Top Sailing Vacations for Couples | 3 Romantic Sea Adventures for Empty-Nesters

If you’ve ever dreamed of taking sailing vacations for couples, there’s no better time than when you become an “empty-nester.” Now that the kids have grown and you have a little extra money in your pocket, it’s a perfect opportunity for an adventure.

It’s also time to rekindle your relationship. 

When you’re surrounded by the beauty of the sea, caressed by gentle breezes, and aboard a luxury sailboat, it’s hard not to be charmed. Below, you’ll discover three sailing experiences to take as a couple, from a short day sail to a more immersive trip. Not only will you have the carefree time of your life, but you just might fall in love all over again.

CONTENTS – In this article, you will discover the sailing vacations for couples that are romantic, and make the perfect adventure for empty-nesters. This includes:

Before we get into these amazing sailing destinations, let’s just take a pulse on what you might be going through as an empty-nester.

Coping With Empty-Nest Syndrome

As a couple, you started this journey together when you fell in love. 

Now, years later, you’ve probably been through so much together—from the most wonderful memories to truly challenging times. You raised a family, and it was natural to put your family priorities—the children you love the more than anything in this world—before yourself. 

It’s likely that your schedule was full of things-to-do, and your vacation spots were kid-friendly destinations

And when finally your efforts paid off, your awesome kids grew up to be independent and left the house.

The only thing is…now what?

What It Feels Like to Be An Empty-Nester 

Maybe it feels a little strange to you that a huge part of your daily activities, space, chaos and youthful excitement in your house went away with your kids. 

You may feel you’ve lost your purpose and mourn the loss of your identity as the care-giver to your beautiful children. Or, you may feel elated at regaining your freedom and are experiencing a new sense of peace and adventure. It’s probably a blend of the two.

And it’s perfectly normal.

Whichever way you are coping with this surreal transition, know that there are good things ahead of you! 

They call it “empty nest” with good reason, and you’ll find lots of ideas on how to fill up your schedule with new things to do, like:

Only you can decide how you redefine yourself in this new chapter.

Reconnecting with Your Spouse or Significant Other

Once you become a so-called empty-nester, you have the perfect opportunity to rediscover your romance and focus on your love for one another as a couple.

Let’s face it, you may have grown apart while raising kids. So it might take a little effort to reconnect.

That means as a couple, you’ll want to do things like:

  • Spend more time together
  • Make small romantic gestures
  • Notice little details and take an interest in each other’s daily lives
  • Savour the time together
  • Dust off that bucket list you put off for so long 

And what is a better way to surprise the love of your life and rekindle your romance than to discover new places together?

Maybe you two have dreamed of visiting Tuscany Italy or taking a romantic sailing holiday. You finally have your chance!

The Ultimate Travel Destinations for Empty Nesters to Fall More in Love  

To help inspire you to travel with your love, we’re sharing the best sailing vacations for couples to get a fresh new perspective on these destinations—and your relationship.

Fireworks in the City

Fireworks over Chicago Illinois viewed from the water
Chicago, Illinois

Plan a spontaneous day in a big city with a spectacular show in the evening of the Independence day. You can take the love of your life to see the fireworks on 4th of July from the waterfront.

As great as it can be to watch the fireworks in the city from land or at home in front of your TV—watching the show from a boat will be even more memorable. 

You’ll find multiple cities where you can enjoy the fireworks on the water. Here’s what you do:

  • Pick your favorite city
  • Plan a day exploring together
  • Surprise your significant other with dinner at a sunset on a boat
  • Follow dinner by enjoying an amazing display of fireworks 

Great Cities for Fireworks

If you’re not sure which city to visit to see fireworks from the water, here are some excellent options:

The largest in all the USA’s fireworks is the annual Macy’s Fireworks on the 4th of July in New York City. Five barges are on the East River, so you’ll have multiple vantage points to see it from the boat. 

Another amazing destination for fireworks is Boston. It is world renown for the Boston Pops performance on The Esplanade, right alongside Charles River. Viewing the fireworks from your private boat rental in Boston is even better!  

A boat on Michigan Lake in Chicago is another great vantage point where you can enjoy spectacular synchronized music and firework shows from the water. 

Californians may opt for Marina Del Rey. You can enjoy this 10-minute spectacular pyrotechnical show from a luxury yacht in Marina Del Rey to get a close-up view.  

If you need help to prepare for your date, go for the one of the best boat rental platforms out there –  sailo.com. For a sailing excursion like this, you’ll have plenty of options of yachts and boats to rent for 2- or 4-hours. You can even contact the boat owner to help you prepare for your night out. 

Don’t forget to bring along a favorite shawl or sweaters so you can both enjoy the evening without getting a chill on the yacht. 

This sailing vacation for couples may just be a day trip, but you’ll feel rejuvenated after such a wonderful experience on the water.

Sail in Nantucket Massachusetts

Nantucket, Massachusetts

Nantucket, Massachusetts offers quiet and romantic places with quite a local flavor.

Why don’t you put on matching guaranteed-to-fade Nantucket reds and explore all this summer island on Cape Cod has to offer for couples?

When you sail into Nantucket, you’ll find beautiful hotels that provide a bit of a remote stay. This is perfect for romantic getaway!

You can also take comfortable shuttles from your accommodations to the center of Nantucket, where you’ll enjoy dining and shopping “in town,” as locals like to say. 

One of the local traditions is to go to Downyflake for a box of fresh doughnuts and get one of those rattan baskets this place is famous for. I can’t think of a better way to start a day! 

Later on, wander cobblestone streets and enjoy gorgeous Victorian architecture. Nantucket is rich with history.

In the late 18th century Nantucket was a whale capital of the world inspired the literary masterpiece, Moby Dick.  Locals can tell you a lot about whales and whaling ships, Also, you can plan a visit to the Nantucket Whaling Museum while you’re there.

And of course, it’s a good idea to have fresh oysters for dinner at the local restaurant in Nantucket. Oysters are supposed to be good for your love life, so why not try a few?

Sailing Holidays in Greece

Poros, Greece 

Greece is home to an amazing history, ancient literature, delicious food, a laid back atmosphere, and thousands of islands to choose from. 

As a sailing vacation for couples, you can bet you and your significant other would love it there. Have you ever heard of anyone who returned from Greece without a smile on their face? This country will captivate your soul forever. 

Yes, it will take a bit of time to plan a sailing trip in Greece. But it is thoroughly worth the time it takes to work out all the details. 

If you opt to stay in Athens, go to the Plaka or Kalanaka areas to lose yourself in the vibrant city. 

Artists from all over Europe have moved to Athens. They brought contemporary art to the street, the young chefs brought new styles of cooking, the musicians, writers, and other creatives have made Athens their own.

But of course, Greece is best explored from the sea. That’s because of the amazing beaches, beautiful island architecture, and turquoise waters. Island-hopping is a popular activity way to see Greece with good reason. 

You can rent a boat for a day or a couple of days and sail away to the mesmerizing islands near Athens: Poros, Hydra, Aegina, Spetses, Tzia/Kea just to name a few. 

Another great way to explore Greece is to fly to Heraklion, the capital of Crete. Explore the beauty of the island and then take about two hours by barge to Santorini. Santorini is well-known for its iconic white and blue buildings and honeymoon atmosphere. You will be at a loss for words at the serenity of this place.

Final Thoughts on Sailing Vacations for Couples

Wherever you go, whatever you do, it is all about spending time with each other and staying in the moment. What better way to enjoy a sailing vacation for couples aboard a luxury sailing vessel together. It’s the perfect place for two of you to savor every moment together and recommit to the future.


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Jackie Gately

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