Nantucket Travel Guide : Your Ultimate Day-Trip Itinerary

Nantucket. The perfect blend of New England summer, coastal grandmother, and upscale beach escape for those who love to don a sweater in the evenings with the cool beach breeze blowing through the cobblestone streets.

Nantucket has been on my bucket list even since my grandmother visited back in the early 2000s with one of her best friends. Their traveling girl’s group made it up to the small Massachusetts island, and I’ve been romanticizing a visit ever since. Mimi had brought back a picture book for me to flip through all of the coastal illustrations and read the tale of Nantucket.

My friends, Reese and Ashley, and I have made a tradition out of traveling together and we shortly set our sights on Nantucket and the Cape. Reese moved up to spend an extended summer in Boston, working remotely out of “Title Town” and planning beautiful weekend excursions to make the most of her time in the northeast. Thankfully, she was able to coordinate our girl’s trip! The logistics of making it to the small island are a little more involved than just hopping off of a plane (although you could do that as an option). I’m here to share a travel guide to Nantucket along with our day-trip itinerary!

We felt like we had made the most of our time on the island - every moment was actually lovely. For a quick peek at our trip, check out this video. You can also peep our Nantucket trip photos on my Instagram highlight.

nantucket and cape cod girl’s trip

GETTING THERE

Nantucket is a small island off the coast of southern Massachusetts. It can be a tad tricky to get there, but is worth the effort.

FLY. You can book a flight directly to Nantucket (ACK), which will most likely connect out of Boston Logan (BOS). Ashley had visited Nantucket in June and mentioned her flying experience involved a puddle jumper to the island. This would be the most convenient and direct travel experience, but perhaps not always the most cost effective.

DRIVE + FERRY. Since we based out of Boston, this is what we did! After spending a full day in Boston, we woke up early for a Nantucket day-trip. We rented a car from the airport after waking up at the crack of dawn (always err on the side of caution and wake up a little earlier than you think) and headed south to Hyannis. NOTE: If you’re traveling “in season” I would account for Cape traffic, which could easily add on 1-2 hours to your 1.5 hour drive if you’re planning to leave Boston anytime after 8:30am. We traveled the weekend after Labor Day and had no issues with traffic, especially since it was early (we were on the road ~6:15am)! We purchased tickets for the high-speed ferry out of Hyannis (1 hour ferry ride vs 2 hours). We booked our ferry tickets, HERE. Would highly recommend the first ferry out and the last ferry back, so you can spend the whole day on the island. We parked in one of the Steamship Authority lots for $15 (off-season pricing, I’m sure) and they had a school bus waiting for us. The bus driver does a great job of making sure you’re at the ferry dock in time for takeoff. New England Wanderlust has a great blog post on travel logistics + details.

STAY

Unless your budget is unlimited, you have a friend on the island who has a house or you manage to find something affordable WELL in advance, the options on the island are a tad limited. We didn’t have the money to drop $$$$ on a hotel for the night, so we stayed in Yarmouth, which is only a 15 minute drive from Hyannis.

Veranda Cap Cod Family Resort. $$. Reese found us this newly renovated motel that also included breakfast + coffee in the morning! It was an affordable option and a clean space to rest our heads after a long day of exploring Nantucket. The muffins in the morning were delicious.

White Elephant Nantucket. $$$$. We biked past this gorgeous hotel on our way to Brant Point Lighthouse. It’s located a couple of blocks from the downtown area, so it’s close enough to walk everywhere but a little bit quieter! Beautiful property.

The Faraway. $$$$. Located right smack in the middle of downtown, this spot is great if you want to be steps from all of the shops and bars. We grabbed cocktails on their patio, which was one of my fave cocktail experiences of all time. It might have had something to do with the fact we were in Nantucket, but the patio also feels like you’re sitting on someone’e boujee backyard patio.

Mackenzie Horan lives on the island and has a wonderful blog on all things Nantucket. She shares her picks for where to stay on the island in her Nantucket Guide.

TO DO

Bike! Biking the island was one one of our trip highlights. Cycling is an easy way to explore the island and enjoy the sights! A day’s rental for three bikes was ~$127 (2022).
Visit a lighthouse. We opted for Brant Point Lighthouse since it was so close to the downtown area, but you can visit more than one (if you’re into it).
The Whaling Museum. Located in the Main Town area, this museum shares the history & industry of Nantucket island.
Shop Main Town. There are SO many stores to explore! We popped in and out of 5-6 stores before deciding to hop on our bikes … and we could have kept shopping!
Wiggle your toes in the sand. Jettie’s Beach has a restaurant and bar on the beach! A crowd fave. Georgie Morley is a Nantucket photographer who lives on the island and has a number of local recs! Check out her instagram, here. She’s almost always on a beach.
Take a photo with the hydrangeas. Duh. They’re everywhere!
Visit Cisco Brewery. You could easily spend an entire afternoon here. It’s a chill vibe.
Grab an ice-cream at The Juice Bar. An iconic Nantucket spot where the scent of waffle cones drifts out of their double doors and into the cobblestone streets.

OUR NANTUCKET DAY TRIP ITINERARY

Note: We traveled to the island the weekend after Labor Day, which was the start of shoulder season. The crowds weren’t bad at all, but the hydrangeas were starting to fade. Pros and cons. Also, be sure to make dinner reservations well in advance. Many places will open up reservations 30 days in advance. Set an alarm to book your ideal dining time!

DETAILS

AM -

Our day began early, early to catch the first high-speed ferry out of Hyannis. I packed Dramamine for the hour-long ride, but we lucked out with smooth waters. The ferry has a snack bar and a BAR bar, so you can have a mimosa if you’d like to get the party started early!

After hopping off of the ferry, it’s an easy walk to downtown (like one block). We worked our way around the ferry crowd and made a beeline to Lemon Press. They have a coffee shop area where you can walk up and order to-go OR you can eat upstairs in the restaurant. We got there before the crowd and snagged a table overlooking Main Street, which was lovely. Our coffees & breakfast sandwiches were delicious and perfect fuel for the start of our day.

After breakfast, we popped in and out of the cutie shops downtown! We were all impressed with the amount of stores in the downtown area and didn’t even hit them all.

Excited to explore the island, we popped into Nantucket Bike Shop and rented bikes for the day (you don’t have to rent in advance - we just walked up)! If you’re planning your day, plan to return the bikes ~5:00pm.

Brant Point Lighthouse is literally around the corner from the Nantucket Bike shop (hop on your bike and take the first right). You’ll pass the White Elephant on your way to the lighthouse.

Note: The lighthouse isn’t as tall as you’d expect and the beach is full of seashells. Consider your footwear accordingly!

Snap a few pics and onwards!

PM -

We biked from the lighthouse to Cisco Brewers, which is located in the middle of the island (~25/35 minutes). Biking through town, we smelled roses, hydrangeas and honeysuckle. It’s was lovely! I was parched when we finally arrived at Cisco (around ~12:15pm) and just about chugged my first beer. They also have cocktails, wine and food trucks on their site, so there’s something for everyone! It does get CROWDED around 1pm, just as a general FYI.

You can grab lunch at Cisco OR bike down the road to Bartlett Farms grocery. Honestly, the sandwich we purchased at Bartlett’s was a foodie highlight of the trip.

Bike back to town, return the bikes, and head over to the Faraway Hotel for cocktails on their patio! This is probably one of your more insta-worthy moments.

Proprietors is literally around the corner, so we left the patio 3 minutes before our dinner reservation. We opted to sit on their back patio, which allowed us to spend our last few hours on the island in the salty & hydrangea-scented breeze.

After dinner, we headed towards The Juice Bar for ice-cream! A wonderful sweet treat before boarding the ferry.

I’d recommend arriving for the return ferry ~20 minutes prior to departure. The Juice Bar is literally around the corner from the dock, so we were in no rush.

Our day was the perfect amount of leisure and activity-based.

WHAT TO PACK FOR A NANTUCKET DAY TRIP

A light backpack or tote to carry all of your items! Like THIS one!
A reusable water bottle to stay hydrated (especially if you’re biking around the island)
Sunscreen! I was a little bit red after biking to Cisco and decided to lather on some SPF for the rest of our day.
Sunglasses. A must.
A light sweater or denim jacket. I mostly needed my sweater for the ferry ride. The island warmed up pretty quickly after the morning hours!
Sandals (if you’re planning to spend some time on the beach). I brought a pair but didn’t actually end up using them! I wore my white tennies the whole day.

NANTUCKET NOTES

The girls and I would insist on renting bikes to explore the island (they come with baskets), especially if it’s your first time visiting the island. It’s a great way to quickly cover ground but still enjoy the scenery.

Note #1: Ashley and Reese wore midi dresses on the island and used binder clips to hold up their dresses while biking, which seems to be effective. I wore a skirt with built in shorts for biking, which was perfect (old, HERE, similar style HERE and HERE). A great way to look cute from day to night!

Note #2: Our Nantucket Bike Shop guy told us it would be a 2 hour ride to Siasconset … and we were in dresses … we opted not to make our way in that direction. However, you could rent a Vespa and make it happen!

Note #3: We packed a card game for our time at Cisco! You can really hang out for a while at the brewery and it was fun to sip our drinks while playing Phase 10.

Note #4: If we had multiple days on the island, I would have planned on getting some sun on Steps Beach, visiting Siasconset and wandering along the ‘Sconset Bluff Walk, grabbing cocktails with a view at the Wauwinet, and sipping on some bubbly while on a sunset sail.

CAPE COD

We were all tucked into our beds ~10:45pm after a full day of exploring Nantucket.

The gal’s and I spent a slow morning at our hotel and then headed to Seagull Beach for a couple of hours. Reese packed beach chairs & towels for us.

For our late lunch, we made the 30-minute drive from Yarmouth to Chatham and grabbed a spot at The Beach House Grill (a Chatham Bars Inn dining experience). They have dining and drinks available on their deck and in the sand, so you can enjoy the ocean view! We’d recommend the lobster nachos and watermelon margaritas. You can also pop up to the Adirondack chairs on the side of the Inn afterwards to enjoy the view of the harbor!

We started our drive back to Boston ~4pm.

Final note - while (of course) staying on Nantucket island would be awesome and allow you to pack in a gaggle’s worth of activities, it is totally doable in a day! Reese and I had never been to Nantucket before and we both felt like we got a full Nantucket experience.