Five Hours in Portland, Maine: From Lighthouses to Little Towns

Portland, the largest city in Maine, is a common port for East-Coast cruises starting out of New York City.

 

This charming seaside city is filled with fun things to do. But when you only have five hours to see it all, it’s hard to know where to begin. To make the most of your short time in Portland, consider taking a tour from a local company. If you’re cruising, there will be plenty of shore excursions offered through your ship. Typically, you’ll find an itinerary that covers all of the hottest local attractions.

For example, Carnival offers a tour called Portland Highlights and Kennebunkport. In just five hours, you get to take in the top sites, and you’ll still have a bit of time afterward to wander on your own. Here’s what you’ll see.

POrtland

Portland Overview

Your tour begins with a drive through Portland itself. You’ll coast along the seaside in a motor coach, taking in the local streets, including some of the most affluent homes in the area. Your guide will tell you about the rich history of diversity and how the homes along the water were once considered undesirable for this exact reason. Today, they are some of the most sought-after abodes in the state.

As you drive along, you’ll catch a glimpse of the stone fortress built to defend the city against the Red Coats, as well as the observation tower that boasts views of the entire city, though you won’t get a chance to test that theory for yourself, as there simply isn’t time to stop here.

As you drive through the heart of the city, you’ll see the home of Henry Wadsworth Longfellow, as well as hear old folk tales of other homes in the community, such as the heavily adorned Wedding Cake House that was built for a bride as her wedding gift many moons ago.

POrtland

Portland Head Light

The first official stop on the tour is to the most photographed lighthouse along the East Coast, Portland Head Light. Looking as picturesque as the many postcards on which it’s been featured, the little lighthouse stands tall as a beacon to sailors passing along the coast of Maine.

portland

You’ll have about 30 minutes to take pictures amid the craggy canyons and rushing waves. A small gift shop offers trinkets and a few locally crafted items at shockingly affordable prices. Snap a few photos, grab, and souvenir, and head back on board the motor coach for the next leg of your five-hour tour.

Kennebunk and Kennebunkport

Next, your tour will take you on a rural drive to see the summer homes of the rich and, well, richer. A few decades ago, the state offered plots of land for $20,000 each. While the land was reasonably priced, it came with a catch: You had to build a home with a certain price tag. The intent was to attract only the upper-middle class to the area. The plan was successful, and most of the homes exceeded the expectations.

POrtland

After about a 45-minute drive from Portland Head Light, you’ll arrive in Kennebunk. The charming little community looks like something out of a Nicholas Sparks novel, and you half expect to see Ryan Gosling strolling the streets hand-in-hand with Rachel McAdams. Colorful cottage-like shops and restaurants line both sides of about a three-block radius and include everything from candy and coffee shops to kitschy souvenir stores and upscale artists’ havens.

POrtland

You’ll get a chance to take in the shops after a short drive through nearby Kennebunkport. If you’re here in the summer months, you’ll see surfers riding the waves on the local beaches, while families gather outside their summer homes for a bonfire and a glass of wine. The brightly colored “cottages” are far more lavish than any typical upscale community and make you long to be one of the next generation of family members who are sure to inherit the tradition.

POrtland

Perhaps the most notable—okay definitely the most notable—local family is the Bushes, who have been spending their summers here for many decades, long before father and son took on the presidential roles of numbers 41 and 43. Like everyone else, they paid $20,000 for their plot of land that stretches like a peninsula into the ocean. The locals tell stories of spotting the secret service in town and George Sr. jumping from airplanes like they are part of their own family histories. It’s just a fact of living here. You will run into one or the other at some point in your lifetime.

Once you’re done your drive, you’ll get about an hour or so to sweep through the Kennebunk shops. If you don’t dawdle, this should be plenty of time. There are an obscene number of stores catering to fashionable canines (my own got several new shirts). And we even had time for a quick snack at one of the popular coffee shops.

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Pro Tip: Be sure to have a whoopie pie, the state dessert. Rumor has it the famous cakes came to be after a woman, tired of the icing coming off the top of the cakes she would wrap in a kerchief for her husband’s lunches, placed an extra piece of cake on top of the icing. When her husband opened his lunch to find the icing still in place, he yelled, “Whoopie!”

Back in Portland

Once you’ve wrapped up your visit to Kennebunkport, you’ll arrive in town with about two hours to spare before you need to be back on board the ship. This will give you plenty of time to walk around the Old Port, which is only about a 10-minute walk from the cruise ship terminal itself. You’ll find lots of one-of-a-kind shops, as well as plenty of places to try the local seafood.

portland

If you’ve only got five hours in Portland, Maine, this is the perfect way to take in the best the area has to offer. What other must-see sights do you recommend? Visit the Wanderlust Wayfarer Facebook group to share your ideas.

 

Five Hours in Funchal: From Gondolas to Street Toboggans

One of the best parts of cruising is going to places you might not have otherwise considered, like Funchal, Madeira.

 

This picturesque city has slightly more than 100,000 people and is the capital of Madeira, a Portuguese island in the North Atlantic Ocean. Funchal is magical, but before my ship entered its port, I had no idea I wanted to go there. Heck, I had no idea it existed. Within 15 minutes ashore, I knew it was one of my new favorite places in Europe, and even though I still had the whole day ahead of me, I didn’t want it to end.

I had no idea what to expect so I thought about taking a ship-sanctioned shore excursion. In the end, I decided not to take one. Instead I chose to take my chances on making my own itinerary. I studied the ship’s recommendations and decided I could see the main city sites and still have plenty of time to stroll the streets if I did things on my own. And I was right! I packed in a ton of fun and never once felt rushed. Here are my tips for the best ways to spend five hours in Funchal.

Disembarking

Funchal

To make the most of this beautiful port, I urge you to rise early and beat the crowds. If you get up at 6:30 a.m., you can be dressed, have a bite to eat, and be ready to go by 8 a.m. This was the projected arrival time for NCL Epic.

As soon as I heard the captain give the A-OK to get off the ship, I headed toward the gangway. Trust me when I tell you not to waste a single minute of time you have in this lovely place. I was the very first person to disembark for the day. And I was glad to have the quiet streets to myself for a few hours before most of the other cruisers made it off the ship.

It’s a bit of a jaunt from the ship to the heart of the action, but it’s a well-designed route once you get past the ship dock. Simply walk off the ship and keep going until you reach a fork in the road. Make a right on Avenida Do Mar, and keep on walking. The level pathway, scenic view along the waterfront, and smattering of shops make it an easy stroll. You can turn left at the first main intersection to head straight into the tourist area. But I decided to up the ante and keep walking. I had a special plan for my morning.

Morning

I walked all along the pathway for about 45 minutes at a brisk pace. I had an ulterior motive: to get on the cable cars or, as they’re called locally, Teleférico do Funchal, before the crowds of tourists arrived. I made good time, arriving by 8:45 a.m. Sadly, they didn’t open until 9 a.m. so I could have walked at a more leisurely pace and enjoyed the sights. Still, even as I waited to get inside, throngs of tourists arrived. In fact, three busloads were waiting just behind me.

I swooped in as soon as the doors were unlocked and bought my ticket to the hilltop village of Monte. Monte has lots to offer in its own right, including beautiful gardens. You can purchase tickets to various attractions at the same time as you buy your cable car fare. Just remember, Funchal also has lots to offer too. Watch the clock so you have time to enjoy both places.

Monte

I bought a round-trip ticket and boarded the very first car of the morning. I’m terrified of heights, but I was pleasantly surprised to find it wasn’t so bad. Treetops and roofs appear to be just a stone’s throw away for most of the ride up. There are a few places where you’re suspended fairly high above the ground, but the journey lasts only 15 minutes. You can do anything for 15 minutes, I promise. And the view is so worth any anxiety you may experience.

When you reach the end of your journey, there’s not a lot of signage telling you where to go. Because I was the first tourist at the top, there wasn’t anyone to follow. If you turn right, you’ll head toward the gardens. If you turn left, you’ll make your way toward the Church of Our Lady of the Mount. It’s a short walk either way you turn.

I was hoping for a few shops and cafés where I could while away the morning in Monte, but there were no such thing. After you walk the stairs to the church and take in the exceptional view of Funchal, there’s not a lot else to do…except for maybe the most amazing experience ever. Read on.

Mid-Morning

So the real reason I wanted to make my way to the hilltop town of Monte was so that I could ride in a wicker basket back down the hill. A wicker basket! I believe the locals call it a toboggan, but I call it like I see it. For the high, high price of 25 Euros for one person or 30 Euros for two, you can sit in a basket while two men push you through the village streets at relatively fast speeds. You can’t make this stuff up.

Funchal

The men wear special boots that help them glide along the well-oiled streets. Occasionally, they slow the pace to let a car pass along at a cross road. Along the way, men will pop out from the side streets to snap your picture. You can buy it later for 10 Euros, along with a cute history of the toboggan ride. I figured no one would believe me when I told them what I’d just done without evidence, so I snapped it up. There’s also a little market where you can haggle for souvenirs and a place where you can grab a bite to eat.

Pro tip: If you plan on taking the toboggan ride down the hill, you only need to purchase a one-way ticket for the cable cars. I learned this the hard way and could have saved myself a few bucks. Oh, and try to have cash for the toboggan ride. In theory, they take credit, but it’s a hassle. My “drivers” were quite unhappy about not being paid cash.

Downhill

It’s important to note the basket ride only takes you partway down the hill. There’s still a long way to go to reach the bottom. You have three options, take a tour bus, hop in a taxi, or walk. As I’m sure you’ve figured out by now, I like a good walk. But I can tell you, I am the only person who chose this option. And it was a long walk at a steep angle. I’m glad I did it, but I’m not sure I’d recommend it, unless you’re really keen.

I stopped a few times along the way to take some snaps of my ship in the port. I also caught a few glimpses of locals going about their daily business. I like that sort of thing. It feels more intimidate, which can be hard to achieve with only five hours in Funchal.

Mid-Day

I’d promised my traveling companion I would return to the ship by 11 a.m. so we could spend the rest of the day in town together. Believe it or not, I had already accomplished all of that excitement and got back to the ship 15 minutes early. To my delight, she was already waiting for me outside, leaving us even more time to explore Funchal.

We spent the rest of the day meandering through the city streets. We went into every shop, walked down every alley, and ate gelato. From trendy boutiques, like Dona Hortensia, to the local market, Mercado Dos Lavradores, there are endless unique shopping options. Zara, Mossimo Dutti, Mango, and all of the other major chain stores are present too.

Funchal

It’s hard not to fall in love with the stunning scenery of town square. Quaint cafés, like The Ritz, lush greenspaces, and white buildings and cobblestone streets give Funchal a romantic glow. Praça do Município, the main square, the statue of João Gonçalves Zarco, and Sé Catedral do Funchal are not to be missed. I could spend a month just sitting at a café taking in Funchal’s beauty, writing a romance novel and enjoying the atmosphere.

In the Old Town, the Rua de Santa Maria features a public art project that’s helping to revitalize the area. Known as Arte de Portas Abertas, it features more than 200 doors painted by local artists. It’s a feast for the eyes.

Alas, with only five hours in Funchal, by mid-afternoon, it was time to make our way back to the ship. I was sad to sail away from this fairy tale town, and dream of visiting Funchal again soon.