MEDITERRANEAN

ENJOY A SAILING VACATION IN THE MEDITERRANEAN

The Mediterranean is renowned for its beautiful weather and tideless waters, making it the ideal destination for a sailing vacation. Exploring the area by boat gives you access to some amazing less-traveled areas. There are also a lot of cultural attractions and delicious food to enjoy.

Popular Mediterranean Sailing Destinations: Croatia | Italy | Greece | Spain | Turkey

Greek Island Hopper A Guided Flotilla

Fair Winds Sailing Greece
Availability : Sep 27 - Oct 03, 2026

Set sail on the Greek Island Hopper Flotilla, hosted by Fair Winds Sailing Greece, and experience the beauty of Corfu and the surrounding Ionian islands. Guided by local captains, you’ll visit favorite anchorages, UNESCO World Heritage sites, and charming island towns while enjoying the perfect blend of sailing, culture, and relaxation. Sail aboard modern monohulls or catamarans, share meals and onshore excursions with fellow sailors, and discover Greece as seen through the eyes of those who know it best.

From$2,250
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MALLORCA A GUIDED FLOTILLA

Nautilus Sailing
Availability : May 23 - 30, 2026

Sailing the coastline of Mallorca is a dreamlike journey through the heart of the Mediterranean. As the largest of Spain’s Balearic Islands, Mallorca offers an irresistible blend of rugged coastlines, serene turquoise coves, charming seaside villages, and rich Spanish culture. The island is a sailor’s paradise—calm waters, steady breezes, and countless hidden anchorages create the perfect conditions for a relaxed and unforgettable voyage. Whether you’re exploring remote natural parks, enjoying a beachside paella, or sipping wine beneath the stars, Mallorca invites you to experience sailing at its most beautiful.

From$3,750
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Amalfi Coast A GUIDED FLOTILLA

Whitecaps Sailing
Availability : May 23 - 30, 2026

Set your course for a week of Italian magic on the Amalfi Coast Flotilla. This unforgettable journey blends world-class sailing with iconic stops in Capri, Positano, and Procida. Enjoy crystal-clear waters, gourmet cuisine, and sun-soaked coastlines aboard a luxurious catamaran, all with the perfect balance of freedom and expert support. Limited to just three boats, this is small-group adventure at its finest. Reserve your cabin today and sail Italy like never before.

From$2,750
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Corfu & Paxos Islands, Greece A Learn-To-Sail Vacation

Fair Winds Sailing Greece
Availability : May 05 - 10, May 19 - 24, Jun 09 – 14, & Oct 06 – 11, 2025
101 / 102 / 103 / 104 / 105 / 106 / 114 / 116 / 118

Embark on a week-long journey through the enchanting Ionian Sea aboard the well-equipped training vessel, Starlight. Guided by experienced American Sailing-certified instructors, you’ll gain hands-on sailing skills while exploring the breathtaking beauty of Corfu and Paxos islands.

From$1,790
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LIMITED CABINS AVAILABLE

EXPLORE CROATIA ABOARD CATALEYA A LUXURY CRUISE

American Sailing
Availability : Jul/Sep 2025 & May/Sep 2026

Welcome aboard Cataleya a 30 meter luxury sailing yacht which will be your home for 8 days as you explore the Dalmation coast of Croatia. This trip will include stops in Split, Hvar, Korcula as well as a few anchorages that are the secrets of the captain and the crew. Join us on a once-in-a-lifetime sailing vacation.

From$3,100
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10% OFF

Poros, Greece A Learn-To-Sail Vacation

Athens Sailing Academy
Availability : Sep 20 - Oct 31, 2025
101 / 102 / 103 / 104 / 105 / 106 / IPC

Join Athens Sailing Academy this fall in Greece and learn to sail while exploring the Aegean. With week-long ASA certification courses, private cabins aboard Jeanneau yachts, English-speaking instructors, and hands-on training in real island conditions, you’ll gain confidence and skills while experiencing the beauty of Poros and the Greek islands. Fall discounts available.

From$1,700$1,530
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NEW

Sailing The South of France aboard Chronos A LUXURY CRUISE

American Sailing
Availability : October 2025

Embark on a luxurious sailing trip starting in St. Tropez, exploring Cap Bregancon and the stunning Îles d’Hyères, including Île de Porquerolles. After relaxing on beautiful beaches, return to St. Tropez to discover iconic sites like Place des Lices and the citadel. Experience the best of the French Riviera.

From$4,050
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NEW

EXPLORE MALLORCA ABOARD CHRONOS A LUXURY CRUISE

American Sailing
Availability : October 2026

Embark on a 8-day luxury sailing adventure aboard Chronos Yacht, exploring Mallorca to Menorca with American Sailing. Enjoy personalized service, secluded coves, and stunning coastlines with a small, passionate group. This intimate voyage offers full-board luxury, breathtaking views, and unique experiences in the heart of the Balearic Islands. Set sail for an unforgettable journey this fall.

From$4,250
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Eclipse on the Med, Mallorca, Spain A Guided Flotilla

Whitecaps Sailing
Availability : Aug 08 - 15, 2026

Experience the magic of a total solar eclipse as it unfolds above the waters of the Mediterranean—an awe-inspiring event witnessed from the deck of a sailing yacht off the coast of Mallorca. This once-in-a-lifetime adventure combines the wonder of the cosmos with the natural beauty, rich history, and coastal charm of one of Spain’s most stunning islands

From$3,150
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SOUTH OF FRANCE & MALLORCA ABOARD CHRONOS A LUXURY CRUISE

American Sailing
Availability : October 2026

Your journey begins in the glamorous port of St. Tropez, known for its luxury yachts, vibrant nightlife, and charming old town. As you set sail from this iconic French Riviera destination, the Mediterranean’s turquoise waters will guide you toward Marseille. Along the way, you can enjoy the stunning coastal landscapes, with opportunities for swimming in secluded coves or relaxing on deck.

From$4,250
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