This started as a way to plan trips with my wife, and it became the place I keep every itinerary, route, and venue list in one structured format. The pages here are the real plans, published the same way the rest of this site is built.

Destination Evaluation Methodology & 100-Point Grading Rubric

Every candidate destination is evaluated and scored against verified travel preferences and logistical constraints anchored at Cudahy, WI 53110:

30 Pts Max
Culinary & Beverage: High density of craft microbreweries (>=4.3 stars), artisan pizza and Italian dining, and chef-driven restaurants. Commercial chains and tourist traps incur a -5 pt penalty.
25 Pts Max
Sights & Unique Activities: Iconic natural landscapes, national parks, coastal bluffs, architectural landmarks, and distinctive experiential depth.
20 Pts Max
Logistics & Friction: Transit feasibility from Cudahy, WI: regional drive <= 400 miles (18-20 pts), non-stop flight from MKE (16-18 pts), or non-stop flight from ORD (14-16 pts). Connecting routes capped at 10-12 pts.
15 Pts Max
Lodging & Walkability: Pedestrian-friendly historic or downtown core (0-8 pts) and boutique hotels, luxury lodges, or upscale suites with kitchenettes (0-7 pts).
10 Pts Max
Seasonality & Climate: Historical weather comfort (60-80 F, low rain/humidity) during target calendar dates. Severe freeze or extreme heat (>95 F) incurs a -5 pt penalty.
+5 Pts Bonus
Dog Friendliness: Driveable destinations comfortably accommodating 4 dogs on outdoor trails, park grounds, and outdoor dining patios.
TIER 1 (90-100 Pts): Flagship Priority TIER 2 (80-89 Pts): High-Value Selected TIER 3 (70-79 Pts): Secondary Candidate
Showing all trips

Trips · Upcoming

Whitewater, WI 7-DAY · UPCOMING

UW-Whitewater Nature Preserve & Campus Prairie Walk (Single-Day Fall Outing)

Oct 25 - 25, 2026
Updated:
Day Trip
$38 to $52 per person
Door County, WI 7-WEEK · UPCOMING

Door County Holiday Quiet Season & Winter Wine Trail

Dec 22, 2026 - Jan 02, 2027
Updated:
12 Days / 11 Nights
$648 to $813 per person
Whitewater, East Troy & Elkhorn, WI 7-WEEK · UPCOMING

Nordic Winter Ski Trails & Alpine Valley Holiday Getaway

Dec 22, 2026 - Jan 02, 2027
Updated:
12 Days / 11 Nights
$422 to $514 per person
New Glarus & Green County, WI 7-WEEK · UPCOMING

New Glarus Swiss Holiday & Winter Getaway

Dec 22, 2026 - Jan 02, 2027
Updated:
12 Days / 11 Nights
$440 to $540 per person
Lake Geneva, WI 7-WEEK · UPCOMING

Lake Geneva Holiday Lights, Santa Cruise & New Year's Winter Getaway

Dec 22, 2026 - Jan 02, 2027
Updated:
12 Days / 11 Nights
$634 to $799 per person
Palm Springs, CA 7-WEEK · UPCOMING

Palm Springs & High Desert Winter Vacation Itinerary

Jan 13 - 16, 2027
Updated:
4 Days / 3 Nights
$796 to $936 per person
Whitewater, WI 7-DAY · UPCOMING

Natureland Park Winter Walk & Whitewater Indoor Market (Single-Day Winter Outing)

Feb 20 - 20, 2027
Updated:
Day Trip
$99 to $135 per person
Whitewater & Janesville, WI 7-DAY · UPCOMING

Ice Age Trail: Whitewater Lake Segment Winter Hike & Janesville Lunch (Single-Day Winter Outing)

Feb 26 - 26, 2027
Updated:
Day Trip
$92 to $135 per person
Orlando, FL 7-MONTH · UPCOMING

Walt Disney World Summer Nights & Skyliner Travel Guide

Jul 14 - 20, 2027
Updated:
7 Days / 6 Nights
$4,508 to $5,022 per person

Possible Suggested Destinations

Door County, WI TIER 1

Door County Autumn Harvest & Wine Trail Escape: Itinerary & Travel Guide

Sep 17 - 19, 2027
Updated:
3 Days / 2 Nights
$648 to $813 per person
Traverse City, MI TIER 1

Traverse City Summer Wine Trail & Coastal Dunes Getaway: Itinerary & Travel Guide

Jul 09 - 12, 2027
Updated:
4 Days / 3 Nights
$805 to $983 per person
Charleston, SC TIER 1

Charleston Spoleto Festival & Historic Lowcountry Architecture Tour: Itinerary & Travel Guide

May 26 - 30, 2028
Updated:
5 Days / 4 Nights
$1,530 to $1,890 per person
Washington, D.C. TIER 1

Washington D.C. Cherry Blossom Festival & National Mall Capital Tour: Itinerary & Travel Guide

Apr 06 - 09, 2029
Updated:
4 Days / 3 Nights
$1,158 to $1,453 per person
Savannah, GA TIER 1

Savannah Historic District & Coastal Lowcountry Spring Getaway: Itinerary & Travel Guide

Mar 18 - 22, 2027
Updated:
5 Days / 4 Nights
$1,380 to $1,730 per person
Austin, TX TIER 1

Austin City Limits Music & Hill Country Culinary Weekend: Itinerary & Travel Guide

Oct 08 - 12, 2027
Updated:
5 Days / 4 Nights
$1,500 to $1,860 per person
San Diego, CA TIER 1

San Diego Coastal Winter Escape & Balboa Park Promenade: Itinerary & Travel Guide

Jan 20 - 24, 2028
Updated:
5 Days / 4 Nights
$1,465 to $1,820 per person
Mackinac Island, MI TIER 1

Mackinac Island Lilac Festival & Historic Carriage Road Weekend: Itinerary & Travel Guide

Jun 09 - 12, 2028
Updated:
4 Days / 3 Nights
$903 to $1,088 per person
Sedona, AZ TIER 1

Sedona Red Rock Winter Sun & Oak Creek Canyon Getaway: Itinerary & Travel Guide

Feb 16 - 20, 2029
Updated:
5 Days / 4 Nights
$1,485 to $1,860 per person
Santa Fe, NM TIER 1

Santa Fe Historic Plaza, Pueblo Arts & Wine & Chile Fiesta Getaway: Itinerary & Travel Guide

Sep 28 - Oct 01, 2029
Updated:
4 Days / 3 Nights
$1,198 to $1,518 per person
Newport, RI TIER 2

Newport Oceanfront Gilded Age Mansions & Coastal Festival Weekend: Itinerary & Travel Guide

Jul 20 - 23, 2029
Updated:
4 Days / 3 Nights
$1,298 to $1,618 per person
Asheville, NC TIER 2

Asheville Blue Ridge Mountain Craft Beer & Autumn Foliage Getaway: Itinerary & Travel Guide

Oct 13 - 16, 2028
Updated:
4 Days / 3 Nights
$1,153 to $1,473 per person
Bar Harbor, ME TIER 2

Acadia National Park & Mount Desert Island Coastal Escape: Itinerary & Travel Guide

Aug 14 - 21, 2027
Updated:
8 Days / 7 Nights
$2,463 to $2,978 per person
Yellowstone National Park, WY TIER 2

Yellowstone & Grand Teton Wilderness Flagship Expedition: Itinerary & Travel Guide

Aug 11 - 17, 2028
Updated:
7 Days / 6 Nights
$2,050 to $2,525 per person
Grand Canyon National Park, AZ TIER 2

Grand Canyon South Rim & Colorado River Wilderness Expedition: Itinerary & Travel Guide

May 18 - 23, 2029
Updated:
6 Days / 5 Nights
$1,683 to $2,068 per person

Trips · 2026 Archive

Whitewater, WI ARCHIVE · 2026

Ice Age Trail: Blackhawk Segment & Lake La Grange Loop (Single-Day Fall Outing)

Oct 17 - 17, 2026
Updated:
Day Trip
$52 to $70 per person
Palmyra & Elkhorn, WI ARCHIVE · 2026

Ice Age Trail: Bald Bluff Overlook & Stone Elephant (Single-Day Fall Outing)

Oct 18 - 18, 2026
Updated:
Day Trip
$48 to $66 per person