From America’s Cup-style sailing to a jazz band on a catamaran, there’s something for everyone on these early-evening jaunts
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 downeastwindjammer.com
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 schoonerwoodwind.com
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 reefroamersnorkel.com
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 blackdragoncruises.com
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 schoonerpride.com
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 sbsail.com
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 sailtrilogy.com
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 redandwhite.com
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 madmaxmarina.com
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 argosycruises.com