Sailing Trips for Solo Travelers: The Ultimate 2025 Guide

If you’ve ever dreamed of feeling the wind in your hair, the horizon stretched endlessly before you, and the thrill of discovering new destinations at your own pace—this is your year. Sailing trips for solo travellers are booming in 2025, offering the perfect blend of adventure, connection, and personal growth. Whether you’re new to sailing or already an experienced hand at the helm, there’s never been a better time to embark on a sailing vacation designed just for you.

From the best sailing trips in the world—like Sailing in Croatia or Cruising in Antarctica—to practical planning tips, this guide will walk you through everything you need to know to set sail on your own.

Why Sailing is the Perfect Adventure for Solo Travelers

Instant Community

Unlike typical holidays, sailing trips for singles instantly immerse you in a small, like-minded group. You’ll bond quickly over shared tasks, breathtaking views, and on-board experiences—whether you’re tacking into the wind or enjoying a sunset dinner at anchor.

Balance of Solitude and Socializing

Sailing alone doesn’t mean being lonely. When you want company, there’s plenty of conversation and laughter to share. When you want solitude, there’s always a quiet deck corner to enjoy the horizon and your thoughts.

Safety in Numbers

Even when traveling solo, you’re part of a team. Being with a crew means extra security—ideal for those trying new sailing destinations or unfamiliar waters.

Skill Building and Participation

Many sailing holidays for singles encourage hands-on participation. You can learn to hoist sails, navigate, and even take the helm under the skipper’s supervision—returning home with newfound confidence and skills.

Types of Sailing Trips for Solo Travelers

Travel Agency Specializing in On-Water Adventures

Working with an expert travel agency such as Neptune's Daughter ensures you’re matched with the right boat charter or cruise, based on your comfort level, interests, and budget. They can arrange sailing vacations for singles that fit your exact style—from hands-on adventures to laid-back luxury.

By-The-Cabin Charters and Cruises

Perfect for meeting others, you’ll book a cabin on a shared yacht or small cruise vessel. It’s a cost-effective way to join sailing trips for singles without needing your own group.

Skippered Charters

Hire a skipper to handle navigation and safety while you enjoy the ride. Great for first-time solo sailors who want the experience without the responsibility.

Flotilla Holidays

A fleet of yachts sails together along a set itinerary. You can join a crew or sometimes even skipper your own boat—benefiting from the support network of other boats and a lead crew.

River Cruises

Not all solo sailing is at sea. River cruises offer a relaxed way to explore inland destinations while still enjoying a nautical experience.

Special Expeditions

Diving safaris, wildlife photography trips, or educational expeditions—special interest voyages let you combine your passion with cruises in unique destinations.

Top Sailing Destinations for Solo Travelers

The Mediterranean

The Med offers rich history, delicious food, and varied coastlines.

Greece

Sailing in Greece is a bucket-list adventure with island-hopping, ancient ruins, and crystal waters. Perfect for both flotillas and skippered charters.

Croatia

Sailing in Croatia brings you along the stunning Dalmatian Coast, dotted with UNESCO sites and charming fishing villages.

Italy

From the Amalfi Coast to Sicily, Italy delivers romance, culture, and cuisine—plus plenty of sheltered bays for overnight stays.

Turkey

A blend of Eastern charm and Western comfort, Turkey’s Turquoise Coast offers warm hospitality and breathtaking anchorages.

Spain

Sail the Balearics—Ibiza, Mallorca, Menorca—for vibrant nightlife, hidden coves, and Mediterranean sun.

The Caribbean

The Caribbean is synonymous with turquoise waters, soft sands, and easy sailing.

British Virgin Islands (BVI)

Sailing in British Virgin Islands is famous for its calm waters and short hops between islands—ideal for solo sailors and first-timers.

The Bahamas

An island chain offering countless secluded beaches and superb snorkeling, with both adventurous and laid-back itineraries.

The Pacific & Beyond

The Galapagos Islands

Sailing in Galapagos Islands offers unmatched wildlife encounters, with small-ship options perfect for solo travelers seeking nature immersion.

Thailand

Thailand combines tropical beauty with warm hospitality. Phuket is the starting point for island-hopping adventures.

Canary Islands

A year-round sailing destination, ideal for winter sun and steady trade winds.

French Polynesia

Tahiti, Bora Bora, New Caledonia, and the surrounding islands offer a stunning blend of turquoise lagoons, lush volcanic landscapes, and vibrant Polynesian culture. Ideal for island-hopping adventures, these waters are a paradise for both relaxed cruising and more adventurous sailing trips.

Fiji

Warm waters, coral reefs, and traditional island villages create a dreamy South Pacific escape.

Tonga

Remote, authentic, and whale-friendly waters make Tonga a unique sailing destination.

Antarctica

Cruising in Antarctica is the ultimate expedition for adventurous solo travelers. Small ships and Zodiac landings create once-in-a-lifetime moments.

South America

From Patagonia to Brazil’s coast, South America offers dramatic landscapes and rich cultural experiences.

Scandinavia and Northern Europe

Norway's Fjords

Towering cliffs, cascading waterfalls, and midnight sun—Norway’s fjords are magical under sail.

Sweden

The Swedish Archipelago offers thousands of islands to explore at a relaxed pace.

The Arctic Circle

Cruising in the Arctic brings polar bears, icebergs, and the ethereal glow of the midnight sun.

Indian Ocean Gems

Seychelles

Granite boulders, turquoise lagoons, and palm-lined beaches make Seychelles a paradise for sailors.

Maldives

A mix of luxury and adventure, with reef-protected waters and overwater bungalows.

Madagascar

Exotic wildlife, remote anchorages, and warm hospitality await in Madagascar.

Planning Your First Solo Sailing Trip

Choosing Your Destination

Think about your comfort level—do you want calm waters like the BVI, cultural exploration like Greece, or wild expeditions like Antarctica?

Booking Your Charter

Decide between a private boat charter, a by-the-cabin option, or a cruise. A specialist in sailing vacations for singles can advise based on your interests and experience.

What's Included vs. Additional Costs

Review trip details carefully—meals, excursions, and equipment rental may be extra. Additional land excursion might come with a premium as well. Many solo travelers worry about single supplements, but some companies waive them during special promotions.

Do You Need Experience?

Not necessarily. Many trips welcome beginners, offering a safe and supportive environment to learn.

Your Adventure Begins with a Conversation

Your perfect sailing holiday for singles starts with a chat—with a travel professional, a skipper, or even fellow adventurers online. With so many sailing trips and special cruises available in 2025, your only challenge will be choosing where to drop anchor first.

FAQs

Do I need sailing experience to go on a solo sailing holiday?

No. Many trips cater to beginners and include a skipper to handle the boat.

Is it safe for a solo traveler?

Yes—reputable operators prioritize safety, and you’ll be traveling with a crew or group.

What is the typical age range on these trips?

Groups often include people from their 30s to 70s, depending on the style of trip.

What should I pack for a solo sailing trip?

Pack light, with quick-dry clothing, non-slip shoes, sun protection, and personal items.

Do I need sailing experience to go on a solo trip?

No—many sailing trips for singles are designed for first-timers.

Will I be lonely on a solo sailing trip?

Unlikely—you’ll be sharing the experience with other travelers and crew.

Are sailing trips expensive for solo travelers?

Costs vary, but boat charters and by-the-cabin trips can be affordable, especially during off-season or single supplement waiver promotions.

What are some of the best sailing trips in the World?

Top picks include sailing in Greece, sailing in Croatia, sailing in British Virgin Islands, Cruising in Galapagos Islands, Cruising in Antarctica, and Cruising in the Arctic.

Traveling alone doesn't mean you will be lonely! Antarctica Expedition