Top 10 Sunset Cruises

From America’s Cup-style sailing to a jazz band on a catamaran, there’s something for everyone on these early-evening jaunts at sea.


Top 10 Sunset Cruises: Downeast Windjammer Cruises

Photographer Julie Qiu

Downeast Windjammer Cruises

Cherryfield, Maine

Sailing from Bar Harbor on the Margaret Todd, this 90-minute cruise caters to a variety of viewers: Pet owners can bring dogs on a leash to mingle with Maggie, the Newfoundland salty dog. Couples cozy up to the romantic view, and families will enjoy the live folk, guitar, fiddle, or banjo music.

The view: Depending on the wind direction, the coastlines of Acadia National Park and Frenchman Bay islands provide plenty of opportunities for viewing wildlife including bald eagles, seals, and waterfowl.

When to go: Mid-May through mid-October

Rate: $35; 207/288-4585 or


Top 10 Sunset Cruises: Schooner Woodwind

Photo: Schooner Woodwind

Schooner Woodwind

Annapolis, Maryland

Choose your own adventure aboard the 74-foot Woodwind or Woodwind II with daily themed cruises that might include regional microbrew sampling or America’s Cup-style racing. (Weekend sails are not themed.)

The view: Monuments from the United States Naval Academy—including Triton Light and the Annapolis skyline

When to go: May through September, or private charter sunset sails during October

Rate: $37 (themed sails), call for private charter prices; 410/263-8994 or


Top 10 Sunset Cruises: Reef Roamers Sunset & Snorkel

Reef Roamers Sunset & Snorkel

Key Largo, Florida

This catamaran cruise combines snorkeling, sunset, and a Champagne toast. Passengers have the option to dive into the sea, or watch the show aboard the boat.

Tip: Bring an underwater camera to catch sea life illuminated by the hues of the sky.

The view: Snorkel and float alongside parrot fish, angelfish, blue tangs, yellowtail snapper, turtles, and colorful coral at the only living coral reef in North America.

When to go: April through October

Rates: $30 ($37 with equipment rental fee); 877/453-0110 or


Top 10 Sunset Cruises: Black Dragon Cruises

Photo: Black Dragon Cruises

Black Dragon Cruises

Port Isabel, Texas

You don’t have to walk the plank, but you can hunt for treasure aboard The Black Dragon, an authentic reproduction of a 17th-century Spanish galleon. Below the waterline, the boat is a modern seaworthy vessel, but up on deck the experience is a trip back in time—complete with cannons, pirate stories, water pistol battles, sword fighting, and music led by a cast of pirates.

The view: Scan the gold horizon for dolphins.

When to go: Year-round

Rates: $43 (adults), $28 (kids 3–12); 956/943-6283 or


Top 10 Sunset Cruises: Schooner Pride Tall Ship

Photo: Schooner Pride Tall Ship

Schooner Pride Tall Ship

Charleston, South Carolina

Help raise the sails on this 84-foot ship, or just sit back and relax with a glass of wine. The two-hour itinerary sails past historic buildings, steeples, and wildlife including dolphins and pelicans.

The view: Castle Pinckney, Battery Park, and the Civil War forts of Charleston Harbor,  including Fort Sumter

When to go: Mid-March through mid-November

Rate: $39; 800/344-4483 or


Top 10 Sunset Cruises: Santa Barbara Sailing Center

Photo: Santa Barbara Sailing Center

Santa Barbara Sailing Center

Santa Barbara, California

Take a romantic, relaxing sail on the Santa Barbara Channel. The center’s Double Dolphin catamaran offers three options: cocktails-only cruise (cash bar), dinner buffet cruise, and the Friday night sunset jazz cruise.

The view: California living—volleyball players at West Beach, luxury homes tucked along the Santa Ynez Mountains, whales, and dolphins

When to go: Sunset cocktail cruises, year-round; dinner buffet and jazz cruises, April through September

Rates: From $25; 805/962-2826 or



Top 10 Sunset Cruises: Trilogy excursions

Photo: Trilogy Excursions

Trilogy Excursions

Maui, Hawaii

Ahoy, foodies! This two-hour family-friendly cruise serves gourmet appetizers, including mango lobster summer rolls and lemon grass chicken kebabs. Capt. Coon and most of the crew are certified naturalists, so feel free to ask about scenic wonders (volcanoes!) along the way.

The view: Neighboring islands Molokai and Lanai, spinner dolphins, and flying fish

When to go: Tuesdays, Thursdays, and Saturdays year-round

Rate: $64 (including tax and two drinks); 888/225-6284 or


Top 10 Sunset Cruises: California Sunset Cruises, Red and White Fleet, San Francisco’s Original Bay Cruise

Photo: California Sunset Cruises, Red and White Fleet, San Francisco’s Original Bay Cruise

California Sunset Cruises, Red and White Fleet, San Francisco’s Original Bay Cruise

San Francisco, California

Enjoy live guitar music, snacks, dessert, and a complimentary drink aboard the Royal Prince luxury ship. Great photo ops abound on the two-hour cruise.

The view: San Francisco landmarks including the Transamerica Pyramid, Coit Tower, Alcatraz, Angel Island National Park, and the shorelines of Tiburon and Sausalito

When to go: April through early November

Rate: $54; 415/673-2900 or



Top 10 Sunset Cruises: Mad Max

Photo: Mad Max

Mad Max

Martha’s Vineyard, Massachusetts

Sit back, sip wine (BYOB), and pretend you’re a Kennedy aboard this 60-foot twin-hull catamaran. The cruise glides past homes once owned by whaling ship captains in the 1800s. Wind direction determines the route—passing either Chappaquiddick Island or the town of Oak Bluffs.

The view: Edgartown Lighthouse, sailboats in Nantucket Sound, and yachts

When to go: Memorial Day weekend through September

Rate: $55; 508/627-7500 or



Top 10 Sunset Cruises: Argosy Cruises

Photo: Argosy Cruises

Argosy Cruises

Seattle, Washington

The Tillicum Village cruise sails across Puget Sound and includes a salmon bake on Blake Island. Or, passengers can solve a murder mystery that’s part of an improv comedy routine.

The view: Seattle’s skyline, the Cascade and Olympic mountains, and harbor seals

When to go: Murder mystery cruise, year-round; Tillicum Village cruise, March through October

Rates: $75 (murder mystery cruise), $80 (Tillicum Village cruise); 888/623-1445 or



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