The Caribbean · SUNSET CRUISES

Caribbean Sunset Cruises: The 15 Best Sailings

79 tours  ·  from $36

Sundown from the water beats sundown from a hotel terrace by a distance. The 15 below are priced and timed, with a note on which serve real food and which hand you a plastic cup.

Aruba Sunset Sail with Appetizers and Open Bar - Finding your place on the catamaran
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Aruba Sunset Sail with Appetizers and Open Bar

1.Aruba Sunset Sail with Appetizers and Open Bar

★★★★★★★★★★4.5 · 2,024 reviews · from $92Our pick

Meet the Red Sail Sports crew at Piet’s Pier Bar at 5:30 pm for a two-hour catamaran sail past Palm Beach. Sip rum punch, beer, and tropical cocktails while the crew, including entertainers such as Junior, Brandon, or Lizzie, adds music, stories, and dancing. Seating can be limited, so arrive early.

“Fun adventure! Boat a little crowded, seating was tight, but we were fortunate to have fun people around us. Captain & staff were very friendly and accommodating which enhanced the adventure. Snorkel was fun.”

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Afternoon Snorkel, Pizza & Sunset Tour departing from St. Thomas & St. John - Pizza Pi and Drinks After Swimming
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Afternoon Snorkel, Pizza & Sunset Tour departing from St. Thomas & St. John

2.Afternoon Snorkel, Pizza & Sunset Tour departing from St. Thomas & St. John

★★★★★★★★★★5.0 · 1,498 reviews · from $120Top rated

Join Ocean Surfari’s Reef Surfari for two snorkeling stops in Virgin Islands National Park, followed by pizza from Pizza Pi, drinks, music, and a sunset dance party. Captains and guides such as CJ, BK, John, Sydney, Darian, and Andy keep the trip lively. Pickup is available in Red Hook and Cruz Bay.

“From the time we were picked up to the time we bid farewell the trip was very entertaining. We met John and Darien first and they were very nice. Captain CJ was very interactive with everyone and along with John and Darien made the whole trip so fun. The sunset dance party was the icing on the cake. Thank you guys for making it worth experiencing”

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Aruba Happy Hour Sunset Sail with Savory Bites and Cocktails - Why the 40-foot trimaran feels more relaxed
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Aruba Happy Hour Sunset Sail with Savory Bites and Cocktails

3.Aruba Happy Hour Sunset Sail with Savory Bites and Cocktails

★★★★★★★★★★4.5 · 1,488 reviews · from $84

Set sail from Palm Beach on a two-hour sunset trip aboard a 40-foot trimaran for up to 34 people. Crew members such as Shaka, Jose, Richard, Vino, and Martin may keep drinks and appetizers moving while you enjoy cushioned seating, sea views, music, and Aruba Ariba cocktails. Boarding requires a short shuttle-boat ride through shallow water.

“The crew was very friendly and helpful. Drinks were frequently offered. The padded bench seating was comfortable. The snacks were good. The small boat portage was a fun way to access the sailboat”

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San Juan Sunset Harbor Boat Ride - Boarding at the marina or using hotel pickup
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San Juan Sunset Harbor Boat Ride

4.San Juan Sunset Harbor Boat Ride

★★★★★★★★★★4.5 · 1,320 reviews · from $109

Cruise San Juan Bay for 90 minutes with guide Rafael and the Rico Sun Tours crew. You’ll pass Old San Juan, El Morro, Paseo de la Princesa, La Fortaleza, and Casa Bacardi while enjoying rum punch, local beer, soft drinks, water, and light snacks. Expect a friendly sightseeing trip that shifts into a casual music-and-dancing party.

“We had a great time! Learned a lot about PR history. The facilitator and captain were very knowledgeable and made us all feel welcome and comfortable.”

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Sunset & Harbor Lights Dinner Sail from the Marriott's Frenchman's Cove - Setting sail aboard the 54-foot VI Cat
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Sunset & Harbor Lights Dinner Sail from the Marriott’s Frenchman’s Cove

5.Sunset & Harbor Lights Dinner Sail from the Marriott’s Frenchman’s Cove

★★★★★★★★★★5.0 · 1,176 reviews · from $119

Sail from Marriott’s Frenchman’s Cove aboard the 54-foot VI Cat for a sunset and Charlotte Amalie harbor lights dinner. Enjoy an open bar, tacos on Tuesdays or barbecue on Wednesdays, Fridays, and Saturdays. The crew, including names such as Captain Dave, Mike, Isaac, and Anders on some departures, handles the food, drinks, and sailing during this relaxed two-hour outing.

“Staff was professional and friendly. The food was good but should have a dessert to offer your guests.”

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2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only) - Grace Bay views, reef water, and a gentle pace
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2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only)

6.2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only)

★★★★★★★★★★5.0 · 1,010 reviews · from $121

Board Ocean Vibes’ 48-foot Island Magic for a two-hour sunset sail along Grace Bay. You’ll get Champagne, wine, local beer, rum punch, soft drinks, and island snacks such as conch fritters. Captain Maycock and crew members including Reggie, Erickson, and Tae are known for a lively, social ride. Expect to wade through shallow water when boarding.

“We had the best time - super fun crew, great music, drinks were never empty and island appetizers! Nothing beats a cruise at sunset with a glass of champagne in hand while you watch the sun melt into the ocean. Super communication prior to the cruise, very responsive to all questions.”

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Aruba Sunset Cruise plus Seaside Dinner - Open bar, snacks, and the changing sky
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Aruba Sunset Cruise plus Seaside Dinner

7.Aruba Sunset Cruise plus Seaside Dinner

★★★★★★★★★★4.5 · 960 reviews · from $122

You’ll sail from Pelican Pier aboard a catamaran, with an open bar, snacks, music, and a sunset over Aruba’s coast. The crew may include hosts such as Sam, Reggie, Jackie, or Pepper, though staffing varies. After the cruise, sit outdoors at Pelican Nest for a set seafood dinner and one glass of wine or soda.

“Cruise portion amazing, sunset was beautiful & crew was professional & fun! Dinner is a set seafood menu but you can choose other options, if you go over $30pp you pay the difference.”

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Cocktail Sunset Cruise from Sapphire Beach Resort - Leaving Sapphire Beach Marina around St. Thomas
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Cocktail Sunset Cruise from Sapphire Beach Resort

8.Cocktail Sunset Cruise from Sapphire Beach Resort

★★★★★★★★★★5.0 · 748 reviews · from $130

Set out from Sapphire Beach Marina with New Horizons & Breakaway Charters for a two-hour sunset cruise around St. Thomas and nearby islands. The crew provides island commentary, Champagne, an open bar, bottled water, and appetizers. Captains Nate, Stewart, and Dave, along with crew members Max, Whitney, and Breezy, have earned high marks for warm service and lively music.

“I hope Dawn wins the steak knife set she was wonderful! It was a great experience the crew was wonderful and knowledgeable great food! Amazing music choices OAR for the win!”

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Historical San Juan Bay Sunset Sailing Tour - The sunset portion is the real payoff
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Historical San Juan Bay Sunset Sailing Tour

9.Historical San Juan Bay Sunset Sailing Tour

★★★★★★★★★★4.5 · 710 reviews · from $115

You’ll sail San Juan Bay for about two hours aboard a 30-foot J/30 racer-cruiser with a captain such as Ivan, Joe, or Carlos. Expect views of El Morro, harbor traffic, local history, and sunset photos. Beer, sangria, rum and Coke, water, and light refreshments are included. The boat is small and sporty, not a yacht or party catamaran.

“Unfortunately, we were not able to sail with this company and ultimately we were not able to communicate with them at all about our problem with the excursion.”

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Champagne Sunset Sail from Margaritaville - What the catamaran ride feels like
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Champagne Sunset Sail from Margaritaville

10.Champagne Sunset Sail from Margaritaville

★★★★★★★★★★4.5 · 691 reviews · from $130

Sail from Margaritaville aboard a modern catamaran for about two hours, with champagne, rum punch, Painkillers, cocktails, soda, and substantial snacks included. The crew, including captains such as Big Tuna and Danny Boy, serves drinks while you watch St. Thomas slip into sunset and the moon rise. Expect a social, barefoot boat outing rather than a sightseeing tour packed with island facts.

“10/10 recommend!! i find water to be so calming & this experience was everything. the views were beautiful, the vibes were great & the crew was top tier!! would do it again hundred times over :))”

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Beach Sunset on Horse Riding in Punta Cana(Private Option) - A short taste of Dominican farm life
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Beach Sunset on Horse Riding in Punta Cana(Private Option)

11.Beach Sunset on Horse Riding in Punta Cana(Private Option)

★★★★★★★★★★5.0 · 684 reviews · from $73

Ride from a family-run ranch to Punta Cana’s beach as the sun goes down. Beginners receive riding help, choose from available horses, and can meet guides such as Miguel and Chris. The outing includes round-trip transport, a beach ride, sunset photos, and a small look at local coffee and cacao production.

“We had a great experience!!! Staff was very professional and accommodating! The beach and sunset was perfect! We enjoyed every minute of the tour!!!”

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Aruba Sunset Sail Cruise Aboard The Dolphin Catamaran - The north-coast ride and the first drink
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Aruba Sunset Sail Cruise Aboard The Dolphin Catamaran

12.Aruba Sunset Sail Cruise Aboard The Dolphin Catamaran

★★★★★★★★★★4.5 · 649 reviews · from $59

Spend about two hours aboard The Dolphin, a 45-foot catamaran sailing from the Hyatt Regency beach. Enjoy Caribbean music, an open bar, light snacks, sunset views, and a swim stop with a rope swing and waterslide. Check in with Olga or John at Delphi Watersports, then board by shuttle boat.

“The site i was in listed DePalm Pier as the beginning spot. We purchased the excursion for all 4 of us. As it turned out, the site was incorrect. Departure was Pelican Pier.”

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Historic Old San Juan Sunset Walking Tour - Plaza de la Barandilla and the everyday city
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Historic Old San Juan Sunset Walking Tour

13.Historic Old San Juan Sunset Walking Tour

★★★★★★★★★★5.0 · 634 reviews · from $39Best value

This two-hour Old San Juan walk starts at Plaza Colón and covers plazas, churches, La Fortaleza, Cuartel de Ballajá, and views of El Morro. Guides including Melanie, Antonio, and Jorge bring Puerto Rican history and culture into the streets. You will walk on hills, steps, and cobblestones, but fort entry is not included.

“Melanie was amazing! She brought Old San Juan to life with her deep knowledge of the city’s history, culture, and architecture. I especially appreciated how she connected the past to Puerto Rico’s current political landscape in such a cRead more”

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Private Sunset Horseback Riding in punta cana beach - The countryside trail is part of the experience
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Private Sunset Horseback Riding in punta cana beach

14.Private Sunset Horseback Riding in punta cana beach

★★★★★★★★★★4.5 · 625 reviews · from $77

Ride a calm Dominican horse for about two hours through countryside and along Punta Cana’s coast. Guides such as Fausto, Miguel, and Sammy lead private groups, provide water, and often stop for photos. Hotel pickup and drop-off are included, though beach time and sunset views can vary with weather, timing, and trail conditions.

“It was easy to schedule. Not far from breathless punta cana. Staff was grest and ensured our safety.”

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San Juan Catamaran Sunset Sail with Drinks Included - Setting out across San Juan Bay
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San Juan Catamaran Sunset Sail with Drinks Included

15.San Juan Catamaran Sunset Sail with Drinks Included

★★★★★★★★★★5.0 · 622 reviews · from $119

Join Sail PR for a two-hour sunset sail from San Juan Bay Marina aboard a 37-foot catamaran limited to six people. Captain Rafael, Hector, Victor, Sophia, Diego, or another crew member may point out El Morro, the San Juan Gate, and the island’s second-oldest executive mansion while you enjoy rum punch, sparkling wine, beer, soft drinks, and water.

“Our experience was about as perfect as I could have asked. We lucked out with some weather that passed thru just in time, and had a magnificent sunset to enjoy the cruise to. A relaxed paced tour around the bay of San Juan, amazing view of El Morrow at sunset, Rafa (our captain) was a gracious host and the First Mate was attentive to ensuring everyone had what they needed (great drinks!), and threw in some history about some of the buildings and scenery as we went along. The passengers are limited to six (we were three) and we shared the ride with another couple and enjoyed nice conversation together…”

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New in Sunset Cruises

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★ 5.0Puerto Rico Sunset Magic: Bio Bay Kayaking Tour from FajardoFrom $66199 reviews
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★ 5.0Klein Curacao Sunset Cruise with Open Bar and BBQFrom $14033 reviews
★ 4.5Cruise Sunset Party in CastriesFrom $8976 reviews
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★ 5.0100% Private Sunset Sail on the most spacious monohull of BonaireFrom $24646 reviews
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