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Honeymoon Travel Guide: New England

Editor’s Note: Since I’m moving to Boston in the next week (eee!), I thought this honeymoon travel guide I wrote a few years (September 2014) ago was fitting! Next Wednesday, I’ll share another trip to Martha’s Vineyard.


Entry No. 49: New England

I finally had some free time to edit my photos from my New England girls’ trip I took in September! To refresh, I took off with my BFF, B, to her family’s home in Gloucester, Mass., (and had the most amazing time meeting her family!) and then B&I hit the road for Salem, the Cape and the islands. Oh, we squeezed a little trip to Maine in there, too, with her parents!

P1170191B’s dad gave us the “official” Gloucester tour and I loved this (oft photographed) shot of the wharf. I had such a great time hearing Mr. W share all the Glosta gossip and news – did you guys know Whoopi Goldberg lives in Gloucester? And it was wonderful walking with B and her fam down to the water at night – magic!

P1170200B’s sister, J, joined B&I for a day in Salem and you better believe the Hocus Pocus house was at the top of my list! I was surprised and impressed that it looks just like it did in the movie and it’s even right next to the harbor. We also spotted Allison’s house and a few other landmarks from the movie. After a tour of the House of Seven Gables and some spiked coffee at The Witches Brew Cafe, we drove over to Gallow’s Hill and later to the Rebecca Nurse homestead. Great day!

P1170413Later in the week, we drove down to the Cape and spent a night in Falmouth before boarding the Island Queen to Martha’s Vineyard.

P1170218We stayed in Oak Bluffs and this cute little blue house was on the same street as our charming hotel [details on lodging in the tips section below]. Once we dropped our luggage off, we rented bikes downtown and peddled our way over to Vineyard Haven for a lobstah roll at The Black Dog Tavern. Next, we biked over to Edgartown to explore and then took a bus back to Oak Bluffs so we’d make it back in time to turn our bikes in. Long, wonderful day.

P1170403 P1170397 P1170231The next morning, we woke up bright and early to catch a flight over to Nantucket:

P1170277 P1170294 P1170305

While I definitely favored Martha’s Vineyard to Nantucket, I have to say I truly adored the amount of patriotism on Nantucket. Red, white and blue was flying high at every turn of the island – beautiful.

P1170336P1170315 P1170318 P1170321 P1170329 P1170338And when it was time to leave ACK, our pilot asked if anyone would like to co-pilot. Can you believe I was the only one who raised my hand?




– Lodging for Martha’s Vineyard and Nantucket. We stayed at the Pequot Hotel on the Vineyard and I cannot say enough wonderful things about it. Tucked away on a quiet street in Oak Bluffs, the staff were extremely kind and gracious; our room clean and charming. In the afternoons, guests can enjoy homemade cookies and tea (with fresh mint from the garden) on the porch rockers/swings. Bliss! I would definitely return to the Pequot. // In Nantucket, we stayed at the Vanessa Noel Hotel Green. This hotel was smack-dab in the center of the cobblestoned downtown and definitely had charm. It’s an eco-friendly hotel and the bathroom was shared but we didn’t have any issues – everything was clean and nice and I have no complaints. However, if I were to re-visit ACK, I think it would be more fun to rent a beachhouse or something outside of town. One last note on lodging: If you’re looking to save some $$$, book your days on the islands during the week rather than weekends. Rates on Sat/Sun soar.

– Getting to the islands. We booked our hotels first and then had the pleasure of figuring out transportation. During the summer months, this probably wouldn’t be a problem but as we were going in mid-September, ferry services were a bit limited. We made it work but ended up having to book two flights that we didn’t know we’d have to book. So learn from our experience and check out transportation so you know what you’re getting into before you book. It all worked out well for us but we had a moment of panic when we didn’t know how we were going to get from the Vineyard to ACK and back. That said, I highly recommend the Island Queen ferry out of Falmouth and CapeAir.

– Rent bikes. My favorite memory from the Vineyard was biking from Oak Bluffs to Vineyard Haven and having lunch seaside at the Black Dog Tavern. It’s a super touristy thing to do but it was so fantastic. We watched golden retrievers play in the surf by the BDYC while we chowed down on lobstah and listened to Dave Matthews. For a second, I totally thought I had died and gone to heaven.

– Explore Oak Bluffs. We met a guy on the harbor who turned out to be a tour guide as he had grown up on the island his entire life. He told us where to go to explore the area of tiny Gingerbread houses (and he told us that his grandfather once bought his grandmother one of the tiny little houses as an anniversary gift – how sweet is that?) It was already getting dark so I didn’t get many good photos but the area was truly magical … little dollhouses lined up in circles in all shades of pastels with a gorgeous open-air tabernacle in the middle.

For next time:

– Rent a jeep. I’m hoping J&I can return to the Vineyard next year and one of the top things I want to do is rent a jeep and head out to Aquinnah / Gay’s Head to watch a sunset. I’d love to explore more of the island by bike, as well.

If you have any tips, insights, suggestions or comments, I’d love to hear them! Did you miss the other entries of CB’s Travel Journal? Click here to catch up!

Images by moi.


  1. Robert E Williams Robert E Williams

    Betsey and I loved having you visit our home here in Gloucester, Ma. The blog was great! Where was the picture of the big chair & the submarine? That was the high light of your trip to the Port Smith Navel ship yard.

    • LOL! You’re right – I totally forgot to include the chair photo, lol! That will be our secret little gem to cherish, haha! 🙂 Thank you and Betsey so much for welcoming me in your lovely home – I had a truly wonderful time and I’m so glad I got to meet you both as well as Jen and her family! xoxo

  2. We did a honeymoon road trip to New England and freaking LOVED it. So, so beautiful and fun!

    • That’s the coolest, Cris – I love it! I hope we get to hang out soon – we can swap notes about our New England favorites! 🙂 xx

  3. I am just crazy about these photos–dying for a trip back home right about now! There are few places lovelier, in my humble opinion, than New England!

    • Thanks so much, Lena! And I couldn’t agree more with you – New England will always have my heart! <3

  4. Jennifer Jennifer

    Best week ever hope to do it again 😉

    • Yes, ma’am! Would love that!! xx.

  5. Svitlana Poptop Svitlana Poptop

    Ohh wow! Nice ideas to have a lovely honeymoon in NE. I like the most – getting to the islands.

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