Portland Day Cruises

Explore Portland's best day cruises including sunset sails, lighthouse tours, and private charters on vintage and wooden boats. Book your perfect day on the water!

No tours match these filters.

2 Hours Sunset Private Charter on Heart's Desire in Casco Bay

This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds. Sail aboard He

★ 5.0 (2)

From $675.00 USD

Casco Bay Morning Windjammer Sail

Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the perfect way to experience the beauty of the rugged coastline, c

★ 4.9 (40)

From $61.00 USD

Casco Bay: Private Afternoon Charter on Heart's Desire

This two-hour afternoon private cruise is the perfect way to experience Maine's coast, your special event, or a family get-together that will never be forgotten

★ 4.0 (1)

From $650.00 USD

Large Group Private Wooden Boat Sightseeing & Lighthouse Charter

100% Private Charter for Groups up to 16 — Flat Rate Pricing This exclusive 2-hour boat tour is designed for private groups seeking an authentic, intimate expe

★ 4.7 (7)

From $850.00 USD

Maine Fall Foliage Private Lobster Boat Cruise with Local Drinks

Experience COLORFUL Maine on this 2-hour sightseeing tour, where you’ll take in the vibrant fall foliage and the best coastal sights in the Portland area. It do

★ 4.6 (11)

From $380.10 USD

Portland Tall Ship Cruise on Casco Bay

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make y

★ 4.6 (243)

From $101.66 USD

Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

100% PRIVATE TOUR! Step aboard a vintage Maine Lobster Boat for a private, 2-hour lighthouse viewing & sightseeing charter. Leave the crowds behind as we cruise

★ 4.9 (70)

From $380.10 USD

Private Sunset Charter on a Vintage Lobster Boat with Drinks

Leave the crowds behind and step aboard a vintage Maine Lobster Boat for a private 2-hour sightseeing and lighthouse viewing charter, ending with a breathtaking

★ 5.0 (44)

From $407.40 USD

Small Group Sunset Lighthouse Boat Cruise With Local Drinks

Board the Elizabeth Grace to cruise around Portland Harbor while sipping local craft beer. This 1.5-hour harbor cruise will take you out into Casco Bay. Keep yo

★ 4.7 (121)

From $89.00 USD