Your host – Matt Houtby
I’m thrilled to be hosting this luxurious Caribbean getaway aboard Windstar’s sailing ship Wind Surf. We’ll visit exclusive island ports including Nevis, Dominica, Guadeloupe and St.Barts, all while being pampered in luxurious Windstar service. Join me to make some unforgettable memories, share in special hosted onboard events and experience the Caribbean in classic sailing yacht style.
Sunny days, chic little harbours, and lots of time to play, this Classic Caribbean sailing with your host Matt Houtby blends postcard beaches with European-tinged island towns. Expect a relaxed vibe where you can snorkel, stroll, or just kick back with your beverage of choice and a sea view.
Day 1 – Philipsburg, St. Maarten
Kick off on the lively Dutch side with a boardwalk stroll and turquoise-blue bay views. Browse boutiques, grab a beach chair on Great Bay, and toast sail-away with Matt as the harbor slips away.
Day 2 – Charlestown (Nevis)
Gingerbread houses, hot springs, and palm-soft beaches set the tone. Wander the heritage-rich town, then sneak away to a quiet stretch of sand for an unhurried swim.
Day 3 – Roseau (Dominica)
Enjoy island vibes with waterfalls, rainforest, and bubbling springs. Choose a guided river or falls visit, or snorkel Champagne Reef where warm vents fizz up from the seafloor.
Day 4 – Mayreau (St. Vincent & the Grenadines)
Tiny, dreamy, and blissfully slow. Think powdery beaches, calm coves for snorkelling, and a laid-back beach bar for fresh grill and a cold rum punch.
Day 5 – Les Saintes (Guadeloupe)
French-Caribbean charm with café terraces. Hike up to Fort Napoléon for sweeping views, then drift back down for a swim and a buttery pastry break.
Day 6 – Basseterre (St. Kitts)
Colourful squares meet emerald hills. Ride the scenic railway, hop to a golden-sand beach, or cross the channel for a Nevis beach lunch.
Day 7 – Gustavia (St. Barts)
Yacht-speckled harbour, chic shops, and oh-so-pretty beaches. Window-shop, linger over a long seaside lunch, then find a tucked-away cove for late-day sun.
Day 8 – Philipsburg, St. Maarten
Back where it began, perfect for last-minute souvenirs or one more dip. Say your goodbyes, or add a beach day before flying home with memories of this Caribbean cruise.
Your hosted cruise includes:
Total Price:
Double Occupancy
(B) Ocean View Stateroom – $8056 CAD total for two guests (Deck 1)
(BX) Ocean View Stateroom – $8582 CAD total for two guests (Deck 1 Mid-ship)
(A) Ocean View Stateroom – $8846 CAD total for two guests (Deck 2)
(AX) Ocean View Stateroom – $9374 CAD total for two guests (Deck 2 Mid-ship)
(TX) Deluxe Ocean View Stateroom – $10,430 CAD total for two guests (Deck 3)
(STE) Deluxe Suite – $15,708 CAD total for two guests (Deck 3)
Single Occupancy
(B) Ocean View Stateroom – $6704 CAD total for one guest (Deck 1)
(BX) Ocean View Stateroom – $7165 CAD total for one guest (Deck 1 Mid-ship)
(A) Ocean View Stateroom – $7396 CAD total for one guest (Deck 2)
(AX) Ocean View Stateroom – $7858 CAD total for one guest (Deck 2 Mid-ship)
(TX) Deluxe Ocean View Stateroom – $8782 CAD total for one guest (Deck 3)
(STE) Deluxe Suite – $15,249 CAD total for one guests (Deck 3)
Taxes and fees included
Pricing and staterooms subject to availability
Deposit:
15% of cruise fare (based on category)
Deposit refundable less $50 per person cancellation fee. Cancellation penalties begin at 120 days prior to sailing.
Final Payment Due:
90 days prior to sailing
The 342-guest Wind Surf is Windstar’s iconic sailing flagship, turning heads as she glides into port with her towering sails. Guests enjoy elegant public spaces, serene staterooms with fresh fruit and Egyptian cotton linens, and the World Spa by Windstar offering regionally inspired treatments.
As part of Windstar’s Setting Sails: A Wind Class Refresh, Wind Surf is undergoing a multi-year redesign featuring refreshed staterooms, new teak decks, a redesigned lounge, and a new pool and pool bar with the full transformation completing in 2026.
