helps someone! This itinerary is perfect for a couples trip without the kids.

4 Days on Nantucket without kids

There is no casual way to get to Nantucket. That is entirely the point.

The island sits thirty miles off the coast of Cape Cod and getting there requires a ferry, a small plane, or a combination of both. Plus, a fair amount of patience. If that sounds like a lot, it is. It's also what keeps Nantucket from becoming every other beach destination. The effort becomes a filter. You and your travels friends have to be committed.

Getting There

You have a few options and both have merit depending on where you're coming from and how much you value your nervous system.

Option one is flying direct into ACK. It's the easiest way to get there, full stop. The catch is that direct flights are more limited in shoulder season (May & June or September & October). And if you end up on a Cape Air connection, just know that they will ask your weight before boarding. They’re not being mean. Their fleet is small, the planes are smaller, and if you have any anxiety about flying you will want to prepare yourself accordingly. It's fine. People do it every day. Just don't say I didn't warn you. These flights are also canceled or delayed often due to fog or other weather issues.

Option two and my personal preference is flying into Logan or Providence, taking a car service to Hyannis, and catching the ferry over. If you're coming through Logan, you could stop in Hingham for lunch on your way down. I’m just off exit 36 or as the longtime South Shore residents say, Old 15.

Once you're in Hyannis, you have two ferry options: the Hy-Line ferry or the Steamship Authority fast ferry. Both get you there, hy-line has more options. I’ll take whichever one lines up with my plans. The trip is about an hour and the time on the water is how I decompress and shift gears from the mainland. It's the official start of the trip.

Before you board, grab lunch at the Black Cat, Baxters or Spanky’s, they’re all right there and set the right tone with your standard Cape Cod dining options. One important note for 2026: if there is construction at the Bourne Bridge, Cape traffic can be brutal. Give yourself more time than you think you need.

Two non-negotiable ferry rules: remember your luggage bin number, take a picture of it. The chaos at bag claim on the other end is real. And do not overpack. Dragging a rolling suitcase across Nantucket cobblestone is a punishment you are inflicting entirely on yourself.

Arrival

If you're staying at a larger hotel, there will likely be a bellman waiting at the luggage carts if you come off the hy-line boat. If you're in a rental, grab a cab at the stand by the Club Car or arrange a rental car in advance. We love Windmill Car Rentals, they'll often meet you right at the ferry with your keys.

Here is something worth knowing before you arrive and remembering every single day you're on the island: Nantucket is a small place and it does not always move fast. My Floridian friends are familiar with the term “island time” and this is an island. The ferry is crowded, the cabs take a minute (and will remind you of your mom’s old Chrysler mini-van), the cobblestones are uneven. If you are fussy, you will not have fun. Take a breath. You made it. That was the hard part.

Settling In

Drop your bags. Hydrate. Rest if you need it. Then send half your group to Nantucket Meat and Fish while the other half showers or gets settled because you already have dinner plans and you need to move.

At Nantucket Meat and Fish, do not ask prices. You're on vacation, it's just money, and you can make more. Pick up cheese, crackers, charcuterie, and wine. Their wine selection is exactly what you'd expect, perfect and expensive. Grab late night snacks and something for breakfast tomorrow while you're at it. Someone will come home hungry. Someone always does. I’m usually someone. And there isn’t any viable options on Nantucket for late night delivery food.

Tonight: Bar Yoshi and Cru

Hopefully someone in your group was organized enough to book a reservation at Cru weeks ago. That's a tough one to get. Extra credit if they requested the back bar table with a later reservation time.

Before dinner, start at Bar Yoshi for a margarita, either in the main bar or at O Bar. It's the right way to arrive on the island. Just don't be late for your Cru reservation. They will not hold the table. Note: at the time of writing this, there was some discussion about Bar Yoshi being open in the 2026 season, check to see if that changed.

At Cru, order the Crucomber because you have to say you did. Their by-the-glass wine list is excellent and their sommelier knows what they're doing if you want a bottle. You need to start with some local oysters. I’m a fifth-bend or Pocomo fan. The lobster roll is a solid choice, albeit small, the fries are One more thing, if someone in your group doesn't eat seafood, order them the chicken. Not sure what the 2026 menu will be but you’re there for the views, people watching and vibe more than the food.

Walk home along Main Street after dinner. You may hear some singing from the Club Car on Main St. Personally, I would stop in for a night-cap. It will be shoulder to shoulder but singing along with the piano player and a room full of well dressed strangers is an opportunity I’ve never turned down.

After the club car I would typically go home. I’m far too old for the Chicken Box crowd but that is an option if you aren’t ready to call it a night. It’s ok if you stay out, you were smart enough in your planning to know that most adults-only trips tend to go a little harder on night 1 and tomorrow is just a casual beach day. Professional level planning that you can take credit for.