Kennebunkport Maine Destination Wedding and Honeymoon

Honeymoon Roadtrip Itinerary for New England

You have just said "I do" and now it's time to jet off on a honeymoon adventure. While most people immediately think of a beachfront honeymoon or  a stay in an all-inclusive luxury resort, a honeymoon road trip is a great way to see different places and really spend some quality time together. New England offers innumerable road trip itineraries. You can easily spend weeks exploring one attractive and welcoming town after another.

We spent seven days in New England, traveling from the coast to the mountains. Here is a detailed look at what we think is the best itinerary for a honeymoon roadtrip in New England. 

1 Night in Boston, Massachusetts

3 Nights in Woodstock, Vermont

1 Night in Portsmouth, Massachusetts

2 Nights in Kennebunkport, Maine

1 Night in Cape Elizabeth, Maine

Here we go...

Day 1: Boston

Just one night in Boston? Many Bostonians would probably argue that this is simply not enough time. While we do a agree, a road trip is about getting out there and seeing different places. So if you have just one night in Boston, it's enough time to check into a nice hotel and have a tasty dinner before heading out on the road the next day.

Where to Stay in Boston:

fifteen-beacon- boston boutique hotel

Photo credit : XV Beacon Hotel

XV Beacon Hotel 

The XV Beacon Hotel is a luxury boutique hotel located right on iconic Beacon Street. Here, you can easily walk to restaurants and nightlife venues. This 1903 landmark Beaux Arts building has 63 uncluttered  rooms fully equipped with a fireplace and luxe amenities.

Days 2-4: Boston to Woodstock, Vermont

After grabbing breakfast in Boston, head out on the 2.5 hour drive to Woodstock, Vermont. You should have your camera ready to stop and take photos along the way. Vermont, the Green Mountain State, is absolutely picturesque with its covered bridges, barns, and endless groves of trees. The drive is actually one of the best parts of a trip to Vermont, so you should pay attention to the scenery. The town of Woodstock is quant and romantic - a perfect first stop on your honeymoon.

Downtown Woodstock Vermont destination wedding

Where to Stay in Vermont

Woodstock Inn, Vermont

Woodstock inn Vermont Wedding and Event Venue 2

The Woodstock Inn is a boutique hotel with all the amenities of a five-star luxury resort. The rooms are cozy. Some have fireplaces, and all have that attractive only-in-Vermont charm. There is a full service spa, a golf course, a fitness center, and several restaurants on property. The Inn is a large resort, yet it still feels like you are at a small boutique hotel.

What to do in Vermont:

Spend a day visiting the local farms and breweries. A day of cheese tasting and beer tasting should be on every Woodstock itinerary. Honeymooners can head over to Quechee and visit the Simon Pearce factory for lunch and shopping. After that, they can make a visit to the historical Billings Farm and Museum.

Vermont destination wedding views bridges

Day 4: Woodstock to Portsmouth, New Hampshire

The cute little seaside town of Portsmouth, New Hampshire is not to be missed on a New England road trip. The entire town can be walked in about 20 minutes, so it's a great overnight stop as you travel from Vermont to Maine.

Where to Stay in New Hampshire 

Ale House Inn Portsmouth New Hampshire boutique hotel

Ale House Inn

The Ale House Inn is a small, hip boutique hotel located in the historic Portsmouth Brewing Company building. With just a dozen rooms and a fun reception/lounge area, it's a perfect place to call home for a night or two while exploring Portsmouth. For beer enthusiast, this building is not to be missed. What is not to love about being greeted with a local craft beer upon arrival? This hotel really offers the quintessential Portsmouth experience. 

If you only have a night in this New Hampshire haven, we recommend a “Portsmouth restaurant crawl.” All you have to do is grab a map and mark off a handful of places that you want to try. Make it a "mission" to try them all before the night is through. You should order an appetizer or a small plate to share at each venue, and try to limit cocktails or beers to one per location. Yes, you will be able to see and taste most of Portsmouth in a short period of time. You will also meet some great people along the way. We highly recommend a visit to Franklin Oyster House for happy hour. You should also try a craft brew at the Portsmouth Brewery. 

Day 5-6 - Portsmouth to Kennebunkport, Maine

It's a quick 45-minute drive from Portsmouth to Kennebunkport. We recommend taking the scenic route and stopping for a lobster roll or two along the way. Kennebunkport is a picture perfect coastal Maine town. It is a great honeymoon destination for foodies.

Where to stay in Maine

Hidden Pond Kennebunkport Maine wedding and Honeymoon Location fire pit

The Hidden Pond, Kennebunkport, Maine

The Hidden Pond is a retreat-style resort that offers 36 uniquely designed cottages spread throughout the private and exclusive grounds. Hidden Pond is perfect for a honeymoon in Maine. It's close enough to town, but it feels so secluded you really do not have to go anywhere to "escape the crowds." You can use the complimentary beach cruisers to explore the grounds of Hidden Pond. People in search of some pampering can spend a day at the Tree Spa or lay poolside and sip on cocktails from the Farm Bar. Have dinner at the resort's farm-to-fork restaurant, Earth, and then enjoy after-dinner campfire cocktails and s'mores at the firepits. Hidden Pond is like a summer camp for adults: sophisticated and fun.  

Hidden Pond Kennebunkport Maine wedding and event venue farm bar and pool

Day 6 - Kennebunkport to Cape Elizabeth, Maine

After a couple relaxing and fun days in Kennebunkport, honeymooners can head another 40 minutes north to Cape Elizabeth. Stop in at the Cape Elizabeth lighthouse and grab a lobster roll at Bite of Maine before heading to the Inn by the Sea for a final night of honeymoon bliss.

Where to Stay in Cape Elizabeth

Inn by the sea Cape elizabeth maine wedding and event venue. sunset

Inn By the Sea, Cape Elizabeth, Maine

Inn By the Sea is a picturesque boutique hotel and spa located right on the water in Cape Elizabeth, which is just 15 minutes from Portland, Maine. Take advantage of the full service day spa and spend the afternoon on the private beach at the Inn by the Sea. Head into Portland to grab dinner or happy hour at Eventide Oyster House. After dinner, head back to the Inn by the Sea and have an after-dinner martini at the lobby bar and reminisce about your week-long adventure.

Inn by the sea Cape elizabeth maine wedding and event venue. beach

More Reviews and Planning Tips for New England

Wedding Weekend Guide for Woodstock Vermont

Inn by the Sea Review

Experiencing Hidden Pond

Have you honeymooned in New England or had a romantic road trip in New England? Share your itinerary with us in the comments section...