Fun & Sun: A Remote Caribbean Getaway

with Windstar & Steady for Life

Bask on remote beaches resplendent in natural beauty during this relaxing, unrushed, and uncrowded 7-day getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from Windstar’s onboard Watersports Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda.

Windstar takes you to the secret beaches and invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.

March 14 - 21, 2026

Wind Surf

Departing PHILIPSBURG, ST. MAARTEN on Saturday, March 14, 2026

7-night cruise visiting:

View Cruise Information

About the Sailing

172 days to go

Wind Surf

Windstar Cruises

Departing Philipsburg on Saturday, March 14th 2026

7-night trip going to Caribbean - All (Caribbean)

Visiting: Philipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, Gustavia

Itinerary | About the Ship | Deck Plans | Ports of Call

Deposit: $550/person (Full cost based upon stateroom selection.)

Final Payment: January 10, 2026

Included: 7-night cruise; all meals onboard ship; 24-hour room service; onboard entertainment; taxes and port charges

Exclusively for Steady for Life offered only by Cruise Planners:

unlimited beer, wine, cocktails by the glass
unlimited Wi-Fi
prepaid gratuities
complimentary group cocktail reception

Not included: Optional travel protection, airfare, shore excursions

Airfare: Flights are provided through Holland America Flight Ease. Pricing to be updated soon.

Note: Queen Beds are offered onboard Wind Surf, with limited availability to separate beds.

Sat Mar 14 - Philipsburg, St. Maarten

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

Sun Mar 15 - Falmouth Harbour

It’s said that Antigua has 365 beaches – one for every day of the year. See how many you can discover as our stay in port stretches into the evening to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.

Mon Mar 16 - Road Bay

With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean. It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats. Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby.

Tue Mar 17 - Soper's Hole

Arrive at the boardwalk of Pusser’s Landing and mingle with other yachtsmen in the utterly charming marina at Soper’s Hole. Find a deserted stretch of beach to kick back and ponder this tiny port’s rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime romantic sunset Sail Away.

Wed Mar 18 - Jost Van Dyke, Great Harbour

For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.

Thu Mar 19 - Virgin Gorda / Prickly Pear, British Virgin Islands

The beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Although uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns.

Please note: only guests with shore excursions booked through Windstar can be tendered to Gun Creek.

Fri Mar 20 - Gustavia

Affectionately known as St. Barts, the Caribbean’s most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island’s signature ti punch as kite surfers fly by.

Sat Mar 21 - Philipsburg, St. Maarten

Today, your Caribbean exploration comes to an end as you return to Philipsburg and disembark for your flight home.

Staterooms

Suite

Stateroom Type: Suite

SUITE Deck 3 Forward/Aft or Midship CABIN TYPE: SUITE 376 sq. feet With 376 square feet, you’ll find the perfect space for time together — and plenty of room for time to yourself. You’ll even enjoy two full separate bathrooms. All the amenities of the staterooms await you, plus a beautiful sitting area, and two flat-screen television sets with DVD players.

Per Guest

Guest 1: $5,377.00

Guest 2: $5,377.00

includes all applicable taxes and fees

See All Occupancy Pricing

DELUXE: TX

Stateroom Type: Ocean View

CATEGORY TX DELUXE Deck 3 Forward/Aft or Midship CABIN TYPE: STATEROOM 188 sq. feet Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L'Occitane & reg; bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.

Per Guest

Guest 1: $3,577.00

Guest 2: $3,577.00

includes all applicable taxes and fees

See All Occupancy Pricing

DELUXE: AX

Stateroom Type: Ocean View

CATEGORY AX DELUXE Deck 2 Midship CABIN TYPE: STATEROOM 188 sq. feet Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.

Per Guest

Guest 1: $3,217.00

Guest 2: $3,217.00

includes all applicable taxes and fees

See All Occupancy Pricing

CATEGORY A: A

Stateroom Type: Ocean View

CATEGORY A Deck 2 Forward/Aft CABIN TYPE: STATEROOM 188 sq. feet Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.

Per Guest

Guest 1: $3,037.00

Guest 2: $3,037.00

includes all applicable taxes and fees

See All Occupancy Pricing

DELUXE: BX

Stateroom Type: Ocean View

With 188 square feet, you’ll find the perfect space for time together — and plenty of room for time to yourself. You’ll even enjoy two full separate bathrooms. All the amenities of the staterooms await you, plus a beautiful sitting area, and two flat-screen television sets with DVD players.

Per Guest

Guest 1: $2,947.00

Guest 2: $2,947.00

includes all applicable taxes and fees

See All Occupancy Pricing

Itinerary

Day

Date

Port

Arrive

Depart
Day 1

Date 03/14/2026

Port Philipsburg

Arrive --

Depart 7:00pm
Day 2

Date 03/15/2026

Port Falmouth

Arrive 8:00am

Depart 6:00pm
Day 3

Date 03/16/2026

Port Road Bay, Anguilla

Arrive 8:00am

Depart 6:00pm
Day 4

Date 03/17/2026

Port Tortola

Arrive 8:00am

Depart 6:00pm
Day 4

Date 03/17/2026

Port Great Harbour, Jost Van Dyke BVI

Arrive 7:00am

Depart --
Day 5

Date 03/18/2026

Port Great Harbour, Jost Van Dyke BVI

Arrive --

Depart 10:00pm
Day 6

Date 03/19/2026

Port Leverick Bay, Virgin Gorda

Arrive 8:00am

Depart 5:00pm
Day 7

Date 03/20/2026

Port Gustavia

Arrive 8:00am

Depart 10:00pm
Day 8

Date 03/21/2026

Port Philipsburg

Arrive 6:00am

Depart --

About the Windstar Cruises Wind Surf

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea.

Details and Deck Plans

Year Built	1990	Capacity	342
Year Refurbished	2003	Elevators	2
Registry	Bahamas	Restaurants	2
Tonnage	14,745	Bars	2
Cabins	154	Pools	2
Wheelchair Accessible Cabins	N	Theaters	N
Shops	Y	Library	Y
Meeting Rooms	Y	Casino	N
Spa	Y	Disco	Y
Fitness Center	Y	Children's Program	N
Internet Cafe	N

Star Deck

Bridge Deck

Main Deck

Deck Three

Deck Two

Deck One

Ports of Call

Philipsburg (Days 1, 8)

An exquisite blend of Dutch and French cultures, St. Martin boasts stunning beaches, crystal clear waters, and incredible duty-free shopping. Whether you lunch at a charming French cafe or explore the lively Dutch capital of Philipsburg, you will find the dichotomy of St. Maarten perfectly charming.

Attractions & Activities

Compete in an actual race on an America's Cup shortened course. Grind a winch, trim a sail or just sit back and enjoy. Professional sailors will give you a quick lesson, then you're off to compete on Stars and Stripes, one of the most famous sailboats in the world.

Falmouth (Day 2)

Tour Nelson's Dockyard, which was originally built as a way station in the 18th century for warships of the British Royal Navy. This historic district has been restored to its former glory and you can sit upon the old fortifications and observation posts that line the harbor. As you evoke the port's nautical past, close your eyes and you can hear the revelry of sailors coming ashore for leave.

Road Bay, Anguilla (Day 3)

Tortola (Day 4)

Twenty-one-square-mile Tortola is the largest of the British Virgin Islands, an unspoiled archipelago that lies in the path of welcome trade winds. Try fishing, snorkeling and sailing excursions out of Road Towns serene harbor or horseback riding in the shadow of Mount Sage.

Attractions & Activities

Rent a private boat and forge your way out to Norman Isle, a former pirate den across Drake Channel from Tortola and real life deserted island today. Legend has it that Norman Isle served as Robert Louis Stevenson's inspiration for Treasure Island. You can venture into caves, some of which are excellent snorkeling spots. Or hike to Spy Glass Hill. This is a journey you'll never forget.

Great Harbour, Jost Van Dyke BVI (Days 4, 5)

Great Harbour is the main anchorage on Jost Van Dyke and the center for nightlife on this beautiful island. The holding for anchors in Great Harbour can be tricky and now there are some mooring balls to make life easier. Great Harbour has the island’s police station and customs and immigration office. It’s “main road” is just a sandy strip. A small beach, dotted with dinghy docks, runs the length of the bay.

Leverick Bay, Virgin Gorda (Day 6)

Gustavia (Day 7)

You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in the evening. Parking in Gustavia is a challenge, especially during vacation times. A good spot to park is rue de la République, alongside the catamarans, yachts, and sailboats.

Terms and Conditions

120-90 days before commencing travel	15% of gross fare (deposit)
89-60 days before commencing travel	35% of gross fare
59-30 days before commencing travel	50% of gross fare
29-0 days before commencing travel	100% of gross fare