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Tours With Sailing & Boat Activities

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Adirondack, NY Rail & Sail

Experience the natural beauty of the Adirondacks with our Rail & Sail tour! Enjoy a scenic train ride through breathtaking landscapes and a relaxing cruise on serene waters, all while exploring the charm of upstate New York.

Duration: 3 Days
Date: 9/10/2025
Annapolis, MD Fall Lighthouse Cruise

Set sail on a picturesque Fall Lighthouse Cruise in Annapolis with Starr Tours. Enjoy scenic views, historic landmarks, and autumnal charm on this unforgettable nautical adventure.

Dates: 10/25/2025 and 11/8/2025
Ark Encounter and Creation Museum: Cincinnati, OH

Explore the wonders of biblical history with Starr Tours' visit to the Ark Encounter and Creation Museum in Cincinnati. Immerse yourself in interactive exhibits, life-sized displays, and captivating experiences that bring history to life.

Duration: 6 Days
Date: 7/27/2025
Assateague Island Boat Cruise - Ocean City, MD

Discover the natural beauty of Assateague Island and Ocean City, MD, on this exciting getaway. Enjoy a scenic boat cruise, spot wild ponies, and explore charming coastal attractions.

Multiple dates available
Baltimore, MD Crab Feast & Boat Cruise

Enjoy a cruise on Baltimore's spectacular waterfront and an all-you-can-eat crab feast including delicious local specialties!

Dates: 8/16/2025 and 8/23/2025
Boston, MA: Fourth of July

Celebrate the Fourth of July in historic Boston with an unforgettable experience! Enjoy a patriotic atmosphere, watch spectacular fireworks, and explore the city's iconic landmarks, from the Freedom Trail to the Boston Harbor.

Duration: 4 Days
Date: 7/2/2025
Boston, Massachusetts Getaway

Explore the rich history and vibrant culture of Boston on our Massachusetts Getaway tour! Visit iconic landmarks like the Freedom Trail, enjoy world-class museums, and experience the charm of this historic city.

Duration: 3 Days
Dates: 7/25/2025 and 10/17/2025
Cape Cod "2nd Timers Only"

Rediscover Cape Cod with Starr Tours and enjoy a second-time experience, featuring new adventures and hidden gems that will make you fall in love with this coastal paradise all over again!

Duration: 5 Days
Date: 10/8/2025
Cape Cod & Martha's Vineyard

Picturesque Victorian cottages, quaint gingerbread houses, and miles of unspoiled beaches are waiting to charm you. Visit countless historic sites and landmarks, each telling the proud role that Cape Cod has played in American history.

Duration: 4 Days
Multiple dates available
Cape Cod, Martha's Vineyard & Nantucket Island

Embark on a picturesque journey to Cape Cod, Martha's Vineyard, and Nantucket Island with Starr Tours. Explore charming coastal towns, pristine beaches, and iconic landmarks on this unforgettable coastal escape.

Duration: 5 Days
Multiple dates available
Castles of New York

Explore the rich history and grandeur of New York’s castles on our Castles of New York tour! Visit stunning estates, admire architectural beauty, and discover the stories behind these magnificent landmarks.

Duration: 4 Days
Date: 9/4/2025
Charming Ports of the South

Discover the charm of the South's captivating ports with Starr Tours. From the historic elegance of Jekyll Island to the enchanting allure of St. Augustine and Savannah, immerse yourself in rich history, scenic beauty, and Southern hospitality on this unforgettable journey.

Duration: 8 Days
Date: 11/15/2025
Chicago Highlights: My Kind of Town

The "Windy City" is just bursting with breathtaking architecture, wonderful museums, fantastic restaurants, a beautiful lakefront, and world-class shopping. Experience all this and more with Starr Tours!

Duration: 7 Days
Date: 7/19/2025
Cocoa Beach, FL Winter Getaway

Escape to the sunny shores of Cocoa Beach, FL, with Starr Tours. Relax on pristine beaches, enjoy water activities, and soak up the laid-back coastal vibe for the perfect beach getaway.

Duration: 14 Days
Date: 2/13/2025
Connecticut: Rail & Sail

Enjoy the unspoiled beauty of New England's Connecticut River Valley by train and by boat on this 2-day weekend getaway.

Duration: 2 Days
Date: 10/9/2025
Crab Feast Cruise at Suicide Bridge & Harriet Tubm

Enjoy a memorable day on Maryland’s Eastern Shore with a scenic cruise and a traditional crab feast. Also included is a visit to the Harriet Tubman Underground Railroad Visitor Center, offering a meaningful blend of history and local flavors.

Dates: 6/26/2025 and 7/31/2025
Ellis Island & Liberty Island

Gaze at the Statue of Liberty and then close your eyes and imagine your ancestors as your ferry takes you to both Ellis and Liberty Islands.

Dates: 6/19/2025 and 9/6/2025
Finger Lakes of New York: Lakes & Grapes

Discover the scenic beauty and rich culture of New York’s Finger Lakes region! Enjoy picturesque vineyards, serene lakes, and charming towns as you explore this stunning destination known for its wine and natural wonders.

Duration: 3 Days
Date: 8/11/2025
Girlfriends Getaway at Lake Morey Resort, Vermont

Escape to Vermont with your friends for a rejuvenating getaway at Lake Morey Resort! Enjoy scenic lake views, activities, fun, and quality time in a peaceful, picturesque setting.

Duration: 4 Days
Date: 9/7/2025
Holland, Michigan Tulip Festival

Join Starr Tours for the Holland, Michigan Tulip Festival and experience a vibrant display of blooming tulips. Enjoy Dutch culture, parades, and beautiful gardens.

Duration: 6 Days
Date: 5/8/2025
Hudson Valley, NY Highlights

See spectacular scenery from your Hudson River Cruise and hear fascinating history amid the backdrop of mansions and museums and, of course, West Point.

Duration: 3 Days
Date: 7/23/2025
Ithaca, NY: Waterfalls, Women, and Wine

Embark on a captivating journey to Ithaca, NY with Starr Tours, where you'll explore stunning waterfalls, celebrate influential women, and savor exquisite wines. Immerse yourself in the natural beauty and cultural richness of this vibrant destination.

Duration: 4 Days
Date: 7/29/2025
Lake George and Lake Placid Fall Splendor

Discover the breathtaking fall splendor of Lake George and Lake Placid with scenic views, historic sites, and vibrant autumn foliage. Enjoy crisp mountain air, charming villages, and the unforgettable colors of the Adirondacks.

Duration: 3 Days
Date: 10/12/2025
Mackinac Island, Michigan

Step back in time onto this enchanting island where bluff cottages, horse-drawn carriages, and historical treasures await you.

Duration: 7 Days
Multiple dates available
Mackinac Island, Michigan "2nd Timers Only"

Return to the enchanting Mackinac Island with Starr Tours for a second-time experience. Enjoy the island's timeless beauty, historic sites, and delightful activities.

Duration: 8 Days
Date: 5/11/2025
Maine and New Hampshire Featuring Ogunquit

Discover the charm of Maine and New Hampshire with a scenic tour through coastal towns, picturesque landscapes, and the renowned Ogunquit Playhouse. Enjoy a captivating performance and explore the best of New England.

Duration: 4 Days
Date: 6/24/2025
Maine Moose, Lobsters & Gems

Discover the beauty and flavors of Maine on this memorable tour featuring a moose-watching excursion, a traditional lobster bake, and stunning natural gems on this unique trip.

Duration: 5 Days
Date: 9/7/2025
Maine's Rocky Coast Featuring Acadia National Park

Discover the breathtaking beauty of Maine’s rocky coast with Starr Tours. Explore Acadia National Park, visit charming seaside towns, and enjoy stunning coastal views on this scenic adventure.

Duration: 5 Days
Dates: 7/13/2025 and 8/24/2025
Myrtle Beach, SC & Wilmington, NC

Join Starr Tours for a coastal adventure to Myrtle Beach, SC, and Wilmington, NC. Enjoy beautiful beaches, vibrant entertainment, and historic charm on this Southern getaway.

Duration: 7 Days
Date: 9/14/2025
Nashville, TN Christmas: 100 Years of Grand Ole Op

Celebrate the magic of the season with Starr Tours on a special holiday tour in Nashville, as we mark the 100th anniversary of the Grand Ole Opry. Experience festive performances and backstage access at Music City's most legendary venues.

Duration: 7 Days
Date: 12/1/2025
New England Rail & Sail

Enjoy two train trips and a beautiful boat ride on Squam Lake on this wonderful New England tour that highlights New Hampshire.

Duration: 4 Days
Date: 6/19/2025
New Hampshire's Railroads

All aboard with Starr Tours! See the breathtaking beauty of New Hampshire up close on three scenic rail excursions that showcase the stunning landscapes of the White Mountains.

Duration: 5 Days
Date: 9/24/2025
New Orleans & Biloxi: Featuring HGTV Hometown

Immerse yourself in the charm of New Orleans and Biloxi with a tour highlighting HGTV favorites. Explore iconic landmarks, indulge in local cuisine, and visit the famous homes featured on "Home Town" in this unforgettable Southern adventure.

Duration: 9 Days
Date: 11/1/2025
New York City by Land & Sea

Explore the best of New York City by land and sea with Starr Tours, with a guided tour of Midtown Manhattan's iconic landmarks followed by a scenic cruise along the Hudson and East Rivers, offering spectacular views of the Statue of Liberty, One World Trade Center, and more.

Multiple dates available
Niagara Falls, NY: Starr Birthday Bash

Celebrate in style at Niagara Falls with our Starr Birthday Bash tour! Enjoy breathtaking views of the Falls, exciting attractions, and a festive birthday celebration at one of the world’s most iconic natural wonders.

Duration: 4 Days
Date: 10/12/2025
Norfolk, VA and NATO Fest Featuring the Tattoo

Explore Norfolk, VA, with Starr Tours and experience the excitement of the NATO Festival. Discover historic sites, vibrant culture, and a dynamic waterfront.

Duration: 4 Days
Date: 4/24/2025
Nova Scotia, PEI, NB, Royal International Tattoo

Experience the vibrant culture of Nova Scotia and Prince Edward Island with Starr Tours. Enjoy the spectacular Royal Nova Scotia International Tattoo and explore charming coastal towns.

Duration: 9 Days
Date: 6/27/2025
Nova Scotia, The Cabot Trail, Prince Edward Island

Experience the breathtaking beauty of Nova Scotia and the Cabot Trail with Starr Tours. Enjoy stunning coastal views, charming villages, and a rich cultural heritage on this unforgettable bus tour.

Duration: 11 Days
Date: 8/16/2025
Ocean City, Maryland: Coastal Treasures

Experience the beauty of Ocean City, Maryland, with Starr Tours. Explore sandy beaches, vibrant boardwalks, and charming coastal treasures on this relaxing getaway.

Duration: 4 Days
Date: 5/12/2025
Outer Banks, NC: Wild and Wonderful

Travel along the North Carolina coastline to discover the history of flight, see remarkable lighthouses, experience beautiful, white sandy beaches, and so much more.

Duration: 5 Days
Date: 9/21/2025
Pennsylvania's Grand Canyon - Wellsboro, PA

Experience the stunning beauty of Pennsylvania’s Grand Canyon in Wellsboro. This tour offers breathtaking views, charming small-town vibes, and a relaxing journey through one of the state’s most scenic natural wonders.

Duration: 3 Days
Dates: 9/12/2025 and 10/3/2025
Savannah, GA & Charleston, SC: Southern Charm

Experience the charm and elegance of the South with our tour to Savannah, GA, and Charleston, SC. Explore historic sites, beautiful gardens, and vibrant local culture on this memorable journey. Photo Courtesy of Adam Goldberg Photography

Duration: 6 Days
Multiple dates available
Seaside Heights, NJ & River Lady Boat Cruise

Cruise the scenic waters of Toms River and Barnegat Bay with Starr Tours, then soak in the vibrant boardwalk vibes at Seaside Heights.

Dates: 8/20/2025 and 9/3/2025
Silver Birches Luncheon Show & Fall Train Ride

Enjoy musical entertainment featuring Eric Kearns along with a buffet meal and scenic train ride on this great getaway!

Date: 9/30/2025
Vermont Culinary Delights: Green Mountain Goodness

Savor the flavors of Vermont with our Culinary Delights & Green Mountain Goodness tour! Enjoy farm-to-table cuisine, explore charming towns, and experience the natural beauty of the Green Mountains on this delicious adventure.

Duration: 4 Days
Date: 8/7/2025
Washington, DC: Cherry Blossom Boat Cruise

Experience our nation's greatest springtime celebration from a new perspective when you view the cherry blossom trees by water.

Dates: 3/30/2025 and 4/6/2025

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