Round Trip
The Classic Grenadines: Bequia, Mustique and Tobago Cays Round Trip
The Classic Grenadines Ring Yacht Charter Itinerary
The Classic Grenadines Ring represents the perfect introduction to this legendary cruising ground, combining the most celebrated destinations with pristine anchorages in a balanced seven-day round trip from Bequia. This itinerary has been refined over decades of charter operations to capture the essential Grenadines experience while maintaining comfortable daily passages and providing ample time for exploration at each destination. Starting and ending at Admiralty Bay gives you the advantage of Bequia's excellent provisioning facilities and relaxed island atmosphere, while the circular route ensures you experience each location only once without backtracking or rushing.
The route takes you progressively south through the heart of the Grenadines, visiting islands that range from exclusive private resorts to completely uninhabited cays. You will experience the glamorous sophistication of Mustique, the pristine marine wilderness of the Tobago Cays, the postcard perfection of Salt Whistle Bay, and the peaceful seclusion of numerous other anchorages that define Caribbean cruising at its finest. The sailing conditions throughout remain consistently excellent, with steady trade winds providing ideal beam-reach and broad-reach passages of 5 to 12 nautical miles between destinations. These manageable distances allow morning departures around 9 or 10 AM with arrivals by early afternoon, leaving plenty of time for swimming, snorkeling, beach exploration, and relaxation.
What makes this itinerary particularly special is its carefully balanced progression. The first half takes you south through increasingly remote and pristine destinations, culminating in the spectacular Tobago Cays at the route's midpoint. The return journey maintains interest by routing you through different anchorages on the western side of the island chain, ensuring continuous variety while working back toward Bequia. By week's end, you will have experienced the full spectrum of what makes the Grenadines one of the world's premier yacht charter destinations, from celebrity hideaways to wilderness marine parks, all while enjoying some of the finest sailing conditions found anywhere in the Caribbean.
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Day 1: Admiralty Bay, Bequia to Britannia Bay, Mustique
Nautical Miles: 10
Travel Time: 2 hours
Your Grenadines adventure begins in the beautiful natural harbor of Admiralty Bay, where Port Elizabeth provides excellent provisioning facilities and a charming island atmosphere for your departure preparations. After completing check-in formalities and stowing your provisions aboard, cast off from your mooring or anchor and set course south toward the exclusive island of Mustique. The passage offers excellent sailing conditions with steady trade winds, typically providing a comfortable beam reach that allows you to make good speed while enjoying views of the surrounding islands. As you leave Bequia behind, its green hills and scattered settlements gradually diminish astern while Mustique's manicured profile emerges ahead.
Approach Britannia Bay on Mustique's western coast and take one of the available moorings or anchor in the designated yacht area, following the island's specific guidelines designed to protect this carefully managed destination. Once secured, go ashore to explore one of the Caribbean's most exclusive retreats, where privacy and understated elegance define the atmosphere. Visit the legendary Basil's Beach Bar for lunch and celebrity spotting, browse the tasteful boutiques in the small village, or arrange beach access at spectacular Macaroni Beach with its pristine white sand and turquoise waters. The island maintains an remarkably peaceful environment despite its fame, with beautiful beaches that often feel almost private. Enjoy sundowners at the Cotton House terrace before returning to your yacht for your first evening at anchor, surrounded by the gentle sounds of the Caribbean and preparing for the days ahead.
Route Highlights
- Departing Admiralty Bay and sailing south with excellent trade wind conditions toward exclusive Mustique.
- Securing moorings in Britannia Bay and stepping ashore on one of the Caribbean's most legendary private islands.
- Visiting famous Basil's Beach Bar and exploring the pristine beaches including spectacular Macaroni Beach.
Caribbean, Grenadines, Britannia Bay, Mustique, View of a beach
Day 2: Britannia Bay to Canouan
Nautical Miles: 11+
Travel Time: 2 hours
Depart Mustique after a leisurely breakfast and continue your southward progression toward Canouan, an island that balances luxury resort development with authentic local Caribbean culture. The passage offers flexibility for detours or swim stops at the small uninhabited cays scattered along this section of the chain, where pristine reefs and crystal-clear waters provide excellent snorkeling opportunities. The sailing conditions remain ideal with consistent trades, allowing you to maintain good speed while enjoying the spectacular scenery of the central Grenadines stretching away in both directions. As Canouan grows larger ahead, you can distinguish both the resort development along the western beaches and the more traditional fishing villages on the windward side.
Round the southern point and head up the western coast to anchor in Charlestown Bay near the island's main settlement, where good holding in sand bottom and protection from the trades create a comfortable overnight anchorage. Canouan provides a welcome change of pace from Mustique's exclusivity, with genuine local interactions available as you explore the small town where fishing boats and modest homes reflect authentic island life. Spend your afternoon visiting the local shops and restaurants, relaxing on the beautiful beaches of Godahl or Grand Bay, or arranging access to the resort's world-class golf course and spa facilities if you prefer more polished amenities. The contrast between the two sides of the island provides interesting insights into Caribbean development patterns. As evening approaches, dine ashore or aboard while watching the sun set over the sea and preparing for tomorrow's highlight: the legendary Tobago Cays.
Route Highlights
- Sailing south through the central Grenadines with optional stops at uninhabited cays for pristine reef snorkeling.
- Anchoring at Canouan and experiencing the unique contrast between luxury resort and traditional fishing village.
- Exploring beautiful beaches and authentic local culture in Charlestown and the surrounding areas.
Overhead View of an Exclusive Caribbean Beach
Day 3: Canouan to Tobago Cays
Nautical Miles: 6
Travel Time: 1 hour
This morning brings the moment many sailors consider the pinnacle of any Grenadines charter: arrival at the world-famous Tobago Cays Marine Park. The short passage from Canouan allows you to depart at a relaxed hour while still arriving with the full day ahead for exploration of this spectacular protected area. As you approach from the north, the scene that unfolds represents the quintessential Caribbean dream: five small uninhabited cays surrounded by brilliant turquoise lagoon waters, all protected by the long barrier reef known as Horseshoe Reef. The colors alone justify the trip, with shades of blue and green that seem almost artificial in their intensity against the white sand beaches and swaying coconut palms.
Navigate carefully through the marked entrance channel and take one of the available moorings to avoid damaging the fragile coral bottom with your anchor. Position yourself with views of the surrounding cays and Horseshoe Reef stretching away to the east. Once secured, the rest of your day belongs to exploration and enjoyment: snorkel or dive the spectacular coral gardens along the reef where healthy elkhorn and staghorn formations host countless tropical fish, swim with the resident hawksbill and green sea turtles that frequent the shallow waters near Baradal Island, explore the pristine beaches of the uninhabited cays, or simply relax in your cockpit soaking up the extraordinary beauty surrounding you. Local vendors arrive by small boat offering fresh lobster, fish, and tropical fruits throughout the day. As afternoon turns to evening and the day-trippers depart, the Tobago Cays transform into a peaceful paradise shared only among the charter yachts anchored for the night, with brilliant stars emerging overhead and bioluminescence sparkling in the water around your hull.
Route Highlights
- Arriving at the legendary Tobago Cays Marine Park, the crown jewel of Caribbean yacht charter destinations.
- Swimming with wild sea turtles and snorkeling the pristine coral gardens of Horseshoe Reef.
- Experiencing the magical evening transformation as the protected lagoon becomes a peaceful paradise under the stars.
Top View of Tobago Cays
Day 4: Tobago Cays to Salt Whistle Bay, Mayreau
Nautical Miles: 3
Travel Time: 30 minutes
Wake early to enjoy sunrise snorkeling in the Tobago Cays before the day boats arrive from the larger islands, then prepare for the very short hop west to Salt Whistle Bay on the island of Mayreau. This brief passage, often the shortest of any Grenadines itinerary, allows you to enjoy a leisurely morning in the Cays while still reaching your next destination with the full afternoon ahead. The route takes you across the channel between the protected lagoon and Mayreau's eastern shore, a journey so brief you might be tempted to stay longer in the Tobago Cays. However, Salt Whistle Bay offers its own brand of perfection that makes the move worthwhile.
Round Mayreau's northern point and enter the stunning natural harbor of Salt Whistle Bay, one of those rare anchorages that exceeds even the most optimistic expectations. The bay presents a perfect crescent of white sand backed by coconut palms, with crystal-clear waters providing excellent holding in sand bottom and good protection from the prevailing winds. Take one of the available moorings or anchor carefully in the designated areas, positioning yourself for easy access to the beach. Spend your afternoon swimming in the impossibly clear water, walking the beautiful beach where a few small beach bars offer cold drinks and simple food, or hiking over the hill to Saline Bay on the windward side for different perspectives and excellent snorkeling along the fringing reef. The tiny village atop Mayreau's central hill is accessible by a steep path and offers spectacular views across the southern Grenadines. As evening settles over the anchorage, enjoy the peaceful atmosphere of this small bay where swaying palms and gentle waves create the perfect Caribbean soundtrack.
Route Highlights
- Sunrise snorkeling session in the Tobago Cays before departing for nearby Mayreau.
- Entering the postcard-perfect crescent of Salt Whistle Bay with its palm-fringed white sand beach.
- Swimming in crystal-clear waters and hiking to Mayreau's hilltop village for spectacular Grenadines views.
Salt Whistle Bay, Mayreau
Day 5: Salt Whistle Bay to Petit St. Vincent
Nautical Miles: 7
Travel Time: 1.5 hours
Depart Salt Whistle Bay and set course south toward Petit St. Vincent, passing between Union Island to the west and the smaller cays scattered along the route. This passage marks your furthest point south in the Grenadines chain, bringing you to the doorstep of Grenadian waters just beyond. The sailing conditions remain excellent with steady trades, and the relatively short distance allows for a relaxed morning departure while arriving with plenty of afternoon time for enjoying PSV's special character. As you approach, the low green profile of this 115-acre private island resort emerges from the brilliant blue waters, its pristine beaches visible along the western and southern shores.
Navigate into the designated yacht anchorage off the western beaches, taking one of the available moorings or anchoring in sand with attention to the resort's guidelines for visiting vessels. Petit St. Vincent has welcomed yachters for decades with its unique combination of exclusivity and accessibility, maintaining high standards while graciously allowing visiting yachts to enjoy the island's beaches and facilities. Once settled, spend your afternoon swimming in the crystal-clear waters, exploring the pristine beaches that rank among the finest in the entire Grenadines, or arranging lunch at the resort's beachfront restaurant where the cuisine matches the spectacular setting. The resort's famous flag communication system, where guests use colored flags to signal staff at their individual cottages, adds charming old-world character to the experience. Snorkeling around the island's fringing reefs reveals healthy coral formations and abundant tropical fish. As evening approaches, enjoy sundowners from your cockpit with views across the channel toward Petite Martinique, knowing tomorrow begins your northward return toward Bequia.
Route Highlights
- Sailing south to reach your furthest point in the Grenadines chain at exclusive Petit St. Vincent.
- Relaxing on pristine white sand beaches that rank among the Caribbean's most beautiful.
- Experiencing the resort's legendary flag communication system and world-class beachfront dining.
Drone shot of Petit St. Vincent
Day 6: Petit St. Vincent to Chatham Bay, Union Island
Nautical Miles: 4
Travel Time: 45 minutes
Begin your northward return journey with the very short passage from Petit St. Vincent to Chatham Bay on the western side of Union Island. This brief hop allows for a leisurely morning departure while arriving with the full day ahead for exploring one of the Grenadines' most beautiful wilderness anchorages. The route takes you north past the channel between PSV and Union Island, with the dramatic volcanic peaks of Union growing larger ahead. Often called the Tahiti of the Caribbean for its mountainous profile, Union Island presents a striking contrast to the low-lying cays and resort islands you have visited over the past days.
Navigate into the well-protected waters of Chatham Bay and anchor in sand bottom with excellent holding, surrounded by lush green hills and with a long pristine beach backing the bay. Despite Union Island's reputation as a busy yacht services hub, Chatham Bay maintains a peaceful, undeveloped character since most commercial activity concentrates in Clifton Harbor on the opposite side of the island. Spend your afternoon swimming from the yacht in the clear protected waters, exploring the beautiful beach that stretches along the bay, or hiking the coastal trails for spectacular views across the southern Grenadines back toward the islands you have just visited. A few simple beach bars and local restaurants offer cold drinks and authentic island food, but the bay retains its wilderness feel with minimal development. As your penultimate day in the Grenadines draws to a close, enjoy a quiet evening at anchor reflecting on the week's experiences and preparing for tomorrow's final passage back to Bequia.
Route Highlights
- Sailing toward Union Island's dramatic volcanic peaks, known as the Tahiti of the Caribbean.
- Anchoring in pristine Chatham Bay, a peaceful wilderness anchorage surrounded by lush green hills.
- Exploring the long beach and hiking coastal trails for spectacular views across the southern Grenadines.
Chatham Bay on Union Island, Saint Vincent and the Grenadines, Lesser Antilles
Day 7: Chatham Bay to Admiralty Bay, Bequia
Nautical Miles: 14+
Travel Time: 2.5 hours
Your final sailing day takes you north from Union Island back to Bequia, completing the classic Grenadines ring and returning you to where the adventure began. The passage offers excellent sailing conditions with the prevailing trades typically providing a comfortable broad reach or run, making for relaxed sailing on your final day. The route can be direct for those eager to maximize time in Admiralty Bay, or include optional stops at interesting locations along the way such as the small anchorages on Canouan's less-visited eastern side or brief swim breaks at uninhabited cays. As Bequia grows larger ahead, you begin to recognize familiar landmarks from your departure day, now seen from the opposite direction and perspective.
Round West Cay and re-enter the welcoming embrace of Admiralty Bay, where the colorful waterfront of Port Elizabeth and the surrounding green hills create a fitting conclusion to your Grenadines exploration. Take a mooring or anchor in the spacious bay, settling back into the comfortable surroundings that launched your journey a week earlier. Spend your final afternoon and evening enjoying Bequia's relaxed atmosphere, perhaps visiting destinations you missed on departure day or simply relaxing at one of the excellent waterfront restaurants while watching the constant parade of yachts and local boats moving through this busy harbor. The Bequia Maritime Museum offers last-minute cultural enrichment, while the shops along the waterfront provide opportunities for final provisioning or souvenirs. As night falls over Admiralty Bay on your final evening, celebrate a successful completion of the Classic Grenadines Ring, having experienced the essential highlights of one of the world's finest cruising grounds across 65 nautical miles of perfect Caribbean sailing.
Route Highlights
- Completing the Classic Grenadines Ring with excellent sailing conditions on the northward passage.
- Returning to the welcoming harbor of Admiralty Bay where your Grenadines adventure began.
- Celebrating your successful 65-nautical-mile journey with a final evening in Port Elizabeth's vibrant waterfront.
Admiralty Bay, Bequia
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