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

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
0
View Details

Croatia A Learn-To-Sail Vacation

Adriatic Sailing Academy
Availability : Apr 26 - May 03 & Jul 19 - 26, 2025
101 / 103 / 104

Navigate Croatia’s breathtaking coastline, where hidden bays, historic cities, and crystal-clear waters await. Indulge in the rich local cuisine as you sail through a perfect blend of adventure, relaxation, and discovery—creating an unforgettable experience on the open sea.

From$2,100
0
View Details

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
0
View Details

Corfu & The North Ionian Sea, Greece A Learn-To-Sail Vacation

Fair Winds Sailing Greece
Availability : Jul 28 - Aug 02, Aug 04 - 09, Aug 11-16, & Aug 25-30, 2025
101 / 102 / 103 / 104 / 105 / 106 / 114 / 116 / 118

Sail the sparkling waters of the Ionian Sea and experience the magic of Greece with Fair Winds Sailing. Departing from the stunning island of Corfu, this all-inclusive adventure blends world-class sailing instruction with island hopping, swimming in turquoise bays, and exploring charming coastal towns. With expert guidance from Captain Dimitris Bampakos, a seasoned Greek Navy officer and master ASA instructor, you’ll gain real skills, earn certifications, and live the dream of sailing in one of the most beautiful places on earth.

From$1,890
0
View Details

A Mile-Building Cruise in the Cyclades, Greece A Learn-To-Sail Vacation

Athens Sailing Academy
Availability : Sep 13 - 20, 2025
104 / 105 / 106

Sail through the stunning Greek islands this September with Athens Sailing Academy’s ASA Milebuilder course. Spend 7 unforgettable days aboard a 55’ Beneteau, exploring the Cyclades and Dodecanese, including Lipsi, Arki, and Ikaria. Earn ASA 104, 105 & 106, enjoy expert instruction, local cuisine, night sailing, and up to 400NM of real offshore adventure.

From$1,650
0
View Details

Ionian Sea, Greece A Guided Flotilla

Whitecaps Sailing
Availability : May 24 - 31 & July 05 - 12, 2025

The Ionian Sea offers crystal-clear waters and breathtaking landscapes, and our flotilla combines the thrill of sailing with camaraderie, mythical legends, ancient history, and legendary Greek hospitality.

From$2,195
0
View Details

Poros, Greece A Women’s Learn-To-Sail Vacation

Athen's Sailing Academy
Availability : Jul 13 - 19 & Aug 10 - 16, 2025
101 / 102 / 103 / 104 / 105 / 106 / 114 / IPC

Join our all-women sailing courses in Greece and earn internationally recognized ASA certifications while exploring the stunning Greek islands. With hands-on training, supportive instruction, and a private cabin aboard a Jeanneau yacht, you’ll build confidence, skills, and unforgettable memories. No experience required!

From$1,700
0
View Details
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$3,000
(1 Review)
View Details

Saronic Gulf, Greece A Learn-To-Sail Vacation

Athens Sailing Academy
Availability : Jul 12 - 19, 2025
101 / 102 / 103 / 104 / 105 /106 / 114 / IPC

Embark on an unforgettable sailing adventure with Athens Sailing Academy. Situated in the stunning Saronic Gulf near Athens, we offer a comprehensive sailing curriculum against the backdrop of the beautiful blue Aegean Sea. From our home port on the quaint island of Poros, just an hour’s ferry ride from Athens, explore the diverse landscapes of the Southern Peloponnese, Cyclades, Sporades, and Dodecanese islands.

From$1,800
0
View Details
LIMITED CABINS AVAILABLE

EXPLORE THE AMALFI COAST ABOARD CHRONOS A LUXURY CRUISE

American Sailing
Availability : July 2025

Experience the enchanting allure of the Italian coast – from the picturesque Amalfi and Positano to the captivating islands of Capri and Ischia. Bask in the sun-drenched hillside villages, where the air is imbued with the tantalizing scent of citrus. Indulge in the delights of limoncello and embrace the charm of “Molto Bene.” Embark on a journey of luxury aboard a sailboat, as we navigate the azure waters of the Amalfi Coast in the summer of 2025.

From$4,050
0
View Details

Montenegro A Guided Flotilla

Whitecaps Sailing
Availability : Aug 30 - Sep 06, 2025

Imagine a week exploring the pristine waters of the Saronic Gulf, setting sail from Athens alongside a community of adventurous, like-minded travelers. Discover hidden coves, swim in azure bays, and dock in charming Greek villages each evening, where local culture and cuisine await!

From$2,295
0
View Details

Central Dalmatian Islands, Croatia A Guided Flotilla

Whitecaps Sailing
Availability : Aug 23 - 30 & Sep 13 - 20, 2025

An unforgettable sailing adventure as we explore the stunning islands of Hvar, Vis, and other hidden gems along Croatia’s pristine coastline. Whether you’re an experienced sailor or a newcomer, this journey offers a perfect blend of beautiful sailing conditions, historic towns, and vibrant local culture.

From$2,295
0
View Details

Gulf of Fethiye, Turkey A Guided Flotilla

Whitecaps Sailing
Availability : Sep 20 - 27, 2025

From the vibrant history of Pashas and Whirling Dervishes to the breathtaking ruins of ancient Greek, Roman, and Ephesus cities, Turkey is a land where East meets West in perfect harmony. And now, you can sail its stunning Mediterranean waters with Med Sailing Adventures.

From$2,295
0
View Details

Dubrovnik to Split, Croatia A Guided Flotilla

Whitecaps Sailing
Availability : Sep 06 - 13, 2025

Join our Mile Builder Flotilla for a stunning one-way journey from Dubrovnik to Trogir near Split. Experience the charm of Ston, the natural beauty of Mljet National Park, and the rich history of Korčula before soaking up the vibrant atmosphere of Hvar. This adventure is perfect for building your sailing skills while exploring Croatia’s breathtaking coastline. Set sail with us for an unforgettable week of discovery and camaraderie on the water!

From$2,295
0
View Details
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
0
View Details
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$4,050
0
View Details
SOLD OUT

ST TROPEZ & MALLORCA ABOARD CHRONOS A LUXURY CRUISE

American Sailing
Availability : October 2025

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$4,050
0
View Details