Star Collector: Spectacular Transatlantic Journey - Caribbean to the Azores

Mar 28, 2026 — Apr 18, 2026

Starting from $8,188 Displayed pricing is based off of double occupancy per person. Pricing subject to change based on occupancy and cabin selection.

See more routes around Caribbean

PHILIPSBURG, ST. MAARTEN → LISBON

21 Nights in Wind Surf

1
MAR 28, 2026
Philipsburg, St. Maarten
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

2
MAR 29, 2026
St. John's
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
9

St. John's is a city of Old World charm and elegance which lingers in the varied architecture of Georgian, Victorian, Vernacular, Romantic and International flavors.  The picturesque seafront where tiny, colorful boats are moored, the cheerful wooden buildings carefully refurbished to retain their original features, the vibrant Market Street offering vegetables, fruit and fish and the duty-free Heritage Quay shopping area provide a delightful atmosphere to captivate you.  Sites to see include St. John's Cathedral with its white Baroque towers, the Botanical Garden, St. John's Antigua Lighthouse, and Fort James.

St. Johns, Segway Fort Conqueror

Time
9:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$159

St Johns, Swim with the Stingrays

Time
9:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$109

St. Johns: Presidents Tour

Time
9:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$109

St.John's, Concierge Collection: Sail Snorkel and Beach

Time
9:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$239

St. Johns, Beach Escape

Time
10:00 AM
Duration
4 Hours
Activity Level
Easy
Price
$79

St. Johns, Spectacular Antigua

Time
9:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$79

St Johns, Concierge Collection, Jet Ski Adventure

Time
9:30 AM
Duration
1.75 Hours
Activity Level
Moderate-Strenuous
Price
$379

St. Johns, Open Course Canopy Challenge

Time
9:30 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$139

St Johns, Chocolate and Rum Making

Time
9:30 AM
Duration
3.25 Hours
Activity Level
Easy-Moderate
Price
$209
3
MAR 30, 2026
Road Bay
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
4

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.

Road Bay, Iconic Island Highlights with Salt Tasting and Beach Time

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$189

Road Bay, Concierge Collection: Relaxing Day at Savi with Lunch

Time
8:30 AM
Duration
5 Hours
Activity Level
Easy-Moderate
Price
$439

Concierge Collection: Road Bay, Snorkel Adventure by Speedboat

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$329

Road Bay, Shoal Bay Beach Transfer

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$125
4
MAR 31, 2026
Soper's Hole
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
4

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. 

Soper's Hole: Cane Garden Bay Beach Break

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate
Price
$89

Tortola, Tortola Jeep & Beach Tour

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate
Price
$199

Tortola, Snorkel Adventure at Peter Island

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$135

Tortola, Scenic Drive & Beach

Time
8:30 AM
Duration
4.5 Hours
Activity Level
Easy
Price
$109
Jost Van Dyke, Great Harbour
ARRIVE
7:00 PM
DEPART
11:59 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

5
APR 01, 2026
Jost Van Dyke, Great Harbour
ARRIVE
12:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
2

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.

Jost Van Dyke, Sail and Snorkel

Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$159

Jost Van Dyke, Catamaran Cruise & Swim to Norman Island

Time
8:15 AM
Duration
4.5 Hours
Activity Level
Moderate-Strenuous
Price
$259
6
APR 02, 2026
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
2

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. Althought 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

Virgin Gorda: Highlights & Bath Tour

Time
8:15 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$89

Virgin Gorda: Snorkel Adventure

Time
9:00 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous
Price
$239
7
APR 03, 2026
Gustavia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
6

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.

St Barts, Concierge Collection: St. Barthelemy Beach Day

Time
10:30 AM
Duration
6 Hours
Activity Level
Easy-Moderate
Price
$499

Gustavia, Concierge Collection: Scuba Dive 1 Tank

Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$339

St. Barts, Concierge Collection: Sunset Cruise

Time
5:00 PM
Duration
1.5 Hours
Activity Level
Easy-Moderate
Price
$199

Gustavia, Concierge Collection: Scuba Dive 2 Tank

Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$499

Gustavia, Concierge Collection: Savor St Barts

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Moderate
Price
$349

Gustavia, Concierge Collection: Jet Ski

Time
8:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$269

Wind Surf

number of decks
6 Decks
yacht length
535 ft (163 meters)
yacht crew size
191 Crew Members
yacht guest capacity
342 Guests

Available Staterooms

Category A

Cabin
29 Cabins
Max. Occupancy
2 Passengers
Room Size
188 Sqft
Amenities

Officer's Suite

Cabin
1 Cabins
Max. Occupancy
2 Passengers
Room Size
242 Sqft
Amenities

Category BX Deluxe

Cabin
34 Cabins
Max. Occupancy
3 Passengers
Room Size
188 Sqft
Amenities

Suite

Cabin
18 Cabins
Max. Occupancy
3 Passengers
Room Size
376 Sqft
Amenities

Category B

Cabin
21 Cabins
Max. Occupancy
2 Passengers
Room Size
188 Sqft
Amenities

Category TX Deluxe

Cabin
32 Cabins
Max. Occupancy
2 Passengers
Room Size
188 Sqft
Amenities

Category AX Deluxe

Cabin
34 Cabins
Max. Occupancy
2 Passengers
Room Size
188 Sqft
Amenities

Available Dates