Having only been sailing on Serendipity for four years, just two of those as full time cruisers, we’ve mostly stuck to the east coast of the US and parts of the Caribbean. Although we’ve been to so many beautiful places and I count myself lucky almost every day that we’re out here living this lifestyle, there haven’t been many places on our list of travels so far that I would categorize as exotic or far flung. In my mind those areas described as unusual or excitingly strange tend to relate to isolated regions of beauty, normally a remote set of islands probably somewhere in the South Pacific. But we had never been any place that met that kind of criteria. At least in my mind at the time.
So when LOOK Insurance Services gave a list of their Top 5 Most Exotic Sailing Locations in the World and asked us to lend them a hand with what we thought our most exotic location was, one area shot straight to the front of my brain. I remembered that we now have been to an area of isolated beauty that’s unfamiliar, fascinating, and definitely romantic. The Atlantic Islands of Portugal.  Lying approximately 800 nautical miles off the coast of Portugal, they should be a top sailing destination for every cruiser and even fit into my mind’s criteria of exotic. Yes they are isolated, yes they are kind of far flung, and Yes, THEY ARE GORGEOUS!!
The specific Portuguese Atlantic Islands I’m including in my list the Azores Archipelago and the Madeira Island Group, and here are a few reasons of why we love them so much.
The sea life is amazing.
It never fails that no matter what port we’re in between any of these islands, there are always tours set up for whale watching, dolphin watching, and seal spotting. And with good reason too. They’re everywhere! Coming in to the ports of Ponta Delgada, Sao Miguel Azores, and Funchal, Madeira, we had pods and pods of dolphins leading the way in. To the point that I actually got sick of watching them, which should really be a felony, because really, how can one ever become sick of watching dolphins glide and jump through the water? Plus even though we arrived fairly late in the season, we actually spotted whales! Short finned pilot whales mostly, but for a couple that couldn’t even spot a single bald eagle while traveling up the Potomac where they’re supposedly hanging off every buoy, getting even one whale sighting in for us was huge.
The views from the water are staggering.
I have never been any place that has offered such great views of said place from the water in my life. When you come up on any of these islands from the water you’re normally greeted with sheer cliff drops into the water and rolling green hills of farm and/or white buildings with terracotta roofs flowing inland. It’s almost like stepping back in time to an era before resorts and hotels and super-malls blocking out any area of civilization, to when it was just nature and and the locals living off the land. Don’t get me wrong, there are still some resorts and hotels and mega malls tucked in here and there, but you can’t tell it from looking. Â If we didn’t have to go through the trouble of getting in and out of a marina berth, I could honestly spend my days just cruising back and forth along the coastline. Â If there was ever an area for daily pleasure cruises, this would be it.Â
The climate is a perfect balance of warm and cool.
You’d think that with such a northern latitude, equivalent to where you’d find yourself in the US anyway, would have fairly cool days and much cooler nights. Not quite, as the Gulf Stream runs just close enough to the Azores leaving them in a subtropical climate all year meaning it is warm but not overly hot. Spending most of August and September in the Azores we’d experience highs in the mid to upper 70’s and low’s in the upper 60’s. Getting to Madeira even later in the season in October, approximately 600 nm south of the Azores, we experienced much of the same there. This meant that the days were warm, even hot sometimes when the sun was beating down on you, but it was never stifling and there were always pleasant sea breezes blowing off the harbor. The nights cooled down just enough that it reminded you fall might be around the corner, that perfect temperature where it’s nice to bundle up in a sweater but know you’ll be able to peel it off the next morning.
The landscapes are incredibly diverse
Think of basically any kind of landscape you’d like to see on a trip or vacation, and it’s likely you’ll be able to find it here. Large volcanoes towering out of the sea? Check. Deserts surrounded by beautiful jagged cliffs? Check. Opulent forests sprawling into rolling green hillsides? Check. Golden sandy beaches leading into clear (sub)tropical waters? Check. Isolated villages that look like they haven’t been touched in a hundred years, or large and upscale metropolitan cities? Check and check. At least one area in these islands, and usually multiple, will give you all of these and more. It’s literally the place that offers everything.
The cities are like something out of a storybook.
Do you remember the photos I shared from Picturesque Horta? How incredibly surreal and beautiful everything looked? Trust me, that wasn’t just for the cameras. Every direction you turn your head in these areas holds parks, markets, beautiful old world architecture or churches that have been standing for a hundred years, and all of them looked like they were set up to be part of a movie except it was actually real life. Â There hasn’t been a single area in any town or village we’ve visited where ours jaws have not been on the floor due to their charm and grace.
Island hopping is easy and enjoyable*
Situated in an area with steady north to northeast tradewinds make moving east, west, or south between the islands incredibly easy. Granted, we did most of our traveling through here in the fall where the weather was a little stronger than normal, but plan your visit from mid-late spring through summer and you’ll find reliable 15-20 knot breezes under brilliant sunny skies to carry you from one destination to the next. In the Azores, the nine islands are clustered together in three groups meaning that most sails are within sunrise to sunset distance of each other, but never more than a day and a half apart. Getting between the Azores and Madeira is about a five day travel, but if you’re moving south you’ll have the wind and current at your back to push you smoothly along.
*Don’t base this on our own travels of the area where every weather forecast was wrong and we ended up with strong winds on our nose. That’s not the norm.
The cost of living is not very high
I may not categorize this with the extreme cheapness we were experiencing in Central America, but I’d say that our costs here are on par with, or even a little lower than what we were paying in the US.  Our main expenses were groceries and marina charges, and although I might have to consult our monthly costs, I think we’re on average below what we were in Florida.  We’d heard that Europe is expensive, and when we arrived here we were blown away with the cheap prices we’ve been finding everywhere.  I will say that we’ve heard Portugal has the lowest cost of living between countries in the EU, but to only have to pay 1€ for a bag of sandwich rolls, 1€ for a bag of potato chips, 1,25€ for a bag of coffee grounds, or 0,60€ per bottle of beer, we’ve been doing pretty good.
I could go on and on about the million other tiny reasons of why we fell so deeply in love with this area. The history, the cleanliness, the safety, plus it’s European flavor. Trust me, the cheap espressos, wine, and cheese have not gone unnoticed. Â Plus all of the impromptu (and free) festivals, concerts, and other events always going on.
Needless to say, if the season and our Visas allowed us, we could spend months and even into years enjoying these island groups. Besides Guatemala, it’s the only place we’ve ever seriously considered buying property because we never wanted to leave. If you’re thinking of spending a long time on a place you’re probably going to fall in love with, make sure to secure the right visa first with the aid of consulates, such as the Italian Consulate Los Angeles.
Unfortunately they’re not on a highly traveled cruising route. The best way to get to the Azores is heading east across the Atlantic, although Madeira wouldn’t be too far out of the way for those making their way south upon leaving the Med. So if you ever find yourself with the opportunity to visit any of these islands, hop on that chance right away. I promise it will be something you’ll never regret. The allure of these islands isn’t just in their beauty, rich history, and effortless charm—it’s also in their potential for real estate investment.
With tourism steadily rising and visitors falling in love with the laid-back yet culturally vibrant atmosphere, vacation rentals and boutique hotels have become a profitable avenue. Sustainable developments, particularly eco-friendly lodgings and locally integrated properties, are gaining traction as travelers become more conscious of their environmental impact. From cozy seaside cottages to high-end retreats, the demand for unique stays continues to grow.
Additionally, commercial properties catering to tourism—such as cafés, artisanal shops, and co-working spaces—are proving to be lucrative for investors looking to tap into the islands’ economic potential. As with any foreign investment, securing the right permits and understanding local regulations is crucial, but the rewards of owning property in such a sought-after destination are undeniable.
Owning property in a paradise setting is a dream, but maintaining it in top shape is what keeps that dream profitable. With high humidity, salt air, and an ever-rotating cast of guests, vacation rentals demand consistent upkeep. It’s not just about fixing what’s broken—it’s about anticipating what could go wrong and addressing it before it becomes a five-star review killer.
This is where professional property maintenance services come into play. Whether it’s routine inspections, pest control, or ensuring eco-friendly systems are running efficiently, a trusted team makes all the difference. Many seasoned owners work with specialists like Property Care Harrogate, whose attention to detail and preventative strategies help keep properties not only beautiful but resilient—no matter the climate or foot traffic.
Beyond tourism, the islands present broader economic opportunities tied to trade and infrastructure development. The strategic location of these archipelagos along transatlantic routes has made them increasingly relevant for maritime logistics and commerce. Governments are investing in port expansions, transportation networks, and energy-efficient initiatives to support both local businesses and international trade. This kind of development isn’t just beneficial for the islands themselves; it also signals potential growth for industries such as manufacturing, warehousing, and shipping logistics.
Investors interested in diversifying their portfolios may find opportunities beyond tourism, particularly in industrial and commercial real estate. Companies like Orlando Industrial Real Estate specialize in helping investors navigate these markets, offering insights into emerging opportunities that balance profitability with long-term economic sustainability. As global trade evolves and new hubs emerge, forward-thinking real estate investments in these regions could prove to be both financially rewarding and strategically sound.
When navigating real estate investments, especially in rapidly developing regions, having a reliable service is crucial to ensure that your properties are managed with precision. From tax strategies to financial reporting, comprehensive accounting services offer the expertise needed to maximize returns and ensure long-term profitability. Professionals like DMR Consulting Group provide tailored services, helping investors streamline their financial management and maintain compliance with regulations—giving you the peace of mind to focus on growth.
Moreover, understanding local market trends and tax implications is vital when expanding your portfolio. Specialized services in real estate accounting can help uncover opportunities for strategic investment, ensuring that you’re not just keeping up with the market but staying ahead of it. With the right guidance, real estate ventures, whether in tourism or commercial sectors, can become a cornerstone of a diversified, profitable portfolio.
But now that I’ve shared our favorite and most exotic sailing location with you, I’d like to know, what’s yours?
*I will note that if there is one big downside to cruising this area it’s that protected anchorages are very hard to come by. If you sail here be prepared to spend a majority of your time in a marina. The upside to this though is they usually cost a fraction of the price they do back in the States. Our 34 ft boat was usually 14€/night.
