It’s a big year for Jared and me, we both turned 30 and we celebrated our 5-year wedding anniversary. To do it big we decided to take a trip to Nantucket. Nantucket has been on our bucket list since we were in college, so when we decided to travel domestically it was our first choice. It can be a little tricky to navigate so I thought I would share where we stayed, what we did, and where we ate in a comprehensive Nantucket Travel Guide.

Nantucket Travel Guide

How To Travel To Nantucket

If you aren’t familiar Nantucket is an island off the coast of Massachusetts not far from Cape Cod and neighboring Martha’s Vineyard. It can be a little tricky to travel to Nantucket, the main two forms of transportation are by plane or ferry. We chose to fly because of our starting point in Houston but I will say the flights to the island are limited and fog may impact your flight. If you are planning to fly I’d try to plan for a longer layover so you aren’t cutting it close. Some days there are only one flight to the island a day so you don’t want to miss it! There’s also a high-speed ferry option which is really popular for people who live in the northeast.

Where To Stay in Nantucket

The island is very historic and unique so you won’t find major hotel chains or high-rise condos, everything is very quaint and historic. All buildings on the island actually have to be constructed of select building materials (siding or wood shingles) and every building has to be approved by the Historic District Commission.

When choosing a place to stay the best route is to either stay at a resort like The Hotel Nantucket or The White Elephant, opt for an Airbnb, or lastly, the route we took which is a bed and breakfast style house. We stayed at The Chapman House, an old historic house from 1830 owned and operated by The Nantucket Resort Collection. We chose The Chapman House for two very apparent reasons. One was for location, it’s very close to everything making it a breeze to walk or bike everywhere we wanted to go. The second reason was that the rooms had private bathrooms. When I was researching where to stay, a lot of the historic bed and breakfast houses had community bathrooms. Having a private bathroom was key for us just because we didn’t want to be fighting for a shower or counter space with other guests.

Because The Nantucket Resort Collection owns multiple houses each property has different events or breakfasts if you want to pop back and forth between. The Regatta Inn, which was about a block away from The Chapman House, had more of a buffet-style breakfast so we popped over one morning to enjoy it.

We really enjoyed our stay at The Chapman House, however, for the steep price the amenities and service were pretty minimal. For our next trip to Nantucket, Jared and I both agreed we’d likely stay at the Faraway House. This quaint house is so adorable and is home to one of our favorite places we ate at, Sister Ship. I’d be willing to share a bathroom or splurge a little more for the extra charm and amenities. Although it’s a little pricier I do think it would even itself out with the complimentary amenities like bikes being provided to guests. We ended up paying about $250 for bike rentals for the week so that could have evened out if they were provided.

Our Itinerary

We were on the island from Sunday to Thursday. This ended up being the perfect time because Sunday the island was VERY busy because of Labor Day Weekend, Monday people were packing up to head home, and then Tuesday and Wednesday were very calm and quiet with Thursday getting busier as people came in for the weekend again.

Sunday

We flew in early so that we could enjoy as much of the island as possible. Once we arrived we took an Uber to The Chapman House, dropped our bags off, and explored our surroundings. We grabbed some coffee at StokeACK and a sandwich at Walters Deli, then popped into all the shops. Some of my favorite shops were Skinny Dip, Murrays, and Lilly Pulitzer (of course). We then ended the night with dinner at Via Mare inside The Greydon House.

Monday

On Monday morning, we grabbed some more coffee at Handlebar and then rented bikes from Cooks, we rented them for the entire time we were there, but in hindsight, we should have just done day rentals because it rained one full day and we didn’t use them. After our bikes were all set we hopped on and rode around the island for a little while. This was fun at first but then very quickly turned out not fun lol! We rode down to Brant Point Lighthouse and then to the access point of Jetties Beach. After that, we thought we would keep going down the coast but somehow ended up on a bike path and 4 miles later I was not having fun. Our leisure bike ride ended up being almost 8 miles later. So I’d definitely recommend bringing a map or sticking to the roads by the cute houses. We managed to make it down to The Tavern for lunch. I don’t know if I would eat here again because it was essentially overpriced bar food, but we were desperate.

After the killer bike ride, we both took a nap, freshened up, and went back out on our bikes to explore more of the cute houses. This time it was much more leisurely! Then we cleaned up and headed to dinner at The Nantucket Tap Room. The food here was absolutely AMAZING and the vibe was perfect with a lively outdoor patio. We ended the night with some ice cream from the iconic Juice Bar.

Tuesday

Unfortunately, rain was in the forecast all day but we decided to make the best of it and we started the morning out slow with breakfast at the Regatta Inn. From there we made our way over to the Whaling Museum which was super cool. We spent about an hour and a half in the museum and it was really cool to learn about the history of the island and the whaling industry that made it.

Following the museum, we hopped in an Uber to enjoy lunch at Cisco Brewers, it was still raining at a light sprinkle but the brewery had covered seating. They offered more than just beer with great cocktail options as well as wine and seltzers. They also had multiple food trucks/tents. This was a little unexpected but it was so fun and very relaxing. It definitely felt more like a local spot than a tourist hangout.

The purchase of our Whaling Museum ticket also gave us free admission to the Hadwen House, which was an old historic home turned into a museum. This museum was filled with exhibits about the lighthouse baskets which was my favorite part. They also had a demonstration which was super cool to see in person.

After a busy day of museums, we cleaned up and were off to dinner. We had a little snafu with our dinner reservations because of the time change we thought we had an extra hour for dinner so we headed to grab drinks and apps at Or, The Whale when we got a notification our table was ready at Sister Ship. We wrapped it up quickly and luckily Sister Ship was still able to accommodate us and thank goodness they did because this was our favorite restaurant and favorite meal of the trip. The food was delightful and the restaurant is so stinking cute! 10 out of 10 would recommend Sister Ship.

Wednesday

 Wednesday was the day I was really looking forward to because we booked a sailing trip with Endeavor. Before heading over to get on board, we grabbed coffee and sandwiches for lunch later at Provisions. The boat departed at 10 AM and we sailed for about an hour and a half. This was seriously SO much and I can’t recommend it enough. The captain was so nice and it was just such a unique experience. This was by far my favorite part of the trip.

After sailing, we enjoyed our sandwiches on a bench by the water and then headed back to the room. We both got splashed by a big wave while we were sailing so changed into different clothes and then took an Uber to the other side of the island to do the Bluff Walk. The Sconset Bluff Walk is a trail that runs along the bluff of the water through the backyards of some of the most gorgeous houses I’ve ever seen. It was so cool to wander through these stunning houses with a gorgeous view. At the end of the trail there’s the Sankaty Head Lighthouse. It’s about a mile and a half walk one way but totally worth it, however, we started walking back and tried to call an Uber and it took a long time to confirm a driver. I think because it’s a more secluded part of the island, so plan accordingly.

After that, we grabbed a bottle of wine and some snacks and enjoyed a little mid-afternoon break back at the courtyard of The Chapman House. To end the night, we kept it casual and went to Brotherhood of Thieves which is another iconic spot with the likes of an old-school pub. The food was delicious and the drinks were great! To end the night, we wandered down to post-dinner drinks at Or, The Whale and finished the evening with a stroll through the yachts.

Thursday

For our final day, we woke up early and biked down to the beach. We spent an hour or so taking in the sunrise and ocean breeze. Don’t let that fool you though it was chilly along the water.

Our flight wasn’t until later in the evening so we went back to the room to pack up and change then we rode our bikes for the final time down to the Brant Point Lighthouse.

We then had lunch at Cru, which everyone raves about…however, in my opinion, it wasn’t worth it. The vibe was cool and the food was good but it was crazy overpriced. If you want to go where everyone talking about and see the hype then go, but if you want good food I think you can find better elsewhere. Our lunch was close to $200 and I didn’t think it was worth it.

After lunch, we hopped back on our bikes for a little stroll. The first stop was to see the oldest house on the island which was built in 1686. It was amazing to see something that was older than this country! From there we rode down to the Old Mill which was an old windmill used for corn in 1746. We had a very extensive tour from the guide there who was so nice and informative.

The guide at the windmill gave us a tip to check out the Hospital Thrift Shop which is a non-profit thrift store in an old historic house. If we weren’t flying home I would have walked away with a lot more. I did manage to score a vintage Lilly Pulitzer skirt!

We squeezed in one last trip to Juice Bar before returning our bikes and heading to the airport!

Final Thoughts

We absolutely LOVED Nantucket and are already planning our next trip back! Jared and I were both very obessed with the preppy trend in college and we kept saying “our college selves would be so proud of us”. The weather was absolutely perfect with a high in the low 80s during the day and in the high 60s at night. The whole island just felt like our vibe and felt like we fit in there. We passed by a sign that said “You made the best decision you could ever make by spending September in Nantucket” and I couldn’t agree more!