After switching your clocks to island time and setting off on the adventure of a lifetime, you'll find yourself sailing across the Sir Francis Drake Channel towards Norman Island. Once you've picked up a mooring ball, head over to The Willy T, an iconic floating bar and restaurant, for a fun lunch with a lively atmosphere and an afternoon swim in turquoise waters. As sunset rolls around, wrap up the day with dinner at Pirate's Bight, offering fresh seafood and delicious Caribbean cuisine in a serene waterfront setting.
Lunch 🥪 The Willy T
Dinner 🍝 Pirate's Bight
Sail to Cooper Island Beach Club, where you can snorkel the crystal-clear waters of Cistern Point, known for its colorful fish and coral. After working up an appetite, enjoy lunch at the Beach Club, which serves fresh, locally sourced seafood, vegetarian-friendly dishes, and craft cocktails. Relax on the beach or visit their eco-friendly boutique before continuing your journey.
Lunch 🥪 Cooper Island Beach Club
Take a slow afternoon sail over to Brandywine Bay and watch take in the gorgeous sunset aboard your yacht. In the evening, enjoy an elegant dinner at Brandywine Estate Restaurant, a Mediterranean-inspired fine dining experience with breathtaking ocean views.
Dinner 🍝 Brandywine Estate Restaurant
Start the day with a sail over to The Baths, Virgin Gorda’s most famous natural wonder, where you can hike through giant granite boulders, swim in hidden pools, and explore caves. After a morning of adventure, grab a well-deserved lunch at the Top of the Baths before an afternoon relaxing on Devil’s Bay Beach.
Lunch 🥪 Top of the Baths
Head round to Spanish Town in the late afternoon and then to dinner at CocoMaya around sunset for stunning views and then enjoy a lovely long dinner of Asian-Latin fusion dishes, fresh sushi, and tropical cocktails. CocoMaya has a great vibe and often turns into a party so make sure you're ready for a boogie!
Dinner 🍝 CocoMaya
From Spanish Town, set sail for Anegada For dinner, enjoy the island’s famous Anegada lobster at The Lobster Trap, or opt for fresh seafood and Caribbean flavors at Anegada Reef Hotel or Potter’s By The Sea, where you can dance under the stars.
Dinner 🍝 The Lobster Trap & Anegada Reef Hotel or Potter's By The Sea
Start your second day in Anegada and rent a Moke or Jeep to explore the island’s secluded beaches. Visit Cow Wreck Beach or Loblolly Bay, both offering pristine white sand and excellent snorkeling. For lunch, visit Anegada Beach Club (ABC) for casual island bites, followed by an afternoon of kite surfing or lounging in a beachfront hammock. Dinner at Sid’s in Pomato Point is a must, featuring home-cooked Caribbean specialties in a cozy setting - their tacos are our favourite!
Lunch 🥪 Anegada Beach Club
Hidden Gem 💎 Sid's Pomato Point
Wake up and off we go! Head over to the North Sound for an afternoon of pure bliss and luxury. Once in The North Sound, head over to Bitter End Yacht Club for a day of water activities, including kayaking, hobie-cat sailing, and paddleboarding or simply lounging on the beach. In the evening, enjoy dinner and drinks at Saba Rock, an intimate restaurant set on a private islet. Alternatively, dine at upstairs at Leverick Bay, a local hidden gem offering delicious Caribbean fare with stunning waterfront views.
Lunch 🥪 Bitter End Yacht Club
Dinner 🍝 Saba Rock
Hidden Gem 💎 Upstairs Leverick Bay
You've got a second day in the North Sound and endless opportunities! Head to Saba Rock for some brekkie and then spend the day hopping between Bitter End and Saba Rock if you didn't get the chance yesterday. Or if you’re up for a change of scenery, sail to Nova at Oil Nut Bay, where you can enjoy a luxurious overwater dining experience with fresh seafood and craft cocktails, alternatively head up to Hog’s Heaven, another hidden gem known for its incredible views and BBQ dishes. For dinner, head to Sugarcane, or if you're really looking for a unique, luxurious dining experience Ikigai Omakase in Biras Creek offers a 12 course Japanese-Caribbean Omakase Menu - totally one of a kind!
Breakfast 🥞 Saba Rock
Lunch 🥪 Nova, Oil Nut Bay
Dinner 🍝 Sugarcane
Hidden Gem 💎 Hog’s Heaven & Ikigai Omakase, Biras Creek
Head ashore to Bitterend and grab some coffee and delicious pastries for a relaxed brekkie on the beach. Then set sail for Trellis Bay and Marina Cay. Pick up a mooring ball and head to Marina Cay first for a swim, some water sports and laid-back lunch. Wrap up the evening with dinner at Trellis Bay, there are countless options but our favorites are Marche, known for its refined Caribbean cuisine and great sushi, or Loose Mongoose, a casual beachfront eatery with a wide Caribbean-inspired menu.
Breakfast 🥞 Bitter End Yacht Club
Lunch 🥪 Marina Cay
Dinner 🍝 Marche or Loose Mongoose, Trellis Bay
Head ashore to Trellis Bay for a relaxed breakfast at Jeremy’s Kitchen then get ready to set sail for Cane Garden Bay. Once you've picked up a mooring ball in this beautiful horseshoe-shaped bay, spend your day soaking up the sun on one of Tortola’s most picturesque beaches, then bar-hop all the way up until dinner. We'd start with lunch at Myett’s or Elm Beach Bar for a taste of local flavors and in the evening we'd head to Indigo’s, Paradise Beach Club, or our secret spot Bananas, each offering a mix of Caribbean and international cuisine.
Breakfast 🥞 Jeremy's Kitchen
Lunch 🥪 Myett's or Elm Beach Bar
Dinner 🍝 Indigo's or Paradise Beach Club
Hidden Gem 💎 Bananas
Spend another morning in paradise with breakfast at Rhythm & Sands and a stroll along the beach. Then sail over to Diamond Cay and head ashore to Foxy's Taboo. Follow the arrows and hike past the Jost Van Dyke sign to the Bubbly Pool - a natural jacuzzi! Head to B-Line Beach Bar for some lunch and then to Foxy's Taboo for dinner after an afternoon aboard.
Breakfast 🥞 Rhythm & Sands
Lunch 🥪 B-Line Beach Bar
Dinner 🍝 Foxy's Taboo
Start the day with a visit to White Bay, home to the world-famous Soggy Dollar Bar, where you can sip a Painkiller cocktail while lounging in a hammock. Have lunch at Soggy's or Hendo’s Hideout, known for its fresh seafood and laid-back vibe. As the sun sets, head over to Foxy’s in Great Harbour for a legendary beach party with live music and dancing.
Lunch 🥪 Soggy Dollar Bar or Hendo's Hideout
Dinner 🍝 Foxy's
Head back to White Bay for some brekkie at Soggy's and a stroll on White Bay. Then kiss Jost goodbye and head over to Soper's Hole on Tortola. Either spend the afternoon shopping or take a short excursion (by foot or by taxi) to Smuggler’s Cove, a secluded beach with great snorkeling. For dinner, choose between Admiral’s, Omar’s Fusion, or Pusser’s Landing, all offering waterfront dining with a mix of Caribbean and international flavors.
Breakfast 🥞 Soggy Dollar Bar
Dinner 🍝 Admiral’s, Omar’s Fusion, or Pusser’s Landing
Start your day ashore with breakfast at Omar’s Coffee House, where you can enjoy island-roasted coffee and fresh-baked pastries. End your trip with a luxurious visit to Peter Island Resort, where you can relax on the pristine beaches, enjoy a spa day, or go on a guided snorkel or diving trip. For dinner, indulge in an elegant meal at the resort’s restaurant, featuring fresh seafood, premium meats, and vegetarian-friendly options, all set against a breathtaking island backdrop.
Breakfast 🥞 Omar's Coffee House
Dinner 🍝 Peter Island Resort
Enjoy one last morning swim in paradise and a coffee on the bow before heading back to Nanny Cay, making sure you have enough time to complete the check-in procedure at our dock. Your flights will be reconfirmed, your taxi already booked and soon you’ll be on your way home, already planning your return!