Bailey Island Maine: How to Plan a Day Trip to Breathtaking “Lands End”

This is much of what I love about Maine. The rugged wilderness. The untamed Atlantic. A string of islands close to Harpswell’s shore made of shoal and sediment and sand—and perfumed by wild roses that somehow manage to take root. So, it should come as no surprise that the charming, ocean-swept Bailey’s Island makes an extraordinary destination. Learn why you might want to plan a day trip (or longer) to Bailey Island Maine with a visit to scenic “Land’s End,” too.

Editor’s Note: We updated this post in July of 2022 to keep it current and add new information.

A view of the Atlantic Ocean and islands as seen from Bailey Island Maine

CONTENTS: In this article, you will learn everything you need to know about planning a trip to Bailey Island Maine, including:

Our Visit to Bailey Island Maine

My mother and I, along with my college-age son, took a road trip to Maine. We spent the better part of an afternoon exploring Bailey Island in Harpswell before meeting friends for dinner.

We could have lingered much longer.

Bailey Island makes for a great scenic road trip in itself or combined with other stops along a longer scenic Maine drive. It’s also an excellent destination for inflatable kayaks and all sorts of other outdoor activities.

As it is all saltwater at Bailey Island, you can pick yours from the list of best inflatable kayaks for ocean.

Like at many coastal towns on the rugged Maine Coastline, you can expect to find beautiful scenery, quaint New England fishing communities, and an independent way of life.

The region is home to some of the few remaining working harbors on the Maine coast.

Keep reading to learn all about this beautiful destination, and why you’ll enjoy visiting Baily Island, Maine.

Related Article: Travel further inland to discover picturesque Bethel, Maine.


Where is Bailey Island Maine

Map pointing out Bailey Island Maine

You’ll find Bailey Island in the Greater Portland and Casco Bay region of Maine. It’s about an hour-and-a-half drive (50 miles) from Portland, and 15 miles south of Brunswick, Maine.

From Boston, it’s 140 miles by car.

Bailey Island is one of three islands—Bailey Island, Orrs Island, and Sebascodegan or “Great Island.” Each is connected to the mainland or each other by bridge.

The islands make up the town of Harpswell.

More specifically, Bailey Island is part of the 216 miles of rocky coastline that comprises Harpswell Neck.

It’s also the last stop on Route 24.

History of Bailey Island

Known as “Newaggin” when settled in the 1600s, Bailey Island is the smallest of the three islands. It’s a charming coastal town in New England with a year-round population of just 400. (Source: 2000 Census).

The name of the island is for Deacon Timothy Bailey of Massachusetts.

Bailey is said to have bought the island in 1750 for 1 pound of tobacco and 1 gallon of rum. Then, he named the island for himself.

How to Get to Bailey Island Maine

There are two ways to get to Bailey island: by land or by sea.

In order to get there from the mainland, you must travel Route 24 across the Cribstone Bridge. This bridge is the only one of its kind in the world. More on that, below.

Related: Before you hit the road, be sure you consider the pros and cons of traveling by car.

Crossing The Cribstone Bridge

Cribstone Bridge in Harpswell Maine, crossing over to Bailey Island Maine

Built in 1927, the narrow Cribstone Bridge is made entirely of large stacked granite blocks. The bridge is a historic civil engineering landmark, listed on the National Register of Historic Places.

It’s 1,122 feet long and gravity alone holds together the blocks. This unique design allows water to flow freely through the open cells without disturbing the structure as the tide changes.

The Cribstone bridge connects the islands of Bailey Island and Orr’s Island in the town of Harpswell.

We pulled over in the dirt lot to the right before crossing to take some photos and to watch the boats gracing the waterway. (If the light isn’t right, you can always use a photo retoucher to correct the shot.)

If you’re looking for a bite to eat overlooking the water, Cook’s Lobster & Ale House is right around the corner from the bridge.

How to Get to Bailey Island Maine by Sea

The other way to get to Bailey Island is by sea.

Casco Bay Lines offers scenic tours departing from Portland, ME. Among others, the tours include Bailey Island and Mackerel Cove or Eagle Island. Both tours provide for a 2-hour layover on Bailey Island for lunch at Cook’s Lobster & Ale House.

You can also arrive by sea on a sailing charter, lobster tour, or even charter your own private tour.

Here are a few options you might consider for arriving at Bailey Island by sea:

  • Tevake Sailing Charters
  • Casco Bay Sites-N-Lights
  • West Wind Lobster Tours

Related Article: Read our review of this great lobster tour departing from Portland, Maine.

What to See and Do On Bailey Island Maine

Boats on the water at the Cribstone Bridge in Harpswell Maine

As you can imagine, the pace is slower, here on Bailey Island. It’s an ideal destination for someone who loves to meander about, taking in stunning ocean views, eating the freshest seafood, and enjoying incredible photo opportunities.

My recommendation is to just take your time to casually explore this quaint little island on your own.

But if you prefer a more solid plan, there are a number of attractions you might put on your itinerary.

In fact, let’s go ahead and design a treasure hunt for you, even though you are likely to stumble upon many of these attractions yourself.

Bailey Island Maine Treasure Hunt

Listed in random order

  • Cook’s Lobster & Ale House
  • Bailey Island Bridge
  • Bailey Island Beach
  • “BIGS” – Bailey Island General Store
  • Casco Bay
  • Mackerel Cove (one of the most photographed places in Maine)
  • Giants Stairway Trail
  • Betty’s Seaside Creations
  • Abner Point
  • Giant Stairs Grille
  • Bailey Island Lobster Co.
  • Glen’s Lobsters
  • Johnson Field Preserve at Mackeral Cove
  • MacIntosh Lot Preserve
  • Garrison Cove
  • Harpswell Honey
  • Harpswell Heritage Land Trust (lots of trails)
  • Cedar Beach
  • Morse’s Cribstone Grill
  • Land’s End Gift Shop

One of my favorite scenic stops is Land’s End.

To get there, follow along Route 24 until it literally ends. You’ll know you’re getting close when you see a sign that warns “Road Ends 500 feet.”

Related Article: Find out what to pack for a Fall Trip to New England here.

Take A Side Trip to Nearby Portland Maine

And if you have a bit of time, definitely stop by Portland Maine on your way to Bailey Island.

While you’re in Portland, you can take part in an amazing, 2.5-hour historical tour of the area. Tickets start at $40 per person and include expert commentary on over two-hundred years of history from a local guide.

You’ll start the tour on Commercial Street. Then, you’ll take a leisurely stroll through the town’s many cobblestone lanes as you explore the Old Port. Finally, you’ll end up at the downtown waterfront area in Portland.

Along the way, you’ll admire the town’s famous lobster statue, see the former residence of Henry Wadsworth-Longfellow, visit the Eastern cemetery, stop by the Abyssinian Church, and end the day with a complimentary sweet treat from a local food vendor.

Portland Maine is a great place to visit. It’s ony about an hour’s drive from Bailey Island.

From Portland, you could even plan a quick visit to the quaint Peaks Island.

What is Land’s End in Harpswell ME?

Lands End in Harpswell (Bailey Island Maine)

Land’s End is a scenic destination at the southernmost tip of Bailey Island.

At Land’s End, you’ll find mesmerizing views of the Atlantic Ocean, Turnip Island, and Jaquish Island. You’ll also see a myriad of other small outcroppings on the horizon. (Fun Fact: About 200 islands of Harpswell are reachable only by boat.)

You’ll also find the “Maine Lobsterman” sculpture, as well as narrow walking paths along the shale.

The view is especially breathtaking from the deck of the Land’s End Gift Shop—not to be confused with the mail-order clothing catalog.

Where to Park at Land’s End

You’ll find two free parking lots next to and across from Lands’ End Gift Shop.

Plus, it’s worth noting that if nature calls, you can use the portable restrooms in the first parking lot next to the gift shop.

Exploring Land’s End

While visiting Land’s End, you might choose to:

  • Relax on the small, sea-glass strewn Bailey Island Beach
  • Watch the boats cruise Casco Bay
  • Admire the iconic ‘Maine Lobsterman’, a bronze statue created for the 1939 World’s Fair
  • Walk along the rocky trail ending at the Giant’s Stairway
  • Cool off and shop the gift store for unique Maine-made souvenirs

At Land’s End, follow the path that meanders along the coastline to enjoy the stunning views of Casco Bay. You may even catch a glimpse of seals, seabirds, and other sea life.

Here’s a great aerial video of the area to give you a taste of the natural beauty you can expect while visiting Land’s End:

If you follow along the coastal path, I’m told you will arrive at what’s known locally as “The Giants Steps.” This is a natural rock formation that looks like stairs leading down to the sea. (Tip: Watch out for poison ivy.)

On the trail, you’ll encounter a small rocky beach called Pinnacle Rock. That’s where you’ll want to keep your eyes out for beautiful sea glass.

You can watch for the waves crashing in “Thunder Hole,” too.

A Must-See: The Gift Shop

Lobsterman Statue at Lands End Maine

Land’s End has a large gift shop with home-made fudge, light snacks, water, and an extensive selection of Maine-made souvenirs.

Two floors are filled with artisan goods, trinkets, t-shirts, and more, crafted by nearly 100 Maine artisans. Trust me, you’ll want to spend some time here to take it all in. This is souvenir heaven.

Land’s End Gift Shop has been owned and run by the Hutchins family since 1959. It was originally a small snack bar and store opened by Ed Hutchin’s grandparents in the 1930s.

The building was fully remodeled in 1978 after a damaging January storm.

Today, Land’s End is run by Ruby and Ed’s son, Howard Hutchins, along with his wife Karen.

In addition, the shop provides plenty of benches on the wraparound deck (alive with whirligigs) overlooking the waterfront. It’s a perfect resting point if you want to sit comfortably and take in the view of Casco Bay.

That’s what I did. I loved catching some rays here, sipping a ginger beer, and taking it all in.

Best Time of Year to Visit Land’s End Gift Shop

Despite Harpswell’s reputation as a seasonal community, Land’s End Gift Shop is open seven days a week from April through October. It’s also open on weekends in December, school vacation week in February, and weekends in March.

New England winters can be bitter cold, especially on the coast. A visit to Land’s End in the spring, summer, or fall might be the better timing.

Land’s End Beach

Adjacent to Land’s End Gift Store, you’ll find the diminutive Land’s End Beach. Just a few steps down from the small parking lot, it’s known for sea glass and its lovely views of the ocean.

You may also enjoy swimming in the soft sandy bottom beach. But remember, the ocean water at Maine beaches can be cold!

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Land’s End is at the southern tip of Bailey Island, one of three small islands in Harpswell that are connected to the mainland by bridge. (The other ~200 islands of Harpswell are only reachable by boat.🚤) . At Land’s End, you’ll find a path that meanders along the coastline, offering stunning views of Casco Bay. There’s also a small rocky beach called Pinnacle Rock. (Keep your eyes out for sea glass!) #baileyisland #harpswell #itsamainething #visitmaine #enjoytravellife #newengland #visitnewengland #falltravel #autumnfoliage #fallfoliage #cascobay #giantsstairs #giantssteps #bayview #maine_igers #mainething #vacationstyle #mainevacation #newengland_igers #newenglandlife #travelblogger #travelwriters #travelpicture #travelpictures #traveltheworldwithme #ísland #maineislands #ilovemaine #roadtripusa .

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This beach reveals a lot of sea glass at low tide. For the best chance to find some sea glass for your collection, check the tide charts. Then, plan to arrive an hour or two before low tide.

Where to Stay on Bailey Island

When we visited this area, we were staying in the nearby town of Brunswick. This was a great day trip, but I could have easily been persuaded to overnight on Bailey Island.

In addition to several cottages on the island, you might consider one of these excellent lodging choices.

Bailey Island Motel

Just over the Cribstone Bridge and on the water’s edge, is Bailey Island Motel.

This is a great family-friendly option within walking distance to popular attractions. You’ll find decks overlooking the water, evening campfires, and complimentary use of their kayaks, too.

Waterside rooms at this modest but comfortable motel are well-priced at $130 per night and include complimentary breakfast.

A typical breakfast at Bailey Island Motel consists of coffee, tea, and delicious, freshly baked muffins. You’ll also enjoy cable TV, free Wi-Fi, ocean views, mini-fridges, and access to a private dock.

Click to see Bailey Island Motel Rates & Availability.

Log Cabin Island Inn

You’ll find breathtaking sunset views of the bay and a firsthand look at lobster boats at Log Cabin Island Inn.

Plus, each room is uniquely styled. Some suites are quite spacious with full kitchens and a jacuzzi. All are well-appointed.

If you stay at Log Cabin Island Inn, you’ll enjoy a full complimentary breakfast. You may also opt for a delicious dinner with your stay, too.

Click to see Log Cabin Island Rates & Availability.

The Driftwood Inn

The Driftwood Inn is the oldest inn on Bailey Island. It has been in continuous operation for over 100 years.

It offers pristine, private cabins for rent on their three-acre oceanfront location overlooking beautiful Casco Bay. Hosting includes housekeeping services and the use of their saltwater swimming pool.

Or, rent “The Mansion,” which literally sleeps a full house of up to 16 guests.

Click to See The Driftwood Inn Rates & Availability.

Capt. Lawrence E. Johnson House

Perhaps one of the most luxurious accommodations on Bailey Island is the Capt. Lawrence E. Johnson House.

It comfortably hosts up to ten guests, making it perfect for family holidays and events.

Each room includes ensuite bathrooms, luxury linens, and cozy sitting areas. They offer different view of the inlets and sounds surrounding the island.

The wrap-around deck provides outdoor dining with a gas grill and a three-burner outside range. Plus, you’ll want to check out the rooftop deck complete with a wet bar.

You might even be tempted to rent this property for a month at a time.

Click to see Capt. Lawrence E. Johnson House Rates & Availability.

Final Thoughts

Bailey Island makes a memorable day trip if you happen to be within driving distance of Harpswell, Maine.

And if you’re further away, even better. Plan to stay over on the island so you can fully experience the relaxed vibe, coastal beauty, and “Down East” hospitality you’re sure to encounter.

Jackie Gately of Enjoy Travel Life at Bailey Island Maine

Do you love Maine’s coastal islands, like I do? Then you might want to check out this article about Peaks Island, too!


This article may contain affiliate links. As always, all opinions expressed are my own. For more information, please see the following Disclosure.

Resources

In alphabetical order

Bailey Island General Store (“BIGS”)

2124 Harpswell Islands Road
Bailey Island, ME 04003
Phone:  +1 (207) 833-2400
More Info

Bailey Island Lobster Co.

51 Abner Point Road
Bailey Island, ME 04003
Phone: (207) 833-6099

Bailey Island Motel

1951 Harpswell Islands Road
Bailey Island, Maine 04003
+1 (207) 833-2886
Website: baileyislandmotel.com
Email: [email protected]
Check Rates & Availability

Betty’s Seaside Creations

47 Washington Avenue
Bailey Island, ME 04003
Phone:  +1 (207) 833-6645
More Info

Capt. Lawrence E. Johnson House

1965 Harpswell Islands Rd
Bailey Island, ME 04003-2573
Phone: +1 (207) 541-9187
Email: [email protected]
Check Rates & Availability

Casco Bay Lines

P.O. Box 4656
Portland, ME
04112-4656
Phone: +1 (207) 774-7871
Email: [email protected]
Website: https://www.cascobaylines.com/

Casco Bay Sites-N-Lights

1945 Harpswell Island Road
Bailey Island, Me. 04003
Phone: Cell – +1 (207) 837-1788 | Home – +1 (207) 406-2124
email: [email protected]
Website: https://cascobaysightseeing.com/

Cook’s Lobster & Ale House

68 Garrison Cove Road
Bailey Island, Maine 04003
Phone: +1 (207) 833-2818
Menu: https://www.cookslobster.com/

Driftwood Inn

1958 Harpswell Islands Road
Bailey Island, ME 04003, USA
Phone: +1 (207) 833-5461
Email: [email protected] | [email protected]
Check Rates & Availability

Giant Stairs Seafood Grille

2118 Harpswell Islands Road
Bailey Island, Maine 04003
Phone: +1 (207) 833-5000
More Info

Glen’s Lobsters

Abner Point Rd
Bailey Island, Maine 04003
Phone: +1 (207) 833-6138
More Info

Harpswell Honey

W. Shore Road
Bailey Island, ME 04003
Phone: +1 (207) 833-5858

Lands End Gift Shop

2391 Harpswell Islands Road
Bailey Island, ME
Phone: +1 (207) 833-2313
Email: [email protected]

Log Cabin Island Inn

5 Log Cabin Road
Bailey Island, ME 04003
Phone: +1 (207) 833-5546
Check Rates & Availablity

Morse’s Cribstone Grill

1945 Harpswell Islands Road
Bailey Island, ME 04003
Phone:  +1 (207) 833-7775
Menu: https://www.morsescribstonegrill.net/

Tevake Sailing Charters

Sea Escape Charters 
3 Sea Escape Lane
Bailey Island, ME 04003
Phone: +1 (207) 841-9125 (cell) | +1 (207) 833-5531
Website: https://seaescapecottages.com/sailing-charters/

West Wind Lobster Tours

1945 Harpswell Islands Road
Bailey Island, Maine 04003
Phone: +1 (207) 939-5481
Website: https://www.westwindlobstertours.com/

Frequently Asked Questions About Bailey Island, Maine

Below are answers to some of the most common questions about Bailey Island.

What town is Bailey Island in?

You’ll find Bailey Island in the town of Harpswell, Maine. It’s part of Cumberland County. This charming little town right on the coast overlooking Casco Bay. Bailey Island is–as you might have guessed–an island. It’s connected to the mainland by a Cribstone bridge you can drive over.

How long is Bailey Island Maine?

Bailey Island Maine is very drivable at 2.5 miles long and just a half mile wide. You’ll find scenic vistas just about everywhere.

What is Land’s End in Maine?

At the southern tip of Bailey Island, you’ll find Land’s End. This scenic destination offers amazing views to the Atlantic Ocean, as well as views to smaller islands and outcroppings, like Jaquish Island and Turnip Island. Trails wrap around this part of the rugged Maine coastline, perfect for walking to enjoy a nature break and wildlife. Or, stop into the gift shop for some souvenirs and a cool beverage.

Have a question not answered by this article? Just post it in the comments below!

Don’t forget to save this post for future reference on Pinterest.

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How to Plan a Trip to Scenic "Land's End" on Bailey Island Maine, from Enjoy Travel Life.
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Jackie Gately

Jackie Gately is a seasoned travel writer, photographer, and marketing consultant who is passionate about travel. She loves casual-luxury experiences, coastal getaways, cultural attractions, and local, wholesome food and wine pairings. A perfect day ends with her toes in the sand or by chasing the sunset with her camera--ideally both.

42 thoughts on “Bailey Island Maine: How to Plan a Day Trip to Breathtaking “Lands End”

  • July 15, 2022 at 11:44 am
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    I would love to visit Bailey Island and Land’s End in Maine someday. It reminds me of the English Land’s End, which I visited a few years ago. It is however completely different. I like that there is a small beach there, as well as plenty of nice places to spend the night too. I would definitely buy a handmade souvenir from the gift shop.

    Reply
    • July 15, 2022 at 8:08 pm
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      Interesting to know there is an English Land’s End! I’m glad this Maine destination sounds like someplace you would like to visit. You’ll have plenty of souvenirs from which to choose.

      Reply
  • July 14, 2022 at 12:34 pm
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    Bailey Island looks so enchanting to me, I really love the New England part of the USA. Eating fresh lobster here would be a must for a seafood lover and I know it’s popular in this part of the country. You’re right about the rugged landscape and pretty Land’s End. It’s really on my list should I revisit the USA and Maine one day again.

    Reply
  • July 14, 2022 at 8:15 am
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    I did a road trip through Maine a few years ago and missed Bailey Island and the whole area of the Harpswell Neck. I’m a huge fan of Portland and love that this is so close yet a completely different experience. Would love to spend time relaxing on Bailey Island Beach and searching for beach glass.

    Reply
    • July 14, 2022 at 8:53 am
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      Your Portland trip sounds wonderful, Sherianne, but I’m sorry you missed Bailey Island and Harpswell Neck. Hope you get a chance for a return trip to get these spots on your itinerary! (I love Portland, too!)

      Reply
  • July 13, 2022 at 5:32 pm
    Permalink

    What a hidden gem you’ve found! I’ve not heard of Bailey Island in Maine. But knowing that it’s the smallest of the 3 islands, and only a population of 400, it immediately gets my attention. It is super quaint and charming, exactly what I look for in a destination.

    Reply
    • July 13, 2022 at 9:29 pm
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      Renee, it truly is a hidden gem. Your description is spot on. Glad to hear it’s your kinda place!

      Reply
  • July 13, 2022 at 12:51 pm
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    Looks amazing, I love rugged landscapes like this and the coastal areas there look fantastic. It’s nice that they are also connected by bridges so they are easy to access and see everything with a short scenic drive. I would definitely love to explore more of this beautiful region and the island attractions.

    Reply
    • July 13, 2022 at 9:30 pm
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      Coastal Maine is a great take, Noel. The bridges are so convenient for the drive over. Hope you get the chance to do some exploring here!

      Reply
  • July 13, 2022 at 8:29 am
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    Wow! This is scenery and place is so stunning. Reading about Land’s end wants to make me go to Bailey island. This will definitely in my to do list on my next trip to the U.S.

    Reply
  • July 12, 2022 at 8:22 pm
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    This part of the US looks stunning and I wish I could have visited last time I was there. I will certainly be adding it to my list for next time. I would love to do the tour of the area and learn the history of it. I also want to see Lands End and visit the little gift shop and I want to stay in Driftwood Inn too or maybe the Log Cabin Island Inn.

    Reply
    • July 12, 2022 at 9:14 pm
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      Glad to give you some inspiration to come back, Clare! This area of New England is just gorgeous.

      Reply
  • July 12, 2022 at 7:47 am
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    I’ve never heard of Bailey Island, but Land’s End Beach sounds like a lovely road trip idea to see the water and enjoy the summer weather with family! Thank you for the varied list of accommodations that fit every budget or luxury requirement, love to support local inns and hotels if possible!

    Reply
    • July 12, 2022 at 6:26 pm
      Permalink

      You are very welcome, Alice! Happy to have brought Bailey Island to your attention. I’m sure the local inns and hotels would love to host you!

      Reply
  • July 12, 2022 at 12:16 am
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    It sounds like a great day trip from Portland, I always wanted to visit! The treasure hunt to do in the island seems like such a fun activity, can’t wait to explore 🙂

    Reply
    • July 12, 2022 at 6:28 pm
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      Maine offers so much, Amalia – you’ll love both Portland and Bailey Island. Enjoy exploring!

      Reply
  • July 28, 2020 at 11:58 pm
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    It’s so wonderful to read that three generations took a road trip together to Maine. I loved your video. I felt i was there exploring the region with you. I love exploring small and offbeat places. I would love to explore Bailey Island for its quaint charm.

    Reply
    • July 29, 2020 at 4:03 pm
      Permalink

      It was such a treat to take a multi-generational trip. I’m so glad you enjoyed exploring Bailey island in this post and video. It certainly is quaint and charming!

      Reply

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