Emerson Goes to Nantucket | 2024
Emerson goes to Nantucket, again!
Mike and I took our annual family vacation to Nantucket in June and it was Emerson’s second time traveling to the island. This year, we flew out of Lexington, which is always nice, except the check-in counter took so long, they told us we were unable to check our bags. The lady said that we could try to take everything (even the big bags) through security so that’s what we did along with all the other families left waiting to check-in.
When we go to Nantucket, I check the Uppa stroller (strollers don’t count as a bag) and use the Doona through the airport so we have a carseat if needed once we arrive. That meant I had 2 strollers, our 2 bags, 2 carry ons and a baby to take through security. Since my bag was too big for the belt, I had to unpack everything and put my items in several bins to scan. The Uppa had to come out of its travel bag which I, of course, had Mike do initially, so I had no clue had to get it back in the bag. At this point, Mike was taking his golf clubs back to the car because those were not allowed. After a stressful 20 minutes, we got all our things through security and were able to gate check all the items we would have checked at the counter. By this point, I was sweating and Emerson was crying but we made the flight with all of our things. Again, we used this padded bag for gate checking the Doona and were able to sneak a few more items in it.
We only had two flights and arrived on Nantucket by lunch. Emerson didn’t sleep on the first flight and was pretty pissed the second flight until she fell asleep as we landed.
WHERE WE STAYED: As our family (8 adults and 5 kids this year) has grown over the years, we are too big to fit in one house so we stay at The Nantucket Hotel. The staff could not be better! They go above and beyond, not only remembering us each year but always gifting Emerson a dog stuffy when we get there (and one for baby boy this year!) and are pretty quick to get at least one room ready early for us to use for naps.
This year, our family stayed in the Mainmast Suite and they had a pack-n-play and high chair ready for her. I think there are at least two of this type of room because ours actually had a hallway and door to close off the bathroom and master from the rest of the living space. This room can actually sleep up to 5 and I love having a separate room for the babysitter to be in.
The Slumberpod and Hatch came with us and I rented a jumparoo (that Emerson never wanted to be in lol) and a hook up chair from Nantucket Baby. Next year, I figure baby boy can be in a crib while Emerson tries the pull down twin that is essentially on the floor.
The hotel has two pools (one is adults only) and girlie loved it more and more as the week went on. We can’t wait for her to be big enough for their complimentary Kids Club camps but the play room is open anytime when camp is not in session. It gave the babysitters a place to take the big kids and Emerson, too.
TRAVEL MUST: We traveled again with the Wyze Camera and it was ideal for watching Emerson nap and still being able to workout or have a cocktail downstairs, which we did most nights after dinner. This camera only works on wifi networks that require a password. The hotel’s public wifi did not require a password but when I explained the issue, they quickly provided the password to another wifi so we could set it up.
Another hotel perk we love is that they have a laundry room. I travel with this stain remover which we love. (Pro tip: Buy both the large and small bottles and use the smaller one for travel.)
2024 ITINERARY: I was in charge of the dinner reservations this year as well as babysitters for all three families. There are several nanny services on island but luckily I was able to use past sitters and recommendations from them to cover all of us.
There were some tried and true places that we always visit but I also added in some we hadn’t been to in years. We try to just plan dinners so everyone else can set their own schedule for their kids. We did 3 full family dinners this year and I think we will go down to one or two next year. Thirteen is just chaos! I will say, Slip14 and Sea Grille were great with our large party.
Mike and I celebrated our two year anniversary and took the boat to Topper’s one night which is such a fun thing to do if you have not! You catch their boat at the White Elephant wharf and enjoy a 50 min ride to the Wauwinet that is then paired with a 3 course dinner menu. We ended up taking the shuttle home to avoid getting drenched by the waves due to weather.
The Critter Cruise was also a big hit this year! It is only an hour and perfect for a wide age range. They catch crabs and lobsters and then let you fish at the end. Emerson was entertained as were the big kids and adults. While we didn’t end up doing the Endeavor this year, I highly recommend it if you plan to visit!
Besides our itinerary, here are more recommendations below of our favorite places.
Kid-Friendly Restaurants:
Sea Grille
Brant Point Grill (at the White Elephant hotel)
Brotherhood
Ventuno
Or, The Whale
Millie’s (lobster quesadilla is a must)
Sandbar at Jettie’s
Surfside
Club Car
Fav Dining Spots:
Galley Beach
Lola41 (tres leche dessert is a must)
Oran Mor
Sister Ship
Cru (order the lobster roll - also great for lunch and can bring kids)
Straight Wharf (where we had our rehearsal dinner)
Slip14
Chanticleer
Grab a Drink At:
The Gazebo (their mudslide is a must)
Cisco Brewery (food trucks, live music, cocktails & kid-friendly)
Club Car (live piano at night)
Misc:
Rent bikes from Young’s or use an app and take an electric bike out for a day
Ice cream at The Juice Bar (there is always a line)
Coffee at The Hub or Sister Ship
Breakfast sandwiches at Born & Bread or FRESH
Bagels at Provision’s
Juice, smoothie or healthy breakfast/lunch at Lemon Press
Sandwiches from FRESH (breakfast and lunch)
Playground at Children’s Beach and Hinsdale Park
If you need a photographer on island, we love Emily and used her for our wedding!
Overall, Emerson did great this visit! She was on the move walking everywhere and did great with the various babysitters she had at night and during the day.
Our flights home were better than coming and snacks were key. I did buy a few new toys (here, here and here) that provided short entertainment but cheerios and pouches over everything right now.
TBD on our next trip with Emerson as we wait for baby boy to arrive in January!
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