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American Pioneer Sailing Dates and Sailing Calendar

For more information, prices, and detailed day-by-day American Pioneer itineraries, please click one of the American Pioneer sailing dates below.

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Sail Date

Itinerary Name and Ports

Duration

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Priced From(per person)

Jun 27, 2026

(Saturday)



8 Night Cape Codder Cruise and Land Tour

From Boston, Massachusetts to Boston, Massachusetts

Ports: Boston, Provincetown, Plymouth Massachusetts, Cruising Cape Cod, Massachusetts Maritime Academy, Newport, Martha's Vineyard, New Bedford, Cruising Cape Cod, Boston

8 Nights

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$7,415

Balcony (double occupancy)

Includes taxes & feesLearn More
Jul 18, 2026

(Saturday)



8 Night Cape Codder Cruise and Land Tour

From Boston, Massachusetts to Boston, Massachusetts

Ports: Boston, Provincetown, Plymouth Massachusetts, Cruising Cape Cod, Massachusetts Maritime Academy, Newport, Martha's Vineyard, New Bedford, Cruising Cape Cod, Boston

8 Nights

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$7,415

Balcony (double occupancy)

Includes taxes & feesLearn More
Oct 3, 2026

(Saturday)



8 Night Cape Codder Cruise and Land Tour

From Boston, Massachusetts to Boston, Massachusetts

Ports: Boston, Provincetown, Plymouth Massachusetts, Cruising Cape Cod, Massachusetts Maritime Academy, Newport, Martha's Vineyard, New Bedford, Cruising Cape Cod, Boston

8 Nights

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$7,835

Balcony (double occupancy)

Includes taxes & feesLearn More
Oct 10, 2026

(Saturday)



8 Night Cape Codder Cruise and Land Tour

From Boston, Massachusetts to Boston, Massachusetts

Ports: Boston, Provincetown, Plymouth Massachusetts, Cruising Cape Cod, Massachusetts Maritime Academy, Newport, Martha's Vineyard, New Bedford, Cruising Cape Cod, Boston

8 Nights

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$7,835

Balcony (double occupancy)

Includes taxes & feesLearn More
Oct 17, 2026

(Saturday)



8 Night Northeast Harbors Cruise and Land Tour

From Boston, Massachusetts to New York, New York

Ports: Boston, Plymouth Massachusetts, Cruising Cape Cod, Newport, New London, Sag Harbor New York, Old Saybrook Connecticut, New York

8 Nights

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$7,835

Balcony (double occupancy)

Includes taxes & feesLearn More
Oct 26, 2026

(Monday)



11 Night American Revolution Cruise and Land Tour

From Philadelphia, Pennsylvania to Washington DC, District of Columbia

Ports: Philadelphia, Annapolis Maryland, St Michaels, Cruising the Atlantic Intracoastal Waterway, Norfolk, Yorktown, Mount Vernon, Washington DC

11 Nights

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$9,595

Balcony (double occupancy)

Includes taxes & feesLearn More
May 7, 2027

(Friday)



15 Night Grand Florida Coast and Keys Cruise and Land Tour

From Tampa, Florida to Fernandina Beach, Florida

Ports: Tampa, St. Petersburg, Punta Gorda Florida, Marco Island Florida, Key West, Key Biscayne Florida, West Palm Beach, Port Canaveral, Green Cove Springs, St. Augustine Florida, Cruising the Tolomato River, Fernandina Beach

15 Nights

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$13,150

Balcony (double occupancy)

Includes taxes & feesLearn More
May 28, 2027

(Friday)



8 Night Cape Codder Cruise and Land Tour

From Boston, Massachusetts to Boston, Massachusetts

Ports: Boston, Provincetown, Plymouth Massachusetts, Cruising Cape Cod, Massachusetts Maritime Academy, Newport, Martha's Vineyard, New Bedford, Cruising Cape Cod, Boston

8 Nights

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$7,415

Balcony (double occupancy)

Includes taxes & feesLearn More
Oct 22, 2027

(Friday)



8 Night Northeast Harbors Cruise and Land Tour

From Boston, Massachusetts to New York, New York

Ports: Boston, Plymouth Massachusetts, Cruising Cape Cod, Newport, New London, Sag Harbor New York, Old Saybrook Connecticut, New York

8 Nights

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$7,835

Balcony (double occupancy)

Includes taxes & feesLearn More
Mar 24, 2028

(Friday)



8 Night Puget Sound and San Juan Islands Cruise and Land Tour

From Tacoma, Washington to Tacoma, Washington

Ports: Tacoma, Cruising Puget Sound, Anacortes, Friday Harbor, Cruising the San Juan Islands, Port Angeles, Ferry Travel, Victoria, Ferry Travel, Port Angeles, Port Townsend, Bremerton, Tacoma

8 Nights

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$6,995

Balcony (double occupancy)

Includes taxes & feesLearn More
Mar 31, 2028

(Friday)



8 Night Puget Sound and San Juan Islands Cruise and Land Tour

From Tacoma, Washington to Tacoma, Washington

Ports: Tacoma, Cruising Puget Sound, Anacortes, Friday Harbor, Cruising the San Juan Islands, Port Angeles, Ferry Travel, Victoria, Ferry Travel, Port Angeles, Port Townsend, Bremerton, Tacoma

8 Nights

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$7,415

Balcony (double occupancy)

Includes taxes & feesLearn More
Apr 7, 2028

(Friday)



8 Night Puget Sound and San Juan Islands Cruise and Land Tour

From Tacoma, Washington to Tacoma, Washington

Ports: Tacoma, Cruising Puget Sound, Anacortes, Friday Harbor, Cruising the San Juan Islands, Port Angeles, Ferry Travel, Victoria, Ferry Travel, Port Angeles, Port Townsend, Bremerton, Tacoma

8 Nights

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$7,415

Balcony (double occupancy)

Includes taxes & feesLearn More
Apr 14, 2028

(Friday)



8 Night Puget Sound and San Juan Islands Cruise and Land Tour

From Tacoma, Washington to Tacoma, Washington

Ports: Tacoma, Cruising Puget Sound, Anacortes, Friday Harbor, Cruising the San Juan Islands, Port Angeles, Ferry Travel, Victoria, Ferry Travel, Port Angeles, Port Townsend, Bremerton, Tacoma

8 Nights

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$7,415

Balcony (double occupancy)

Includes taxes & feesLearn More
Apr 21, 2028

(Friday)



8 Night Puget Sound and San Juan Islands Cruise and Land Tour

From Tacoma, Washington to Tacoma, Washington

Ports: Tacoma, Cruising Puget Sound, Anacortes, Friday Harbor, Cruising the San Juan Islands, Port Angeles, Ferry Travel, Victoria, Ferry Travel, Port Angeles, Port Townsend, Bremerton, Tacoma

8 Nights

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$7,415

Balcony (double occupancy)

Includes taxes & feesLearn More
Apr 28, 2028

(Friday)



8 Night Puget Sound and San Juan Islands Cruise and Land Tour

From Tacoma, Washington to Tacoma, Washington

Ports: Tacoma, Cruising Puget Sound, Anacortes, Friday Harbor, Cruising the San Juan Islands, Port Angeles, Ferry Travel, Victoria, Ferry Travel, Port Angeles, Port Townsend, Bremerton, Tacoma

8 Nights

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$7,415

Balcony (double occupancy)

Includes taxes & feesLearn More
May 5, 2028

(Friday)



8 Night Puget Sound and San Juan Islands Cruise and Land Tour

From Tacoma, Washington to Tacoma, Washington

Ports: Tacoma, Cruising Puget Sound, Anacortes, Friday Harbor, Cruising the San Juan Islands, Port Angeles, Ferry Travel, Victoria, Ferry Travel, Port Angeles, Port Townsend, Bremerton, Tacoma

8 Nights

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$7,835

Balcony (double occupancy)

Includes taxes & feesLearn More
May 12, 2028

(Friday)



8 Night Puget Sound and San Juan Islands Cruise and Land Tour

From Tacoma, Washington to Tacoma, Washington

Ports: Tacoma, Cruising Puget Sound, Anacortes, Friday Harbor, Cruising the San Juan Islands, Port Angeles, Ferry Travel, Victoria, Ferry Travel, Port Angeles, Port Townsend, Bremerton, Tacoma

8 Nights

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$7,835

Balcony (double occupancy)

Includes taxes & feesLearn More
May 19, 2028

(Friday)



8 Night Puget Sound and San Juan Islands Cruise and Land Tour

From Tacoma, Washington to Tacoma, Washington

Ports: Tacoma, Cruising Puget Sound, Anacortes, Friday Harbor, Cruising the San Juan Islands, Port Angeles, Ferry Travel, Victoria, Ferry Travel, Port Angeles, Port Townsend, Bremerton, Tacoma

8 Nights

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$7,835

Balcony (double occupancy)

Includes taxes & feesLearn More
May 26, 2028

(Friday)



8 Night Puget Sound and San Juan Islands Cruise and Land Tour

From Tacoma, Washington to Tacoma, Washington

Ports: Tacoma, Cruising Puget Sound, Anacortes, Friday Harbor, Cruising the San Juan Islands, Port Angeles, Ferry Travel, Victoria, Ferry Travel, Port Angeles, Port Townsend, Bremerton, Tacoma

8 Nights

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$7,835

Balcony (double occupancy)

Includes taxes & feesLearn More
Jun 2, 2028

(Friday)



8 Night Puget Sound and San Juan Islands Cruise and Land Tour

From Tacoma, Washington to Tacoma, Washington

Ports: Tacoma, Cruising Puget Sound, Anacortes, Friday Harbor, Cruising the San Juan Islands, Port Angeles, Ferry Travel, Victoria, Ferry Travel, Port Angeles, Port Townsend, Bremerton, Tacoma

8 Nights

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$7,835

Balcony (double occupancy)

Includes taxes & feesLearn More

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