Alex the Traveler (and Philip, too!)

Kittery, Maine: Lobsters. Candy. Pigs.

June 30, 2025

Kittery Maine is the place we always went right before school started for our back to school shopping. But it’s not just about the back to school outlet shopping – Kittery is just around the corner from one of my favorite ports, York. And you can’t forget about Portsmouth, NH just over the bridge. Now, it’s a great halfway stop when we’re en route to visit the bonus mom who lives in mid-coast Maine.

My mother would probably roll in her grave if I didn’t start with a blog post about Kittery by talking about the best store in the entire world: Yummies. It’s EXACTLY what it says on the box. It’s literally a bulk candy store. But it’s not just a bulk candy store – they also sell pretty much every candy under the sun. Looking for that obscure random Italian candy? I’m personally a fan of the gigantic bags of shoestring licorice that they sell. Philip laughs at me because the first bag usually doesn’t even usually make it home…an hour and a half away. (We don’t stop at Yummies on the way TO bonus mom…that’d be dangerous.)

Candy at Yummies (photo credit: Yummies)

I started with Yummies, but Kittery is mostly famous for its shopping. Like North Conway, Kittery has an abundance of outlet shopping. It’s not just the standard stuff, either. Each time we go, we find a new corner of the outlet mall to explore. This past year, we discovered a restaurant supply outlet store and bought a bunch of new silverware. We needed new silverware because I’m a bit of a scatterbrain. If I’m eating out of a takeout container with silverware, I have a tendency to accidentally throw out forks with the container. It drives Philip bananas. And I don’t usually notice until I suddenly only have one fork left.

Hawkeye Yelena Belova GIFfrom Hawkeye GIFs

Anyways…also nearby is one of the best lobster pounds in New England (besides Woodman’s. But we haven’t covered all of Massachusetts yet). Chauncey Creek Lobster Pier. I’m obsessed. I’m a true New Englander. Pretty much all I need in life is lobster with butter. Or mayo, if we’re going lobster roll. And for Philip, they have a fry-o-later and can make pretty awesome fries and chicken fingers. Chauncey Creek is right on the water. It’s the kind of place you can pick out your lobster, grab a picnic table, and chill. And yes, it’s absolutely worth the drive from our house. I vote if you’re easing into the lobster life, start with a lobster roll. It’s summer in taco form. **Lobster rolls are tacos. I will fight on this.**

Chauncey Creek Lobster Pier (photo credit: Chauncey Creek)

Just one town over from Kittery, York is home to the adorable New England B&Bs most people imagine when they think of New England. Bonus mom and I used to stop at one on the way home from camp. It’s no longer there, but I still have dreams about that first post-camp burger. That said, you can still find plenty of B&Bs for a weekend away. Or places to sail.

And before you leave Kittery, be sure to stop at When Pigs Fly bakery (and pizzeria), They have the bakery itself, with fun flavors of bread and jam (and scones and dough and on and on), but they also have a great sit down restaurant. My go to there is their amazing meatball sub. Philip usually leans towards their pizza.

I love their logo!

Kittery is a perfect day trip from central to eastern Massachusetts, but it’s also a great weekend away. Portsmouth, NH has a more standard hotels (and a few concert venues!), and York tends towards the more smaller inns and bed and breakfasts. Both are great options, either way, you can’t go wrong.

Places to stay:
* The Water Street Inn
* Kittery Inn and Suites

Places to Eat:
* When Pigs Fly
* Chauncy Creek Lobster Pier
* Rudders Public House

Happy Travels!
Berkshires…Western Mass is your perfect weekend getaway.

June 26, 2025

When I think of the Berkshires, my first thought is for Tanglewood, the summer home of the Boston Symphony Orchestra. I in my post about North Conway that I was a band geek who worked at one of the best music camps, Camp Encore/Coda. If my life had been slightly different, I would’ve been a music teacher. Alas, I was an awful teacher. Like, REALLY awful. But I was a halfway decent bassoonist. Good enough I made All-State every year of high school and that I was part of the New England Conservatory Youth Symphony Orchestra, Massachusetts Wind Ensemble, and the Greater Boston Youth Symphony Orchestra. Oh, and also honors level band and orchestra in my high school. So Tanglewood feels like my home away from home. I’ve seen Tanglewood from all sides – on stage in Seiji Ozawa hall and The Shed, and also from the seats and the lawn.

Tanglewood (photo credit: bso.org)

But that’s not all there is to see in the Berkshires, the last time I was out there, my college besties and I rented a house with our significant others and spent the weekend wandering around. We made a point of finding some new places we hadn’t been before. And we also went to some old favorites, too.

One standout for us? Gould Farm, a local farm with an on-site sandwich shop (the Roadside Cafe) we went to near our B&B in Monterey. What made this place even more special was that the farm works with those in need of mental health support. Because everyone needs help sometimes. They let you wander the farm (Philip and I made good friends with a baby cow!), and the cafe had some of the best quiche I’ve ever had.

I couldn’t find the cat we made a friend with. Also, yes, there was snow on the ground in May. It melted same day.

I’m also a fan of wandering around the shops of Great Barrington. I’ve found summer tourist towns have the best mix of kitsch and fancy. And nearby is the Barrington Brewery and Restaurant. I love a good pub burger, and theirs definitely hit the spot.

Barrington Brewery. (Photo credit: Boston Globe)

Also in the Berkshites is the Massachusetts Museum of Contemporary Art (aka MASS MoCA), one of the best places for contemporary art. They always have a few really fascinating installations. It’s in an old printworks factory, and it’s always got something new to find. They also partner with the Solid Sound Festival, and host the gamut of other performing arts – it’s not just about the visual art. If you can’t make it to a performance piece, it’s still worth a wander – I love that every wall in the space seems to have a different feeling.

MASS MoCA – Carly Govinski: Almanac (Photo credit: MASS MoCA)

And last, but certainly not least, Six Flags New England is just a hop skip and a jump away from the Berkshires. It’s about an hour away, but if you’re driving from the east it’s worth it. Especially if you’re a fan of coasters.

Places to Stay:
* The Red Lion Inn (we had the best ice cider at their restaurant!)
* East Rock Inn
* The Black Swan

Places to Eat:
* Champney’s Restaurant at the Deerfield Inn
* The Lion’s Den at the Red Lion Inn
* The Proprietor’s Lodge

Happy Travels!
North Conway, NH: Outlets, Trains, Games

June 23, 2025

So those who don’t know me are always shocked to learn that I went to band camp. I also WORKED at band camp. It was back in my “I totally won’t suck as a teacher” phase. I was a counselor at Camp Encore/Coda (now owned and run by my favorite former camper and fellow NYU alumna, Cara Bergantino!). One summer when I was working, my mother decided she missed me and drove the 3 hours from Massachusetts just to see me on my day off. The two of us decided that North Conway was the answer to all of our troubles. So we drove from Sweden, ME over to North Conway for a day of outlet shopping and eating.

I’m on the bottom right. Camp owner is next to me. Don’t judge the outfit, it was the early 00s. (© Camp Encore/Coda 2004)

For the record, I thought my mother was pranking me about this visit because I had recently called her on her birthday to prank her by telling her I broke my leg. “Surprise! Kidding! Happy birthday, Mom!” Her response was “You little &#$*! You failed for your second semester at NYU! KIDDING! You made Dean’s List!” (We had a very strange relationship and I miss her dearly.) I’m pretty sure the visit was a detente between us.

We got to North Conway around 9AM and started with some shopping. The first stop in North Conway is always Zeb’s General Store. I’m a sucker for penny candy (more on that when we discuss Kittery and York, ME), and my mom loved all the random crap that you don’t need…but you actually do. It’s easy for someone to get lost in Zeb’s, each shelf has something different to explore.

The famous talking moose at Zeb’s (photo credit: Zeb’s General Store)

From there, go for a train ride on the Conway Scenic Railroad. Even in summer, the ride is a beautiful tour through the mountains. They have all kinds of tours, from short one hour ones, to a longer five hour scenic excursion. Another option is their murder mystery train, which is exactly what it says on the box – a murder mystery party while riding the rails.

When we’re in town, we like to lunch at Flatbread Company. Flatbread is actually a local chain (with one random location in Maui?), but it is all about locally sourced ingredients. I’ll admit, I went to the Providence one first, but the North Conway one is also great. They have a Street Taco pizza with cotijo cheese…excuse me while I daydream a bit about it. I haven’t yet been to their new location, but they just relocated (as of June 16th) down the road.

Now that you’re all full of delicious pizza, I recommend some more retail therapy. North Conway is home to the Settlers Green Outlets. I wouldn’t miss an opportunity to stop by The Met. The Met Coffeehouse, that is. They have great drinks and their chocolate croissant is perfection. They’ve got two locations in North Conway – one right in the outlets, the other is downtown.

When you’re exhausted and have spent large amounts of money in the outlets, if you need a place to crash, I recommend the White Mountain Hotel. It’s gorgeous and honestly looks exactly what I see in my head when I think of a New England resort. If you’re into golf, there’s also a golf course on site.

White Mountain Hotel (Photo credit: Tripadvisor)

The next morning, if you’re looking for some adventure, head over to Storyland. It’s a rite of passage as a New Englander to go to this amusement park. That and Canobie Lake Park and Water Country (Water Country…water country…have some fun! IYKYK). Storyland is known for being one of the best kids amusement parks in the northeast. If you’ve got kiddos, definitely spend a day there.

Places to stay:
* White Mountain Hotel
* North Conway Grand
* Stonehurst Manor

Places to eat:
* Barley and Salt <- the tap list is incredible!
* Flatbread Company
* Moat Mountain Brewery (and Smokehouse) <- go for the brisket!

Happy Travels!
Mid-coast Maine. Puffins, Lighthouses, Family.

June 19, 2025
Every summer, Philip and I head up to Rockland in mid-coast Maine to visit my bonus mother. After my sister and I left our hometown, she moved up to Maine to work for their state government, and has been there ever since. She usually comes down to Massachusetts for Thanksgiving, so we try to head up there over the summer for a long weekend.

Philip and me in Camden with bonus mom and her other half

Rockland, Camden, Thomaston. These are the main areas we hang out in. But we also take a day in Boothbay. Each of the towns has their own feel: Rockland is known as a bit of an artist colony, Camden is home to a Shakespeare festival each summer, and Thomaston is known for its harbor…and for being where Shawshank Redemption was based.

For us, since we base ourselves in Rockland, we always start our weekend by going to Archer’s on the Pier for dinner. I’m a sucker for seared scallops, and I swear that Archer’s has the best. It doesn’t hurt that it’s pretty darn close to bonus mom’s house and that the views can’t be beat.

If you’re wandering around Rockland during the summer, be sure to check out the Farnsworth Art Museum. They currently have a mural project expected to last through 2027 which is incredible. Unfortunately, the homestead and the Olsen house are both closed this season for refurbishment, but they are supposed to be back open in 2026. If you need a snack after the museum, hit up Bixby Chocolate, a local women-owned chocolatier whose products are all created in a former ice plant by the marina. I’m also partial to her because she went to NYU like me.

Also worth a visit is the Rockland Breakwater Lighthouse. If you’ve been reading the blog, you’ve noticed that I really like lighthouses. I think it’s just because I grew up in New England. It’s in my blood or something. I’m just required to find them fascinating. Also near Rockland in Owl’s Head is the Owl’s Head Lighthouse. That lighthouse has a Keeper’s Museum which is adorable. I’ll level with you guys…the museum is a room next to the gift shop. But it’s cute. The lighthouse itself is worth a visit though!
When you’ve finished wandering around Rockland, head up to Camden. Many of the old schooners summer in Camden harbor, so it’s a great place to take a boat tour. In particular, Schooner Appledore does coastal tours on their fast tall ships. Then wander downtown and check out The Owl and Turtle Bookshop. Because, like lighthouses, I can’t resist a good locally owned bookstore.

If you’re up for heading down the coast, you can get some puffin tours out of Boothbay. Also in Boothbay are the Coastal Maine Botanical Gardens. They are HUGE. They make Tower Hill look like the baby sister. And, to top it all off, they have some of Thomas Dambo‘s Giant Troll installation. The ones at the gardens are the “Guardians of the Seeds.”

Gro

Roskva

Søren

Places to stay:
* Rockland Harbor Hotel
* 250 Main Hotel
* Camden Windward House

Places to eat:
* Archer’s on the Pier
* Rock City Coffee
* Home Kitchen Cafe (where I had some AMAZING huevos rancheros)

Happy Travels!
Smuggler’s Notch, Vermont – Not Just a Ski Vacation

June 16, 2025

When you think of Smugglers Notch and Stowe, Vermont, your first thoughts are probably about skiing, snowboarding, and winter. You’d be surprised – central Vermont is actually an amazing summer vacation!

We’ve already covered a couple of places that my family used to go when I was growing up such as Martha’s Vineyard, MA, and later Newport, RI, but we had a timeshare at Smuggs for the bulk of my teen years after my parents split and my dad sold the Vineyard condo. With the timeshare, we’d end up in Vermont two to three times a year. We usually had one ski week and one summer week, and one week at a random time of year (that we often traded for other vacations). Our summer week was usually the last week of August, so it was kind of a last hurrah at the end of the summer. Plus, on the way north from Massachusetts, you drive through Waterbury. You can’t drive through central Vermont on vacation and NOT stop in Waterbury, Vermont and visit the Ben & Jerry’s factory. As I mentioned in the Martha’s Vineyard blog, Mad Martha’s has something called a “Pig’s Delight.” The Ben & Jerry’s equivalent is a Vermonster. And yes, you get to keep the bucket.

The entrance to the Waterbury Factory

Prohibition Pig’s Fried Pimento Cheese Balls. I was in AWE.

Smuggs has something for everyone. For the families, they have kids clubs and camps. The summer camps are usually weekdays and range from arts and crafts to outdoor activities such as ropes courses, boating, and swimming. For the adults, there’s hiking, mountain biking, breweries nearby and more. But our family often would just sit and relax and look at the scenery. Every year, my mother and I would bring a gigantic stack of books. There was usually an unspoken competition as to who could read more that week. We always did a few days where my mother and I would sit on the balcony and just read, because the views are just gorgeous, and sometimes a summer vacation is less about running around seeing everything and more about just chilling out. At the end of the day, we’d drive through the Notch and find a good hiking spot and a dinner spot.

I know there’s snow, but my sister love Smuggs.

Total Eclipse, 2024

2024 was really exciting because we got to bring the niblings since we went up to the full eclipse. Although unfortunately, it was too early in the season for the notch to be open so they didn’t get to fully experience driving through the winding mountain roads.

So what do I recommend you do? Well, first and foremost, you want to hike Mount Mansfield. Even if you don’t want to or can’t hike the whole way, there’s a way you can drive up the mountain and it’s short walk to the overlook. It’s gorgeous. Nearby is the Stowe Resort which has a gondola to their Cliff House Restaurant with beautiful scenic dining. One thing I will say, if you were staying at Smuggs, the food does leave something to be desired. It is great kid’s food, but that’s about it. It’s mostly ski lodge food – burgers and beers, but it’s not the best you’re gonna ever eat. So I recommend it’s best if you plan to eat in downtown Stowe or head down into Jeffersonville rather than sticking to the resort.

Von Trapp Family Lodge (CondeNast traveler)

Downtown Stowe (Visit Stowe)

Other things you can do is because it’s so close to everything you can take a day trip up to Montreal, or you can go wander towards Lake Champlain. Also nearby is the Von Trapp family lodge, which was where the Von Trapps went after leaving Austria. Vermont is also known for its covered bridges, and there are plenty you can wander towards. And if you’re looking for a day spa, One of the best spas I’ve ever experienced is at the Stoweflake Mountain Resort. The spa itself is currently under construction, but it’s expected to be back up and running soon.

Places to stay:
* Smugglers Notch Resort
* Stowe Resort
* Stoweflake Mountain Resort

Places to eat:
* Von Trapp Family Lodge Restaurant
* Prohibition Pig (Waterbury)
* Skinny Pancake

Happy travels!
Newport, Rhode Island: Come for the Mansions, Stay for the Sailors (the Portuguese Sailor Sandwiches that is)

June 12, 2025

About a week after I arrived at NYU for my sophomore year, I got a phone call from my parents.
“We bought a house!”
“WHHHAAAT?!”
“Yeah, we stopped for a vacation in Newport, RI and fell in love with a house that was for sale!”

My room was in the back. Also not visible? The incredible widow’s walk.

So that’s what started my love affair with Newport. That next summer, I jumped back and forth between New York and Newport. I got my first taste of the Newport Folk Festival and the Newport Jazz Festival. And Del’s! I had SO MUCH DEL’S that first season. The memories continued – my sister and her husband got married on First Beach (aka Easton’s Beach). It became a haven for the family. Seasons didn’t matter (although summer is peak Newport!), so whoever had time would show up and hang out. I even ran my first half marathon in Newport (the hills and wind are killer!).

My favorite part of the house (other than the widow’s walk) was simply where it was. Newport, Rhode Island. I needed culture? Wander down Bellevue and head to the mansions. Want a beach? First beach is just over the hill. Food? Thames Street. Want to fly a kite? Brenton Point. Need Portuguese sweet bread? Franklin Spa. Festivals are at the Fort. Don’t want to drive? You can bike everywhere. Or rent one of those three-wheel scooter things.

And that’s what Newport is. Need a getaway this summer? Here’s where I’d start:

You probably need breakfast, right? I mentioned Franklin Spa. I’ve been known to visit about five times for a four day trip. Now that I’m back in Massachusetts, I’ve been known to drive down just for brunch. I tend to switch between their Bolo Benedict and the Portuguese Sailor.

There should be two halves of that Portuguese Sailor…but I was too hungry to take a photo.

After breakfast, head down Bellevue to view the summer “cottages.” I’d recommend starting with either The Breakers or Marble House. Rosecliff is also a winner. It’s modeled after Versailles, and the gardens behind it are the annual location of the Newport Mansions Wine and Food Festival. When you’re done with the cottages, you can wander back via the Cliff Walk, a 3.5 mile path overlooking the water.

Marble House

The Breakers

Rosecliff

If you’re ready for the beach, the end of the Cliff Walk kicks you out right near First Beach. Normally, you can ride the Carousel and get some snacks, but due to 2023 storms, both are under construction. Either way, there’s probably a Del’s Lemonade truck in the parking lot, so be sure to get some frozen lemonade.

After the beach, you’re probably ready for some more food. You can either take a cab or walk the 1.5 miles (uphill!) towards Thames, the downtown area. I highly recommend stopping into the Black Pearl to get (New England) Clam Chowder.

The Black Pearl off of Thames Street

If, after all that you are still not relaxed? One of the most relaxing places is Spa Fjör at the Hotel Viking. You can relax by the Himalayan Sea Salt wall or by the spa pool. Plus their services are amazing. They’re known for their facials, but I’m personally a huge fan of their royal honey massage.

Finish your day up by grabbing a drink on the Lawn at Castle Hill Inn. The views are stunning, and the prices are right. Get there early for a good spot.

The Lawn at Castle Hill

Places to Stay:
* Hotel Viking
* Castle Hill Inn
* OceanCliff

Places to Eat:
* Franklin Spa
* Safari Room at OceanCliff
* The Black Pearl
* TSK (Thames Street Kitchen)
* The Red Parrot

Happy Travels!
Packing List – Alaskan Cruise

June 10, 2025

Our next trip is for Philip and my 5th Anniversary. We’ve been married for 5 years?! I still can’t believe it. So to celebrate our anniversary we decided to take a trip to Alaska. Philip has never been and I haven’t been since I was about 12. But since we got Covid married, we decided to invite everyone we couldn’t invite for our actual wedding.*

*Our actual wedding was in my sister’s living room. Complete with Lego castle.

So now we’ve got all our friends and family joining us, but we still need to pack. We leave in about two weeks, and we’re spending some time in Seattle to meet up with a cousin before we head to Vancouver. While it’ll be great to see our Seattle cousins, it makes our packing list is a little bit complicated. Between Seattle, Vancouver, and the Inside Passage (while on a cruise ship), we’ve basically got about three separate climates we need to pack for.

For starters, Seattle – Seattle is pretty darn similar weather-wise to Boston, which makes it a little bit easier for us. Basically, we can get away with the same thing we would wear here. We plan on doing things like MoPop and the Space Needle and all of those types of touristy things. Most of those things are indoors and probably heavily air conditioned, meaning an extra layer. From there, we head up to Vancouver, which will be a little bit cooler and then with the equivalent of fall in New England. When we get up to Alaska will be lucky if it hits 60°F.

I am always a heavy packer; it’s a problem. I’m the person with the gigantic suitcase, the carry-on suitcase, and a personal item. The exception to the rule is when I’m traveling for my stats job. Business professional outfits are pretty simple, so I can get by with packing just a laptop bag and a carry-on.

Basically, this is one of my “do as I say, not as I do” situations. For a client taking this 10-day trip, I’d recommend packing 7 days of light layers. Things they can mix and match, things they can take off but are thin enough to throw around a waist or shove in a day pack. One or two nicer outfits for the main dining room’s dress to impress nights. But for me? I’m a slob who spills things and is incapable of only packing the bare minimum. (As I write this, I’m somehow covered in homemade chicken tikka marsala sauce…)

The Seattle and Vancouver segments are pretty much just clothes – we’ll be at hotels that provide basics if needed, but unless you stay in a suite-level stateroom on Royal Caribbean, you are only provided with a 3-in-1 shower wash. I’m pretty lax with my hair care, but even I draw the line there and plan on packing some shampoo! I have become a big fan of bar shampoo.

So let’s get down to brass tacks. Here’s my packing list for this upcoming trip:

My personal item:
* Wallet with cash for tips, credit cards, ID, Global Entry card, Passport card
* Passport
* Kindle preloaded with all the books I could possibly need (book recs are coming in another post!)
* Laptop
* Headphones of some sort
* Camera
* Phone
* Printouts of ALL of my travel documents (I know they’re all digital, but things happen)
* Backup battery
* Medications
* Water bottle

My carry-on suitcase:
* Basic toiletries – toothbrush/toothpaste
* A small tube of sunblock
* A change of clothes
* A pair of flip-flops (because I can wear flip-flops in any weather)
* Chargers
* Sunglasses
* First aid kit (including pain relief, seasickness relief, band-aids, etc)
* Light raincoat

My big suitcase:
* 10 outfits, mostly tech long sleeve shirts and hiking pants
* Underwear/socks/etc for 10 days
* 1 nice outfit (including nice shoes)
* 1 swimsuit/Turkish towel
* Pajamas
* Makeup
* Other toiletries – shampoo/conditioner, deodorant, lotion, etc
* Lanyard for cruise card (I’ve recently switched to a mag-safe phone wallet)
* Backup sunglasses
* Magnets for cruise door
* Hiking boots (and maybe poles)
* Cheap gloves
* Spare shoes
There Once was a Girl Who Went to Nantucket…

June 9, 2025

So far we’ve talked about Martha’s Vineyard, but it’s now time to discuss the other Massachusetts island, Nantucket. Similar to the Vineyard, high season is the summer. You can visit other times, but be prepared for off-season closures.

Nantucket is famous first and foremost for its whaling history. So much so that Captain Ahab and Starbuck from Moby Dick are both from Nantucket! Nowadays, it’s much more famous for its historic homes, cobblestone streets, and stunning beaches.

The first place I always stop into is the Whaling Museum. I loved it as a kid, but I have to admit that despite all the hate about Gilmore Girls: A Year in the Life, I love it even more after watching the scene with Emily Gilmore as a docent. And yes, they do have a sperm whale skeleton. And yes, it’s pretty epic.

If you can stomach some food after that museum, head to Walter’s Deli which is basically across the street. My recommendation is the lobster roll. Not only is it the epitome of New England…they are just amazing and delicious.

From there, go see some lighthouses. Nantucket is famous for them. There are three total, the most photographed is probably Brant Point, but my personal favorite is Sankaty Head. It’s just past Baxter Road in Siasconset.

Great Point

Sankaty Head

Brant Point

Dinner? I recommend The Nautilus. They have a Boston seaport location, but the one on Nantucket is the original. Be sure to try the Blue Crab Fried Rice. And also get a Blueberry and “Soda.”

As you head back to the ferry, wander around the cobblestone streets and see some of the hydrangeas. The whole island is historic. Don’t forget to stop for a beer at Cisco Brewers, Whale’s Tale Pale Ale is delicious. They usually host live music during summer evenings.

Happy travels!
Martha’s Vineyard, Beyond the Sharks

June 5, 2025

Martha’s Vineyard is one of my favorite places in the universe. I used to spend the last two weeks of the summer near South Beach just outside of Edgartown. We would take the ferry from Wood’s Hole, and once I could feel the salt air I knew I was heading somewhere wonderful.

Martha’s Vineyard Ferry

We always had a list of things to do there, most of which included just hanging out on the beach, but we also needed food and entertainment!

While the Vineyard does have islanders, the peak season for tourism is usually Memorial Day to Columbus Day. During July and August, you have to pre-book the ferry if you want to bring your car to the island. But you can have a great time even without a car – the Vineyard Transit Authority has a great bus system to get around the island, and the busses stop right at the ferry terminals.

The Pink House

Flying Horses Carousel

A gorgeous gingerbread house

So where do you start? I recommend Oak Bluffs! Oak Bluffs is home to the beautiful gingerbread houses (part of the Martha’s Vineyard Camp Meeting Association). One of my good friends in high school spent her summers there, so I’ve got memories of sitting on a brightly painted porch listening to Red Sox games on the radio. They’re just so gorgeous to wander around! The most famous one is the “Pink House,” so be sure to check it out. After you’ve wandered around there, mosey over to the Flying Horses for a carousel ride. It’s the oldest platform carousel in the United States. If you catch the brass ring, you get a free ride!

The Black Dog Tavern

Bunch of Grapes

From there, head over to Vineyard Haven (or start there if that’s where your ferry goes!). Bunch of Grapes Bookstore is a must do for every bibliophile. It’s independently owned and has been there since longer than I can remember. After you grab your stack of books, head over to the Black Dog Tavern. Dinner is what they’re famous for, but I love the bakery for their sweets.

South Beach

Edgartown

When you’re ready to explore further, head to Edgartown for some shopping. Be sure to stop at the Vineyard Vines store! Just past Edgartown is a famous beach – South Beach! It’s known for where Jaws was filmed. As you drive there, you’ll pass a few sights from the movie as well.

Before you leave Martha’s Vineyard, you have a few more necessary stops…you simply can’t go to the Vineyard without watching at least one Menemsha sunset. It’s one of the only places in Massachusetts where you get a beach sunset! Before sunset, grab some lobster at The Homeport. It’s where we used to go for my brother’s birthday every year. I’m a huge fan of the strawberry shortcake. Don’t forget ice cream at Mad Martha’s. They have three locations on island. And a famous dessert called the Pig’s Delight. It’s ordered by saying “Oink”!

Places to Stay:
* The Edgartown Inn
* The Dockside Inn
* Mansion House Inn

Places to Eat:
* The Black Dog Tavern
* Mad Martha’s
* The Homeport

Happy Travels!
Passenger Princess

June 1, 2025

I have to confess that I am the passenger princess in this relationship. From our very first trip together, Alex has done 95% of the planning. To be fair, the first three trips were planned before I existed in her life. So it was a simple matter of her adding me on to plans that were already made. Of course it would make sense that she would handle that. Sometimes the patterns of a new relationship takes hold and develops a momentum of its own. This is not always a bad thing, though it can be. But it is a real thing and it happened with us and travelling.

I am thankful for this. I get all of the pleasure of traveling with hardly any of the hassle. Like none of the hassle. I feel guilty, but all I need to do is make sure I navigate the airport, be supportive during the hard parts of travel, and answer the questions when asked during the planning stage. Alex is kind of awesome and I am fully included in the decision making process. These aren’t her trips, she makes sure they are our trips. She likes the planning. The problem solving. The research. Planning a trip is second nature to her.

There is a spectrum of Passenger Princesses and I have to admit that I am way out there. I’m not a 1 or 2 where I could jump in at any point, but lets my partner person take point. I am like an 8-9 where I am sure I could handling changing a reservation if needed, but I have never done it. What’s JetBlue’s phone number? *shrug* Where is our Marriot Rewards Number? Somewhere? Maybe? I do know where my passport is and how to make sure I get on the right flight on time. So I am not a 10. But the hard logistics of all? Nope. It’s like someone asking you to do the dishes and your response is, “Honey, where’s the dishwasher?” Sitcom dad, I am at the sitcom dad side of the spectrum.

How do I dig myself out of this hole? I roll with it. I am honest about it. I appreciate what she does. I enjoy our trips. And I contribute to her blog.

And that is the key to being a passenger princess, appreciate it all. All the effort, all the emotional labor, and all the thought that goes into it. You participate where needed. That includes during the trip and during the hard parts of the travels. The scales may never balance, but what matters is the journey, the adventure, the memories, and being together. You support their travel hobby by being a person that is enjoyable to travel with.