Last year I was researching a fresh new vacation destination and happened upon the beautiful and quaint island of Nantucket! I was super excited because I had been wanting to take my husband on a vacation somewhere along the Northeast coastline for years.

We actually drove down from Maine, (which I will share in another post) but we parked at Hyannis Port to catch the Steamship Authority Ferry.

Now this might sound crazy, but I was incredibly worried about taking the Ferry such a far distance across the sound as someone who has been sea sick before. Trust me, once you get sea sick, you never ever want to feel that way again! Luckily, I had a friend who had taken the ferry to Martha’s Vineyard and assured me I had nothing to worry about. The ferry was super easy and relaxing! It is about a one hour ride. I would recommend getting there a bit early just because there’s a long line waiting to board.

We got lucky and had 2 rows of seats with a long table between on the way there and on the way back! I was pleasantly surprised that the ferry wasn’t overly crowded. Especially since we were traveling right at Memorial Day Weekend!

Once we arrived, we were with a huge group of others rolling our luggage through the cobblestone streets, which was comical. As with most of our vacations, we ended up booking this pretty last minute (I think less than a week before!). We booked a room at 21 Broad and it was a perfect little boutique hotel!

After a long day of travel on a cold and rainy day, I made myself a cup of tea, put on the cozy robe, and sat to recharge. The room was a bit smaller than a hotel room but it was so charming!

After our short tea break, we went out around the town to explore. We visited the cutest shops and stopped at multiple restaurants.

We started at Brotherhood of Thieves where I ordered the Lobster Bisque. It came out in a puff pastry and it was delicious! I loved the service, food, drink and atmosphere of Brotherhood of Thieves! Highly recommend!

We also stopped for a drink at Nantucket Prime’s outdoor patio and I remember how delightful the heaters were on a chilly evening!

The next day we started off with the lovely breakfast at 21 Broad out on the patio!

We spent most of our morning walking around and going to lots of local shops.

Everywhere we happened upon was just as picturesque as you would expect Nantucket to be! Or as I like to call it, Pleasantville. I remember we would walk down the street hearing beautiful bells ringing.

We walked to the Straight Wharf area and signed up for a sunset boat tour! I was dying to try Cru but they were closed! Instead we stopped at The Tavern for lunch. Which ended up being perfect. Great service and Food!

I had seen White Elephant Hotel online so I really wanted to check it out while we were there. The staff was incredibly friendly and invited us to try Brant Pointe Grill.

Brant Pointe Grill ended up being one of the highlights of our trip! It was right on the water, they had Frosé, and the bartender was super friendly!

If we didn’t have a boat to catch, we would have spent our entire afternoon into evening in this spot!

It was actually our 7th wedding anniversary, so we made sure to go to a celebratory dinner. We picked SeaGrille, which ended up being pretty far from everything else (we had to uber), but it was well worth it!

I ordered the cod with lobster mashed potatoes, which is basically what I wish I could eat every night for dinner!

Will got the lobster fettuccine which was also outstanding.

We headed back to our hotel to change into warmer clothing for our sunset sail.

We loved Endeavor Sailing because they allow you to BYO food & drink!

They also let you sit back, relax, and enjoy the sunset without a lot of talking. To me, this made our sail almost like our own and so much more relaxing and enjoyable.

Again, no worries here about sea sickness.

This was another big highlight of our time in Nantucket and the perfect way to spend our 7th Wedding Anniversary!

Don’t miss the Sunset Sail with Endeavor Sailing if you go to Nantucket!

Where to stay:

21 Broad https://www.21broadhotel.com/

White Elephant https://www.whiteelephantnantucket.com/

Where to Eat:

Brotherhood of Thieves https://www.brotherhoodofthieves.com/

The Tavern http://nantuckettavern.com/

Brant Pointe Grill https://www.whiteelephantnantucket.com/dining/brant-point-grill

SeaGrille https://www.theseagrille.com/

What to do: Endeavor Sailing http://www.endeavorsailing.com/

If I get the chance to go back, I’d also like to try Cru, Galley Beach, The Nantucket Hotel, and rent one of those cute bikes but I didn’t get to fit any of that in this trip.

I hope this helps you plan your Nantucket vacation!

XOXO,

Amy