Today’s blog prompt is to plan a seven day vacation where I can do anything I want – and have unlimited money to go with it 😀 Sounds fun, right? The other piece of this challenge is that it has to be reasonable (i.e. I should account for travel time and such!). Basically, at the end of it, I should be able to say hey, if I raise X amount of money I could actually go on this seven day (maybe 8 to 9 day with initial travel) adventure!

I recall only once being in Pennsylvania and also another time in Washington D.C. and Virginia – however, the northern New England states, I’ve never had the joy of adventuring to!

Screen shot of 7 day New England Trip Adventure

Cape Cod, MA (Day 1)

I’m assuming I would arrive into Cape Cod with the entire day to spend adventuring about.

As I only have 24 hours, the two biggest things I’d want to do would be to go dolphin and whale watching and watch the sunrise at the beach. In addition, I’d want to stumble onto some delicious food. Commercial Street also seems like a good place to just go people watching!

Boston, MA (Day 2, 3)

Day 2, I would wake up, hop into my rental car and head North for Boston. The drive would take well less than 2 hours so I would have almost the entire second and third days to explore the town of Boston.

I’d first want to go along the Freedom Trail and learn the history of Boston. Then I’d head off to Fenway park to hopefully catch a game. Hopefully, I’d find time to check out the Boston Public Library, as it’s supposed to be gorgeous. In addition, I’d want to visit the Museum of Fine Arts, the North End and maybe check out a microbrewery or two.

Portsmouth, NH (Day 4)

At the end of Day three in Boston, I would spend another two hours driving North and check into my hotel in Portsmouth, NH.

In this coastal town, I would want to check out it’s microbreweries, grab some delicious seafood and walk around Strawbery Banke, a gorgeous neighborhood of centuries-old colored wooden houses and an open-air museum.

Portland, ME (Day 5, 6)

Day 5, I would wake up and drive under an hour to visit the city of Portland. Maine has been close to my heart since I started watching M*A*S*H and fell in love with the main character, Alan Alda. He was from Crab Apple Cove, Maine. After countless searches, I couldn’t find this place… (maybe it exists, maybe it doesn’t). However, Maine is on my definite to-see list.

I’d also want to see the Portland Museum of Art, Casco Bay Islands and check out the Portland Observatory. It is here I’d also want to see the many lighthouses, little shops and the waterfront – maybe even catch a sunrise!

Acadia National Forest (Day 7)

At the end of the day on day number six, I would pack my things and make the longest drive yet! Almost three hours North to the Acadia National Forest. It is here I would get a good nights sleep before my next day (Day 7) of outdoor adventures. Here I’d most want to climb the summit of Cadillac Mountain and just look out at the beautiful view of the endless Atlantic Ocean!


One piece of adventure I wasn’t able to squeeze in, realistically, is Prince Edward Island. It is here that Lucy Maude Montgomery set her stories of Anne of Green Gables. As I fell fast in love with this book series, I’ve also been anxious to visit this little Island in Canada. If I were to add anything to this trip, I’d add a few days and a flight to explore the island and all that it has to offer.


If you had 7 whole days and an unlimited budget, where would you adventure to? Have you ever been to the New England states? Which ones? What was your favorite part? Be sure to share in the comments below!

  • Sounds like such a fun road trip!!! I’m so sad you didn’t post any pics, I bet it’s so lovely this time of year!!!
    Danielle Greco

    • Hey Danielle! Actually, I haven’t taken this trip! I want to 🙂 The blog post prompt for today in the October Blogging Challenge was to plan out a 7 day trip – and since I’ve never been to the New England states, I planned this one! Thanks for dropping by!