Windward Ways & Tobago Cays
Ocean Cruise Memorii Pick
Windstar Cruises  ·  Star Legend

Windward Ways & Tobago Cays

From Bridgetown to Oranjestad  ·  Caribbean  ·  8 nights

Departure 4 Dec 2026
Return 12 Dec 2026
Duration 8 nights
Ports of call 7 ports
Ship Star Legend
Journey type Ocean Cruise
From
$2,824
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
4 Dec 2026
Bridgetown

The tiny eastern Caribbean island of Barbados has long been a favourite for British holiday makers, thanks in no small part to the platinum sands and warm, crystal clear waters of the west coast. But there's more to Barbados than just beaches; the delightful architecture of the old garrison in Bridgetown, the capital, is fully deserving of its UNESCO World Heritage status, and the island interior is littered with old sugar plantations and natural wonders such as Harrison's Cave. Perhaps the island's biggest asset, however, is the Bajans themselves, who are some of the friendliest people you're ever likely to meet.

Memory Tip: Don't miss Barbados is packed with historic houses, signal stations and sugar mills – one of our favourites is Sunbury Plantation House.
2
5 Dec 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.

3
6 Dec 2026
At Sea
4
7 Dec 2026
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
8 Dec 2026
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
9 Dec 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.

7
10 Dec 2026
At Sea
8
11 Dec 2026
Willemstad

The gabled houses of Willemstad lend an undeniably Dutch feel to the capital of little Curaçao, with a splash of Caribbean colour thrown in. The island itself is not your typical lush tropical paradise - the landscape is characterised instead by thorny shrubs and cacti - but there are some fantastic beaches and quaint little villages.

9
12 Dec 2026
Oranjestad

The tiny Dutch Caribbean island of Aruba, located just off the coast of Venezuela, lies outside of the hurricane belt, meaning it enjoys a largely dry climate, and boasts some of the best beaches in the region, if not the world.

Memory Tip: Our tip Aruba is rightly known as one of the safest islands in the Caribbean – make time to speak to the friendly local people. Their local language is Papiamento but speaking English is just fine.
What is included

Fare inclusions

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