Windward Islands Surf & Sunsets
Ocean Cruise Memorii Pick
Windstar Cruises  ·  Star Legend

Windward Islands Surf & Sunsets

From San Juan to San Juan  ·  Caribbean  ·  7 nights

Departure 10 Jan 2028
Return 17 Jan 2028
Duration 7 nights
Ports of call 6 ports
Ship Star Legend
Journey type Ocean Cruise
From
$2,343
per person
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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
10 Jan 2028
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
11 Jan 2028
At Sea
3
12 Jan 2028
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.

4
13 Jan 2028
Bequia

Bequia is an incredibly friendly, laid-back island blessed with pristine golden sand beaches and some excellent restaurants. It’s also a popular sailing destination; the yachts tend to congregate around Admiralty Bay, where you’ll find the little waterfront town of Port Elizabeth.

5
14 Jan 2028
Mayreau

Situated just to the west of the Tobago Cays, Mayreau is a tiny, barely inhabited island that can only be reached by boat. There is very little to do, which is the main attraction for those lucky few who wash up here; the palm-fringed beaches and gently lapping waters are the Caribbean island idyll par excellence.

6
15 Jan 2028
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
16 Jan 2028
Marigot

Marigot is the gateway to an intriguing little Caribbean island with a dual personality: the Dutch side, St. Maarten, is the livelier of the two, with shopping malls, casinos and more of a nightlife scene, while French-speaking St. Martin is a more refined (and more expensive) affair, with a laid-back, continental air and a host of exclusive resorts and restaurants.

8
17 Jan 2028
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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