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18 shown • 18 matching itineraries

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View of New York CityDesigned

AskTryps traveler

3-night New York City

This Midtown afternoon packs New York’s most recognizable civic landmarks into a walkable stretch where skyscraper drama meets elegant public spaces.

✦4 days · 2 adults

✦New York City

Priority

Romantic

Interest

Luxury / hotels

Food

Fine dining
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View of Cape MayDesignedPhoto source

AskTryps traveler

4-night Cape May

Cape May’s historic core is defined by its preserved Victorian streetscape, where shopping, sightseeing, and local history sit within an easy walk of one another.

✦5 days · 2 adults · 2 kids

✦Cape May

Priority

Shopping

Interest

Parks
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View of HonoluluDesigned

AskTryps traveler

5-night Honolulu

Waikiki Beach and Kalakaua Avenue are the classic Honolulu pairing, where oceanfront strolling meets polished resort energy.

✦6 days · 2 adults · 1 kid

✦Honolulu

Priority

Wellness

Interest

Beach

Food

Chinese
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View of PhiladelphiaDesigned

AskTryps traveler

2-night Philadelphia

Philadelphia’s Independence Mall and Old City concentrate the city’s founding story into a compact, walkable historic core.

✦3 days · 5 adults

✦Philadelphia

Priority

Shopping

Interest

Markets
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View of VancouverDesignedPhoto source

AskTryps traveler

3-night Vancouver

Granville Island blends a working market with waterfront arts, so this morning feels distinctly Vancouver rather than just another shopping stop.

✦4 days · 2 adults

✦Vancouver

Priority

Sports

Interest

Hiking

Food

Japanese
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View of ArubaDesignedPhoto source

AskTryps traveler

14-night Aruba

Aruba Aloe and Heritage Factory is a compact indoor stop that gives useful context for the island beyond its beaches.

✦15 days · 2 adults · 2 kids

✦Aruba

Priority

Scenic views

Interest

Beaches

Food

Mexican
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View of DenverDesigned

AskTryps traveler

7-night Denver

LoDo and Union Station show Denver at its most walkable, where restored brick warehouses, rail-era architecture, and lively plazas meet in one compact afternoon.

✦8 days · 2 adults · 2 kids

✦Denver

Priority

History

Interest

Museums

Food

Chinese
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View of MontrealDesignedPhoto source

AskTryps traveler

10-night Montreal

Downtown and the Golden Square Mile show Montréal at its most polished, where university buildings, major museums, and sleek towers sit within an easy urban stroll.

✦11 days · 2 adults

✦Montreal

Priority

Scenic views

Interest

Food

Food

Italian
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View of BermudaDesignedPhoto source

AskTryps traveler

7-night Bermuda

This morning is Bermuda at its most geologic, where a short drive leads underground into gleaming chambers and then back to surface attractions centered on nature and wildlife.

✦8 days · 2 adults · 2 kids

✦Bermuda

Priority

Outdoor

Interest

Historical sites

Food

Chinese
View itinerary Community trip
View of SeattleDesigned

AskTryps traveler

3-night Seattle

Pike Place and the central waterfront are Seattle’s most immediate visitor zone, with food stalls, harbor views, and pier-side attractions.

✦4 days · 2 adults

✦Seattle

Priority

Local neighborhoods

Interest

Food halls

Food

Seafood
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View of Cape MayDesignedPhoto source

AskTryps traveler

4-night Cape May

Cape May’s oceanfront is defined by its broad promenade, soft-sand beach, and the classic resort façade that frames the waterline.

✦5 days · 2 adults · 2 kids

✦Cape May

Priority

Family

Interest

Beaches
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View of San FranciscoDesigned

AskTryps traveler

3-night San Francisco

San Francisco’s waterfront begins with a blend of working-harbor history and postcard Bay views, making this one of the city’s most distinctive first looks.

✦4 days · 2 adults

✦San Francisco

Priority

Scenic views

Interest

Museums

Food

Japanese
View itinerary Community trip
View of PrincetonDesignedPhoto source

AskTryps traveler

3-night Princeton

Morven Museum and Princeton’s historic gardens give Princeton a stately, compact window into the town’s colonial and civic past.

✦4 days · 2 adults · 2 kids

✦Princeton

Priority

History

Interest

Parks

Food

Steakhouses
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View of Key WestDesignedPhoto source

AskTryps traveler

3-night Key West

Old Town Key West packs the island’s most recognizable 19th-century character into a compact, walkable afternoon of porches, palms, and lively streets.

✦4 days · 12 adults

✦Key West

Priority

Scenic views

Interest

Parks
View itinerary Community trip
View of Olympic National ParkDesignedPhoto source

AskTryps traveler

2-night Olympic National Park

This afternoon frames Olympic National Park at its most dramatic, moving from alpine overlooks to the gateway atmosphere in Port Angeles.

✦3 days · 2 adults

✦Olympic National Park

Priority

Culture

Interest

Beaches
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View of ChicagoDesigned

AskTryps traveler

3-night Chicago

This afternoon brings together Chicago’s signature museum core and its most recognizable public art, so the day feels both cultural and unmistakably urban.

✦4 days · 2 adults · 2 kids

✦Chicago

Interest

Zoos / aquariums
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View of Olympic National ParkDesignedPhoto source

AskTryps traveler

4-night Olympic National Park

This afternoon sets the tone for Olympic National Park with its alpine overlook country and the gateway feel of Port Angeles.

✦5 days · 2 adults

✦Olympic National Park

Priority

Beach

Interest

Parks

Food

Japanese
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View of Cape MayDesignedPhoto source

AskTryps traveler

7-night Cape May

Cape May’s beachfront day is defined by its wide, walkable shore and the gentle, resort-town rhythm of the promenade.

✦8 days · 2 adults · 2 kids

✦Cape May

Priority

Adventure

Interest

Luxury / hotels

Food

Chinese
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