Yep, that’s what we did! I had my first road trip in USA with a crazy amazing friend, from New York to Maine 😊 ❤️ 💝 💕 And in this New York to Maine Road Trip post, I’ll be sharing what-when-who all the details.

Dates: May 5-10 2019
Duration: 5 nights, 6 days
Destination: Maine (far away), Portland, Boston, Hamptons
Rented car: Audi from amazing Turo, (save $25 off with my link)
Stayed: Bed and breakfast, hotel, and Airbnb, (save $45 off with my link)
Total accommodation costs: ?
Total car rental and gas costs: $423 for the car rental. Gas?

Oh boy, where to start?

Ok here it is. One cold April day, one of my close friend’s friend whom I met briefly messaged to me, saying “hii, how are you? I’m coming to New York for a bachelorette party, oh also I was gonna do a road trip but my friend bailed on me.” I think she didn’t even ask me if I want to do it, or I didn’t give her a chance to ask, because I quickly responded, I’ll come with you!

I asked where are we going? And she had no idea! And that’s the best because then I could involve with the planning, which I enjoy a lot.

So I asked her without knowing much to go to North Carolina, New Orleans, etc… She said too much driving and she already went to New Orleans twice. So my next suggestion was to offer my dream trip to go to Maine… I asked gently, how about Maine, Portland, Vermont.. (at the time didn’t know Vermont is kinda different area) She agreed…

Highlights – Summary:

  • I was not sure if I can still drive, but turned out, you can’t forget how to drive, especially if it’s an automatic car.
  • Similarly, you don’t learn how to reverse park in your dreams, so I’m pretty bad at it still…
  • You can not wear a Yankees hat in Maine, Portland or Boston! Got tremendous attention, and warnings! Bought a Red Sox hat from Boston and looks like New Yorkers don’t like it either!!! 🤪(So a perfect way to grab attention is to challenge them with their not liked team’s hats I guess…)
  • I was food poisoned before the trip started, so ate lots of bananas and toasted bread. Thankfully I could try the best fish ever in Portland.
  • Where we stayed didn’t matter as long as it was a central location.
  • We didn’t have a destination much. It was Elysia’s birthday on May 8th, and we didn’t want to be on the road that day, lucky that worked well.

The Rental Car:

It’s a road trip, and obviously what’s a road trip if you don’t love driving? So I love driving, not necessarily to go to a destination but just purely driving, with music, maybe singing, maybe a bit speeding and all my attention is on the road, surroundings and so.

New York to Maine Road Trip, Girl On The Bike
We tried to turn on the top cover for 30-45 minutes. In the end, made it! 😎

Our beautiful, oh soooo beautiful fancy convertible car did have a Bluetooth and I downloaded songs on my phone to listen since I knew we would lose connection in the woods and roads. After picking the car, we understood that Bluetooth only works to TALK. Music doesn’t work 😮We spent easily an hour or so to figure that out. This is no good. I can’t function well when there is no music. And driving is BEST when there is good music. (Similarly, I bike with music, I walk with music. That’s called a constantly busy mind, working on it to quiet it down.)

New York to Maine Road Trip, Girl On The Bike
Ahhhh, soo loved this car. Would love to own an electric version of this so much one day…

Soon to be learned, when you have the worst, you get happy whatever you get. The radio becomes our best friend and enemy. Thankfully there was a switch at the steering wheel under my fingertips, and that was helpful. Every 5-10 minutes we switched songs and looked for new ones.

New York to Maine Road Trip, Girl On The Bike
The first day, first moments of driving…
I’m a very careful good driver but have my weaknesses too…

We used an app to rent the car, it’s called Turo. We originally rented a Mustang 2013, but that car got canceled on us. I used an old email address and barely saw it was canceled. Then Turo helped us and covered the additional costs and rented the Audi A4 convertible beautiful little thing. That was a beautiful car. When first went to New Jersey to pick up the car, a part of me was yelling in my mind, “how can they trust and give this beautiful thing to us?!!! Am I gonna drive it??”

My dear friend had no idea of my driving skills.. or why I really wanted to go to Maine, and why never went before… More on that later.

A few friends told me, if you have a Mustang, it’s telling to cops “stop me, cause I may be speeding or something” so it was a really “lucky” thing we got rid of the Mustang naturally and instead got the Audi.

I recommend everyone who wants to rent a car to use TURO, it’s like Airbnb directly from the owners. Very very very smooth experience and I messaged so many times to the owner and he responded so quickly 🙂 And prices very good. I recommend their cheapest version of insurance. I don’t think it really matters if you get the premium or basic insurance.

Maine was cold! But that didn’t stop us converting the car! 😂 Seats are heated too.

Also used Waze app most of the time, and I simply can’t imagine driving without it… You can see where there is a construction, police, gas station, accident, etc, instantly shared by other users.

So at some point in Maine, we didn’t have any signal, I shut down my Waze mistakenly so it couldn’t find the route without internet, and we were so lucky that the GPS works with internet or not, on Google maps. I just followed the map, we had the destination saved so could see it, I also could see where my GPS location is and then just found the way like that for around 1-2 hours.

Accommodation

We stayed in Airbnb in Boston, Hotel in Portland, and Bed and Breakfast in Maine. They were all great in different ways.

My first choice of place to stay is always Airbnb, you get the local experience, good prices, reviews from real people. If first time using it with this link, then you get $55 off, (or if you start a new account) 🙏

In Maine, close to Acadia Park, there was only a few Airbnb options, and when my friend sent me link to the bed and breakfast place, I said yes! Let’s do it. It was next to a lake, the host was renting her two rooms, cooking delicious breakfast, OMG, and it was a pleasant experience. I’ll share the link if you’d like to take a look.

The place we stayed in Maine, so magical! (credit: http://www.threepinesbandb.com/)

I told the BnB host, why she’s not listing her rooms on Airbnb and oh boy, she’s just against the idea of people renting their room vs she got certified to do a hotel business. So that’s a bit misfortunate she’s taking this personal and not using the Airbnb but instead Expedia and every other commercial website.

Acadia Park

Hmm.. I’ve never been to a big national park like this before. (While writing I remembered I was at a beach in Florida, no one was there, and that was a national park).

New York to Maine Road Trip, Girl On The Bike
Beehive trail, on top…

Acadia became a favorite place for me, each corner or hike turns to be a uniquely magical place.

Beehive, Bubble Rock, Secret Beach, Thunder Hole; these are a must!

New York to Maine Road Trip, Girl On The Bike
Thunder Hole

They sell park tickets, $30-35 they are valid for a week. The couple we met in Portland in a restaurant told us “we left our tickets in a gas station, for someone else to use it, since there are no names or plate numbers, you can use it again.” We went to that gas station, they had no idea what we were talking about. I think it could be to support the local business, etc. Just keep in mind…

New York to Maine Road Trip, Girl On The Bike
Beehive is the most amazing hike trail for me. We went up, and then went down the same way. Intense 😁

I heard Acadia gets really hot in summer. So I think the best time is May – June. Not July or August unless you like it hot…

Bubble Rock hiking. Very cool!!!! I almost didn’t go to this one, said I’ll wait for you here, although saw the rock from away. It’s so cool closer.

Maine

Maine is very special to me, thanks to Stephen King, most of his books are happening in Maine, always wanted to make a New York to Maine road trip because of him and when we drove to his house, and the gate was open, and I was truly wishing not to see King yet!

First I’m terrified, he’s a genius or he actually has super abilities to talk to his characters in his books somehow. And you know he writes pretty scary stuff. Hahah.

What I didn’t tell my friend was I went to Maine to “Well, let’s go and see if we’ll make it back” We could have been captured by serial killers, aliens, ghosts, monsters, locals – oh secretive locals, maybe a local police taking us to a weird place, maybe our car’s tire blew and we stuck there till a car picker truck comes… I didn’t tell those to my friend.. But I asked another of my friend if we pulled over, and the police come to our window, can I ask him to show his ID first   😳🤓🤔

In Maine, we stayed in a gorgeous bed and breakfast place. There were very few Airbnb’s, and now thinking BB was phenomenal. She cooked fresh eggs from the chickens and waffles and muffins. OH SO YUM!

New York to Maine Road Trip, Girl On The Bike

That night, we hit the bed, less than 1 minute I was sleeping Elysia told me… “You sleep like a log!” she said 😀 ( no idea what a log is ☺️

It was completely dark and quiet.. Except for the heaters sound, which I actually love a bit of noise…. just a bit to remind me I’m in this world and dimension …

I forgot to go out and look at the stars!!!!! ⭐️ ✨ 😢I can’t wait to see the sky and all the stars and lay down and watch them… Maine was freezing at night, that’s my excuse of forgetting to take a look outside…

Portland

Hmm… Portland is adorably cute. Why? Lighthouses, beach, seafood restaurants… Actually one place I found.. I can drive there, fly there to eat there again…

J’s Oyster. A hidden spot next to big touristic traps. So although I was a bit of food poisoned from New York, I had to try this food, thinking I need nutrients. Ordered a fish… THAT WAS THE BEST fish I ate in the USA! Elysia got a mix of all seafood stuff… Looked amazing. Okay, I found my review I wrote for them explains my then feelings:

“Oh my… I got this melting fish in my mouth, super fresh, delicious…. yummmmmmm My friend got the seafood casserole, said amazing. The clam chowder was also amazing..”

New York to Maine Road Trip, Girl On The Bike
J’s Oyster is a small hidden gem, so delicious with friendly staff 😋🤤

Boston

I’ve been in Boston many times, (3 probably), and I loved it each time visited. This time with a car, terrified if we can find a parking spot and it’s not difficult at all. We stayed in a local neighborhood Summerville in an Airbnb apartment, met a friend of mine there, walked a lot!!! Went to an amazing live jazz music show, lots of talented musicians there studying in schools.

My Elysia insisted she wants to drive by the Red Sox stadium and knowing Yankees stadium or any stadium areas not a cool spot to see outside, I agreed and ended up buying a Boston Red Sox hat and winter gloves!

Cross Sound Ferry

We decided that instead of coming to New York and then she goes to Hamptons for the bachelorette party, we drive there. And then I drive back to city and then to Jersey to drop the car.

From Boston to Hamptons, we found there is a ferry called Cross Sound Ferry, and decided to take it.

  • It’s a pretty nice way, with view and ocean, breakfast, tea, coffee..
  • Don’t pay extras, just get the basic ticket, because it doesn’t matter.
  • Unless it’s summer and you’re not so flexible with time in case it’s fully booked.

Know that, after that big car ferry, there is 2 or 3 little more ferry we had to take to arrive at Hamptons. I had no idea about that, and that means more costs! And getting in and out of the ferry, driving is a bit weird…

Hamptons

Such a beautiful place. Interestingly because of the season we chose, Maine didn’t have greens and leaves yet, it was empty branches. When we arrive in Boston it was colorful greens, and when we arrived at Hamptons, Sag Harbor old streets, amaazing! I loved it. I saw the first deers, squirrels.. (I didn’t see any animal in Maine really!)

We didn’t get stopped or seen any police car in this 1250+ miles trip, except Hamptons. I’ve seen so many, waiting, hiding, all around… I guess they are ready for the party-goers.

New York to Maine Road Trip, Girl On The Bike
Last day, driving at Hamptons, tired! 😴

Oh, so we arrived at Sag Harbor and drove till the end of Montauk; passed the city, beach and arrived at this National Park.. Haha, it was the “end of the world”. Because we were at the end of the map. I hope you can see the video, it was very unique, scary, out of the world experience for me.

Road Trip Buddy

Very important. I can’t highlight enough.

I was lucky she was amazing, easy-going, like to laugh, caring, honest. Because when you’re driving a long time, even if you like each other, amazing person; there will be times you both will disagree on things. How you communicate on these conflict times are the key to the success of the road trip. Because if you clashes, you don’t wanna be sitting next to your friend, the trip becomes a mess.

New York to Maine Road Trip, Girl On The Bike
Elysia opening her birthday cards! Have no idea what this tradition is. I never do cards, and she was very strict about it 🤔😍Oh this is the beach at the Acadia National Park… Pretty nice…

So I was lucky, because when we disagreed on something, oh wait, we didn’t so much. She didn’t mind what we do, where we go, what music we listen, how fast we drive, etc… That was perfect. I may get a bit control freak, I like to do things in the best way, and mostly it’s my way. Or I prefer doing it alone. (I’m much better now, working on to go with the flow, less control I have, more relaxed I am, but still, I’m not a person like her, that easy-going)

She was strict on having enough water, drinks, snacks, so we made sure to stop for these. I mean, she drinks A LOT of water! A lot!!! 😂And gets panic when there is no water bottle in her hands. Real panic! And if there is only 1 bottle left, she keeps it to herself till we get new bottles…. hahaha 😂

Also, she wanted to hike a lot. I agreed, which turned out amazing, I wouldn’t hike that much myself. But oh yes, she minded that, and so I went to her way. (Except now I remember, I waited for some little lake and so hikings in the car… I was tired 😝)

Oh, also, she didn’t trash any of those bottles, looking for recycling, and I had no idea what she was looking for real, till I saw the recycling machines in Hamptons. It was a big deal for the supermarket manager, she was demanding to use the recycling machines outside which were giving “full” error. Well, we kept all the bottles, and then trashed in the last days.

And other times, it was all amazing. So fun. Feeling the breeze, oh wait again, what breeze? Do you mean cold air? Yes! We converted our car’s top, and opened it most of the times, it was cold May days! And we heated our seat, and put our jackets, hats, glasses, and drove like that 😆😂 😍

I had such a fun time driving with her. She is pure fun. Silly jokes, British accent, the view.

New York to Maine Road Trip Suggestions:

Well let’s make this part where I give my personal suggestions:

  • Choose your road trip buddy carefully, be open-minded, relax, and be clear of how you feel about things in the beginning so you don’t grow negative emotions inside.
  • Wanna save money on nice accommodation? Use Airbnb, start a new account, save $55 on your rental and experiences.
  • Read reviews, wherever you decide to stay, reviews are so important to learn the hidden details. I care most about cleanliness, centeredness, and safety.
  • Have a few more days extra, so you don’t have to drive everyday like us… (Elysia’s tip)
  • No time to research? Ask your host, receptionist, in a friendly way, where they eat or hangout. These are the best places most of the time.

Do you have your New York to Maine road trip tips? Please share with us in the comments!!! And now photos 😃I took a lot of photos:

More Trip Photos