Couple standing on sailboat bow at sunset over calm sea

Sail Skiathos & Skopelos: Sunset Cruises, Private Charters, Day Trips

Experience crystal-clear waters, iconic Mamma Mia beaches, and bespoke sailing aboard Aeolus Sailing.

Featured Tours & Experiences

Choose a Sunset Private Cocktail Tour, Semi-Private Day Trip, or Private Day Trip aboard the Aeolus II.

Outdoor Water Activities: Sunset Private Cocktail Tour by Aeolus Sailing

Experience the magic of a Greek sunset aboard a private sail with Aeolus Sailing. Glide over clear waters, visit idyllic islands, and enjoy drinks as the sky turns vibrant colors—perfect for a memorable evening.

Outdoor Water Activities: Sunset Private Cocktail Tour by Aeolus Sailing

water activities

Skiathos

7-Hour Sailing Adventure with Aeolus Sailing in Skiathos

Spend a day sailing the clear waters of Skiathos and Skopelos with Aeolus Sailing. Swim, snorkel, and paddle board your way through famed Mamma Mia beaches and secret caves on this 7-hour adventure.

7-Hour Sailing Adventure with Aeolus Sailing in Skiathos

water activities

Skiathos

Private Sailing Adventures with Aeolus Sailing in Skiathos

Sail the crystal-clear Aegean aboard Aeolus II, visiting hidden gems like Skopelos, Lalaria, and Tsougria. Swim, snorkel, and savor gourmet meals on a private, crowd-free day trip.

Private Sailing Adventures with Aeolus Sailing in Skiathos

boat charters

About Aeolus Sailing

Aeolus Sailing operates sailing experiences based in the Skiathos region, offering private and semi-private tours around Skiathos and neighboring islands. The company runs a 3-hour Sunset Private Cocktail Tour that cruises around Skiathos with drinks and snacks, visits islands such as Skopelos and Tsougria, and includes opportunities for swimming in clear Aegean water.

For longer excursions, Aeolus Sailing offers a Semi-Private Day Trip lasting approximately seven hours. That trip explores Skiathos and Skopelos, visits iconic beaches featured in media, provides snorkeling, paddle boarding, fishing, and includes an onboard lunch with drinks.

Aeolus Sailing also operates private full-day charters aboard the Aeolus II. Private Day Trips visit Skopelos, Lalaria, Tsougria, Dasia, and Arkos, and focus on swimming, snorkeling, and a relaxed, crowd-free experience with meals served on board.

All trip descriptions, routes, and vessel names are provided by the operator. Schedules and availability vary by season; guests are advised to review current departure times and booking details when reserving. The business is featured on The Adventure Collective, where trips and itineraries are listed and described.

Contact and booking information is available through the operator’s official listings and The Adventure Collective profile. Guests looking for sunset cruises, private sailing, snorkeling, or island-hopping around Skiathos and Skopelos can find specific itineraries, inclusions, and practical details on the booking pages.

Local regulations, safety briefings, and crew instructions are included with each booking to ensure a smooth trip. Pricing and group size details are listed per tour on booking pages and may change seasonally. Updates.

Group jumping off yacht into clear coastal sea for summer swim

Skiathos Sailing & Skopelos Boat Tours with Aeolus Sailing

Aeolus Sailing offers a range of boat trips around Skiathos and Skopelos focused on island-hopping, snorkeling, and scenic cruising. Featured on The Adventure Collective, the operator provides clear itineraries for sunset cruises, semi-private day trips, and private full-day charters aboard vessels including the Aeolus II.

Popular Trip Types

Sunset Private Cocktail Tour (3 hours) — A compact sunset cruise around Skiathos with drinks, snacks, and swimming near Skopelos and Tsougria. Ideal for couples and small groups seeking a memorable Aegean sunset.
Semi-Private Day Trip (≈7 hours) — A shared day experience visiting Skiathos and Skopelos beaches, snorkeling spots, sea caves, and offering paddle boarding, fishing, and onboard lunch.
Private Day Trip (Full day aboard Aeolus II) — Private charter exploring Skopelos, Lalaria, Tsougria, Dasia, and Arkos with swimming, snorkeling, and meals served on board.

Why book Aeolus Sailing for Skiathos sailing

High-interest itineraries that include iconic Mamma Mia beaches and lesser-known coves.
Multiple trip formats: intimate sunset cruises, semi-private day trips, and private charters to match group size and preference.
Hands-on water activities such as snorkeling, paddle boarding, and fishing integrated into day trip itineraries.

What to expect on board

Clear, factual itineraries listing islands visited: Skopelos, Tsougria, Lalaria, Dasia, Arkos, and local swimming stops.
Onboard refreshments: the sunset tour includes drinks and snacks; the semi-private day trip includes an onboard lunch and drinks.
Opportunities to swim in the Aegean, snorkel at clear-water spots, and explore sea caves accessible from the vessel.

Practical booking information

Departure points are centered on the Skiathos area; exact boarding locations and schedules are listed on booking pages.
Trip durations range from a 3-hour sunset option to approximately 7 hours for semi-private day trips and full-day private charters.
Guests should consult the operator’s listing and The Adventure Collective profile for up-to-date pricing, seasonal availability, and group-size details.

Keywords & search terms

For travelers searching online, relevant terms include: Skiathos sailing, Skopelos boat tours, Sunset cruise Skiathos, private sailing Skiathos, Aeolus II charter, day trip Skiathos Skopelos, Mamma Mia beaches boat tour, snorkeling Skiathos, and island hopping Skiathos.

Final notes

Information on itineraries, vessel names, and inclusions is provided by the operator and listed on The Adventure Collective. Prospective guests should review specific trip pages for exact routes, safety notes, and booking requirements before reserving to ensure the chosen experience meets expectations.

Aerial view of sailboat anchored in turquoise Mediterranean waters

Reserve a Sailing Experience with Aeolus Sailing

Book a sunset cruise, semi-private day trip, or private charter around Skiathos and Skopelos — check availability and itinerary details before booking.