Historical Tours


SAILING WORLDWIDE

15 Best Historical Tours Worldwide

The best days on the water.

The 15 most popular historical tours. What each sail costs, how long you are on the water, and which crews run it well.

15 Best Historical Tours Worldwide

Historical San Juan Bay Sunset Sailing Tour - Your boat: the 30-foot J/30 racer-cruiser experience (and what to expect)
Cruises & Boat Tours, Evening Experiences, Historical Tours, Sailing, San Juan, Sunset Sails, Tour Reviews, Tours

Historical San Juan Bay Sunset Sailing Tour

/

1.Historical San Juan Bay Sunset Sailing Tour

Two-hour small-group sunset sail from San Juan Bay past El Morro. Complimentary drinks, light bites, and calm Caribbean sailing.

Most Popular★ 4.5

“Beautiful views and outstanding service. It was a busy day out on the water and our captain showed off his skills navigating us through all the boats coming in from their fishing tournament. He was very knowledgeable and gave us details about San Juan. Such a worthy experience.”

710 reviewsFrom $115.00by Sail San Juan Bay

Check Availability →Read the review →

Lisbon: Sunset Sailing with Portuguese Wine and History - Doca de Santo Amaro: the meeting point that keeps things easy
Cruises & Boat Tours, Evening Experiences, Historical Tours, Lisbon, Lisbon Sailing Trips, Sailing, Sunset Sails, Tour Reviews, Wine Tours

Lisbon Sunset Sailing with Portuguese Wine and History

/
Lisbon: Sunset Sailing with Portuguese Wine and History - Doca de Santo Amaro: the meeting point that keeps things easy
Cruises & Boat Tours, Evening Experiences, Historical Tours, Lisbon, Lisbon Sailing Trips, Sailing, Sunset Sails, Tour Reviews, Wine Tours

Lisbon: Sunset Sailing with Portuguese Wine and History

/

3.Lisbon: Sunset Sailing with Portuguese Wine and History

Sail Lisbon at sunset on a 12-meter boat with Portuguese wine and easy history stops from Belém to Praça do Comércio.

★ 5.0

“This was a highlight of my stay in Lisbon Loved the trip out on the river at sunset, the opportunity to see key land marks from a different perspective and the stories that went with each one The green wine was really good too. The guides were really good, very hospitable and friendly Lovely experience…”

270 reviews2 hoursFrom $49by Breeze Passion Nautical Experiences

Check Availability →Read the review →

Nydri: Sailing Through History. Daily Cruise with Beach BBQ - Papanikolis cave: the stop that makes the whole day feel special
BBQ, Cruises & Boat Tours, Dinner & BBQ Cruises, Historical Tours, Ionian Islands, Sailing, Tour Reviews

Nydri: Sailing Through History. Daily Cruise with Beach BBQ

/
Parasailing over the Historic Key West Seaport - Sunset Watersports: A 36-Year Local Operation You Can Trust
Historical Tours, Key West, Key West Sailing Trips, Parasailing, Tour Reviews

Parasailing over the Historic Key West Seaport

/
Camden: Historic Schooner Day Sailing Trip - Where You Meet and How Early to Get There
Camden Maine, Cruises & Boat Tours, Historical Tours, Sailing, Tall Ships & Sailing Boats, Tour Reviews

Camden: Historic Schooner Day Sailing Trip

/

6.Camden: Historic Schooner Day Sailing Trip

Sail Camden’s rocky coast on the Appledore II schooner. Help hoist sails, steer the wheel, spot wildlife, and buy drinks.

★ 4.7

“The Schooner sail on the Appledore II was so much fun allowing volunteers to help raise the sails. Captain & Crew were personable & we got a little history & views of the area. We would definitely do this sail again! Sue & Kevin”

181 reviews2 hoursFrom $59by Schooner Appledore

Check Availability →Read the review →

San Juan Historical Bay Daytime Sailing Tour - Old San Juan’s Landmarks Look Better From the Water
Cruises & Boat Tours, Historical Tours, Sailing, San Juan, Tour Reviews, Tours

San Juan Historical Bay Daytime Sailing Tour

/
Sailing on Historic Schooner Yacht in Salem, MA - Two hours under sail on Salem Sound: what the ride actually feels like
Cruises & Boat Tours, Historical Tours, Luxury Yacht Trips, Sailing, Salem, Tall Ships & Sailing Boats, Tour Reviews

Sailing on Historic Schooner Yacht in Salem, MA

/

8.Sailing on Historic Schooner Yacht in Salem, MA

Classic North Shore schooner sailing in Salem Sound: help hoist the sails, sip cider and cocktails, and spot Marblehead and island views.

★ 5.0

“100% recommend. The view is amazing. We went pretty far, getting to see a lot of coast line. It was late October and nippy- so bring a jacket. I brought a beanie( Floridian).”

172 reviews2 hours (approx.)by Sunset Sail Key West

Check Availability →Read the review →

Scenic Cruise & Guided Walk on Historic Motor Yacht Lake Te Anau - Stop 1: Fiordland National Park (Te Wahipounamu) forest walk with mountain views
Cruises & Boat Tours, Guided, Historical Tours, Luxury Yacht Trips, Sailing, Te Anau, Tour Reviews, Walking Tours

Scenic Cruise & Guided Walk on Historic Motor Yacht Lake Te Anau

/

9.Scenic Cruise & Guided Walk on Historic Motor Yacht Lake Te Anau

Historic yacht cruise on Lake Te Anau plus a guided Fiordland walk, with live commentary and afternoon tea in a small group.

★ 5.0

“The gracious crew who served us well and allowed us to fully enjoy the peaceful cruise with wonderful views of the lake. The afternoon tea was excellent. As there were only our family onboard we got to have a turn at steering the boat and helping put the sails up. The crew did very well…”

165 reviewsFrom $102.39by Fiordland Historic Cruises

Check Availability →Read the review →

Camden: Historic Schooner Day Sailing Trip - Where You Meet and How Early to Get There
Camden Maine, Cruises & Boat Tours, Historical Tours, Sailing, Tall Ships & Sailing Boats, Tour Reviews

Camden: Historic Schooner Day Sailing Trip

/
Key West Historic Schooner When And If Sunset Cruise - The Boat and Crew: General Patton Heritage Plus Real Deck Work
Cruises & Boat Tours, Evening Experiences, Historical Tours, Key West, Key West Sailing Trips, Sunset Sails, Tall Ships & Sailing Boats, Tour Reviews

Key West Historic Schooner When And If Sunset Cruise

/
Lisbon Small Group Day Cruise with Historic Commentary & a Drink - The river route: Belém to Almada viewpoints in one smooth loop
Cruises & Boat Tours, Historical Tours, Lisbon, Lisbon Sailing Trips, Small-Group Sails, Tour Reviews

Lisbon Small Group Day Cruise with Historic Commentary & a Drink

/
Salem: Historic Schooner Sailing Cruise - Where the cruise starts: Pickering Wharf Marina in downtown Salem
Cruises & Boat Tours, Historical Tours, Sailing, Salem, Tall Ships & Sailing Boats, Tour Reviews

Salem: Historic Schooner Sailing Cruise

/
Private Morning Sail, Dolphin and History Tour on Mystique - Charleston Battery and pre-antebellum waterfront homes: the first big view
Charleston, Charleston Sailing Trips, Cruises & Boat Tours, Dolphin & Whale Sails, Dolphin Watching, Historical Tours, Morning, Private, Private Sailing Charters, Tour Reviews, Tours

Private Morning Sail, Dolphin and History Tour on Mystique

/
Scenic Cruise & Guided Walk on Historic Motor Yacht Lake Te Anau - Stop 1: Fiordland National Park (Te Wahipounamu) forest walk with mountain views
Cruises & Boat Tours, Guided, Historical Tours, Luxury Yacht Trips, Sailing, Te Anau, Tour Reviews, Walking Tours

Scenic Cruise & Guided walk on Historic Motor Yacht Lake Te Anau

/

More Historical Tours Worldwide

Scroll to Top

Explore by Destination

The sailing ports worth the trip, grouped by the sea they sit on.

The Mediterranean

The Atlantic Isles

The Gulf

The Caribbean

The Pacific