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Summer Maine Vacation Guide

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This is your perfect summer Maine vacation guide. A no stress guide to seeing all the pretty sights and eating all the delicious food without having to stick to a schedule. 

Summer Maine Travel Guide - Orr's Island

I have always DREAMED of moving to Maine. I read Sarah, Plain and Tall when I was a kid and the way Sarah talked about the sea made me want to pack my bags and move. However, it wasn’t until just a few years ago that I actually made my way to Maine. And you know what? I was hooked. That state knows how to lure you in and make you love it. Of course, I have only gone in the summer so my lust is completely ignoring the very cold and snowy winters. BUT pay no mind to snow and cold because today I’m talking about Maine in the SUMMER!

First, Maine is a pretty big state (with parts of Maine basically being full on wilderness) so this guide doesn’t exactly cover ALL of Maine. Instead, I’m going to talk about the Portland area of Maine. I’m going to show you places to eat, stay and explore in Portland, Kennebunkport and Orr’s Island. So, grab a whoopie pie and a lobster roll and enjoy the show!


Summer Maine Travel Guide - Portland Love Locks

I love Portland SOOOOOOOO much! It’s got the perfect Maine feel with a hefty dose of coolness and funk. Plus, the food in this town is pretty spot on!

Where to stay?

Summer Maine Travel Guide - Portland Mercury Inn

Mercury Inn

First, there are a lot of places to stay in Portland but one of my favorite (in town) places to stay is Mercury Inn. It’s got that cute bed and breakfast feel without any of the creepiness that sometimes comes with places like that. The breakfast is top notch and made with a lot of local and in-season ingredients. The rooms are all freshly updated with super comfortable beds and each room has air conditioning. I know, most people can live without AC in Maine but I’m pretty high maintenance when it comes to sleeping. I need it cold without even a hint of warm in the air.

Another perk about Mercury Inn is the ability to park your car and walk. It’s close to the center area of town so you don’t have to necessarily rely on driving around and parking your car to see the sights.

Summer Maine Travel Guide - Portland Inn at Diamond Cove

Inn at Diamond Cove

Ok, first you need to know you have to get to this hotel via a ferry or private boat. {We took the UB85 private charter boat!}  It’s still considered Portland it’s just on Great Diamond Island instead of being on the mainland. Personally, I loved this hotel! It was quiet and peaceful and is perfect for a relaxing weekend away. Plus each room is amazing! Our luxury suite came with a private balcony (the type of balcony you want to wrap yourself in a blanket and go read a book!) kitchen, living room, big bedroom and beautiful bathroom. It had just been re-done and was 100% worth the stay.

Also, there is parking in mainland Portland for your car. Once you arrive on the island the hotel will pick you up on a golf cart and take you to the hotel.

Fun fact: The hotel and surrounding buildings used to be a military complex!

What to do?

Summer Maine Travel Guide - Portland Lucky Catch Lobster Tour

Lucky Catch Lobster Boat Tour

If you’re looking for something fun to do in Portland you need to go out on a lobster boat! You can get up close and personal with a lobsterman and learn how to bait a trap, pull it out of the water and do a ton of other lobster related things.

Soakology – aka: Treat yo self!

YOU GUYS! This place is seriously like heaven on earth. First, it smells fantastic when you walk in and second, the people who work here have magic hands.

Brewery Tours

I have done the Shipyard Brewery tour with a few friends and it was a blast. It doesn’t take too long and at the end, you get to sample BEER! The hardest part of the tour was withstanding the urge to put a glove on the line of beer bottles in the factory. Props to those who get what I’m talking about.

Although I have never done this I have heard awesome things about the tour at the Allagash Brewery. I have had their beer before and I luuuuuuurve it! Plus, we all know brewery tours are fun!

Cabot Farmers’ Annex

You can sample and shop for cheese PLUS there are lots of fun gifts and other local Maine products to sample. PLUS CHEESE!

Hiking and more!

If you’re an active person you’ll love Maine. There are tons of hiking trails, running paths, places to kayak and paddle board PLUS it’s Maine so there are tons of beautiful lighthouses to look at.

Where to eat?

Summer Maine Travel Guide - Portland Lobster Company

Portland Lobster Company

There are mixed feelings from friends on this choice. Some day it’s too touristy and there are better lobster shakes in the area BUT I really like the Portland Lobster Company. The food is fresh, the lobster roll is cold and delicious and the beer is also cold – which is very important. I always go for the classic Maine lobster roll while my husband usually orders a lobster roll AND a whole belly clam roll. Full disclosure – I hate whole belly clams but my husband really seems to love them.


They fry their french fries in duck fat. Do I need to say more? Ok, I will. They also have ahhhhhhmazing gelato milkshakes that should be consumed while shoveling fries into your mouth. Oh, make sure to spring for the fry dippings sauces. My personal favorite was the garlic mayo BUT the curry ketchup was pretty awesome too.

Mi Sen Noodle Bar

Ok, I don’t need a reason to want to eat noodles BUT the fact that Mi Sen has Tom Kha spicy noodles makes my spicy heart sing. It’s all the flavors of Tom Kha Gai soup but with noodles. You guys – it’s the best!


Vena’s Fizz House

This place is half shopping half drinking! So really I guess it could be in the where to go category too. Lots of fun cocktail glasses and TONS of fun cocktail ingredients – infusion kits, bitters, etc. PLUS PLUS PLUS there is a fun little drink bar where they make totally slamming (and refreshing) mocktails and cocktails. Seriously guys hit this place up! Highly recommended.

Nosh Kitchen Bar

They have a burger that combines a beef patty, cheese, crispy pork belly, bacon, foie gras paté, mayo, cherry jam all piled onto a grilled brioche bun. Do I need to say more?

The Holy Donut

DONUTS! These delicious potato donuts are a MUST if you visit Portland. I have had a lot of their flavors but my personal favorites are the pomegranate glazed and the Holy Cannoli STUFFED donut.

Summer Maine Travel Guide - Cape Elizabeth Lobster Shack at Two Lights

The Lobster House at Two Lights (Technically in Cape Elizabeth, ME)

This lobster house is a bit out of town BUT 100% worth it! We sampled SOOOOOOO much food from here and everything was delicious. Here is what we got and what I recommend – the lobster roll boat, the lobster stew and the mini blueberry pie.


Summer Maine Travel Guide - Kennebunkport

Last summer was my first time in Kennebunkport and to be honest I wasn’t sure what to expect. I had always envisioned it being super rich and nothing more. Well, yeah, it was a little ritzy BUT I had so much fun! It’s walkable with lots of delicious food and tons of fun shopping.

Where to stay?

Summer Maine Travel Guide - Kennebunkport Inn

The Kennebunkport Inn

You know in movies when you see cute little quaint hotels? The Kennebunkport Inn is exactly one of those! The rooms were clean, updated and quiet. Our room wasn’t huge but it came with a king size bed and AC. Plus it has a cute little patio where I spent a few hours chatting with friends.

What to do?

Summer Maine Travel Guide - Kennebunkport


If there is one thing Kennebunkport is not short on its places to shop. We strolled all around town and found everything from a store that was full of just hot sauce to a store where I could look at jewelry that cost more than my house. I also almost bought a Maine rope bracelet but chickened out last minute because I was afraid it looked too bulky on my wrist. Ugh. I sorta wanna go back to Maine to buy one…

Summer Maine Travel Guide - Kennebunkport

The Bush Compound

Why I love to see big houses I could never afford I’ll never know but it was pretty neat. Plus I had an excuse to climb on some rocks and play near the ocean.

Where to eat?

Summer Maine Travel Guide - Kennebunkport Earth at Hidden Pond Dinner

Earth at Hidden Pond

The meal I had at Earth is in my top 5 of amazing meals. First, we started our time at Hidden Pond with a fun seasonal mixology class and then followed up with a private dinner. We ate ahhhhmazing food and I left so stuffed I thought I might have to be rolled out of the place. Favorite item of the night – chicken wings covered in a squid ink sauce.

Summer Maine Travel Guide - Kennebunkport The Clam Shack

The Clam Shack

As my husband I drove past this shack he said to me “Oh that place is good.” so I reply “Umm, have you been there?” his reply “Nope. But you can tell from the outside that it’s an awesome place.” Well, he was right. It serves up fried seafood baskets that are PACKED full of food. Lot’s of crinkle fries and delicious fried shrimp.

Summer Maine Travel Guide - Kennebunkport Rococo Ice Cream

Rococo Artisan Ice Cream

Good ice cream is a necessity on any vacation. So I and a few friends stopped in and had some amazing sweet treats. I had a scoop of coffee and dark chocolate and then dropped the chocolate all over my white shirt. Sigh. I cannot be trusted with wearing white.

Summer Maine Travel Guide - Kennebunkport Salt & Honey bloody mary

Salt & Honey

I had breakfast here twice and each time was delicious! Their wild Maine blueberry pancakes with lemon curd are delicious! And they make a hash out of short ribs – yeah! Oh, and if you’re a bloody mary fan you need to try theirs because not only is it delicious it comes with bacon.

Orr’s Island

Summer Maine Travel Guide - Orr's Island

I just got back from Orr’s Island this year and LOVED it! I was invited to stay with some of my friends and it was an amazing time. Very quiet, relaxing and perfect for people who want to get away. We also caught an awesome lightening storm on our last night that we watched for hours.

Where to stay?

Summer Maine Travel Guide - Orr's Island Ferris Lodge

Ferris Lodge

I stayed in a rental home with my friends and it was fabulous. Now, the rental home is a bit older but what I loved most is that it was big with lots of character and stunning views of the bay. I’m such a sucker for a house with a view! The room I stayed in came with a private sink that was the smallest private sink in the planet earth and my friend Julie stayed in a room that had a second secret hobbit door entrance. Seriously, this house had major character.

What to do?

Summer Maine Travel Guide - Orr's Island

Casco Bay Boat Tour

We took a fun narrated noontime cruise around Casco Bay that I highly recommend. It’s $16 and if you can grab a seat outside the view is straight up amazing. It’s actually one island over from Orr’s island {Bailey Island} but it’s easy to get too and afterward you can walk over to Cook’s Lobster & Ale house for seafood and beer – THE BEST!

Where to eat?

Summer Maine Travel Guide - Orr's Island

Cook’s Lobster & Ale House

The location is RIGHT ON the water and the food is damn good. I got myself a warm lobster roll and I insisted we order the lobster dip because who doesn’t love warm lobster dip that can be scooped up with grilled bread. DO IT!



This super simple heirloom tomato tart is made with puff pastry, lemon and fresh herb ricotta and covered with lots of freshly sliced heirloom tomatoes. Ready in just 25 minutes and perfect for an appetizer or a light dinner.
Heirloom Tomato Tart
These no bake strawberry tartlets are the perfect way to end the summer. This recipe only takes 5 ingredients and is prepared in just 15 minutes!
No Bake Strawberry Tartlets