Itinerary - AO Trips

2027 Caribbean Cruise Itinerary

Port arrival/departure times are subject to change

Day 1 – San Juan, Puerto Rico

Arrive San Juan, Puerto Rico and transfer to the port for embarkation on Windstar Star Pride (embarkation begins at 1:00 pm local time)
Lunch onboard the ship (included) or on own in San Juan
Walking Tours of Old San Juan available in the afternoon (included)
Welcome Reception on Deck (included)
Dinner onboard the ship (included) in various ship restaurants or on own in San Juan
Overnight onboard the Windstar Star Pride in San Juan, Puerto Rico

Day 2 – San Juan, Puerto Rico

Breakfast onboard the ship (included) or on own in San Juan
Walking Tours of Old San Juan available in the morning (included)
Optional Excursions available for purchase
Lunch onboard the ship (included) or on own in San Juan
Dinner onboard the ship (included) in various ship restaurants or on own in San Juan
9:30 pm All Aboard
Windstar Signature Sail Away on Deck
10:00 pm Windstar Star Pride departs San Juan, Puerto Rico

Day 3 – Virgin Gorda, Prickly Pear Beach, BVI

Day 4 – Day at Sea

Breakfast onboard the ship (included)
Ship Activities available throughout the day onboard (some included and some for purchase)
Lunch onboard the ship (included)
Dinner onboard the ship (included) in various ship restaurants

Day 5 – St. Lucia

7:00 am Windstar Star Pride arrives St. Lucia
Breakfast onboard the ship (included)
Optional Excursions available for purchase
Lunch onboard the ship (included), or included in select optional excursions, or on own in St Lucia
4:30 pm All Aboard (Group 2: 3:30 pm All Aboard)
5:00 pm Windstar Star Pride departs St. Lucia (Group 2: 4:00 pm departure)
A-O Trips Reception on deck as we sail through the Pitons (included)
Dinner onboard the ship (included) in various ship restaurants

Day 6 – Antigua (For group 2, Day 6 will be St Kitts/Nevis)

9:30 am Windstar Star Pride arrives Antigua (Group 2: Arrives 8:00 am)
Breakfast onboard the ship (included)
Optional Excursions available for purchase
Lunch onboard the ship (included) or included in select optional excursions, or on own in Antigua
BBQ Deck Dinner onboard the ship (included) or on own in Antiqua
9:30 pm All Aboard
10:00 pm Windstar Star Pride departs Antigua

Day 7 – St. Kitts / Nevis (For group 2, Day 7 will be Antigua)

8:00 am Windstar Star Pride arrives St. Kitts (Group 2: arrives 10:00 am)
Breakfast onboard the ship (included)
Optional Excursions available for purchase
A-O Trips Beach Day at Carambola Beach Club with Activities (Included)
Lunch at Carambola Beach Club (included)
Dinner onboard the ship (included) in various ship restaurants or on own in St. Kitts
9:30 pm All Aboard
10:00 pm Windstar Star Pride departs St. Kitts

Day 8 – St. Barts

8:00 am Windstar Star Pride arrives St. Barts
Breakfast onboard the ship (included)
Optional Excursions available for purchase
Lunch onboard the ship (included) or included in select optional excursions, or on own in St. Barts
Dinner onboard the ship (included) in various ship restaurants or on own in St. Barts
10:30 pm All Aboard
11:00 pm Windstar Star Pride departs St. Barts

Day 9 – Day at Sea

Breakfast onboard the ship (included)
Ship Activities available throughout the day onboard (some included and some for purchase)
Lunch onboard the ship (included)
Farewell Reception on deck (included)
Dinner onboard the ship (included) in various ship restaurants

Day 10 – San Juan, Puerto Rico

7:00 am Windstar Star Pride arrives in San Juan, Puerto Rico
Breakfast onboard the ship (included)
Optional Excursions available for purchase with included transfer to the airport
8:00 am Disembarkation begins
Transfers to San Juan Airport based on flight time – departing either from the pier or from Hotel Rumbao
9:00 am – 2:00 pm A-O Trips Hospitality Room at Hotel Rumbao; scheduled airport transfers from hotel to airport provided throughout the day
Depart San Juan, Puerto Rico on flights to home cities