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Luxury cruise ship Wind Surf sailing in Caribbean
14 NightsCaribbean
Windstar Cruises

14-Night Eastern Caribbean Escape

Windstar CruisesWind SurfDeparts from Port Everglades4.3 Rated (30 Reviews)

Vessel Specifications

Gross Tonnage14,745 GT
Decks6 Guest Decks
Pass Capacity342 guests
Crew Size210 staff

Customize Estimate & Fares

Configure origin markets, travelers, and dining tiers to dynamically recalculate stateroom fares.

Stateroom Tiers & Rates

Select a cabin type below. All fares are estimates based on your selected departure origin market and traveler composition.

Stateroom CategoryInclusionsPrice per Guest
Interior CabinPerfect budget option, cozy retreat with standard cruise amenities.
USD 7,140USD 6,283Save USD 857!
Ocean ViewFeatures a large picture window or porthole to enjoy natural light and ocean views.
USD 8,692USD 7,649Save USD 1,043!
Balcony CabinIncludes a private verandah with floor-to-ceiling glass doors and seating.
USD 10,865USD 9,561Save USD 1,304!
Junior SuiteSpacious layout with a dedicated sitting area and full bathtub.
USD 14,053USD 12,367Save USD 1,686!
SuitePremium living room, priority boarding, and luxury bath amenities.
USD 18,397USD 16,189Save USD 2,208!
Luxury SuiteElite suite with a private hot tub on the deck, concierge service.
USD 27,086USD 23,836Save USD 3,250!
Owner's SuiteThe ultimate cruise luxury, dining room, wet bar, and butler service.
USD 41,360USD 36,397Save USD 4,963!
Family CabinDesigned for up to 6 guests, bunk beds, and double vanity bathroom.
USD 13,037USD 11,473Save USD 1,564!
Accessible CabinWider doorways, roll-in shower, grab bars, and accessible closet rods.
USD 7,761USD 6,830Save USD 931!
Solo CabinSpecifically sized and priced for solo travelers, avoiding single supplements.
USD 6,211USD 5,466Save USD 745!

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Day-by-Day Voyage Itinerary

1
Day 1

Fort Lauderdale

Embarkation

Embark and settle into cabins • Safety briefing • Sailaway deck party

Dining

Main Dining Room, Specialty Italian Restaurant

Evening Show

Acrobatic / Aerialist Theater Show

2
Day 2

Cruising at Sea

At Sea

Relaxing by the pools • Onboard shopping specials • Mini-golf tournament

Dining

Coastal Kitchen, Seafood Shack

Evening Show

Comedy Night, Nightclub dancing

3
Day 3

San Juan

02:00 PM - 10:00 PM

Tour historic El Morro Fort • Walk the cobblestone streets of Old San Juan • Salsa dancing lesson

Shore Activities

Old San Juan Walking Tour & El Morro Fort, El Yunque Rainforest Hiking Tour

Dining

Barrachina (birthplace of Piña Colada), Main Dining Room

Evening Show

Late night Salsa bar crawl, Movies on Deck

4
Day 4

St. Thomas

08:00 AM - 06:00 PM

Sunbathing at Magens Bay Beach • Ride tramway to Paradise Point • Duty-free shopping in Charlotte Amalie

Shore Activities

Magens Bay Beach Escape, St. Thomas Island Tour & Mountaintop

Dining

Gladys' Cafe, Main Dining Room

Evening Show

Caribbean steel drum party on pool deck

5
Day 5

Nassau

10:00 AM - 07:00 PM

Visit Atlantis Waterpark • Climb Queen's Staircase • Straw Market shopping

Shore Activities

Atlantis Aquaventure Day Pass, Pearl Island Beach Day & Lunch

Dining

Graycliff Chocolatier lunch, Main Dining Room

Evening Show

White-Hot Deck Party, Adult comedy night

6
Day 6

Cruising at Sea

At Sea

Galley tour • Spa luxury massage • Bingo games • Packing bags

Dining

Specialty Steakhouse, Main Dining Room

Evening Show

Farewell Variety Show, Live Jazz in the lounge

7
Day 7

Fort Lauderdale

06:00 AM - Disembarkation

Final breakfast • Express walk-off departure

Dining

Buffet breakfast

8
Day 8

Fort Lauderdale

Embarkation

Embark and settle into cabins • Safety briefing • Sailaway deck party

Dining

Main Dining Room, Specialty Italian Restaurant

Evening Show

Acrobatic / Aerialist Theater Show

9
Day 9

Cruising at Sea

At Sea

Relaxing by the pools • Onboard shopping specials • Mini-golf tournament

Dining

Coastal Kitchen, Seafood Shack

Evening Show

Comedy Night, Nightclub dancing

10
Day 10

San Juan

02:00 PM - 10:00 PM

Tour historic El Morro Fort • Walk the cobblestone streets of Old San Juan • Salsa dancing lesson

Shore Activities

Old San Juan Walking Tour & El Morro Fort, El Yunque Rainforest Hiking Tour

Dining

Barrachina (birthplace of Piña Colada), Main Dining Room

Evening Show

Late night Salsa bar crawl, Movies on Deck

11
Day 11

St. Thomas

08:00 AM - 06:00 PM

Sunbathing at Magens Bay Beach • Ride tramway to Paradise Point • Duty-free shopping in Charlotte Amalie

Shore Activities

Magens Bay Beach Escape, St. Thomas Island Tour & Mountaintop

Dining

Gladys' Cafe, Main Dining Room

Evening Show

Caribbean steel drum party on pool deck

12
Day 12

Nassau

10:00 AM - 07:00 PM

Visit Atlantis Waterpark • Climb Queen's Staircase • Straw Market shopping

Shore Activities

Atlantis Aquaventure Day Pass, Pearl Island Beach Day & Lunch

Dining

Graycliff Chocolatier lunch, Main Dining Room

Evening Show

White-Hot Deck Party, Adult comedy night

13
Day 13

Cruising at Sea

At Sea

Galley tour • Spa luxury massage • Bingo games • Packing bags

Dining

Specialty Steakhouse, Main Dining Room

Evening Show

Farewell Variety Show, Live Jazz in the lounge

14
Day 14

Fort Lauderdale

06:00 AM - Disembarkation

Final breakfast • Express walk-off departure

Dining

Buffet breakfast

15
Day 15

Fort Lauderdale

Disembarkation

Embark and settle into cabins • Safety briefing • Sailaway deck party

Dining

Main Dining Room, Specialty Italian Restaurant

Evening Show

Acrobatic / Aerialist Theater Show

Shore Excursions

Optional activities available at your ports of call.

Best of Fort Lauderdale

Free
Free Activities Full-Day Tours

A wonderful full-day tours exploring the sights of Fort Lauderdale. This free activities covers main landmarks, guided by a local historian.

Secrets of San Juan

$247
Private Tours Half-Day Tours

A wonderful half-day tours exploring the sights of San Juan. This private tours covers main landmarks, guided by a local historian.

Secrets of St. Thomas

$261
Private Tours Half-Day Tours

A wonderful half-day tours exploring the sights of St. Thomas. This private tours covers main landmarks, guided by a local historian.

Highlights of Nassau

$116
Luxury Experiences Full-Day Tours

A wonderful full-day tours exploring the sights of Nassau. This luxury experiences covers main landmarks, guided by a local historian.

Scenic Route of Fort Lauderdale

$194
Water Sports Half-Day Tours

A wonderful half-day tours exploring the sights of Fort Lauderdale. This water sports covers main landmarks, guided by a local historian.

Best of Fort Lauderdale

$75
Paid Excursions Full-Day Tours

A wonderful full-day tours exploring the sights of Fort Lauderdale. This paid excursions covers main landmarks, guided by a local historian.

Discover San Juan

$141
Family Activities Full-Day Tours

A wonderful full-day tours exploring the sights of San Juan. This family activities covers main landmarks, guided by a local historian.

Best of St. Thomas

$73
Paid Excursions Full-Day Tours

A wonderful full-day tours exploring the sights of St. Thomas. This paid excursions covers main landmarks, guided by a local historian.

Scenic Route of Nassau

$206
Cultural Tours Half-Day Tours

A wonderful half-day tours exploring the sights of Nassau. This cultural tours covers main landmarks, guided by a local historian.

Highlights of Fort Lauderdale

$92
Adventure Tours Full-Day Tours

A wonderful full-day tours exploring the sights of Fort Lauderdale. This adventure tours covers main landmarks, guided by a local historian.

Highlights of Fort Lauderdale

$96
Adventure Tours Full-Day Tours

A wonderful full-day tours exploring the sights of Fort Lauderdale. This adventure tours covers main landmarks, guided by a local historian.

Onboard Life & Entertainment

Culinary Experience

Included Complimentary Dining
Grand Dining RoomOceanview Café (Buffet)
Specialty Fine Dining Options
Pinnacle Grill SteakhouseTuscan Grille ItalianJacques French BistroRed Ginger Pan-Asian
Dietary Accommodations
Vegetarian
Vegan
Halal
Kosher
GlutenFree

Vessel Entertainment & Activities

Onboard Thrill Activities
Fitness jogging trackShuffleboard
Amenities Overview
1 Swimming Pools
Luxury Spa & Salon

Reserve Your Voyage

No immediate online payment is required. Select a stateroom from the fare table to lock in these estimated rates, and one of our dedicated cruise consultants will contact you to finalize cabins, routes, and optional excursions.

Full consultant support, 100% refundable reservation until payment.

Guest Reviews

Realistic feedback from verified cruise bookings.

Guest Traveler 14.2

Dining options were amazing. Specialty restaurants were worth the cover charge. The theater shows were Broadway quality. Slipped off to 14-Night Eastern Caribbean Escape and had a fantastic time.

family4 Voyage • 2026-07-08
Guest Traveler 24.4

Refined atmosphere, excellent service, and beautiful ship design. Excursion slots filled up quickly, so book early. Slipped off to 14-Night Eastern Caribbean Escape and had a fantastic time.

group Voyage • 2026-07-03
Guest Traveler 34.2

Dining options were amazing. Specialty restaurants were worth the cover charge. The theater shows were Broadway quality. Slipped off to 14-Night Eastern Caribbean Escape and had a fantastic time.

family4 Voyage • 2026-06-28