Sailing the Caribbean: Best Islands to Visit by Yacht in 7 Days

There’s something unforgettable about seeing the Caribbean from the deck of a yacht. The water shifts from turquoise to deep blue, trade winds fill the sails, and every stop has its own rhythm. Whether it’s your first charter number 101, a 7-day sailing trip lets you slow down, explore multiple islands, and still have time to work in those tan lines.

Here’s a 7-day Caribbean itinerary that blends easy sailing routes with unforgettable anchorages.

Day 1 – Tortola, British Virgin Islands (BVI)

Tortola is the natural starting point for many Caribbean yacht charters. The island has a protected harbor, plenty of provisioning options, and calm waters to ease into your trip.

• 🏝 Top stop: Cane Garden Bay for your first Caribbean sunset.
• ⛵ Why it’s great: Short, easy sail to your next destination.
• 🍹 Local tip: Grab a painkiller cocktail at a beach bar — they’re legendary here.

Day 2 – Norman Island

A short hop from Tortola, Norman Island is known for its crystal-clear snorkeling spots and pirate legends.

• 🐠 Must-do: Snorkel “The Caves” — said to have inspired Treasure Island.
• 🛥 Anchor: Bight Bay, well-sheltered and calm.
• 🌅 Evening: Dinghy to the floating bar for sunset drinks.

Day 3 – Virgin Gorda

Sail north to Virgin Gorda, home to one of the Caribbean’s most iconic natural wonders: The Baths. Giant granite boulders form a maze of pools and tunnels that are best explored in the morning before the day-trippers arrive.

• 🏊 Don’t miss: Devil’s Bay — a natural swimming pool.
• 🧭 Sailing tip: Arrive early for mooring balls near Spanish Town.
• 🌿 Vibe: Quiet, scenic, and unforgettable.

Day 4 – Anegada

Unlike the hilly islands nearby, Anegada is low and flat — a coral atoll that feels totally different.

• 🐢 Top activity: Snorkel Horseshoe Reef — the largest barrier reef in the Caribbean.
• 🦞 Foodie bonus: Try freshly caught lobster right on the beach.
• 🧭 Sailing tip: Anegada has shallow waters, so careful navigation (or a skipper) is a must.

Day 5 – Jost Van Dyke

A small island with a big reputation. Jost Van Dyke is famous for its barefoot beach bars and laid-back vibe.

• 🍸 Must-do: Visit Soggy Dollar Bar, where the Painkiller cocktail was born.
• 🏖 Best anchorage: White Bay (get there early — mooring balls go fast).
• 🕺 Vibe: Chill during the day, lively at night.

Day 6 – Cooper Island

On your way back toward Tortola, Cooper Island is a quiet, eco-friendly stop to recharge before your final sail.

• ☕ Highlight: A small beach club with craft coffee, local rum, and epic sunsets.
• 🧘 Vibe: Relaxed and peaceful — the perfect reset after Jost Van Dyke.

Day 7 – Return to Tortola

Sail back to Tortola at your own pace, maybe stopping at Peter Island for a quick swim. Most charters require returning the boat by late afternoon or evening.

• 📝 Pro tip: Schedule your flight for the next day to allow time to check out, refuel, and relax ashore.
• 🛳 End your trip: with dinner by the marina as the boats roll in.

🧭 Quick Tips for Your Caribbean Yacht Charter

• Best time to go: December through May (calm seas, steady winds)
• Type of charter: Ideal for both crewed and bareboat trips *read about the differences
• Experience level: Beginner-friendly route — great for first timers
• Packing essentials: Lightweight clothes, snorkel gear, reef-safe sunscreen, dry bag

✨ Why This Route Works

This itinerary is popular for a reason:

• Short sails between islands (usually under 3 hours)
• Mix of vibrant and quiet stops — snorkeling, exploring, relaxing
• Easy access from major airports via Beef Island (EIS)

Whether you’re celebrating a special occasion, traveling as a couple, or sailing with friends, this weeklong route is a perfect introduction to Caribbean yacht life.

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