What to Pack for a Summer in Maine

Maine Packing List

Alternative Apparel Tee


Maine Packing List


August kicked off with C and my first road trip together: NY to Maine!

We’ve always wanted to road trip New England and a coastal drive up to Maine seemed like the perfect summer getaway. We just got back home, are deeply tanned and covered in mosquito bites, but the trip was lots of fun!

Here are tips for what to pack for Maine and a quick recap of my favorite summer outfits throughout the trip!


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what to wear in kennebunkport maine



Outfit Details:

I'm obsessed with polka dots lately! Love how this ‘dress' is actually a versatile 2 piece set.


1 / Polka Dot Bodysuit Top

 Note: this is a thong bodysuit made of a forgiving neoprene fabric. On sale!!

Similar 2 piece set: red polka dot blouse + short set, or red polka dot bandeau


2 / Polka Dot Midi Skirt

high-waisted & hits below the knee. On sale!!

Similar set: asymmetric top + midi skirt set or cowl neck dress


3 / Cork Crossbody Purse

A fun, summer bag made from cork.


NYC to Maine Road Trip

We rented a Volvo XC60 for the trip and got upgraded to a hybrid car the morning of. Although we started off a little later than we had planned, it ended up being such a treat! I think this Volvo is the swankiest car I’ve ever been in. Now granted, living in NYC I don’t drive around much but this car was so beautiful that it made both of us want to buy a car just to enjoy it more.

The interior was roomy (I could definitely buy all the furniture I like at Home Goods with this car!) and the front panel was entirely digitized. The car had parking assist, let you know speed limits as you drove, and even showed you all the songs on every radio channel.

You didn’t even need to plug-in the key to drive it! When you locked the car it automatically turned in the side mirrors which is nice if you parallel park frequently.

Are all cars nowadays digitized like this? I am definitely out of the loop on cars but we were both really impressed by it. Plus, it’s an electric-gas hybrid car, so we only had to fill up the tank twice in 10 days, after driving for 780+ miles. Not bad!

For our road trip, C handled 100% of the driving as I’ve never driven a car by myself and we made it without killing each other. I like to think I was a pretty good navigator. There was just this one incident where we drove off the road and needed a truck to tow us out… but it was pretty much smooth sailing :)

 Read more:  Follow this Essential Maine Road Trip Itinerary!




flynn skye dress



Outfit Details:

I loved the cheery yellow flower print, but it also comes in different patterns and solid colors, as well as a mini dress option, wrap around skirt version & adorable off the shoulder jumpsuit


1 / Yellow Off the Shoulder Dress

Selling fast! Limited availability on:

AmazonZappos, Shopbop, Revolve and Flynn Skye


2 / Gold Lariat Lariat Necklace

I've been obsessed with necklaces lately and rotated between this delicate chain and a fun hamsa hand necklace for the trip.



Visiting Maine

We wanted to explore as much of Maine as we could, so we hit up Kennebunkport, Scarborough, Portland and Rockland on our trip, and took a couple days to sail on a traditional Maine sailboat. Out of all the stops, Kennebunkport was hands down our favorite.

Not only is the town adorably charming, Kennebunkport offers the best of both worlds. For example, you can try glamping, pick a beautiful marina hotel or stay a charming bed & breakfast. For food, there are tons of great restaurants in town, from Michelin quality dining to tasty road side lobster shacks!

 Read more:  Where to Stay in Portland, Maine




flynn skye maxi dress


Sailing on a Windjammer Cruise

Our of our entire Maine vacation, sailing on a windjammer cruise for 4 days was probably the most unique experience.

The best way to describe it would be “camping on a boat”. It was a little unexpected, and we were definitely a bit of our comfort zones, but we had a lot of fun getting in touch with our adventurey-nature sides and the sunsets were beautiful.

Some days we sailed all day, others we disembarked into tiny local Maine towns and uninhabited islands. We even had a traditional lobster bake for dinner, cooked in seaweed!

 Read more:  Everything You Should Know Before Sailing in Maine




the fifth label idyllic top and shorts set



Outfit Details:

I'm all about the 2 piece sets this summer.


1 / Checked Gingham Top

I don't think I've ever worn yellow before but this was so cute! I would size down on the top, it's a little boxy. Comes in a dress version too.

Also love this white sweetheart dress & smocked top


2 / Gingham Ruffle Shorts

These are cute both with the matching top, or on their own. Available on:

Shopbop & Nordstrom




Maine Food

The specific itinerary we booked was called ‘Lobsters & Lighthouses‘ and focused on a culinary experience for the week.

Once we got on board, we learned that the chef was actually the Captain’s wife! They met on board a different schooner when they first started their careers (her as a mess cook and he as a deck hand) and gradually honed their skills until they got married and purchased their own windjammer. One of their daughters also helped out as part of the crew. It was nice to see the family business in operation.

Annie is an INSANE cook, with experience at the CIA and restaurants across Maine. She made 3 heavenly meals a day and if only for her cooking alone, you should book a trip on the J & E Riggin! What we really liked was that all the meals were different and filling, but had a ton of vegetables so it didn’t feel too indulgent.




cmeo collective dress with polka dots



Outfit Details:

Wore this for dinner at the White Barn Inn, a gorgeous fine dining spot in Kennebunkport. The restaurant is in a rustic barn!


1 / Polka Dot Dress

Love the swingy movement of the bottom of the dress. Made from silk and super comfortable

Similar: polka dot blouse, red polka dot dress, 2 piece polka dot set


2 / Nude Leather Sandals

comfy leather sandals that I got on sale at the Jack Rogers summer sale! sold out, but similar here.



Our Foodie Sailing Cruise

We took one of her cookbooks home with us (she has three!) and have already earmarked some recipes to try ourselves. The menu on board was really varied – unexpectedly so! For example, we tried everything from a traditional Lobster bake steamed with seaweed, to rustic smores over an island campfire, to Bibimbap bowls and pulled pork tacos.

The desserts? Don’t even get me started. Annie whipped up espresso creme brule, shortbread peach cobbler and my hands down favorite, a dark chocolate tart in the flakiest crust (recipe is in her 2nd cookbook here)

On the last day, I peeked into the ship kitchen to watch her prep (she was making pop tarts from scratch) and I was shocked to see her cook up such a feast given how tiny the space is! It’s about half the size of my NYC kitchen… and I thought I had it bad (ha)

To make things more complicated, the ship uses a vintage wood fired stove, so she wakes up every day around 4am just to build the fire. It’s a long process to get the ancient stove up to the proper temperature – breakfast was usually served around ~7:30 am.

 Grab A Copy:  At Home, At Sea: Recipes from a Maine Windjammer Cookbook




everlane wide leg crop pant



Outfit Details:

Probably my favorite outfit from the trip and super comfortable.


1 / Bralette Crop Top

I wanted a white crop top since the pants sit really high on the waist. Really cute and affordable! Available on:

Shopbop, Free People, Macy's & Zappos


2 / Everlane Crop Pant

High waisted with wide legs and a cropped hem. I liked the thick but soft cotton, comes in lots of colors but I thought the salmon was so different!


3 / Hamsa Layered Necklace



Maine Packing List

Now for what to bring to Maine!

Definitely bug spray – I’m itching furiously as I type this. As a result of spending so much time in the outdoors, we’re both riddled with mosquito bites and wish we had packed buy spray!

I recently heard about mosquito patches so I think I’ll stock up on those along with those mosquito bracelets for my next trip into the woods.

Fun summer outfits aside, here’s what you absolutely should pack for Maine. The state is famous for its natural beauty, beautiful coastline and great outdoors so lots of casual clothes and gear for all weather situations is key!




revolve lpa dress



Outfit Details:

Interesting necklines and puffed sleeves are all the rage this summer. When I saw this cute pink gingham printed dress, I wanted it right away.


1 / Puff Sleeve Checkered Dress

The pastel pink checkered print is perfect for summer! The dress ended up fitting a little loose for me on the top, so it's better for a bigger bust. Also love this 2 piece set that's very similar.


2 / Converse Shoes

Like the hidden platform in these, but I have to admit they're not the most comfortable!


3 / Statement Flower Earrings

Sold out, but similar versions here, here and here.



1. Summer Clothes, But Bring a Windbreaker

We visited Maine in August, and found the days got HOT early. Sunrise was around 5:30am and it felt like mid afternoon by 6:45am. I lived in breathable cotton tops and dresses and definitely plan to get more of these super soft jersey shirts –  they were sooo comfortable!

In the early mornings or late evenings, it can cool down quite a bit, so do pack a rain jacket and umbrella along with a pullover or sweatshirt. We had a full day of pouring rain and a couple foggy nights out on the open water. If you do a whale watching tour, those boats will sail far out from the coastline in order to spot whales so temperatures can be a little cooler.


2. Comfortable Shoes.

Comfortable shoes are a must for traveling anywhere, but especially in Maine. If you’re visiting Acadia National Park or doing any camping, bring your hiking boots. We packed ‘shower’ flip flops and boat shoes for our sailing trip, which really came in handy for the ‘heads’, or bathrooms.




rye swim triangle bikini and high waisted bottom
everything but water rye swim


Rye Triangle Top & High Waisted Full Coverage Bottom



3. Insect Repellent

This one is a must. Maine jokes that the mosquito is it’s state animal and boy did I get eaten alive. Get OFF wipes, bug spray, mosquito repellent bracelets and even patches – those suckers are vicious! There were multiple times that we hit mosquitoes feasting on us and had streams of blood on our arms and legs.


4. Swimsuit

I packed like 5 bathing suits and barely got wet, ha. The Atlantic is pretty cold all year round, but in August the water warms up to a balmy 60 degrees.

Pack a swimsuit anyway! You never know if you’ll stumble on a beautiful beach (we liked Higgins Beach in Scarborough) or if your hotel will have a gorgeous pool.






Outfit Details:

On the Windjammer, I stuck to no makeup and comfy clothes.


1 / Stars Henley

If you love vintage-inspired lounge wear and super soft clothes, you will love this brand! I wore 3 pieces from the brand on our trip because I never wanted to take them off! Available on:

Nordstrom, Zappos & Alternative Apparel

Also love their distressed teescropped stars tee, fleece jogger pant


2 / Lobster Bikini (old, TJ Maxx)

I had to pack this – our cruise was themed ‘lobsters & lighthouses'!




Maine Windjammer Packing List

If you’re going sailing on a Maine windjammer, you’re in for a treat!

These narrow schooners are historic vessels and really unique to cruise with, but require a little extra packing assistance.

 Read more:  7 Things to Know Before Booking a Windjammer Cruise


Here’s what you should add to your packing list:

Duffel Bag – there’s no space for rolling suitcase on board. I brought my Vera Bradley large duffel, which is super roomy but folds up to the size of an envelope when empty

Portable Chargers – it will be an unplugged getaway at sea, so pack extra camera batteries and chargers for your electronics. A solar charger is great!

Outdoor Chair – we didn’t have this but another couple on board did and it really came in handy! there are limited seats on board so having your own outdoor chair is really nice.

Waterproof Bags – ships are always damp and if it rains, rain did get into some people’s cabins. Pack your clothing in separate seal-able, re-usable waterproof bags.




what to pack for maine



Outfit Details:

Casual outfit for our long driving days.


1 / White Pullover

Slightly over sized and super soft with a deep v neck. Available on:

ShopbopZappos, Macys & Revolve


2 / Everlane High Waisted Shorts

my first pair of ‘mom jeans'. These have a nice relaxed fit and you can wear them cuffed or unrolled to show the raw hem


3 / Cork Crossbody Bag

A fun, summer bag made from cork.



Lightweight Jacket – windjammers have a tugboat with a motor, but the best days are sailing days when the wind pushes you forward! It gets chilly as a result, and early morning / late evenings in Maine can also be quite cool. Pack at least 1 sweatshirt, preferably 2 as the tight quarters mean people don’t shower frequently.

Boat Shoes – Maine’s Penobscot Bay has hundreds of tiny islands and inlets to explore. Most don’t have docks, so good shoes with grip are a must to easily get on and off the boat to shore.

Bathing Suit – the sea is a refreshing 60 degrees in the summer, so bring a swimsuit and your own quick drying towel if you want to take a dip! We went paddle boarding and sailing on the smaller row boat.

Ear Plugs – the cabin walls are quite thin, so we heard everything from our neighbors. If you’re sensitive to noise, you might want ear plugs.

Flash Light – the small cabins can get dark at night, so if you have a flash light they’re great to bring along.




Australia Gold SPF 50 Spray / Drunk Elephant Tinted SPF 30 / Laura Mercier Oil Free Tinted Moisturizer with SPF 20 / PCA Skin SPF 45 Physical Sunscreen / Coola Makeup Setting Spray with SPF 30 / Australian Gold Tinted Sunscreen


Sunscreen – on a sail boat, you’ll be totally exposed when the boat is moving. Get yourself some heavy duty SPF and check that it protects against both UVA and UVB! I recommend Biore or PCA Skin for face sunscreen. Lately I’ve been really liking tinted sunscreens that function as a tinted moisturizer and sunscreen – Australian Gold makes a great inexpensive one or Drunk Elephant has a nice thicker one.

Wet Wipes – these will really come in handy! Whether you just want to quickly clean yourself off or feel grimey after a day at sea, get yourself a pack.

Towel – the ship provides a body towel, but I always prefer to bring my own and these are a nice quick drying microfiber! Also doubles as a beach towel or camping towel.

Water Bottle – the schooner brings enough fresh water on board for the journey, but it’s a good idea to bring a water bottle so you can refill. We also brought some rose and wine to enjoy on the journey – its BYOB

Binoculars – we spotted some ospreys and porpoises on the sailing cruise, and the seals were especially cute (one guy seemed to be holding a dinghy and leisurely floating on his back). They won’t come too close to the sailing vessels, so bring a pair of portable binoculars like these if you want to see them up close!




what to wear in maine



Outfit Details:

Another polka dot outfit – this cute but casual day dress is pretty versatile!


1 / Off the Shoulder Dress

Love the subtle polka dot print, off the shoulder sweet heart neck and small waist cut out. It's a nice thick cotton material too. Available on:

Amazon, Shopbop, Nordstrom & Bloomingdales


2 / Converse Shoes

Like the hidden platform in these, but I have to admit they're not the most comfortable!




Maine Souvenirs

If you forget to pack a layer, don’t worry – you can always pick up a fun tourist shirt in Kennebunkport! There’s everything from presidential tees (the Bush clan vacations there) to “Kennebunkport” sweaters. We got a red “MAINE” sweatshirt on our last day so we could exit like proper tourists, ha.

Or, if you really love to shop, include a road stop in Freeport, where LL Bean is located. We drove through on our way up and saw tons of factory outlet stores from brands like Ralph Lauren, Patagonia, Brooks Brothers, Calvin Klein – you name it.

In the Maine town of Kittery, just over the New Hampshire border, you can visit the Kittery Trading Post if you want to load up on hunting / fishing / boating and outdoor gear.





What’s your favorite road trip that you’ve done? 


Visiting Maine – Trip Planning Checklist

Road Trip | We rented a car for our 10 day road trip. It ended up being a great and cost-effective way to explore Maine, as our hybrid Volvo XC 60 really maximized every mile of the 800 mile route. We only had to fill up on gas twice! Check the latest deals on car rentals here.

Accommodation | Maine has some beautiful boutique hotels along its popular coastal towns. Summer is peak season in Maine, so book hotels in advance to save, or check here for last-minute deals. Alternatively, get a fun group together and rent a house on AirBnB for a slightly more budget friendly option.

Insurance | Lastly, be sure to visit Maine with travel insurance. Whether you get injured and need to be hospitalized, or your phone gets stolen, travel insurance will help when you need it most. Get a quote for your trip here.


 You Might Also Enjoy: 


Maine Vacation Planning Articles

A Classic Maine Road Trip: Lobsters, Lighthouses & Coastal Views

What to Wear in Maine: The Ultimate Packing List

Where to Stay in Portland, ME


Coastal Maine

Our Windjammer Cruise Sailing Experience: J&E Riggin Review

7 Things to Know Before Joining a Windjammer Cruise



Where to Stay in Portland


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  1. Samantha
    August 20, 2018 / 1:01 am

    “There was just this one incident where we drove off the road and needed a truck to tow us out… but it was pretty much smooth sailing :)”

    I have follow up questions hahahaha

    • Sher
      August 20, 2018 / 1:35 pm

      LOL its a long story… will tell you I see ya!

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