Island hopping · SUNSET ISLAND CRUISES IN THE USA

The 15 Sunset Island Cruises in the USA That Earn Their Price

21 tours  ·  from $40 a head

The 15 best sunset island cruises in the USA you can book today, with the per-head price, how long the day runs and how many landings you get. Number one is top for a reason; start there.

Island Sunset and Skyway Light Show - 3hr Boat Cruise in St. Pete - Leaving St. Pete beside waterfront estates
Evening Experiences, Island Hopping Tours, Show, Sunset Island Cruises, Sunset Island Cruises in the USA, Tour Reviews, USA Island Hopping Tours

Island Sunset and Skyway Light Show – 3hr Boat Cruise in St. Pete

1.Island Sunset and Skyway Light Show – 3hr Boat Cruise in St. Pete

★★★★★★★★★★5.0 · 1,871 reviews · 3 hours (approx.) · from $80Our pick

Spend about three hours on the water with Coastal Cruises, passing waterfront estates, sailboats, bridges, and possible dolphin-spotting areas. Step onto Sand Dollar Island for sunset and shell hunting, then return beneath the Sunshine Skyway Bridge for its nightly lights. Captains and crew members may include Paul, Gavin, Chase, Dillon, or Noah.

“Aaron and Dillion were great!!! We rode out to an island to see the sunset and then under the sunshine skyway bridge was really colorful!! They were very funny and enjoyable”

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Sunset & Dolphin Catamaran Cruise with Island Time - Key points to know before you book
Catamaran Cruises, Catamaran Cruises in the USA, Dolphin Watching, Evening Experiences, Island Hopping Tours, Sunset Island Cruises, Sunset Island Cruises in the USA, Tour Reviews, USA Island Hopping Tours

Sunset & Dolphin Catamaran Cruise with Island Time

2.Sunset & Dolphin Catamaran Cruise with Island Time

★★★★★★★★★★5.0 · 1,867 reviews · 2 hours (approx.) · from $57

Spend two hours aboard Island Time Sailing’s catamaran, cruising Grand Lagoon past St. Andrews State Park while watching for dolphins and sunset color. The crew, including Captain Clay, Christo, Sara, Audra, Carter, and Emma on various departures, adds music, drinks, photos, and dockside fun.

“Very nice experience! The entire crew was great, they obviously enjoy their jobs. We really enjoyed sailing with no engine, it is exhilarating. Absolutely recommend this tour!”

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Hilton Head Island: Sunset Dolphin Cruise - The dolphin search comes first
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Hilton Head Island: Sunset Dolphin Cruise

3.Hilton Head Island: Sunset Dolphin Cruise

★★★★★★★★★★4.6 · 412 reviews · 1h 30m · from $50

Join Vagabond Cruise at Harbour Town Pier for a 90-minute sunset sail. Your English-speaking captain searches for Atlantic bottlenose dolphins, then heads toward Daufuskie Island and Bull Creek. Expect live nature commentary, open-water views, and drinks and snacks for sale. Bring cash and a warm layer.

“We saw so many dolphins! It was amazing. The tour guide did a fantastic job telling us about dolphin behavior and other facts. We were lucky to be in the Sound when two shrimp boats came in, which attracted even more dolphins. It was a memorable activity and I’m very happy to have gone on this short cruise.”

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Cape May: Cape May Island Sunset Cruise & Dolphin Watching - The first stretch: Cape May from the water
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Cape May: Cape May Island Sunset Cruise & Dolphin Watching

4.Cape May: Cape May Island Sunset Cruise & Dolphin Watching

★★★★★★★★★★4.7 · 382 reviews · 2 hours · from $40Best value

Join Captain Jeff aboard the Cape May Whale Watcher for a two-hour sunset cruise from Miss Chris Marina. Look for bottlenose dolphins, pass Cape May’s lighthouse and Victorian waterfront, hear local stories, and enjoy included pizza and hot dogs. Drinks are available to buy, and the ship is wheelchair accessible.

“It was an incredible experience! Seeing multiple dolphins up close and learning about them was unforgettable. The crew was friendly, welcoming, and helpful from start to finish. As a bonus, we enjoyed a fascinating tour filled with fun facts about the landmarks, buildings, and attractions around the island. I would highly recommend this to anyone visiting the area, you truly get far more than you pay for. I can’t wait to return!”

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Anna Maria Island Dolphin Sunset Boat Tour - What dolphin watching is really like here
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Anna Maria Island Dolphin Sunset Boat Tour

5.Anna Maria Island Dolphin Sunset Boat Tour

★★★★★★★★★★5.0 · 272 reviews · 2 hours (approx.) · from $57

Set out from Waterline Villas & Marina with an English-speaking captain and crew for about two hours on Sarasota Bay. Look for dolphins, manatees, sea turtles, pelicans, and other wildlife, then watch the sun sink beyond Anna Maria Island. Captains may include Ben, Chad, Mike, JD, Luke, or Jake.

“We had a great time and saw a lot of dolphins. Crew was very knowledgeable, friendly, and enthusiastic. They took us to a perfect spot to watch the sunset.”

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South Maui: Sunset Prime Rib or Island Fish Dinner Cruise - Ma’alaea Bay, music, and the first drink
Dining Experiences, Dinner Experiences, Evening Experiences, Island Hopping Tours, Sunset Island Cruises, Sunset Island Cruises in the USA, Tour Reviews, USA Island Hopping Tours

South Maui: Sunset Prime Rib or Island Fish Dinner Cruise

6.South Maui: Sunset Prime Rib or Island Fish Dinner Cruise

★★★★★★★★★★4.7 · 242 reviews · 2 hours · from $149

Sail from Ma’alaea Harbor on a triple-decker catamaran for a two-hour Maui sunset cruise. Choose prime rib, mahi-mahi, chicken, ribs, or vegetarian pasta, then enjoy live music, dessert, two drinks, and views toward Molokini, Lanai, Kaho’olawe, and the West Maui Mountains.

“Great food and breathtaking scenery! Staff was top shelf! Loved that you could go up top outside and the sunset was amazing!”

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Hilton Head Island: Sunset Dinner Cruise - A three-course dinner with four main choices
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Hilton Head Island: Sunset Dinner Cruise

7.Hilton Head Island: Sunset Dinner Cruise

★★★★★★★★★★4.5 · 211 reviews · 2 hours · from $109

Cruise from Harbour Town aboard the Spirit of Harbour Town for a two-hour dinner with personal table service, sunset views, and a chance to spot dolphins. Choose an outdoor upper-deck table or climate-controlled indoor seating. The menu includes mahi-mahi, chicken, pork, vegetarian pasta, and dessert.

“This dinner cruise was lovely. Watching the sunset from the boat was beautiful. The dinner was delicious. We got the chicken. Dessert was also yummy. Great experience.”

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2-Hour Sunset Sailing With Wine In Stock Island - Wine, Beer, Sodas, and a Practical Snack
2-Hour Experiences, Evening Experiences, Island Hopping Tours, Sailing & Yacht Charters, Sailing and Yacht Charters in the USA, Sunset Island Cruises, Sunset Island Cruises in the USA, Tour Reviews, USA Island Hopping Tours, Wine Tours

2-Hour Sunset Sailing With Wine In Stock Island

8.2-Hour Sunset Sailing With Wine In Stock Island

★★★★★★★★★★5.0 · 94 reviews · 2 hours (approx.) · from $125

Spend two hours sailing from Stock Island aboard a schooner with eight wines, five beers, sodas, and charcuterie. The crew, including guides such as Tony, Maria, and Lexi on some departures, serves drinks and helps you enjoy a calm sunset on the water. Ages 13 and up.

“This was an awesome experience. The food and wine selection was great! Staff was awesome! And the views of the sunset were top notch! Would highly recommend!”

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Folly Beach: Sunset Dolphin Boat Tour to Morris Island - Starting at 83 Center Street
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Folly Beach: Sunset Dolphin Boat Tour to Morris Island

9.Folly Beach: Sunset Dolphin Boat Tour to Morris Island

★★★★★★★★★★4.9 · 73 reviews · 2 hours · from $59

Cruise Folly’s creeks and marshes with a local captain such as Will, Davis, or Richard, watching for bottlenose dolphins and seasonal strand feeding. Stop for 20 to 30 minutes on Morris Island to see the lighthouse and search for shells, sand dollars, fossils, and shark teeth before returning at sunset.

“We had such a good time! Captain Davis was wonderful and navigated all sorts of tricky weather and still managed to make it a really great experience for all of us, despite rain and wind. Would definitely recommend. (Plus his play list was *chefs kiss*.)”

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Naples, FL: Manatee, Dolphin, 10,000 Islands Sunset Cruise - Wildlife Along the Way
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Naples, FL: Manatee, Dolphin, 10,000 Islands Sunset Cruise

10.Naples, FL: Manatee, Dolphin, 10,000 Islands Sunset Cruise

★★★★★★★★★★4.7 · 71 reviews · 3 hours · from $129

Join Captain John or Captain Chris for a three-hour sunset cruise from Port of the Islands Marina. Watch for manatees, dolphins, alligators, turtles, and birds, then stop at Whitehorse Key for shelling before the sun drops over Gulf waters.

“Capt. John was terrific and informative, charismatic, wonderfully funny and friendly guide on our private tour. We saw manatees, a crocodile sunning himself on a boat dock and cranes and pelicans & birds. Also we were able to get out of the boat to collect shells - my daughter found 2 live conches which she put back in the water. Then we saw a most beautiful sunset on the boat. Definitely worth it to go on fabulous adventure! Highly recommend it to everyone.”

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Chincoteague: Assateague Island Sunset Boat Cruise - The first part of the 90-minute cruise
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Chincoteague: Assateague Island Sunset Boat Cruise

11.Chincoteague: Assateague Island Sunset Boat Cruise

★★★★★★★★★★4.2 · 69 reviews · 1h 30m · from $59

Cruise from Chincoteague to Assateague Island with local captains such as Shane and guides such as Jen. Over 90 minutes, look for wild ponies, dolphins, eagles, and shorebirds while learning local stories. The boat returns to the harbor after sunset, with free parking and wheelchair access.

“The captain was friendly, honestly sounded like Mater from the Disney cars movie. Jen the commentator was knowledgeable and very passionate. we saw dolphin and the ponies. excellent experience.”

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Waikoloa: Catamaran Sunset Sail with Cocktails - Getting to the boat at Anaeho‘omalu Bay
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Waikoloa: Catamaran Sunset Sail with Cocktails

12.Waikoloa: Catamaran Sunset Sail with Cocktails

★★★★★★★★★★4.8 · 68 reviews · 1h 30m · from $159

Spend 90 minutes aboard the Spirit of Aloha catamaran, departing Anaeho‘omalu Bay for a sunset sail past Mauna Kea and Hualālai. Your ticket includes a premium bar, island-style snacks, shaded seating, restrooms, and crew service. Boarding requires a short barefoot walk through seawater from the beach.

“Everything about the sunset sail was awesome. Beautiful sailing and sunset; as well as expert/kind/wonderful captain and crew. I couldn’t have enjoyed it more.”

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South Pasadena: Island Sunset Cruise and Skyway Light Show - From Gulfport to the Intracoastal Waterway
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South Pasadena: Island Sunset Cruise and Skyway Light Show

13.South Pasadena: Island Sunset Cruise and Skyway Light Show

★★★★★★★★★★4.9 · 17 reviews · 3 hours · from $84

Spend three hours on a 50-foot catamaran with Captain Glenn and the St. Pete Coastal Cruises crew. You’ll cruise the Intracoastal Waterway, look for dolphins, walk ashore on Outback Key, watch the Gulf sunset, and stop beneath the Sunshine Skyway Bridge’s $15 million light show.

“we really enjoyed the cruise. I found a few shell pieces on Shell Island, watching the sky during sunset was fun and seeing the Sunshine Skyway bridge and the other bridges was amazing.”

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Marco Island: Sunset Boat Tour - Leaving Goodland for the Ten Thousand Islands
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Marco Island: Sunset Boat Tour

14.Marco Island: Sunset Boat Tour

★★★★★★★★★★4.9 · 16 reviews · 2h 30m · from $125

Spend 150 minutes with a captain such as John, Nate, or Thomas cruising Marco Island and the Ten Thousand Islands. Look for dolphins, manatees, birds, fish, and stingrays, then step onto a remote barrier island for sunset. Bring snacks and drinks for this six-person boat tour.

“It was a perfect boat ride with Captain Nate to see wildlife and the beauty of the Marco island area. A bathroom on the boat would have been nice.”

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Private Boat Tour, Sunset Cruise, Island Hopping and more! - Setting out from Florida’s central Gulf Coast
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Private Boat Tour, Sunset Cruise, Island Hopping and more!

15.Private Boat Tour, Sunset Cruise, Island Hopping and more!

★★★★★★★★★★5.0 · 15 reviews · 3 - 8 hours

Captain Steve takes up to six people on a private, flexible boat tour from Palm Harbor, Clearwater Beach, or Indian Rocks Beach. Choose dolphin watching, sunset views, sandbars, Caladesi Island, Honeymoon Island, beach stops, or a simple swim in the Gulf. Coolers, water, ice, and water toys are included.

“Capitain Steve has been great. He took us on amazing islands. We had a blast. we got to see Dolphins. it's been an unforgettable moment.”

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