USA · SUNSET CRUISES & SAILS
Every trip has one free day too few. These 15 sunset cruises & sails justify the slot, priced and timed so you can decide in minutes and get back to the fun part of planning.
Sail the Key West coast at sunset on a big catamaran with an open bar, live local music, and filling hors d’oeuvres in about 2 hours.
“Time on the boat was so enjoyable! Not overcrowded. Enjoyed drinks and delicious snacks! The crew was great!!”
Cruise San Francisco Bay for sunset, passing Alcatraz and Angel Island, then go under the Golden Gate Bridge and watch city lights bloom.
“Got to see Alcratraz, Angel Island and the whole bay area... we were lucky to get a fabulous sunset as well.”
Key West sunset dinner cruise with tropical buffet, unlimited drinks, live music, and best water views for photos.
“Was very relaxing. If you wanted to be alone by yourself, you could. if you wanted to party with others you could. Good mix.”
San Francisco sunset cruise on the Bay: Alcatraz, Angel Island, and the Golden Gate Bridge, plus skyline lights after dark.
“My wife and I (early 30s) were in San Francisco for a few days and wanted to get a boat cruise in. This is not a historic tour cruise, so don't expect a guide. It is meant to show the bay area from different views. They have snacks and beverages including alcohol on board for purchase. You can also bring your own food on (no alcohol), so we stopped by Boudin across the street for a loaf of fresh sourdough bread and charcuterie meats. When we got on board, we grabbed a table and purchased a bottle of wine, enjoying the sights for 2 hours. If we got dinner before,…”
Lake Michigan sunset cruise from the Chicago River, skyline views and architecture narration, plus snacks and drinks onboard.
“This was an amazing experience, even with it being cold! I booked this for my sister's birthday, and this was our first time visiting Chicago as well!”
Two-hour Ka'anapali sunset catamaran with open bar, pupus, live music on select nights, and winter whales from the water.
“The crew is professional and friendly! The ride is beautiful and the food was good. We’ll definitely book again.”
Sunset cruise from South Street Seaport area to Lady Liberty with music, indoor comfort, and close skyline views near Brooklyn Bridge.
“Amazing experience and worth every penny. What a beautiful way to see NYC”
Small-group Key West sunset sail with up to eight wines, quality beer, and hors d'oeuvres. Check in on Front St.
“It was wonderful. At first your like where are we going to sit but they have it all figured out. It was perfect.”
A 90-minute St. Augustine sunset cruise with live narration, pontoon comfort, landmark views, and a choice of 21+ or family-friendly onboard vibes.
“Great night on the water! The crew, drinks and atmosphere were amazing! Beautiful sunset too! Definitely would recommend!”
San Francisco Bay sunset cruise on a luxury catamaran past Alcatraz, under the Golden Gate Bridge, with Pier 39 sea lions and 1 drink.
“Cannot say enough about my experience! First, customer service is on point: from office staff to on board - everyone seems like they love what they do. So accommodating to guests, from volunteering to take photos, showing us the ropes, general hosting. The cruise itself was...perfect. Comfortable number of guests allowed all of us to move around at take photos at every angle at leisure. The route and time of the cruise was fantastic. Seriously, SO many incredible photo ops, especially on a clear day like this last Sunday. Unanticipated chill from the winds and splashing water were helped by jackets for everyone to borrow as needed. If you decide…”
A 2-hour Key West catamaran sunset sail with live local music, unlimited drinks, and appetizers, returning for dinner with ocean views.
“The boat can seem crowded and not enough seating for everyone but even when full there’s plenty of room to move around. Deck hands were great and made sure everyone had a good time.”
Small-group Key West sunset sail with drinks included, a rail-side view, and a front-row look at the Sunset Celebration.
“This was a wonderfully relaxing sunset sail. There were only 13 people on board. The drinks were free flowing and the sky was beautiful.”
Two-hour Charleston Harbor sunset cruise on a 45-foot catamaran. Pass landmarks, spot dolphins, and photograph forts and lighthouses.
“The crew were great! There was a lot of history but they did not talk the whole time. I would definitely recommend!”
Boston Harbor Sunset Cruise from Rowes Wharf, see USS Constitution and Boston landmarks, guided narration, onboard bar. 90 min.
“Love it the crew was great. The years of experience in whale watching and safe animal tourism was obvious. We found about 8 humpbacks in a hunting ground and had some truly amazing sites.”
A 2-hour Key West sunset sail on the America 2.0 replica schooner with beer, wine, champagne, and plated hors d’oeuvres.
“Highly recommends to those who appreciate a quiet sail vs a powerboat. Crew was kind and accommodating , drinks were robust and plentiful! We thought appetizers were also fresh and delicious!”
Every kind of day out, and the best of each.
