Last year I was chatting with my daughter, Molly, about our summer 2024 travel plans. I asked her if she could travel anywhere on points and miles where she would choose. She immediately exclaimed, “Stars Hollow!” While Stars Hollow is a fictional town made famous by the show Gilmore Girls, it is based on some areas in Connecticut. I told her I was pretty sure I could make it happen 😉

 

Getting There

I had never been to Boston before, so we decided to tack on a couple of nights in Boston before driving to Connecticut. We flew from IAH to BOS on JetBlue using miles I had earned from opening a JetBlue Business Card. 

My husband came along for the journey as well. It was 25,200 JetBlue miles round-trip + $11.20 for each of us, so 75,600 JetBlue miles + $33.60 total for all three of us. 

 

 

We rented a car from the Boston airport and drove to our hotel in Boston. You do not need a car in Boston, so if Boston was our final destination we would not have rented a car. We were able to valet park for free at our Hyatt hotel thanks to my Globalist status, but if I didn’t have status we would have waited to rent a car until the Boston portion of our trip was over. 

 

Hotel Stay in Boston

In Boston, we stayed at the Hyatt Regency Boston using Hyatt points. The Hyatt Regency Boston is a category 5 hotel, so standard award nights are 20K points each. We were traveling during a peak time, so our two nights were 46,000 Hyatt points (23,000 points/night at peak pricing) + $0 (Hyatt does not charge taxes or resort fees on award stays). 

I booked a standard room with two queen beds, and we were upgraded to a two queen bed corner room at check-in. The extra space and seating was much appreciated! 

 

 

The Hyatt Regency Boston does not have a Club Lounge, so as Globalists we were offered complimentary breakfast in the hotel’s restaurant, Avenue One. We had the option of ordering off the menu or having the buffet. Ted and Molly chose the buffet while I chose to order a la carte off the menu. The adult buffet would have cost $35.00/person and the children’s buffet would have cost $17.50/child. 

The offerings were good, but I don’t think it was worth that cash price and would have skipped it had it not been included with my status. 

 

Overall, I would definitely stay at the Hyatt Regency Boston again. The location is great, the room was comfortable, and the service was good as well. No complaints!

 

Things to Do in Boston

We were only in Boston for two nights, but we made the most of our time there! When we arrived, we went straight from dropping off our bags at the Hyatt to Fenway Park to see a Red Sox game. 

 

 

The next day, I booked an Airbnb experience for us: The Freedom Trail for Kids and Families. I booked it as a private tour, and Michael was a great guide. He is incredibly knowledgeable about the Freedom Trail and also made sure to ask Molly questions and keep her engaged. 

 

 

For food, we loved the lobster roll from Legal Sea Foods and the cannolis from Mike’s Pastry. 

 

Drive to Connecticut

We decided Hartford, Connecticut, was a great place to position ourselves for our Gilmore Girls day out. The drive from Boston to Hartford was less than two hours. We stopped along the way at Adams National Historical Park. We hadn’t bought tickets ahead of time, so we couldn’t tour the house, but the gardens are free and absolutely beautiful! 

 

 

After that we made our way to Harvard. Even though Rory didn’t choose it, we needed to see her other top contender for ourselves. We enjoyed walking around campus!

 

 

Hotel Stay in Hartford

In Connecticut, we stayed at the Hyatt House Hartford North/Windsor. This Hyatt is a category two and an absolute steal! We were able to book the one-bedroom, two-queen suite for just 13,000 Hyatt points/night. We stayed two nights and paid 26,000 Hyatt points + $0 total. 

Our room had two queen beds, a full kitchen, and a living room. The hotel was clean and very comfortable. This hotel offers free breakfast and free parking for all guests (regardless of status). 

 

 

 

Gilmore Girls Day Out

Washington Depot is the primary town in Connecticut that inspired Stars Hollow. We set out early to make our way there, which is about an hour from Hartford. 

We skipped breakfast at the Hyatt in favor of breakfast at Luke’s Diner…I mean Marty’s Cafe. Afterward, we had a day full of “Stars Hollow” goodness. Here’s a complete list of the places we visited (and the order in which we visited them) after we left Marty’s Cafe. 

(1) The Hickory Stick Bookshop—Stars Hollow Books

(2) Titus Park and Garage—Gypsy’s Garage

(3) The Washington Food Market—Doose’s Market

(4) Five Janes—Not part of the show but the owner is a Gilmore Girls fan and there is lots of cute Gilmore Girls merch. 

(5) The Frederick Gunn School—Chilton Preparatory School

(6) Mayflower Inn & Spa—We had lunch here. This Inn is where Amy Sherman-Palladino was staying when she came up with the idea for Gilmore Girls and it inspired the Dragonfly Inn. 

(7) New Milford town green gazebo—Stars Hollow gazebo

(8) Yale—Yale (lol)

 

 

 

 

One Last Night in Boston

Before flying out, we spent one last night in Boston at the Hilton Boston Logan Airport. Our flight back to Houston was very early the next morning, so we decided a hotel connected to the airport was most convenient. I redeemed 70,000 Hilton points + $0 for a two-queen-bed airport view room. 

 

Bottom Line

Points and miles made Molly’s Stars Hollow dreams come true! Our flights to Boston cost only $33.60 out of pocket, and we spent five nights in hotels for $0! I love a luxury vacation, but taking a trip inspired by a TV show we’ve bonded over for years and making memories with my family is extra special. 

 

Related Posts

• Friday Family Vacation to Boston
• Friday Family Vacation: New England Roadtrip with Points
• East Coast National Parks Road Trip