On the water · SUNSET HARBOUR CRUISES
Sunset sailings cost a little more than the same boat at noon and fill up first. These 15 cover the schooners, the dinner boats and the plain hour on deck, with prices and the departure times that actually catch the light.
Spend 90 minutes aboard a 1920s-Bay-Steamer-replica yacht with live English narration from the captain. You will pass Fort Sumter, The Battery, the Ravenel Bridge, Civil and Revolutionary War sites, and more than 75 harbor landmarks. Choose indoor or outdoor seating, watch for dolphins and pelicans, and buy drinks or snacks on board.
“The captain was knowledgeable and full of local stories.”
Watch Old San Juan, El Morro, and the city walls glow at sunset on a 90-minute harbor cruise with Rico Sun Tours. Rafael and the crew mix local history with music and a casual party mood. Beer, rum punch, soft drinks, water, and light snacks are included, but the boat has no bathroom.
“Don’t go. Very poor!!! Awful!! No bathrooms. They forgot to bring wine on board as advertised they would have! Food was pitiful and not as advertised. Not worth the money”
Set sail from Marriott Frenchman's Cove aboard The VI Cat, a 54-foot US Coast Guard-certified catamaran. Enjoy sunset views, Charlotte Amalie harbor lights, a taco or barbecue dinner, and an open bar during this relaxed two-hour evening cruise. Arrive 30 minutes early, and request vegetarian or vegan food at least 48 hours ahead.
“A great way to wind down your day or the end of a visit. The crew was awesome interacted great with the guests.”
Board Captain Cook Cruises’ Sydney 2000 at King Street Wharf for an early-evening meal on Sydney Harbour. You’ll pass the Harbour Bridge and Opera House while enjoying three à la carte courses, with a four-course premium upgrade available. Add a confirmed window seat for clearer views, and expect live music on weekends.
“We had an amazing experience with the harbour cruise with guaranteed window seating. Our waiter, Kevin, was excellent, and the food was terrific. Entertainment was also first class. It was worth every penny.”
Meet Sandlapper Water Tours at the Charleston Maritime Center for a two-hour sunset ride on a 45-foot catamaran. Captain Mike, Victor, Robbie, Tim, JP, and other crew members have been praised for mixing local facts, humor, music, and personal attention. Expect Fort Sumter, the Battery, dolphins, the Ravenel Bridge, and sunset photos, but not a formal narrated tour.
“This was a great sunset cruise. Victor was very fun to talk to. He encouraged everyone to have their pictures taken with the perfect sunset. The music was great. It was a beautiful relaxing evening!”
Meet at Rowes Wharf for a 90-minute English-language cruise around Boston Harbor. You’ll see the skyline, USS Constitution, Logan Airport activity, and the city changing from daylight to evening. A guide provides history and local stories, while the onboard bar sells snacks and drinks. Indoor and outdoor seating are available.
“The weather😂. Everything else was as advertised. The narrator was knowledgable, friendly and really nice to listen to. Thoroughly enjoyed learning all about Boston and its harbour.”
Cruise Boston Harbor for about two hours as sunset colors the skyline and historic waterfront. You will pass the Old North Church, Charlestown Navy Yard, USS Cassin Young, and USS Constitution, whose cannon marks sundown. Choose the open-air deck or heated cabin, and buy drinks or light snacks onboard. Commentary is brief, not a full guided tour.
“Very nice ride around the harbor. The Christmas decorations wade the trip very pleasant. The entertainment was nice too.”
Sail from Rowes Wharf for 90 minutes of live Boston Harbor narration, passing Fish Pier, Logan Airport, East Boston, Charlestown, the USS Constitution, and the North End. You’ll see Boston change from daylight to city lights, with outdoor and indoor seating plus a bar and snacks for purchase. Arrive early for the best upper-deck seats.
“It was super good! Get a seat in the front of the boat and bring a jacket for night cruises. Such a fantastic time!! The microphone was a little quiet in some parts of the ship.”
Set out from Charleston’s Maritime Center on a 45-foot power catamaran for a two-hour evening cruise. You’ll pass the Battery, Fort Sumter, islands, lighthouses, and the Ravenel Bridge, with chances to spot dolphins and shore birds. Captains and hosts such as Mike, Victor, JP, and Robbie mix local stories with music, photos, and drinks available from the onboard bar.
“Captain Robert and Victor were so much fun. Was an amazing way to complete our last night in Charleston.”
Spend two hours aboard the schooner Bay Lady, sailing from Pier 66 as the sun drops behind the Olympic Mountains. You can help raise the sails, take a turn at the wheel, and buy beer, wine, cider, champagne, snacks, or soft drinks. Bring warm layers: the boat sails rain or shine, and the evening breeze can feel cold.
“Best experience we have had here. The captain and crew were tremendous.”
Board the Charles Darwin at Stokes Hill Wharf for a two-hour Darwin Harbor cruise, timed for sunset. You’ll dine on a Territory-style buffet with seafood and local produce, use the top deck for photographs, and buy drinks from the licensed bar. Assigned seating keeps boarding orderly, though commentary is limited.
“An excellent excursion. The barramundi was outstanding. Highly recommend.”
Board the Sea Rocket at 307 Dorchester Street for a one-hour sunset ride through Ocean City Harbor and nearby waters. You’ll see fishing boats, waterfront restaurants, mansions, and the skyline while the crew searches for dolphins. Captains including Owen, Ashton, Chase, and Riley have earned praise for making the trip lively and informative. A full liquor license is available for the 2025 season.
“We didn’t even get to go on the cruise as I was only informed 30 minutes before departure that they didn’t sell enough tickets. Apparently only 12 seats left on the boat isn’t enough to run the cruise.”
Spend one hour on a 10.5-metre catamaran with up to 26 passengers, cruising beneath the Harbour Bridge and past the Opera House at sunset. The friendly crew, including Phil, Adam, Jacob, and others, serve a grazing platter and one soft drink or water. Bring your own alcohol, wear a jacket, and remember that sunset is not guaranteed.
“Great activity, experience and crew! Would absolutely do it again. I also really appreciate the staff. They were so kind and took us on a great excursion.”
Sail Maui’s west coast aboard the 55-passenger Ocean Spirit, a luxury catamaran departing Ma’alaea Harbor for a two-hour sunset outing. You’ll get island-style music, appetizers, coffee, tea, and non-alcoholic drinks, with possible whale sightings in season. Alcohol policies have changed, so confirm current BYOB and liquor-license details before booking.
“We really enjoyed our sunset sail. Our all female crew were fun and hard working (I had no idea of the physical exertion required in hoisting the sail). The food was really good and my beer was cold. But the real attraction was nature itself. Being in the ocean watching the sunset was simply amazing.”
Join Fins Up Clearwater for a 90-minute sunset cruise from 25 Causeway Blvd. You will sail through Clearwater Harbor, look for dolphins, hear local stories from the crew, and watch bridge lights come on after sunset. Bring your own snacks and drinks, or buy water and soda onboard. Captains Matt and guides such as Zach have earned praise for smooth handling and friendly commentary.
“Beautiful Sunset, knowledgeable and friendly crew, on time, safe and smooth ride. We highly recommend!”
Fifty countries, one thing in common: the best view is from the deck.
