

7-night Windward Ways and Tobago Cays Cruise
Aboard
Star Pride
From
Oranjestad, Aruba, Caribbean
1 Sailing
Mar 15, 2026
Published prices from
$3,119
per person*
taxes & fees included
A secluded crescent of calm on Tobago’s lesser-visited eastern coast.

4.9/5 ⭐Google 600+ Reviews | A+ Better Business Bureau

Overview
Man O'War Bay, nestled on the picturesque northeast coast of Tobago, offers cruise visitors a tranquil escape into a pristine Caribbean paradise. This deep, sheltered bay is named for the British naval ships that once anchored here, reflecting its historical significance. Today, it's renowned for its calm, clear turquoise waters, lush surrounding rainforest, and vibrant marine life, making it a favorite for nature lovers and those seeking peaceful relaxation.
The village of Charlotteville, a charming fishing community, sits along the bay, providing an authentic glimpse into Tobagonian life. Man O'War Bay is a haven for snorkeling, diving, and swimming, with its healthy coral reefs easily accessible. It embodies the untouched beauty often associated with the Caribbean, offering a serene counterpoint to more bustling destinations and an opportunity to connect with Tobago's natural splendor and friendly local culture.
Immerse yourself in the vibrant underwater world of Man O'War Bay by snorkeling or diving. The calm, clear waters and healthy coral reefs teem with colorful fish, sea turtles, and other marine life, providing an excellent opportunity for underwater exploration directly from the bay.
Tip: Many local operators offer equipment rentals and guided snorkeling or dive trips from Charlotteville village. Pay attention to currents near the bay's mouth.
Take a leisurely stroll through Charlotteville, the charming fishing village that fringes Man O'War Bay. Observe the local fishermen bringing in their daily catch, browse small shops, and experience the relaxed pace of authentic Tobagonian life.
Tip: Engage with the friendly locals; they often have great stories and insights into the village's history and culture.
Enjoy ultimate relaxation on the tranquil beaches lining Man O'War Bay. With their soft sands and calm, clear waters, these beaches are perfect for sunbathing, swimming, or simply unwinding amidst the stunning natural scenery.
Tip: Bring a towel, sun protection, and a good book to fully embrace the peaceful atmosphere of this idyllic Caribbean bay.
Ascend to Fort Cambleton, a historical site offering panoramic views of Man O'War Bay, Charlotteville, and the surrounding coastline. While largely in ruins, it provides a sense of the area's strategic past and offers fantastic photographic opportunities.
Tip: The path to the fort can be uneven; wear comfortable, sturdy shoes. The views are well worth the effort.
Embark on a guided rainforest hike in the lush hills surrounding Man O'War Bay. This region is part of the Tobago Main Ridge Forest Reserve, the oldest legally protected rainforest in the Western Hemisphere. Look for exotic birds, unique flora, and stunning vistas.
Tip: Hire a local nature guide to fully appreciate the biodiversity and learn about the medicinal uses of plants. Wear appropriate footwear and bring insect repellent.
Savor the incredibly fresh local seafood that is the lifeblood of Charlotteville. Many small eateries or roadside vendors will offer the day's catch, often prepared in traditional Tobagonian styles with a blend of Creole and West Indian flavors.
Tip: Ask for the "catch of the day" and be adventurous! You might find delicious grilled fish, conch, or lobster.



Aboard
Star Pride
From
Oranjestad, Aruba, Caribbean
1 Sailing
Mar 15, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Surf
From
Philipsburg, St. Maarten, The Netherlands
1 Sailing
Jan 4, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Surf
From
Bridgetown, Barbados
1 Sailing
Jan 25, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Surf
From
Bridgetown, Barbados
1 Sailing
Jan 18, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Surf
From
Philipsburg, St. Maarten, The Netherlands
1 Sailing
Jan 4, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Surf
From
Bridgetown, Barbados
1 Sailing
Jan 25, 2026
Published prices from
per person*
taxes & fees included

Our expert consultants and customer service teams are standing by to help with all of your cruising needs.
I was having some trouble finding the right cruise for the right price as a single traveler, but thanks to [our Cruise Expert] I was able to find it with Cruise Web. Thank you very much [our Cruise Expert]!
Camille G.
We have worked with [our Cruise Expert] several times and she makes it so easy and a pleasure to work with. She is very knowledgeable.
Linda F.
[Our Cruise Expert] was informative and very pleasant to work with. I'm not familiar with booking travel online and he made my experience pleasant.
Sharon E.
I would like to mention that for many years I really appreciate to have [our Cruise Expert] taking care of my cruises in the states. So, i'm glad to give five stars for him
Rudi D.
I am working with [our Cruise Expert] as my travel agent...he has been very helpful...he is very informative and knowledgeable about the places that I want to go on my Cruise....I would use [our Cruise Expert] and Cruise Web again to book another cruise...thank you...
Priscilla B.
[Our Cruise Expert] does an exceptional job of planning (with you) and coordinating a trip of your dreams! I can't wait to get started on the next one.
Sheralyn H.
Great working with [our Cruise Expert]! He was a tremendous help and steered us in the right direction every time! Helped us make memories for a lifetime!
Wendy F.
[Our Cruise Expert] always works hard to secure the bookings we have chosen and guides us through the process. She is always available to help and her advise is spot on.
James C.
We are residents in another country, and have used [our Cruise Expert] for years as we try to cruise around the entire world. She offers great service and stellar communication.
Dave O.
[Our Cruise Expert]does a wonderful job for me. I have had no glitches and I can count on things running smoothly when [our Cruise Expert] makes my arrangements.
Barbara H.