5 Hours in Punta del Este, Uruguay: From Beautiful Beaches to Urban Delights

Punta del Este is paradise defined.

With its glistening azure waters and stunning sandy beaches, it's hard to imagine a more perfect place to drop anchor than this resort city on Uruguay's Atlantic coast. While Punta, as the locals call it, boasts a population of fewer than 10,000 permanent residents, the city comes alive for two weeks in January each year, when hundreds of thousands of rich and famous sun seekers swoop in to take advantage of this coastal playground in its peak season.

In recent years, Punta del Este has become a popular port for some of the world's most prominent cruise lines, including Costa, MSC, Celebrity, and Norwegian. One of the best things about cruising is that you get to sample many different parts of the world, and you can always revisit the ones that really stand out. Punta del Este is one of those places.

Cruise Ship Shore Excursions

With only a few hours to explore Punta del Este, it's important to maximize your time. Cruise ships typically offer shore excursions that take you to the most prominent tourist sites. These types of excursions are a great way to ensure you get a good feel for the place you're visiting. However, on this particular cruise, I found the options lacking. I decided to research other options for my day in Punta del Este. I wanted to create a custom experience that met my unique needs. That's when I came across a company called ToursByLocals.

For nearly a decade, ToursByLocals has been connecting travelers with local guides in more than 150 countries around the world. They've sourced the best experts in each community they serve so they can guarantee an exceptional experience every time. What's more, they offer port pick up, the option to create your own itinerary or select from a variety of excursion options, and a "no one left behind" return to ship guarantee.

While the cruise line offered only two ways to spend the day in Punta del Este, ToursByLocals provided a plethora of opportunities. From food and wine to walking and wildlife tours, there was something for every taste. There were also a variety of guides to choose from. You can read their bios to find out their areas of expertise and interests to select the one that's right for you. I opted for the Punta del Este and José Ignacio shore excursion with the delightfully fun and exceptionally intelligent Mariana.

Getting Started

Prior to our arrival in Punta del Este, Mariana contacted me to arrange a meeting time and place—10 a.m. at the very end of the pier. Since we needed to tender ashore, this gave us plenty of time to relax in the morning before our excursion. From the moment your ship drops anchor in Punta del Este, you'll be blown away by its beauty. Just taking in the sun shining over the marina while drinking your morning cup of joe is a enough to make you wish you had more than a few hours in this amazing resort city.

punta del este

We arrived at the pier a little before 10 a.m., and while Mariana was holding a sign inscribed with my name, it was completely unnecessary. We locked eyes on each other long before I was near enough to read the sign. Mariana looked just like her picture, and from the moment we met, it felt like I was reuniting with a long lost friend. After a quick embrace and official introductions (my mother was also traveling with me), we were on our way.

Mariana wasted no time jumping right into guide mode. Though she did it in such a way that you felt you were just slipping into a casual conversation. It was relaxed and easy. She showed us the dockside fish market where stout sea wolves anxiously await scraps of seafood from tourists who are all too eager to feed the massive marine creatures.

From there, we headed toward the car, where we met Mariana's mother, who had graciously agreed to be our chauffeur for the day. This was a pleasant surprise—by not having to focus on driving, Mariana was able to give her full attention to my mother and myself. But this wasn't our only surprise. Mariana had a few sweet treats for us to try, too. One of the two local delicacies included dulce de leche, which is made from sweetened milk that is heated until it forms a thick caramel-like substances, and it's absolutely to die for. The second treat was an alfajor, which is made up of two round cookies with dulce de leche sandwiched between them—also delicious.

We enjoyed our treats as we drove along the coastline, taking in the magnificent mansions lining the shore. All the while, Mariana provided fascinating details about Uruguay, Punta del Este, and the sights we were seeing. Punta is built on a peninsula that extends well into the sea, and a 2.5-mile pathway lines the shore along the peninsula. You can get off the ship and enjoy the breathtaking beauty of the area as you walk along the water.

Embarking on Our Adventure

One of our first stops was to take in the rocky point that marks where the Rio de la Plata river and estuary meet the Atlantic Ocean, creating a completely unique ecosystem. It's at this midpoint that we made a quick pit stop to take some photos and talk about how these two distinct bodies of water converge.

Mariana talked in detail about the diversity of nature found in this place, as well as recounted the discovery and history of the country. She then showed us the remains of two mermaid statues that once stood proud on the rocky shoreline, as well as the site of the first naval battle of World War II. Mariana added a personal touch by telling us how her own grandmother had witnessed the fighting first hand and would often share stories with her grandchildren.

From here, we hopped back in the car, pausing for a quick look at the lighthouse and the beautiful blue Candelaria Church located across from it. Mariana, who teaches touristic geography at the local university, is extremely well educated about the area and provided tidbits of knowledge and fun facts about every site we visited and Uruguay in general. Her zest for life and passion for preserving Uruguay's natural beauty are infectious. It was immediately apparent we were in excellent hands for the day.

As we continued our drive along the coastline, Mariana explained that the river side of the water is called La Mansa, or tame beach, and it's perfect for swimming and relaxing on the sand. The ocean side, called La Brava, or fierce beach, is known for its rough waves and is ideal for outdoor enthusiasts looking for a little adventure in the form of surfing and other water sports. It was here that we made our next stop for a picture with the infamous sculpture of the hand rising from the sand, or La Mano.

From here, we began our long and scenic drive along the Atlantic coastline. Mariana regaled us with countless facts about the scenery and landscapes we passed. She explained that Punta is located in the Maldonado Department, or state, of Uruguay, and we would be traveling to the entire length of this department on our excursion. To begin, we crossed over the wavy bridge—so named for its notorious ups and downs—into the town of La Barra. Located at the northern end of Punta del Este, this idyllic beach resort community is the perfect place to kick back and soak in the sun.

Passing through the countryside, we took in sights of kite surfers, local vegetation, and beaches en route to the town of Manantiales. According to Mariana, Manantiales' Bikini Beach is the place to spot models and other celebrities during the peak season, and lavish condos are available to rent right along the waterfront.

On the next leg of our journey, we made our way to José Ignacio, an ultra chic beach town that serves as a quaint getaway for Latin America's the uber elite. If you're hoping to spot a South American celebrity, this is the place to be. We ventured through the city streets, getting a good feel for the way the other half lives—and boy, do they live. This exclusive community boasts some of the most expensive housing in the area and is the ultimate seaside paradise.

A trip to José Ignacio wouldn't be complete without a visit to the picturesque lighthouse that sits astride the rocky shoreline. It was here that Mariana shared with us the details of some of the important work she does to promote sustainable tourism and environmental awareness.

Roundabout at Rocha

By this time, we were only about halfway through our adventure with Mariana. There was still much to see and do. We continued our journey to the edge of Maldonado via the incredibly cool circle bridge that spans across Laguna Garzón. Once we hit the border with Rocha Department, we turned around and made our way back down the same road. Mariana pointed out rare indigenous cacti and revealed even more interesting facts about Uruguay.

Prior to meeting Mariana, she emailed to ask our dining preferences. She tries to tailor the excursion to individual tastes and wants to ensure her guests have an exceptional experience. Some people are looking for an upscale eatery where they can eavesdrop on the stars. Others seek a seafood extravaganza. Us? We opted for a simple outdoor eatery in Mariana's hometown, La Barra.

Before heading for lunch, Mariana treated us to a glimpse into her own life. We drove past her house and down her street. She even took us down a back road and through a farmer's field where we could glimpse the city from afar. It was an extraordinary and unexpected experience that turned out to be the highlight of our day. And just when we thought it couldn't get any better, we found ourselves at the most delightful little restaurant. At first glance, it looked like nothing more than a tiny log cabin with a few picnic tables set out in the open air. But it turned out to be a truly gourmet experience. We were greeted with a warm embrace by a few of the locals, who seemed to know Mariana well.

Within minutes of our arrival, the small establishment was swarming with hungry patrons. We were delighted to find Mariana's husband and young daughter had arrived ahead of time to snag a table under the shade of the extended rooftop. Immediately, we engaged in conversation, giving us unprecedented insight into life in Uruguay. And have I mentioned the food yet? My goodness, I can't forget the food...it was the ultimate in deliciousness. The restaurant offers three different choices on its menu each day, and at least one is vegetarian. Seeing as I don't eat meat, I opted for the pumpkin quiche, and I was not disappointed. The generous portion was enough to tide me over until a late night dinner seating back on the ship. And it was accompanied by a fresh-from-the-garden salad doused in vinaigrette and sesame seeds that tasted like heaven.

Since there were still a few sights left for us to see, we made quick work of our meal, bid farewell to Mariana's family, and headed back out on the road. As we made our way back toward Punta del Este, we drove through a shantytown to balance the excessive wealth we'd witnessed earlier in our tour. We also drove past the Maldonado university where Mariana works and through Maldonado City.

The last leg of our journey took us to Punta Ballena, or "Whale Point," a small peninsula in the Rio de la Plata. En route, we learned that Punta del Este is the perfect place to view southern right whales from July to November each year. In fact, they come so close to shore that you can "smell" the water they exhale through their blowhole. Mariana is an expert in this particular species and offers specialized whale tours during the peak season.

Punta Bellena is the perfect place to watch the sunset over the river. It's also the ideal location to spread your proverbial wings for a little hang gliding or take a gander at the infamous architecture of Casapueblo. Looking like something straight off of a Santorini postcard, what was once a summer home and workshop for Uruguayan artist Carlos Páez Vilaró is now a hotel, museum, and art gallery. You can take a tour of this incredible location if you'd like to get up close and personal.

All Good Things Must End

As it always does when you're having fun, the time flew by all too quickly. With what seemed like the blink of an eye, our time with Mariana was up. We had spent five perfect hours in Punta del Este, enjoying the area and making new friends. And, just like a good friend, Mariana anticipated my mother and I would like to spend a little time wandering the main street on our own. She gave us the option to be dropped off at the pier or on Gorlero Avenue, where you can find souvenir shops, clothing boutiques, and more.

Needless to say, we opted for the latter, and after saying our goodbyes and snapping a quick selfie, we parted ways with Mariana and her mother. We spent an hour or so meandering in and out of Gorlero's quaint shops. If you're looking to take home a special reminder of your time in Punta del Este, an amethyst is the way to go, and you'll find no shortage of them here.

From the center of town, it's only about a ten-minute walk back to the pier. We grabbed a glass of freshly squeezed orange juice from one of the waterside restaurants and took another walk around the fish market—I just had to see those incredible sea wolves one last time. You'll also find free Wifi near the pier if you want to tell friends and family back home about your awesome adventures in Uruguay.

I have traveled to about 50 countries on 6 continents. I've been on countless cruises and tours, but none have come even close to the amazing experience I had in Punta del Este. I can say with some authority that ToursByLocals has found something truly special in Mariana. If all of their tours are even half as good as the one I took in Uruguay, then they are well worth every penny.

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One Day in the Algarve: From the Seaside to Castles

So you're in the Algarve region of Portugal for just one day, and you want to take in as much as you can.

No problem. Local touring companies offer amazing options for folks who want to pack in as much as they can in one quick trip. The best way to source the perfect tour is to simply ask at the reception desk at your hotel. Prior to my trip to the Algarve, I was so overwhelmed by the variety of tours offered in the area that I didn't book anything. Immediately upon arrival at the Sol e Mar Hotel in Albufeira, my home base for the next three days, I asked the woman who checked me in what she would do if she only had one day. She didn't even need a minute to think about her response—she quickly pulled out a brochure and told me her favorite tour. She then proceeded to call the tour company directly and had me booked in no time flat.

Pro tip: You will need to pay your hotel for the tour, and the payment will need to be in cash. Make sure you have a few extra Euros handy to cover the costs. Also, you can purchase tours from street vendors—they may even be a few dollars cheaper. But if you purchase through your hotel, you can rest assured your tickets will be valid.

Over the course of about 10 hours, the Historical Algarve Tour takes you on a whirlwind adventure through several small town and scenic sites. It's the perfect way to get a glimpse of some of the most popular attractions. Here's what to expect.

Morning

Your hotel will have a designated meeting time and spot for the tour. You'll be picked up promptly at this location and taken to another spot to meet with a larger motorcoach. But your journey hasn't started just yet...first, you need to journey to one more location, where you may need to transfer to another bus, depending on the tour you are taking. This may sound like a lot of work, but it all goes very quickly and smoothly. My pickup time was 8:30 a.m., and by 9 a.m. I was happily en route to my adventure.

The first stop is a traditional Portuguese town called Silves. After parking along a main road, your guide will take you on a brief walk through the narrow, winding streets. A steep climb up the cobbled roads brings you to Silves Cathedral. It will cost you 1 Euro to take a look inside this Gothic gem—a steal by today's standards. Afterward, a short walk brings you to Silves Castle, where, for just 3 Euros, you can get breathtaking views of the city from the sides of its towering walls. Though the castle is the best-preserved in the country, aside from the exterior walls, there is little else to see, unless you fancy a refreshment or two from the adorable cafe in the center of the castle ruins.

You'll have about an hour to spend in Silves. It's not a ton of time, but it will give you a taste of this charming community. If you're fast, you can take in both the castle and cathedral and still have time to roam one or two of the bustling side streets off the main road before returning to your bus. The shops don't have a ton to offer tourists, but it's a great way to peek inside the lives of the locals, even if only for a few minutes.

Once you're safely strapped back into your comfortable seat, your bus will make its way through the winding mountains toward the tiny hilltop town of Monchique. You'll pass through ancient towns, fields of fruit and nut trees, and rolling hills. The sights and stories are truly like something out of a fairy tale. Though you won't have a chance to exit the vehicle in Monchique, you will get to see the quaint cityscape before riding on to Foia, the highest point in the Algarve.

Unfortunately, when I visited Foia, it was very foggy and overcast, so I can't tell you much about what you should see from the top, but I'm told that the view is spectacular. There is a little shop selling souvenirs, including hand-painted tiles, cork purses and shoes, pottery, wool sweaters, and trinkets. But the main event is the tasting of a local liqueur. The line will be long, and you'll feel a little like cattle as you're shepherded through the narrow aisles of the shop to sample the special treat.

You'll have about a half hour to spend at this stop. There are public toilets available to use free of charge, and there is a small cafe where you can grab a quick bite to eat. If you have a few extra minutes to spare, consider spending them outdoors. One of the other travelers on my tour told me it was good luck to pile three rocks on top of each other at the top of Foia. So I did just that. They were the tiniest rocks in the world, but I don't think that has any impact on the outcome.

Afternoon

By this time, you'll likely be feeling tiny hunger pains in the pit of your stomach. Fear not—your coach will make a stop at a family-run restaurant for a hearty meal. But beware...there is a preset menu and the cost of the meal is not included in the price of your tour. For 13 Euros, you'll get your choice of beef, pork, chicken, or fish prepared in a traditional way.

Your tour operator will come around the bus and ask your preference as you make your way to the restaurant so that the meal will be ready when you arrive. In addition to the main course, your table will be set with lettuce and tomatoes, wine, juice, and bread. I had the fish, which was breaded and served with lemon and tartar. I'm not sure what kind of fish it was—I hadn't heard of it before, and the texture was...odd. So I chocked it up as an experience. For dessert, you'll be served traditional sweets made from almond paste, as well as a cup of espresso. The sweet treat was delightful.

I was traveling alone, and I enjoyed my meal with three other women who were also traveling solo. We laughed and shared stories of our travels—it was a highlight of the day for me. The time passed quickly, though I am sure we were there for at least an hour. Before we knew it, the restaurateur had come around to collect our payment, and we were on our way again.

Pro tip: It's a good idea to carry a bit of cash on this tour to cover all of the unexpected extras. About 20 or 30 Euros should do the trick.

Originally, I thought about opting out of  the meal but then realized there may not be another opportunity to eat on the trip, and I was right. If you don't plan to eat at the restaurant, be sure to pack a few snacks in your bag or pick something up that you can take with you at one of the other stops. And keep in mind, there is nothing else to do at the restaurant site. It's a little shop in the middle of nowhere, so there isn't much else you can do while the rest of your group eats.

Following your traditional Portuguese dining experience, you'll make your way to Sagres, Cape St. Vincent, which is the southernmost point in Europe. Here, you'll have about 30 minutes to walk out among the rocks overlooking the sea. If you're daring enough, you can even sit with you legs dangling over the edge of the rocky cliffs. I kept a good distance from the ledge, but many of my fellow travelers climbed across the rocks to get a closeup glimpse of the rough seas below. Here, at the end of the world, you'll also have a chance to visit the strongest lighthouse in Europe, Baleeira. It makes a beautiful backdrop for your already amazing photos of the area.

Evening

Just when you think the tour must be coming to a close, you make your way to one last stop: Lagos. And you'll have about an hour and a half to spend walking through its winding streets. By now, the sun will be low in the sky, but the streets will be alive with the hustle and bustle of busy people. From the picturesque marina to the bountiful boutiques, there's plenty to see and do in Lagos. In fact, the next time I visit Algarve, I'll make it my home base.

The main sites to visit here include the fort, St. Anthony's Golden Church, and the former slave market, which is now a museum. In the time I had, I managed to walk several streets, visit the church, and spend some of my hard-earned cash in the local shops. It was one of the most eventful stops of the day. By the time our visit in Lagos was over, night had fallen, and it was time to return to Albufeira.

The coach dropped me off at the same place it had picked me up that morning, which was just a short walk from my hotel. It was after 7 p.m., and most of the shops had shut their doors for the night, including the 7/11 where I had hoped to pick up a midnight snack. I roamed the quiet streets of the Old Town for a while before settling in at Urban Pizza, a popular restaurant that is always buzzing with activity. As the rain drizzled down outside, I sat next to a warm propane heater while enjoying a fungi pizza. It was a wonderful way to wrap up an amazing day.

Finally, about 12 hours after I left my hotel, I returned for a good night's rest. It was a packed day, and I felt like I had experienced so much of the best parts of the Algarve.

Have you been to the Algarve? What was your favorite part? Share your experience with the Wanderlust Wayfarer Facebook group.

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3 Tips for Choosing a Vacation Destination

With so much world to see, how do you choose a vacation destination?

 

My bucket list is at least a mile long. Israel, Bali, Myanmar, Peru, Portugal, Russia…these are just a few of the places I’m dying to visit. But I’m open to traveling just about anyplace, which means I have a terrible time choosing where to go. Each year, I can only get to three—maybe four—countries. So how do I decide which ones to visit?

Here are three tips to help you choose the perfect vacation destination when you’re not sure where you want to go.

Decide What’s Most Important: Date, Budget, Destination

When you’re searching travel sites for vacations, there are a few different ways you can filter the results: date, price, and place. So before you even begin your search, decide which of these is most important to you. Are you a sun seeker or a skiier? Do you like farms or cities? If you have a specific type of activity you like to do or part of the world you want to see, narrow your search using those details. Otherwise, if you’re open to any destination, your best bet is to base your decision on date and price.

Perhaps, you can travel any time of year, but you only have $1,500. Sort your search by lowest to highest price. This way you won’t end up flipping for something with a hefty price tag that’s out of your budget. You may be surprised by what you find. There are plenty of times I’ve booked a trip someplace I didn’t know I wanted to go because I found a smokin’ deal. But beware…You know how they say not to try on a wedding dress that’s out of your budget because you’ll fall in love and nothing will compare? Well, vacations work the same way. Don’t look at river cruises if you’ve got a Carnival cruise budget—no offence to Carnival. It’s just a lot cheaper than other options.

If you know you only have four days of vacation time, and you can only take days off in September, filter your search by date and number of days. You’ll weed out a bunch of options that don’t apply to you, making your choice for a vacation destination easier. I can’t tell you how many times I’ve found the right place for the right price but then realized it was at a time of year that simply wouldn’t work for me. Talk about disappointing.

Who is Your Travel Companion?

Even though you may be open to all sorts of different places, your travel companion may not be. Consider the types of things the person you’re traveling with likes to do. Does this person like to shop? Then New York City might be the perfect escape. Or maybe your companion really likes animals. You might decide to take a safari together.

There are three people I typically travel with: my mother, my husband, and my best friend. Each one has completely different tastes. So when I look at my bucket list, I think about which vacation destination is right for each person. For example, my mom loves charming seaside villages. A river cruise through France is perfect for her. My best friend? She’s all about the shopping. Vegas or LA are the best types of places for us to hit up together. My husband is a bit more adventurous. For our next trip together, we’re thinking an ATV drive through Machu Picchu, for example.

There are many items on my bucket list that don’t interest my regular travel companions. For these places, I’ll either convince one of them to cave in and go with me, or I’ll look for other options. I might join a tour group, or I’ll simply hop on a place all by myself.

How Do You Like to Travel?

Do you like to create your own schedule while you drive along vast highways? Or do you prefer to let someone else do the driving? Maybe you like a mix of both. These are important factors that can help you narrow down your vacation destination.

If you like to be part of a large group, start your destination search with a look at what tour companies have to offer. If you like being on the open ocean, then look at different cruise lines to see what they have available that interests you. Don’t bother looking at dates and rates for tour or cruise vacations if they’re not your style, but you might want to use them as a jumping off point for planning your own vacation.

There are times when I like to plan every part of a trip—train tickets between towns, bed and breakfasts in little villages, entry fees for attractions. And then there are times when I’m super busy and like to let someone else do all the work. Get a stack of vacation magazines and brochures, and simply start leafing through the pages. See what’s out there that catches your eye. You’ll likely be inspired by a few different itineraries or images. You can either book directly with the company that made the brochure or start booking your own plans based on the itinerary you found.

Want more great ideas for the perfect vacation destination? Follow Wanderlust Wayfarer on Twitter, where we’re constantly sharing cool places to go and things to do around the world.

3 Flight Tips to Help You Arrive on Time for Your Cruise or Tour

Nothing ruins a vacation like arriving late.

 

The ship ain’t gonna wait because your flight got delayed. But how early should you fly to ensure you arrive on time for your cruise or tour? Follow these three flight tips, and you’ll never have to worry again.

1. Fly Direct

If you’re flying the same day as you cruise or tour starts, if at all possible, book a direct flight. The fewer connections you have to make, the less likely you are to run into trouble. So long as your flight takes off as scheduled, there’s no need to worry that you won’t arrive on time.

Pro Tip: There are handy-dandy apps that let you check the accuracy of your flight. They’ll tell you how often your flight takes off as scheduled. Check before you book your flight so you can rest easy knowing you’ll likely arrive on time.

arrive on time

2. Embrace a Long Layover

Sometimes, flight connections are inevitable. You may live in a place that doesn’t have a direct flight to your final destination. Or the cost of a direct flight might be prohibitive. There will be times when you simply can’t avoid taking several flights. If that’s the case, make sure you leave plenty of time between flights. You’re less likely to miss a connection if one flight is delayed if you have several hours to spare. Fewer that two hours between connections could spell disaster if you’re on a tight schedule. And try to book a flight that arrives well before your ship or bus departs. That will give you a bit of wiggle room if you find yourself held up on the runway for any reason.

Pro Tip: If possible, try to connect out of an airport that has regular flights to your final destination. That way, if your flight gets cancelled or severely delayed, there’s a better chance you’ll be able to catch another one.

arrive on time

On a recent cruise out of New York, I decided to take my chances on a same-day flight. The cruise ended on a Saturday, and I wanted to extend my stay at the end of the trip rather than the beginning. But I still took precautions to ensure I would arrive on time. First, I found a red-eye flight that departed just before midnight the night before my cruise set sail. I didn’t have the funds for a direct flight, so I found a connection with a four-hour layover. But I was still sweating bullets right up until we made our connection.

So why not arrive a day early and save myself the heartache? Well, an extra night in New York is a lot of money, so I weighed the pros and cons. The second flight was out of a major airport with plenty of other flights headed to New York should ours be canceled or delayed. I checked the flight history to see how often it arrives on time, and it was nearly perfect. Lastly, I made sure the flight arrived in New York early on the day of the cruise, affording us a bit of time to spare.

As one final precaution, I booked a transfer to the port through the cruise line, even though I could get it elsewhere for a little less money. Why, you ask? Well, you’re supposed to board a cruise no later than two hours before sailing. If something happened, and I arrived with less than the recommended time, I figured the cruise line would likely go the extra mile to help us get on board as quickly as possible.

3. Plan a City Break

Take an extra two or three days off at the start of your trip so you can spend some time in your port of departure. For international flights, you should fly in at least one day to guarantee you’ll arrive on time. It will also give you a chance to adjust your sleep pattern for the change in time zone. Not to mention it’s a great reason to extend your vacation.

arrive on time

When I went on a cruise to the Canary Islands last spring, our ship wasn’t scheduled to set sail until Wednesday. Following my own rules, in order to arrive a day early, I had to take the entire week of work. Since I already had the weekend off, I left after work on the Friday night. I arrived Saturday afternoon and spent three fun-filled days touring Barcelona.

What other tricks do you employ to make sure you arrive on time? Share them with the Wanderlust Wayfarer Facebook group.

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.

portland

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.