Sailing Virgins
Madeira Sailing Adventure

Madeira Sailing Adventure

classic
Monohull
BeginnerIntermediateAdvanced
Max 5 sailors
7 days / 6 nights
From$3,990per person
$3,990
Starting from
7
Days sailing
5
Max crew size
5.0
Avg SV sailor rating

What past Sailing Virgins sailors say

Madeira reviews are coming as our first sailors complete the programme. Until then, here's a sample of what alumni from our Croatia and BVI programmes have written about the experience.

Our instructor created a team/family out of 4 strangers in just 1 day. He taught from a place of deep experience and instilled that confidence in us.
kristen fCroatia · September 2024 · Couples
I went stressed out and came back the most relaxed I have ever been. One of the best trips I've ever been on in my life.
John LeiCroatia · August 2023 · Friends
An amazing experience balancing fun, training and incredible destinations. One week with Sailing Virgins turned out to be one of the best times in my life.
Ruben BCroatia · September 2024 · Couples

Book with confidence

  • Cancel 90+ days before departure for a near-full refund (admin fee only).
  • Full credit or refund if Sailing Virgins has to cancel due to weather, government action, or other force majeure.
  • Goodwill resale — even inside the 60-day window, if we resell your spot we'll refund you minus a small fee.
See full cancellation policy

Select Your Adventure Week

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Course Overview

Wonderful tour of Madeira and surrounding islands on a monohull

Perfect For

  • Adventure seekers wanting to learn sailing
  • Solo travelers looking to meet like-minded people
  • Anyone wanting to explore off-the-beaten-path destinations

You'll Learn

  • Basic to intermediate sailing skills
  • Navigation and chart reading
  • Safety procedures and emergency protocols

What's Included

What's NOT Included

So there are no surprises at checkout — these aren't covered by your course fee:

International flights
Travel insurance
Meals off the boat (shore dinners)
Alcohol and drinks ashore
Optional dive or activity add-ons
Gratuity (if you wish to tip your instructor)

Photo Gallery

Destination Guide

Your Madeira Adventure

Discover what makes sailing in Madeira an unforgettable experience — from the daily rhythm aboard to the stunning destinations you'll explore.

A Day in the Life

From sunrise yoga to sunset cocktails — here's what a typical day looks like on your Madeira sailing adventure.

07:00The 7-7-7 Morning Routine

7min breathing practice, 7min meditation, 7min workout — the Sailing Virgins way. Start your day anchored in a secluded Madeiran cove with the Atlantic stretching to the horizon.

Zen
07:30Atlantic Morning Swim

Dive into crystal-clear waters with visibility exceeding 30 meters. The deep Atlantic blue around Madeira is incomparable — some mornings you might spot dolphins cruising past.

Active
08:30Portuguese Breakfast on Deck

Fresh bolo do caco (Madeiran bread), local honey, tropical fruits, and strong coffee while reviewing the day's passage plan and weather forecasts.

Social
09:30Navigation Theory Session

Learn to read Atlantic weather patterns, understand the unique wind acceleration zones around Madeira's volcanic peaks, and master passage planning for island hopping.

Academic
11:00Hands-On Sailing

Take the helm along Madeira's dramatic south coast. Practice sail trim in the island's variable winds, navigate past towering sea cliffs, and build confidence in open ocean conditions.

High Focus
13:00Lunch in a Hidden Anchorage

Drop anchor in a cove beneath Madeira's famous levada waterfalls. Fresh salads, local cheeses, and espetada stories while the boat gently rocks in the Atlantic swell.

Social
15:00Skill Building: Advanced Maneuvers

Master Mediterranean mooring in Madeiran ports, practice man overboard recovery in deep water, and refine your close-quarters handling.

High Focus
19:00Sundowners & Sunset

Watch the Atlantic sun sink behind Porto Santo on the horizon. Share Madeira wine, swap stories with your crew, and celebrate another day of transformation under sail.

Celebration
Zen
Academic
Active
Social
High Focus
Celebration

See Madeira in Action

Experience what a week of sailing looks like through the eyes of our students and instructors.

The Experience

90 seconds of pure sailing adventure in Madeira

Your Madeira Sailing Route

Our Madeira route takes you along the island's spectacular south coast before venturing offshore to the protected Desertas Islands, then returning via the dramatic eastern peninsula. Expect approximately 100-150 nautical miles of genuine Atlantic sailing, with conditions ranging from sheltered coastal waters to open ocean passages.

Start & Finish
Funchal Marina
1
Funchal Marina
Historic capital city, departure point beneath the mountains
2
Câmara de Lobos
Winston Churchill's favorite fishing village, spectacular cliffs
3
Calheta Marina
Sandy beach, modern marina, Mediterranean mooring practice
4
Desertas Islands
Remote nature reserve, monk seals, incredible stargazing
5
Ponta de São Lourenço
Dramatic volcanic peninsula, wind acceleration training
6
Machico Bay
Site of Madeira's discovery, protected bay for skill refinement
7
Islands
~80
Nautical Miles
Madeira Sailing Route Map showing numbered stops
Loading map...
7-day circular route
Returns to Funchal Marina

This is a sample route — your actual itinerary may vary based on weather, wind conditions, and crew preferences. That's the beauty of sailing!

Welcome to Madeira! Meet your crew and instructors at Funchal Marina, nestled beneath the island's amphitheater of green mountains. After boat orientation and safety briefing, we'll motor out of the harbor for your first taste of Atlantic sailing. Return to Funchal for a welcome dinner overlooking the twinkling city lights.

Sail west along Madeira's dramatic south coast to the picturesque fishing village that inspired Winston Churchill's paintings. Practice your points of sail with the towering Cabo Girão — Europe's second-highest sea cliff — as your backdrop. Overnight in this charming harbor, enjoying fresh grilled fish at waterfront restaurants.

Continue west to Calheta, home to Madeira's only natural sandy beach and a modern marina perfectly sized for practicing Mediterranean mooring. The afternoon brings theory sessions on weather patterns and passage planning, followed by sunset drinks overlooking the marina's golden beach.

Today's highlight: a passage to the Ilhas Desertas, a protected nature reserve 25 nautical miles southeast. These uninhabited volcanic islets are home to monk seals and countless seabirds. Anchor in the lee of Deserta Grande for an unforgettable night under the stars, far from any light pollution.

Sail back toward Madeira's eastern tip, the dramatic Ponta de São Lourenço. This stark, wind-sculpted peninsula feels like another planet — golden cliffs and red volcanic rock contrasting with the deep blue Atlantic. Practice navigation around headlands and identifying wind acceleration zones.

Round the eastern point to Machico, the site of Madeira's discovery in 1419 and the island's second-largest town. This protected bay offers perfect conditions for skill refinement — man overboard drills, close-quarters handling, and final certification assessments. Celebrate your progress with dinner in the historic town center.

Your final morning sail takes you along the southeast coast back to Funchal, with time for last practice maneuvers and stunning views of the island's terraced hillsides. Arrive at the marina by midday for certification ceremonies, fond farewells, and plans for future sailing adventures. You're no longer a passenger — you're a sailor.

Flexible sailing: Routes adapt to conditions. Your instructor will tailor the experience to maximize your learning and enjoyment.

FAQs About Our Madeira Sailing School

Plan to arrive in Funchal by early afternoon on Day 1 to ensure plenty of time for check-in and orientation. Cristiano Ronaldo International Airport (FNC) is just 15 minutes from the marina, with direct flights from most major European cities. We recommend booking accommodation near the marina for the night before if you're arriving late, though many students fly in the morning of and head straight to the boat. Funchal's Old Town is right next to the marina — perfect for exploring if you arrive early.

We typically conclude certifications and say our farewells by midday on Day 7, giving you plenty of time for afternoon or evening flights. The airport is a quick taxi ride from Funchal Marina. Many of our students extend their stay to explore Madeira's incredible hiking trails, levadas, and mountain peaks — if you have flexibility, an extra day or two on the island is highly rewarding.

Madeira's nickname 'Island of Eternal Spring' is well-earned — expect daytime temperatures between 25-30°C from May to October with reliable sunshine. The Atlantic provides consistent trade winds, typically from the northeast, creating ideal learning conditions. Sea conditions are moderate with ocean swells, which is exactly what builds confident sailors. Water temperature hovers around 22-24°C in summer, perfect for swimming. Morning conditions tend to be calmer, with winds building through the afternoon. Our instructors have years of experience reading Madeira's unique microclimates and always plan routes that match your developing skill level.

Pack light and practical: soft-sided duffel bags only (no hard suitcases). Bring quick-dry clothing, swimwear, a light rain jacket, non-marking deck shoes, and sandals for shore. Madeira's sun is intense — bring reef-safe sunscreen, quality sunglasses with a strap, and a hat. Layers are key as evenings can be cooler at sea. Don't forget a headlamp for night watches, seasickness remedies if you're prone, and a dry bag for electronics. We provide all safety gear and bedding. One nice outfit for shore dinners is recommended — Funchal has some wonderful restaurants.

Absolutely — that's exactly what we specialize in! Our ASA 101 course assumes zero prior experience. Most of our students have never set foot on a yacht before Day 1, and by Day 7 they're confidently handling the boat. Our instructors are passionate teachers who break down every skill into manageable steps. You'll be surprised how natural it feels once you understand the basics. The only prerequisite is a willingness to learn, a sense of adventure, and reasonable physical fitness to move around the boat.

Eating well is part of the experience! We provision the boat before departure with breakfast supplies and lunch ingredients — think fresh Portuguese bread, local cheeses, charcuterie, tropical fruits, salads, and plenty of snacks. Morning coffee is sacred. Dinners are typically enjoyed ashore, exploring Madeira's fantastic restaurant scene: fresh-caught fish, traditional espetada (beef skewers grilled on laurel sticks), and incredible local wine. Budget roughly €20-35 per dinner. Let us know about any dietary requirements in advance, and we'll ensure you're well-catered throughout the week.

Our week combines ASA 101 (Basic Keelboat Sailing), ASA 103 (Basic Coastal Cruising), and ASA 104 (Bareboat Cruising). These are internationally recognized certifications that allow you to charter boats worldwide. Assessment is continuous throughout the week — there's no high-pressure exam at the end. Your instructor evaluates your practical skills, knowledge, and seamanship as you sail. Complete the required competencies, and you'll receive your certifications. We also include ICC/IPC (International Certificate of Competence) preparation, which is recognized across Europe and essential for Mediterranean chartering. Most importantly, we don't pass anyone who isn't genuinely ready — our reputation depends on producing capable, confident sailors.

Ready to Start Your Adventure?

Choose your perfect week to sail Madeira

From
$3,990
per person