If you’re dreaming of crystal-clear water, steady trade winds, and island hopping that actually feels relaxed, the Grenadines are hard to beat. This 7-day route starts in Grenada, works its way north through Carriacou, Union Island, Mayreau, and the Tobago Cays, then turns back south to finish in Grenada.
It’s a great starting point for first-time charterers, mixed crews, or anyone who wants a taste of the islands without feeling rushed. If you love the rhythm of this trip, you’ll find that a longer, 10-day itinerary very naturally builds on the same route with more time to explore, sail, and settle into island life.
And if you’re newer to chartering, short on time, or simply want a smoother experience, consider booking a skippered charter with an experienced local captain. You’ll still sail, explore, and make decisions as a crew, but with the benefit of local knowledge, insider tips, and someone who knows these waters intimately.
Day 1: Settle in around Grenada
St. George’s Anchorage or Flamingo Bay
Your first day is about getting comfortable with the boat, your crew, and the pace of Caribbean sailing. Staying close to Grenada keeps things simple while you sort provisioning, systems, and navigation. St. George’s is lively and convenient if you want to wander into town, while Flamingo Bay offers a quieter, more peaceful first night.
Day 2: Hop up to Carriacou
Tyrell Bay
This is your check-out point from Grenada. Tyrell Bay is protected, well serviced, and full of cruising boats, making it a natural gateway into the Grenadines. It’s also a lovely place to spend an evening, with a few beach bars and that unmistakable sailor-friendly vibe that makes you feel immediately at home.
Day 3: Cross into St. Vincent and the Grenadines
Union Island, Chatham Bay or Clifton Harbour
From Carriacou, you’ll sail north to Union Island, your first taste of the Grenadines proper.
In Chatham Bay, you can hire Sekkie to handle your check-in to St. Vincent and the Grenadines, which keeps things easy and efficient so you can stay focused on sailing and enjoying the day.
If you prefer to do it yourself, pick up a mooring in Clifton Harbour, complete your check-in, and take a short walk around town. Either option works well, and both give you a good feel for island life.
Day 4: Classic Grenadines charm in Mayreau
Saline Bay
Saline Bay is what many people picture when they imagine the Grenadines: calm water, clear anchoring, and a slow, easy pace. A short walk up the hill brings you to the tiny village where you can say hello to Robert Righteous and the Youths, a beloved local presence in Mayreau. It’s the kind of stop that reminds you why you came all this way.
Day 5: The Tobago Cays
Overnight in the park
The Tobago Cays are the highlight for many sailors, a necklace of uninhabited islands surrounded by reefs and impossibly blue water. It’s a perfect place to snorkel with turtles, paddle around the shallows, or simply drift and take it all in.
Most crews head to the popular beach lobster BBQ, but it can get crowded. If you’re looking for a quieter, more local-feeling experience, many sailors swear by Lobster BBQ by Tim in nearby Anse le Roche.
Day 6: Back toward Carriacou
Sandy Island or Anse le Roche
On your way south, you’ve got two excellent choices.
If you take a mooring at Sandy Island, be sure to stop and snorkel the newer underwater sculpture garden just off Jack-a-Dan. It’s a unique and surprisingly beautiful experience.
Alternatively, anchor in Anse le Roche for Tim’s lobster BBQ, widely considered the best in the Grenadines. The snorkeling around the large rock at the south end of the bay is excellent and often less busy than the Cays.
Day 7: Return to Grenada
Molinere Point
Finish your week at Molinere Point, where you can snorkel the Caribbean’s first underwater sculpture garden, just off the beach. It’s a calm, memorable final night before heading back into St. George’s in the morning.
Why this route works
This itinerary moves at a comfortable pace, mixes protected anchorages with open-water sailing, and gives you real options based on weather, crew energy, and personal preference. You hit the must-see spots without feeling rushed, and you get a genuine sense of what makes the Grenadines such a beloved cruising destination. Do we recommend spending more days exploring if you can? Absolutely!
Want to go deeper?
If this week leaves you wanting more, that’s exactly why many sailors choose a 10-day itinerary, which follows a similar path but allows for slower days in the Tobago Cays, additional stops around Union Island, and more time to simply live aboard and sail.
For those who want to focus more on the experience and less on logistics, a skippered charter with an experienced local captain is a fantastic option. You’ll still be part of the sailing, but you’ll benefit from local insight, smoother planning, and access to spots you might otherwise miss.
However you choose to do it, this route is a beautiful introduction to one of the world’s most spectacular sailing grounds.
See you on the water!
