Classic Caribbean

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Dining
£1,829pp
sparks

All-Inclusive offer

Drinks, gratuities, and WiFi included plus up to exclusive savings on selected sailings - only with The Cruise Line.

Voyage Code: WIND1020909
moon 7 nights
anchorWind Surf
calendar 26 Dec '26

Cruise overview

From the chic harborfront of Gustavia to the captivating charm of Les Saintes. From hidden coves and secret beaches to exotic markets and lively cafés. Discover the best of this region with one single Caribbean cruise. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.

Philipsburg
Gustavia
Roseau
Mayreau Island
Terre-de-Haut
Basseterre, Saint Kitts
Philipsburg

Itinerary

Day 1

Philipsburg


The capital of Dutch St. Maarten stretches about a mile (1½ km) along an isthmus between Great Bay and the Salt Pond and has five parallel streets. Most of the village’s dozens of shops and restaurants are on Front Street, narrow and cobblestone, closest to Great Bay. It’s generally congested when cruise ships are in port, because of its many duty-free shops and several casinos. Little lanes called steegjes connect Front Street with Back Street, which has fewer shops and considerably less congestion. Along the beach is a ½-mile-long (1-km-long) boardwalk with restaurants and several Wi-Fi hot spots.Wathey Square (pronounced watty) is in the heart of the village. Directly across from the square are the town hall and the courthouse, in a striking white building with cupola. The structure was built in 1793 and has served as the commander’s home, a fire station, a jail, and a post office. The streets surrounding the square are lined with hotels, duty-free shops, restaurants, and cafés. The Captain Hodge Pier, just off the square, is a good spot to view Great Bay and the beach that stretches alongside.

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Day 2

Gustavia

Day 3

at-sea At sea

Day 4

Roseau

Day 5

Mayreau Island

Day 6

Terre-de-Haut

Day 7

Basseterre, Saint Kitts

Day 8

Philipsburg

Gracious Stateroomsfrom£2,169pp
Spacious Suitesfrom£3,139pp
Opulent Bridge Suitesfrom£3,769pp
Owner's SuiteCall for price
Broadmoor SuiteCall for price
Sea Island SuiteCall for price

Gracious Staterooms

from£2,169pp
Enquire now

Amenities

  • Queen or Twin Configuration
  • Lounge Area
  • Shower
  • Toiletries Provided
  • Room Service Available
  • Suite Benefits
  • TV
  • Wi-Fi (Additional Cost)
  • Safe
  • Hair Dryer
  • Desk
  • Vanity Area
  • Telephone
  • Mini Bar (Additional Cost)

Ship features

Wind Surf marries classic sailing romance with modern yacht comforts and upscale amenities.

Overview
Accommodation
Dining
Amenities
Spa
Entertainment
Families
  • Five large sails up to 67.5 m high
  • Full-service spa, fitness centre and wellness offerings
  • Multiple dining outlets including AmphorA, Stella Bistro and Candles
  • Open-bridge policy allowing guest visits
  • Watersports platform with snorkeling, paddleboards etc.
  • Indoor & outdoor lounges, bars, library, photo gallery
  • Pools, two whirlpools and reclining decks
  • Boutique shopping and signature shop