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Vacations Under $5000pp

Find inspiration in the familiar - under the new perspective of an expert's lens - or in destinations beyond your wildest dreams on hand-selected vacations under $5,000, each backed by more than 50 years of travel expertise.

Alaska Railroad
Alaska the Greatland
9 days from $5,499 pp
  • Board the Alaska Railroad’s Denali Star and Glacier Discovery on an escorted vacation
  • Cruise past the glaciers of Kenai Fjords and Prince William Sound searching for wildlife
  • Marvel at North America’s tallest peak while spending two nights at Denali Bluffs Hotel
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Old Faithful, Yellowstone
America's Treasures & Natural Wonders
12 days from $6,299 pp
  • Discover six of America's most scenic National Parks on this epic journey
  • Cross the Continental Divide on a drive along the Going-to-the-Sun Road aboard vintage Red Jammer buses.
  • Enjoy a classic overnight rail journey aboard Amtrak's Empire Builder
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Ross Castle
The Best of Scotland & Ireland
13 days from $6,399 pp
  • Explore Edinburgh and the Scottish Highlands, traveling on three scenic railways
  • Visit historic Belfast, the Titanic Center and the Giant’s Causeway in Northern Ireland
  • Cruise past the epic Cliffs of Moher, visit Blarney Castle and explore Dublin in Ireland
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176 results matching: Vacations Under $5000

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Albuquerque Balloon FiestaAlbuquerque Balloon FiestaAlbuquerque Balloon FiestaAlbuquerque Balloon FiestaAlbuquerque Balloon Fiesta
Last Spaces
Albuquerque Balloon Fiesta by Rail
4.6 stars(67 reviews)
Escorted
2026SepOct
Escorted

Discover the beauty of the Southwest in autumn on this 9-day escorted adventure featuring national parks, historic rail journeys, and the world-famous International Balloon Fiesta in Albuquerque. Travel on the iconic California Zephyr to Grand Junction. View the breathtaking landscapes of Arches and Mesa Verde national parks, before riding...

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9 days from
$3,799 pp $3,499 pp
per person
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Grand CanyonGrand CanyonGrand CanyonGrand CanyonGrand Canyon
Grand Canyon Railway Rails to the Rim Adventure
Independent
2026AugSepOctNovDec
Independent

The classic ambiance of an overnight rail journey meets the splendors of one of America's top natural attractions on this rail vacation to Arizona. Join Amtrak's Southwest Chief on its cross-country route from Chicago to Flagstaff, and then board the 120-year-old Grand Canyon Railway on its route to the Grand Canyon. Uncover iconic views...

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6 days from
$1,195 pp $1,095 pp
per person
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Mount Washington Cog RailwayMount Washington Cog RailwayMount Washington Cog RailwayMount Washington Cog RailwayMount Washington Cog Railway
Last Spaces
New England in a Nutshell
4.4 stars(75 reviews)
Escorted
2026SepOct
Escorted

Behold the brilliance of nature's seasonal finale in New England this fall. For 6 days, find yourself surrounded by sights of gold, rust and crimson as you travel through leaf-peeping hotspots in Massachusetts, New Hampshire and Vermont. Begin with time in Boston, where a guided tour acquaints you with the most historically significant sites...

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6 days from
$2,999 pp $2,699 pp
per person
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Niagara FallsNiagara FallsNiagara FallsNiagara FallsNiagara Falls
New York to Niagara Falls
Independent
2026AugSepOct
Independent

Discover the wonders of Niagara Falls on this 4-day rail adventure. Beginning and ending in New York City, travel aboard Amtrak's Maple Leaf for a full-day journey through upstate New York and into Ontario. Make the most of your two full days in Niagara Falls, enjoying the sights and sounds of the thundering falls and exploring the area's...

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4 days from
$795 pp $695 pp
per person
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Denali National Park wildlifeDenali National Park wildlifeDenali National Park wildlifeDenali National Park wildlifeDenali National Park wildlife
Alaska Wilderness Tour
Independent
Independent

Uncover scenic landscapes and quintessential sights of Alaska on this seven-day independent journey featuring the Denali Star. Travel from Anchorage to Talkeetna, where a jetboat takes you along the Talkeetna and Susitna Rivers, and then embark on a tundra wilderness tour in Denali National Park, with an expert guide revealing the best...

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7 days
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Jacobite Steam TrainJacobite Steam TrainJacobite Steam TrainJacobite Steam TrainJacobite Steam Train
Last Spaces for Summer
Edinburgh, the Highlands and Islands
4.4 stars(1072 reviews)
Escorted
2026AugSepOct
Escorted

Majestic lochs and glens await on this Scottish escape as we explore Edinburgh and cross the Highlands. Traveling on the scenic West Highland and Kyle rail lines, we discover historic castles, sail along glistening lochs, and stay in vibrant cities. Admire the iconic Glenfinnan Viaduct on the world-famous Jacobite Steam train journey...

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9 days from
$3,699 pp
per person
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Moraine Lake in BanffMoraine Lake in BanffMoraine Lake in BanffMoraine Lake in BanffMoraine Lake in Banff
Canadian Rockies by Rail
Independent
2026SepOct
Independent

Over 69,500 square miles of jagged peaks, emerald forests, and alpine lakes spread over two provinces await in the Canadian Rockies. Venture into the jaw-dropping scenery of Jasper National Park aboard VIA Rail's premier overnight train, the Canadian. On arrival, well-planned sightseeing in iconic Rocky Mountain locales, including Jasper and...

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7 days from
$2,795 pp $2,595 pp
per person
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California ZephyrCalifornia ZephyrCalifornia ZephyrCalifornia ZephyrCalifornia Zephyr
California Zephyr Experience
Independent
2026AugSepOctNovDec
Independent

Before embarking on your 2,300 mile journey to San Francisco, take advantage of your time in Chicago by visiting the city's famed attractions such as the John Hancock Observation Deck, ride the Ferris wheel at Navy Pier or window shop down The Magnificent Mile. The city also offers a rich cultural experience with its several museums and the...

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5 days from
$895 pp $795 pp
per person
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Bryce CanyonBryce CanyonBryce CanyonBryce CanyonBryce Canyon
Last Spaces
Great Parks of the Southwest featuring the Grand Canyon
4.7 stars(119 reviews)
Escorted
2026SepOct
Escorted

Discover the natural wonders and rugged wilderness of the Southwest on this scenic rail tour through Canyon Country. This tour has it all: amazing national parks, classic train journeys, and spectacular sightseeing and excursions. Your adventure begins in Chicago with a classic rail journey aboard the legendary California Zephyr to Grand...

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10 days from
$3,999 pp
per person
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Conway Scenic Railroad Conway Scenic Railroad Conway Scenic Railroad Conway Scenic Railroad Conway Scenic Railroad
Last Spaces
Fall Colors, Scenic Trains & Martha's Vineyard
Escorted
2026SepOct
Escorted

 The sites of yesteryear, iconic towns and delightful fall scenery set the backdrop for this New England adventure. Following an itinerary through Massachusetts, Maine, New Hampshire, Connecticut and Rhode Island, this journey presents some of the nation's best autumnal foliage in unforgettable settings. Explore by rail on the Conway Scenic...

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10 days from
$3,799 pp $3,499 pp
per person
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Montmorency Falls, CanadaMontmorency Falls, CanadaMontmorency Falls, CanadaMontmorency Falls, CanadaMontmorency Falls, Canada
Last Spaces
Highlights of French Canada and Nova Scotia
Escorted
2026Oct
Escorted

Eastern Canada's provinces draw the eye and capture the soul. Some of their best elements lie ahead as you explore French Canada's cities and the coastlines of Nova Scotia. In autumn, Canada's fiery fall foliage stands out against a bright blue sky, giving each destination a blazing backdrop. Spend time sightseeing and tasting your way...

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8 days from
$3,599 pp $3,299 pp
per person
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Glacier Parks Lakes and WildflowersGlacier Parks Lakes and WildflowersGlacier Parks Lakes and WildflowersGlacier Parks Lakes and WildflowersGlacier Parks Lakes and Wildflowers
Glacier National Park Escape - Chicago Roundtrip
Independent
Independent

Your two-night stay is in the heart of the unspoiled natural attractions and stunning beauty Glacier National Park. Wondrous displays of nature, historic lodges, and sightseeing through the forests and valleys of this complex ecosystem are highlights of your stay before returning by train to Chicago.

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5 days
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Our customers love our Vacations Under $5000 tours
Great Parks of the Southwest featuring the Grand Canyon
11/Jun
Harry Gregori
5 stars
“Great trip, staff and arrangements all excellent.
Collected by Trustpilot
New England in a Nutshell
06 Nov 2025
Suzanne Howze
5 stars
“Our tour guide was great! Also the trip was well thought out and well-organized. My only suggestion; please have people wear name tags. Please, please.
Collected by Trustpilot
Albuquerque Balloon Fiesta by Rail
27 Oct 2025
Michael Mefferd Jr
5 stars
“This was our first vacation out west and we found it very enjoyable. The scenery was spectacular and the towns were interesting. I loved Santa Fe and would like to visit again. The tour manager, bus driver and all the people on the bus were very friendly. There were some...
Collected by Trustpilot
Edinburgh, the Highlands and Islands
12/Jul
Avril
4 stars
“Very well organized tour and Martin our tour manager was excellent. Hotels services were good and the rooma in the main spacious. We would have liked air conditioning in some of the inner city hotels as the rooms were very stuffy. Choice of meals throughout the tour...
Collected by Trustpilot