preppy heaven: the ultimate guide to nantucket island

back in july, elle, dana, and i made our way to nantucket for a girl’s weekend! we had been talking about going to nantucket for well over a year and in january we finally booked the trip. now, after going to nantucket for four days, i can confirm it is the cutest place we have ever been and i’m officially and expert haha. it is a photographer and influencer dream as the fairly small island is full of beautiful homes and scenery and i truly can’t wait to go back!


how we got there.

since we are in nyc, we had many options on how to get to nantucket. we ultimately decided to fly there (jetblue has nonstop service there from nyc during the summer) and we are so glad we did. the flight is a quick 30-minutes and even though it is a bit pricey, it definitely beats the 6+ hour drive and a ferry ride to the island. 

where we stayed.

when we were planning the trip we originally thought about renting an airbnb as that is what most people do but even in january/february there were slim pickings! we knew we wanted to be walking distance to town as this was our first time to the island. i came across hotel pippa that was an boutique hotel located right in the center of town. the hotel, was laid out more like a house, was newly renovated and very up to date. we stayed on the first floor in the main house and our room had 2 double beds. it was definitely on the small side but fit 3 girls and 6 bags of luggage (judge us) just fine...especially being used to our nyc standards. the one strange thing about our room is that our bathroom was detached but private to only us. as I mentioned, the hotel is more like a house so since there are different rooms not every room has a bathroom attached. we were aware of this going into the weekend and the hotel notified us again before our stay. it honestly didn’t really bother us too much as we didn’t have any awkward encounters with the 2 other rooms that were on our floor. overall, we were very pleased with our stay and couldn’t recommend hotel pippa enough; we definitely want to go back!

 what we did.

on friday, dana and i took an earlier flight than elle and we got to the island around 11. we immediately checked into the hotel and dropped off our bags since we had to wait a little bit before our room was ready. we took that opportunity to pop into goop and enjoy lunch at the whale. once we were able to check in we went to take a nap (we had been up since 6am) and wait for elle to arrive. once elle got to the hotel we did some exploring and got ready for dinner at the nautilus with our two favorite chicagoans jenn and bob! we love jenn and bob and having the opportunity to spend time with them made this trip that much better! the nautilis was fantastic as it is one of jenn’s favorite restaurants on the island. they do not take reservations so bob was a saint and waited in line the morning of for well over an hour to get us a table. after dinner we headed to a bar for one last drink and dessert!  

saturday was a jam-packed day for us. elle obviously woke up early and wanted us to do the same to seize the day (queue the eyerolls from dana and me). we did some exploring in the morning as well as some shopping at ralph lauren, skinny dip, and the other thousands of adorable shops and boutiques. we made our way to the club car for brunch and boy were we hungry. i have to say, here the food was just okay. it was kind of disappointing because everyone said that we had to go here. maybe brunch wasn’t our best option, as we should have gone here for dinner but the reason why we didn’t go here for dinner was because they don’t have outdoor seating and we knew we wanted to eat outside as much as possible. after brunch we made our way to the infamous juice bar to get some ice cream. guys, this ice cream is no joke. it is so good!! we then made our way back to the hotel to rest up before our sailboat sunset cruise with jenn and bob! the sailboat cruise was so much fun and again we loved every second we had with our favorite couple. we took pictures, drank (our new favorite drink fishers island lemonade and veuve), and caught up on life! after the cruise we went to jenn and bob’s hotel at 76 main, which is a beautiful property and spent some time in the courtyard drinking more of those spiked lemonades and playing card games. it truly was the perfect evening and to top things off dana, elle and i made our way to oath pizza to grab a quick bite to eat before going to bed. it was a busy day but so much fun! 

on sunday we went for an adventure in siasconset, which is about a 30-minute or so uber ride from the center of town. we’ve had our eye on this area of the island because this is home to sankaty liighthouse and the bluff walk. i would like to note that going from the lighthouse to the bluff walk it is a long walk. elle of course decided it would be a great idea for us to do this in the heat and 100% sunshine and i was not a happy camper. don’t get me wrong, it was a beautiful walk looking at all the beautiful homes but it was so hot and sunny and this little redhead couldn’t hang (see the green polkadot outfit for how burned my arms got haha. we luckily found a great sandwich place for a quick bite to eat before we made our way back to our hotel. for dinner we ate at cru, which was one of our favorite meals on the island. the atmosphere is beautiful and overlooks all the boats. after our delicious meal we decided to take another uber to the infamous hydrangea driveway. it was about a 10-minute uber ride (you can’t walk there, it is far) and let’s just say there were no hydrangeas. we got out of the car and our mouths dropped and couldn’t believe our eyes. we either were extremely early (even though Instagram told us this was the week to go see them) or they weren’t blooming this year. even though we were extremely disappointed (still not over it) we walked around the area and were basically house hunting for our dream home. every single house was beautiful and we would be happy campers to call any of these home. we ended the evening at juice bar (shocker) and went to bed!


monday was our last day and we were sad knowing we had to go back to the city. we started the morning early by ubering to nantucket bake shop and we got some incredible donuts! we then made our way to brant point lighthouse to take some photos and just to see another lighthouse! our donuts definitely didn’t fill us up (do they ever?) and we went to black eyed susans for some brunch. this place doesn’t take reservations so we had to wait in line for maybe 30 mins but it definitely was a shorter wait considering it was a monday and not on the weekend. we had some time to hangout in the outdoor garden of our hotel before our 6pm flight so we grabbed sandwiches to go at provisions and enjoyed the last couple of hours we had on the island. we made our way to the airport and that is when it all went south. our flight was delayed for 2+ hours. i will spare you the details, but it wasn’t the easiest getting home. at this point even though we were sad we were leaving we wanted to get back to our own beds.

all in all, we had an amazing trip to nantucket. will i be back? definitely. we are already talking about our return next summer! it is a beautiful island with so much to offer. next time we definitely want to try out renting a house and car to really get that local feel of the island!