If you’re dreaming of turquoise anchorages, quiet coves, and a fresh breeze filling your sails, now’s the time to start planning. Booking your 2026 bareboat charter early gives you first pick of boats, the most flexible travel dates, and access to early-booking rates.
Whether you’re envisioning a week exploring Grenada and the Grenadines or a skippered adventure to build confidence before going fully bareboat, planning now means you’ll be ready to cast off when your perfect sailing season arrives.
Why Book Now
Sailboats aren’t unlimited—and neither are ideal travel dates. Peak season in the Caribbean runs from December through April, when steady trade winds and dry skies make for perfect sailing. By midyear, the best boats and weeks are often booked solid.
Here’s why smart sailors plan ahead:
- Choose your yacht: The best-maintained boats, with the layouts and amenities you want, go first.
- Secure your favorite dates: Align your trip with your schedule, crew, or special occasions.
- Lock in lower rates: Early bookings often qualify for shoulder-season pricing or promotional savings.
- Enjoy stress-free planning: More time means smoother coordination for travel, provisions, and crew.
Booking early isn’t just about getting a deal—it’s about creating options. The more flexibility you have, the easier it is to craft a trip that fits your goals and sailing style.
How Bareboat Chartering Works
A bareboat charter is the sailing world’s version of renting a vacation home—except your “home” moves with you from island to island. You take the helm, chart your own course, and decide when to hoist the sails or drop anchor.
Here’s what the process looks like:
1. Choose Your Location
Start with your dream destination. The Grenada and Grenadines are ideal for experienced sailors who want a mix of adventure and relaxation. With steady trade winds, line-of-sight navigation, and uncrowded anchorages, this stretch of the southern Caribbean is made for sailors who like variety—vibrant island towns one day, untouched nature the next.
2. Pick Your Dates and Duration
Most charters run seven to ten days, but you can tailor your trip to match your schedule. Shoulder season (May–June and November) often offers calmer anchorages and attractive pricing, while prime season (December–April) brings the liveliest atmosphere and ideal sailing conditions.
3. Select Your Boat
Your boat is both your transportation and your home.
- Monohulls are great for traditionalists who love the feel of classic sailing and heeling under wind.
- Catamarans offer more stability, space, and comfort—especially nice for groups or newer sailors.
Need help deciding? Our team can walk you through the pros and cons based on your comfort level, budget, and goals for the trip.
4. Add a Skipper (Optional)
If you’re not quite ready to take full command, consider booking a skippered charter. You’ll enjoy the same privacy and flexibility as a bareboat, but with an experienced captain aboard. It’s a great way to relax while still learning hands-on from a pro. Many guests combine this option with training to prepare for future bareboat charters.
Build Confidence with ASA 111: Cruise Crew Review
If you’ve already earned your ASA 104 certification but want a little more experience before skippering your own yacht, the ASA 111 Cruise Crew Review is your perfect next step.
This liveaboard course lets you practice in real-world conditions—anchoring, docking, navigation, sail trim, and crew coordination—under the guidance of a professional instructor. You’ll earn your ASA 111 certification, build confidence, and leave ready to plan your own charter with ease.
The Grenada and Grenadines are a prime classroom for this kind of training: consistent wind, scenic passages between islands, and countless opportunities to refine your seamanship skills while enjoying some of the most beautiful cruising grounds in the world.
Chartering in Grenada and the Grenadines
Sailing from Grenada offers one of the best bareboat routes in the Caribbean. The chain of islands to the north—the Grenadines—includes dreamy stops like Carriacou, Union Island, Mayreau, and the famous Tobago Cays Marine Park.
Each day brings something new: snorkeling with sea turtles, beach bar lunches, lively island music, and quiet nights under the stars. With short hops between islands and consistent trade winds, it’s easy to tailor your route for adventure, relaxation, or both.
Ready to Start Planning?
Bareboat chartering gives you ultimate freedom—the ability to explore the Caribbean your way, on your schedule. But the best adventures start with early planning.
Booking your 2026 charter now means:
- More boat options
- Better pricing
- Time to train, plan, and dream
Whether you’re ready to take the helm yourself or prefer to sail with a skipper while earning ASA 111, now is the time to secure your week on the water.
Start planning your Grenada bareboat adventure today → Email [email protected]
