Top 6 Romantic Sailing Destinations for 2026
Some trips are about doing everything. Romantic sailing trips are about doing less, but doing it better. A calm anchorage. A swim before breakfast. A short sail to a new harbor town. A sunset that turns into dinner under the stars without anyone checking the time.
If you’re planning a couple’s sailing getaway in 2026, these six destinations are easy to fall for. Each of them shines because the sailing itself is the experience, not just a way to get around.
1. British Virgin Islands
The British Virgin Islands is one of the best places in the world for an easy, romantic sailing rhythm. Short hops, plenty of protected anchorages, and lots of spots you can only properly enjoy when you arrive by boat. Sunsail’s base is in Road Town, Tortola, at Wickhams Cay II, just a short drive from the ferry dock or Beef Island airport.
Romantic highlight 1: The Baths, Virgin Gorda
This is a classic for a reason. Big granite boulders, hidden pools, and a beach that feels like a reward when you reach it. It is the kind of shared little adventure that sticks with you.
Romantic highlight 2: Anegada lobster night
Anegada is famous for lobster dinners and wide-open beaches, and it feels like a proper change of pace from the rest of the islands. Plan it as your “special night” and let the evening run long.
2. St. Lucia
St. Lucia brings a more dramatic kind of romance, where lush rainforest, volcanic peaks, and warm Caribbean sailing all come together. Sunsail’s base at Rodney Bay Marina makes it easy to settle into the rhythm of the island before heading south along a coastline that feels wild, green, and unforgettable.
Romantic highlight 1: Rabot Restaurant & Cacao Bar
Set on a cacao estate with sweeping views of the Pitons, Rabot is a perfect “dress up just a little” evening. Think sunset cocktails, chocolate-infused dishes, and a setting that feels special without being overdone. It’s an ideal way to anchor the trip with a memorable night ashore.
Romantic highlight 2: Hike up Gros Piton
For couples who like to earn their views, a guided hike up Gros Piton is a shared adventure you’ll talk about long after the charter ends. It’s challenging, rewarding, and ends with panoramic views that make the effort worth it—followed, ideally, by a well-deserved swim back on the boat.
3. St. Martin
St. Martin is a great mix of cultural experiences, island-hopping, and food. Sunsail’s base is at Marina Fort Louis in Marigot, which is handy for starting the trip and getting into the cruising grounds quickly.
Romantic highlight 1: Grand Case dinner night
Grand Case is known for its French-Caribbean dining scene and it is an easy way to build a romantic evening into the trip without forcing it. Start with a simple sail, end with a long dinner.
Romantic highlight 2: Prickly Pear Cays lunch stop
If you want the “we came by boat” moment, this is it. Clear water, a beautiful beach, and reef snorkeling right there. Great for couples who want a little adventure in the middle of a lazy day.
4. Greece (Lefkas and the Ionian)
For a romantic charter in the Mediterranean that still feels easy, the Ionian is a favorite. Sunsail’s Lefkas base is the gateway to island hopping through places like Meganisi, Kalamos, Ithaca and more, with plenty of sheltered bays and relaxed sailing days.
Romantic highlight 1: Meganisi channel and a swim stop off the stern
This is Ionian sailing at its best. A scenic run, then lunch at anchor with a swim straight from the boat. No big plan needed, just a good bay and good company.
Romantic highlight 2: Harbor night in Ithaca (Kioni)
The Ionian itineraries make it easy to build in a proper “harbor town night”, and Kioni is a great example. Moor up, walk the waterfront, choose a spot for dinner, and take your time.
5. Croatia (Dalmatian Coast)
Croatia is a strong choice for couples who want equal parts sailing and evenings ashore. Sunsail’s base is Marina Agana, a great jumping-off point for the central Dalmatian coast.
Romantic highlight 1: Quiet evenings at anchor with pine-scented air
Croatia does “end the day properly” well. Swim, rinse off, then settle into a calm bay where the only plan is dinner and a sunset you can actually hear.
Romantic highlight 2: Historic town evening on Hvar or Korcula
The Dalmatian islands give you that simple, romantic routine: sail in, tie up, wander old stone streets, then find a table that turns into two hours without trying.
6. French Polynesia
If you want romance that feels like a true escape, Tahiti is hard to beat. Sunsail’s cruising area covers islands such as Raiatea, Tahaa, Huahine and Bora Bora, with itinerary options built around lagoon time, snorkeling and those once-in-a-lifetime anchorages.
Romantic highlight 1: Bora Bora lagoon days
Bora Bora is the postcard, but on a charter you get the version that feels personal. Clear lagoon water, snorkeling, and a day that naturally turns into an unforgettable sunset.
Romantic highlight 2: Tahaa and Huahine slow mornings
These are the “quiet magic” islands. Start the day with a swim, take a short sail, then find a calm spot for lunch and do nothing for a while. That is the point.
Why we love sailing
Sailing makes it easy to be present. You move with the conditions, you earn your views, and you end up sharing small moments that feel bigger because you are out there together.
To enter our 2026 Valentine’s Day contest, share a photo or video on Instagram showing why you love sailing, and use #WhyWeLoveSailing for a chance to win a $1,380 voucher towards your next Sunsail charter. Find us at @sunsailholidays.
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Contributor
Tina Huewe
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