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
$8,384
actual
Memorial Day weekend
May 22–24, 2026 · Long Island, NY
$937
actual
Surf Club / Dewey
Jun 10, 2026 · Dewey Beach, DE
$410
actual
2026 — upcoming & booked
Dewey Beach weekendbooked
Aug 20–22, 2026 · Dewey Beach, DE
$409 deposit paid (Surf Club) · est. $535 remaining
~$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
~$5,738
est. total
2026 — tentative
Avalon w/ Lindi's familytentative
July 2026 (TBD) · Avalon, NJ
~$450 share of house · ~$400 food/alcohol · ~$120 pet care · ~$130 activities & misc
~$1,100
est. total
Portland, Mainetentative
July 2026 (TBD) · Portland, ME
3 paid tickets + companion free (~$1,590) · 3 nights hotel ~$750 · food 4 days ~$600 · activities ~$200 · pet care ~$200
~$3,340
est. total
Fenwick Islandtentative
Jul 27–31, 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
~$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
~$6,750
est. (cash)
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~$1,100
Portland, Maine~$3,340
Fenwick Island~$2,250
NYE — Hyatt Chesapeake~$1,400
Tentative subtotal~$8,090
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