Set Sail for Adventure: Join The Joy of Sailing Carib 2027 and Explore Grenada St Vincent St Lucia Martinique and Dominica

Captain Lynda
2 days ago
4 min read

Imagine waking up to the gentle sway of a sailboat on crystal-clear Caribbean waters, surrounded by lush islands, vibrant cultures, and endless opportunities for adventure. The Joy of Sailing Carib 2027 is ready to make that dream your reality. After a highly successful season with over 10 groups exploring the stunning Caribbean, we are excited to announce our sailing schedule for 2027 — now featuring new destinations like Grenada, St. Lucia, Martinique, and Dominica.

To secure your spot and learn more about costs, call Lynda at 562-652-7374. This year promises even more unforgettable experiences, and spaces fill quickly. Here's pics of a fraction of the 2026 sailing season fun.

Schedule The Joy of Sailing Carib 2027

Please note that weather is always a factor...afterall, this is sailing! Also, dates may be flexible to help you save flight costs so look at flight itineraries and give Lynda a call today!

Why Choose The Joy of Sailing Carib 2027

Last season, more than 10 groups enjoyed the perfect blend of relaxation and adventure on our sailing trips. Participants praised the stunning scenery, friendly crews, and the chance to explore islands that few get to see from the water. This year, we are expanding our itinerary to include four new islands, each offering unique landscapes and cultural experiences.

Our trips are designed for sailors of all levels. Whether you are an experienced sailor or a first-timer, our knowledgeable crew will guide you through every step. The Joy of Sailing Carib offers a perfect mix of sailing, island exploration, and social time with fellow travelers.

New Destinations to Discover in 2027

Grenada

Known as the "Spice Isle," Grenada offers fragrant nutmeg plantations, pristine beaches, and vibrant coral reefs. Sail into secluded bays and enjoy snorkeling among colorful marine life. Onshore, explore the historic forts and bustling markets filled with local crafts and spices.

St. Lucia

St. Lucia’s iconic Pitons rise dramatically from the sea, creating one of the most breathtaking backdrops in the Caribbean. Hike through tropical rainforests, relax in natural hot springs, or visit charming fishing villages. The island’s mix of French and English heritage adds a rich cultural layer to your visit.

Martinique

Martinique blends French sophistication with Caribbean charm. Explore botanical gardens, sample Creole cuisine, and stroll through colorful towns. The island’s volcanic landscapes and black sand beaches provide stunning scenery for both sailing and shore excursions.

Dominica

Known as the "Nature Island," Dominica is a paradise for eco-adventurers. Sail into untouched bays, hike to waterfalls, and swim in natural hot springs. The island’s lush rainforests and diverse wildlife make it a unique destination for those who love outdoor exploration.

Fabulous Repeats from 2026

St. Vincent — The lush, mountainous heart of St. Vincent offers dramatic volcanic scenery, quiet anchorages, and a more off-the-beaten-path Caribbean feel. Explore local villages, hike to breathtaking viewpoints, and enjoy the island’s warm, authentic culture.

Bequia Island — Life Aquatic's home port...Charming and laid-back, Bequia is known for its friendly harbor town, beautiful beaches, and classic Caribbean sailing vibe. Stroll the waterfront in Port Elizabeth, browse local boutiques, enjoy cocktails at the local bar "Rendezvous" where you can catch a backgammon game and get to know the wonderful locals. Snorkeling here is off the charts as is the very active sailing community with its daily fun events including pub crawls, dinghy floats and group dinners.

Union Island — A favorite among sailors, Union Island delivers vibrant island energy with stunning views. We harbor in the secluded Chatham Bay and enjoy a wonderful dinner with our toes in the sand at Sunset Cove Beach Bar and Grill. Tenuta, the boutique resort with an infinity pool and 5 star menu under the tikit bar is a sailors favorite!

Tobago Keys — A true sailing paradise, the Tobago Keys are a protected cluster of tiny islands surrounded by crystal-clear water and coral reefs. Snorkel with sea turtles, relax on powdery white sand, and experience some of the most spectacular turquoise lagoons in the Caribbean. This stop also offers an amazing Fresh Lobster Dinner under the stars.

Canouan Island — Elegant yet naturally beautiful, Canouan blends upscale island charm with pristine beaches and calm, clear waters. It’s the perfect place to recharge because here we enjoy the lifestyle of the rich and famous. We harbor at The Sandy Lane Yacht Club with it's killer pool, bar and Shenanigans restaurant. In the morning we hop over to the French Bakery to grab coffee and fresh baked goods that we enjoy under the cabanas at the natural sea water pool. Sundowns are enjoyed at Scruffy's, the best beach bar in the islands with giant Jenga and incredible views.

What to Expect on Your Sailing Adventure

Our 2027 sailing schedule offers flexible options to fit your travel plans. Each trip includes:

Comfortable sailing vessels equipped with modern amenities
Experienced crew to assist with sailing and local knowledge
Daily excursions to explore islands, beaches, and cultural sites
Opportunities for snorkeling, swimming, and hiking
Delicious meals featuring fresh local ingredients
Paddleboarding, dinghy rides and fun local bars

We tailor each journey to balance sailing time with onshore activities, ensuring you experience the best of the Caribbean’s natural beauty and culture.

Reserve Your Spot!

Spaces for The Joy of Sailing Carib 2027 fill quickly due to high demand. To save your spot or ask about costs, call Lynda at 562-652-7374. She will provide detailed information about trip dates, pricing, and any special offers.

Booking early gives you the best chance to choose your preferred dates and cabin. Whether you want a solo adventure, a romantic getaway, or a group trip with friends, we can help you plan the perfect sailing vacation.

Join the Growing Community of Joyful Sailors

The Joy of Sailing Carib has built a community of travelers who share a passion for the sea and island life. Many guests return year after year, drawn by the welcoming atmosphere and the chance to explore new destinations.

By joining the 2027 season, you become part of this community. Meet new friends, share stories, and create memories that last a lifetime.

Set your course for adventure and discovery with The Joy of Sailing Carib 2027. Call Lynda today at 562-652-7374 to reserve your place and start planning your Caribbean escape. The islands of St. Vincent & the Grenadines, Grenada, St. Lucia, Martinique, and Dominica await your arrival. Don’t miss the chance to sail, explore, and experience the Caribbean like never before.