Masterpieces at Sea: Gems of the Leeward Islands
Ocean Cruise Memorii Pick
Windstar Cruises  ·  Star Pride

Masterpieces at Sea: Gems of the Leeward Islands

From San Juan to San Juan  ·  Caribbean  ·  11 nights

Departure 28 Oct 2026
Return 8 Nov 2026
Duration 11 nights
Ports of call 8 ports
Ship Star Pride
Journey type Ocean Cruise
From
$3,085
per person
Request a Proposal
Voyage overview

What this voyage is

Windstar’s Star Plus Class of vessels – Star Pride, Star Legend and Star Breeze – each carry just over 300 guests and are hugely popular for very good reason.

These small ships accommodate 312 guests in large all-suite
accommodation, following the completion of the Star Plus
refurbishment programme in 2021 which saw the ships lengthened.
There’s a choice of restaurants, comfortable lounges, and plenty of
deck space, while the ship’s marina ensures you can enjoy the
complimentary watersports when anchored in hidden bays and tiny
coves.

Day By Day

Itinerary

1
28 Oct 2026
San Juan

Founded by the Spanish in 1521, Puerto Rico's capital is the second oldest European settlement in the Americas. Modern San Juan is a bustling city, home to over a third of the island's population, but the cobbled streets of the Old Town remain the biggest tourist draw. The colonial-era fortifications have been awarded UNESCO World Heritage status, crowned by the imposing waterfront El Morro fortress, and the Old Town is full of attractive, brightly coloured houses. Outside of the Old Town you can find designer shopping on Avenida Ashford, and the north of the city is fringed by beautiful beaches, including fashionable Condado with its hip hotels and bars.

Memory Tip: Don't miss Here in Puerto Rico it’s all about the history and the sea – you can’t miss the fabulous beaches, and you will enjoy the historic military buildings.
2
29 Oct 2026
At Sea
3
30 Oct 2026
Gustavia

Gustavia is the chic and petite capital of Saint Barths, a tiny French Caribbean island that’s renowned as a haunt of the rich and the famous. You can certainly live well here if you’ve got the means, with an array of gourmet restaurants and luxury boutiques aimed squarely at the A-list. The beautiful beaches, on the other hand, are free and open to all.

4
31 Oct 2026
Basseterre (Saint Kitts)

Laid back and low key, Saint Kitts is an island typified by rolling green hills, characterful beach bars and the lingering remnants of the sugar cane trade that once dominated here. Attractions include the UNESCO-listed Brimstone Hill fortress, the 18-mile Scenic Railway and the faded Georgian elegance of the capital, Basseterre.

5
1 Nov 2026
Falmouth Harbour

Antigua is famously home to 365 beaches - one for every day of the year - and there is an undeniable allure to the many white sand coves dotted along the coast. Falmouth Harbour lies on the south of the island, close to historic Nelson’s Dockyard and the lookout at Shirley Heights.

6
2 Nov 2026
Terre-de-Haut

Eight tiny islands make up the Iles des Saintes, a sparsely inhabited archipelago off the southern coast of Guadeloupe. The most interesting island is hilly Terre-de-Haut, almost entirely populated by the fair-skinned descendants of Breton sailors and home to a beautiful bay reminiscent of a mini Rio de Janeiro.

7
3 Nov 2026
Rodney Bay

The majority of Saint Lucia’s hotels are clustered around the broad sweep of Rodney Bay, where you’ll find some of the best beaches on the island and a host of lively bars and restaurants. At the northern end of the bay is Pigeon Island and historic Fort Rodney, well worth a visit for the splendid views.

8
4 Nov 2026
St George's

Browse the markets of charming St George’s, fragrant with the scent of cinnamon and nutmeg, and you’ll soon understand why Grenada is known as the ‘isle of spice’. This is one of the Caribbean’s most enchanting islands, fringed by gorgeous beaches and largely unsullied by mass market tourism.

9
5 Nov 2026
At Sea
10
6 Nov 2026
Jost Van Dyke

The idyllic island of Jost Van Dyke, named after an early Dutch settler, is known for its laid back vibe and friendly beach bars, including the famous Foxy’s, which counts Keith Richards amongst its past customers. It’s a place to kick back and relax, and the clear blue waters are also perfect for snorkelling.

11
7 Nov 2026
At Sea
12
8 Nov 2026
San Juan

Founded by the Spanish in 1521, Puerto Rico’s capital is the second oldest European settlement in the Americas. Modern San Juan is a bustling city, home to over a third of the island’s population, but the cobbled streets of the Old Town remain the biggest tourist draw.

Memory Tip: Our tip Hunt out the very best chuletas Can-Can and pastelillos – local food at its best is great. Don’t settle for sorry imitations.
What is included

Fare inclusions

Alcohol included
Daytime activities
Meals included
Soft drinks, tea and coffee included
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