Every trip
Chronological2025 — completed
Rehoboth / Dewey Beach
Apr 1, 2025 · Rehoboth Beach, DE
$2,666
actual
Lewes / Rehoboth Beach
Jul 5–10, 2025 · Lewes & Rehoboth, DE
$1,217
actual
Las Vegas
Aug 10–17, 2025 · Las Vegas, NV
$5,441
actual
Dewey Beach house week
Aug 21–25, 2025 · Dewey Beach, DE
$1,359
actual
Ocean City, NJ
Sep 12–14, 2025 · NJ coast
$455
actual
Lewes / Dewey Christmas
Dec 17–21, 2025 · Lewes & Dewey, DE
$513
actual
NYE — Hyatt Chesapeake
Dec 30, 2025 – Jan 1, 2026 · Cambridge, MD
$1,382
actual
2026 — completed
Disney World
Mar 30 – Apr 4, 2026 · Orlando, FL
✈ SW AQ5G26 — 114,000 pts + $44.80$1,710 value
🏨 Hyatt Regency Grand Cypress — Hyatt points$3,022 cash rate · 5 nights
$8,384
actual
✦ 204k pts
~$4,730 saved
Memorial Day weekend
May 22–24, 2026 · Long Island, NY
$937
actual
2026 — upcoming & booked
Dewey Beach weekendbooked
Aug 20–22, 2026 · Dewey Beach, DE (Surf Club Oceanfront Hotel)
$409 deposit paid Jun 10 (Surf Club Confirmation #56208) · early booking discount applied · est. $535 remaining
🏨 Surf Club Oceanfront Hotel — $945 cashConf #56208 · $409 paid
$945
est. total
Turks & Caicosbooked
Sep 24–28, 2026 · Turks & Caicos
$1,320 paid (50% deposit on $2,640 accommodation) + $1,663 flights paid · est. $1,825 remaining
✈ AA NUYKOM — $1,663 cashAmEx ending 1007 · 2 pax + bags
🏠 Villa via Lindi — $2,640 est.$1,320 deposit paid
$5,738
est. total
2026 — tentative
Avalon w/ Lindi's familytentative
July 2026 (TBD) · Avalon, NJ
Lodging free · ~$400 food/alcohol · ~$120 pet care · ~$130 activities & misc
~$650
est. total
Portland, Mainetentative
Jul 5–9, 2026 · Portland, ME
3 paid tickets + companion free ($1,590) · 3 nights hotel $750 · food 4 days $600 · activities $200 · pet care $200
✈ SW BWI→PWM — $1,590 cash + companion freeestimate
🏨 Hotel — $750 est.3 nights
$3,340
est. total
✦ Companion pass
~$530 saved
Fenwick Islandtentative
Jul 25–30, 2026 · Fenwick Island, DE
Fenwick Shores Hilton or Airbnb condo (4 nights $1,500) · food/alcohol $500 · activities $100 · pet care $120 · parking $16/day
$2,250
est. total
NYE — Hyatt Chesapeaketentative
Dec 30, 2026 – Jan 1, 2027 · Cambridge, MD
Based on 2025 actual ($1,382) — same property, same format, no flights
$1,400
est. total
2027 — booked
Cooper's Bar Mitzvah — Long Islandbooked
Mar 12–14, 2027 · Long Island, NY
Hotel already paid · est. remaining: gas $60, dining 2 nights $300, Bar Mitzvah gift $200, incidentals $100
🏨 Hilton Garden Inn Roslyn — $488.94 cashConf #3475716570 · fully paid
$660
est. remaining
2027 — tentative
Spring Break — Baha Mar, Bahamastentative
Late March 2027 · Nassau, Bahamas (Grand Hyatt Baha Mar)
Flights BWI→NAS for 4 ~$1,800 · 5 nights hotel ~$3,500 cash (or points if availability opens) · food/excursions ~$1,200 · pet care ~$250 · Points redemption saves ~$3,500
✈ BWI→NAS — $1,800 est.4 passengers
🏨 Grand Hyatt Baha Mar — Hyatt pts (no availability yet)or $3,500 cash · 5 nights
$6,750
est. (cash)
✦ pts possible
saves ~$3,500
Where the money goes
Completed trips onlyFood & alcohol
$9,200
Activities
$4,085
Flights
$3,599
Accommodations
$2,421
Transport
$1,650
Pet care
$1,115
Shopping
$1,009
Year by year
2026 — booked & completed
Disney World$8,384
Memorial Day — Long Island$937
Surf Club / Dewey$410
Dewey Aug weekend (est.)$945
Turks & Caicos (est.)$5,738
Booked subtotal$16,414
2026 — tentative
Avalon, NJ~$650
Portland, Maine~$3,340
Fenwick Island~$2,250
NYE — Hyatt Chesapeake~$1,400
Tentative subtotal~$7,640
2027 — booked
Cooper's Bar Mitzvah (remaining)$660
Booked subtotal$660
2027 — tentative
Baha Mar, Bahamas (cash est.)$6,750
Baha Mar with Hyatt points$3,250
Tentative subtotal$6,750