Hotel
Begin serious lodging planning around September 2028 for the August 2029 trip.
Planning
Before you go
Use this as the practical checklist for booking, packing, reservations, groceries, transportation, internet, and arrival-day details.
Book Early
Reservation timeline
Trina's planning note is emphatic: decide how many days you want to stay and start saving early.
Film Festival
Plan for African American Film Festival passes well before the trip.
Flights & Ferry
Do not leave either transportation leg until the last minute.
Restaurants
Some dining reservations may need to be made far in advance.
Packing Checklist
What Trina says to bring
The checklist is only for convenience in your browser; it does not save to the website yet.
Food & Groceries
Stock up thoughtfully
- Consider getting groceries after getting off the ferry on the way to your hotel.
- Some food spots are cash only.
- Trina's notes suggest grocery prices may be better in Edgartown or Vineyard Haven than on Circuit Avenue in Oak Bluffs.
Internet
Do not rely on your signal
- Internet service can be unreliable and varies by location.
- Tell someone where you're going ahead of time so the group can still meet if signals fail.
Transportation
Have a backup plan
- The bus is described as dependable.
- Ubers may not be dependable.
- Some guests may rent bikes.
Reservations
Plan popular activities early
Make dining and activity reservations ahead of time whenever possible, especially during busy August dates.