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TUE • MAY 21 • 4:30PM PT

Sail Power For Cruisers

Boost your sailboat’s speed & efficiency while under sail. Master sail configurations & weather tactics for monohulls & catamarans.

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MAY 25 - JUN 1 • 2024

Greece & The Aegean Sea

Sail with us on the Magical Aegean Sea, visit ancient ruins and old castles, and taste the real Greek Mediterranean diet.

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TUE MAY 28 • THU MAY 30 • 4:30PM PT

Rules To Know Around The Race Course

Join champion racer Dave Perry as we master boat-on-boat tactics for successful racing—from start to finish line maneuvering.

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Part 1 • TUE MAY 28 • 4:30PM PT

Rules You Need To Know Around The Race Course

Join champion racer Dave Perry as we master boat-on-boat tactics for successful racing—from start to finish line maneuvering.

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Part 2 • THU MAY 30 • 4:30PM PT

Rules You Need To Know Around The Race Course

Join champion racer Dave Perry as we master boat-on-boat tactics for successful racing—from start to finish line maneuvering.

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JUN 1 • 2024

Dalmation Islands, Croatia

Embark on an unforgettable sailing journey tracing a course across Croatia's beautiful coastline.

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TUE • JUN 04 • 4:30PM PT

Voyage Planning In A Changing World

Learn how to plan and navigate safely with world-renowned sailor Jimmy Cornell as we cover planning essentials for global journeys.

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THU • JUN 06 • 4:30PM PT

VHF Confidence: Mastering Marine Radio Communication

Gain confidence in your VHF skills. Learn how to master VHF communication from common uses to protocol nuances.

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JUN 2024

British Virgin Islands, Caribbean

Find out why cruising sailors refer to the British Virgin Islands as a “sailor’s paradise.”

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2 PART SERIES • TUE JUN 11 & THU JUN 13

ASA 102 Essentials

Learn how to master keelboat sailing essentials, from sail trim to crew roles, in preparation for your ASA 102 Certification.

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PART 1 • TUE JUN 11 • 4:30PM PT

ASA 102 Essentials

In part one of this two-part series, we will dive into a quick ASA 101 review, followed by 102 topics including safety, boat handling, crew overboard, sail trim basics, and more.

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PART 2 • THU JUN 13 • 4:30PM PT

ASA 102 Essentials

In part two of this two-part series, we will continue covering 102 essentials including sail shape, balance, trim techniques for various wind conditions and more.

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Jun 2024

Victoria & the Gulf Islands

Join fellow sailors for a week cruising the beautiful San Juan and Canadian Gulf Islands to Victoria, BC.

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JUN 2024

Islands of Belize

Experience the beauty of Belize on this sailing flotilla. Explore new locations every day, enjoy snorkeling, and more.

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JUN 2024

Greece

Experience Greece's Corfu Islands through sailing, cultural immersion, and personalized bareboat chartering.

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TUE • JUN 25 • 4:30PM PT

Worldwide Anchoring Techniques

Learn how to confidently anchor worldwide, gaining confidence and enhancing your cruising experience.

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2 PART SERIES • TUE JUL 9 & THU JUL 11

Winning Tactics Around The Race Course

Master racing tactics with champion racer Dave Perry in this comprehensive online class series.

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PART 1 • TUE JUL 9 • 4:30PM PT

Winning Tactics Around The Race Course

Elevate your racing game with expert insights from champion racer Dave Perry, covering essential boat-on-boat tactics for competitive success.

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PART 2 • THU JUL 11 • 4:30PM PT

Winning Tactics Around The Race Course

Master boat-on-boat tactics for successful racing with champion racer Dave Perry. Learn strategic positioning for winning races!

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JUL 2024

Islands of Belize

Experience the beauty of Belize on this sailing flotilla. Explore new locations every day, enjoy snorkeling, and more.

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AUG / SEP • 7 DAYS • LIMITED SPOTS

Grand Tour of New England

Join us aboard Arabella, a 157-foot mega yacht, to explore all the sights of Martha’s Vineyard, Nantucket, and Cuttyhunk.
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AUG 2024

Gastro-Sail, Croatia

Explore the ancient city of Dubrovnik, Discover Ston & its well-preserved city walls and salt works.

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AUG 2024

Dalmatian Islands, Croatia

A sailor’s paradise with crystal clear waters, picturesque fishing villages, and scenic coves for anchoring.
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SEP 2024

Turkey

Turquoise waters, secluded anchorages, small restaurants, and amazing gastronomy is the recipe for a memorable flotilla vacation.
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SEP 18-22 • 2024

Seattle, WA

Master racing trim, helming, and boat handling with practical on-water training and shoreside seminars taught by seasoned coaches.
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NOV 2024

Islands of Belize

Experience the beauty of Belize on this sailing flotilla. Explore new locations every day, enjoy snorkeling, and more.

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DEC 2024

British Virgin Islands, Caribbean

Discover why the “Christmas Winds” make December in the BVI a sailing mecca!

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DEC 2024

The Bahamas, Caribbean

Explore turquoise waters, encounter dolphins, reefs, and sea turtles, during this extraordinary Bahamas flotilla - guided by the experts at Whitecaps Sailing.
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DEC 2024

Islands of Belize

Experience the beauty of Belize on this sailing flotilla. Explore new locations every day, enjoy snorkeling, and more.

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JAN 31 - FEB 7 • 2025

British Virgin Islands, Caribbean

Join Annapolis Sailing School for an unforgettable voyage through the British Virgin Island's azure waters. Enjoy daily sailing excursions, island hopping, and leisurely activities like snorkeling and beachcombing.
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JAN 8 - FEB 15 • 2025

British Virgin Islands, Caribbean

Join Annapolis Sailing School for the adventure of a lifetime in a tropical paradise. Sail through azure waters, indulge in leisurely activities like snorkeling and beachcombing while island hopping. 
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JUL 2025 • 8 DAYS • 1 SPOT REMAINING

Explore The Amalfi Coast Aboard Chronos

Join American Sailing as we discover the Amalfi Coast (Amalfi, Positano, Capri, and more) from Luxury Yacht Chronos.