Martha's Vineyard First Timers
 

Hi, Fodorites!
Hoping for help on a first trip to Martha's Vineyard. Nothing booked yet, but I know I have to hop to it. Sorry if I'm leaning too much here. My work has been crazy and I've found so little time to do research, so I thought I'd reach out to see if any experts here.
Some basics: Mother-daughter trip. 5 days/4 nights. In late Sept/early Oct. before 10/11 (Columbus Day). Flying in from Chicago. Don't want to rent a car but can--but definitely not wanting a car on MV. Mom is healthy, but at 79, her walks need occasional stops and bathroom breaks.

Questions:

1. PASSENGER FERRY: Anyone have a reco for which passenger ferry to take to MV? There seem to be several. This will inform our choice of airport. Hoping to fly in/out Boston (more flights, lower fares) but open to others.
2. ON THE ISLAND:
   1. Assuming Edgartown for a first timer but let me know. Looking for most convenience/easier walks to restaurants, shopping for my mom. And honestly, the only thing I really want is a well-made espresso in the morning.
   2. Hotel/B&B: I think I may have to book what's available, but any recos would be appreciated. Would be willing to pay up to $375/night.
   3. Restaurants: We love seafood and is top reason for New England. Is MV famous for any foods?
   4. Tourist Shopping: I've seen lots of 'black dog tavern' tee shirts in my life. Are there shops/restaurants that are long-established and loved by tourists?
   5. Local transportation/Day Tours: If we want to see other areas of the island, any recos for day tours? I believe there's a bus line, probably taxis, but I've not had time to delve into this yet.
   6. History: I'm an 18th-19th century history buff. Is there anything of historical interest on the island from this time?
   7. Beach: Any particular beach for an hour of ocean-gazing and an easy stroll?
   8. Weather: I believe the weather in late-Sept/early Oct should be fine. We're not swimming.
   9. Duration of stay/Side trip: If 4 days on MV is too much, I'd love any ideas for locations near the Ferry to break up the trip. Maybe a night somewhere in Cape Cod?

Thank you, Fodorites. So appreciate any suggestions.

Check Jet blue and Cape Air. They fly to the Vineyard. There also is a bus from Boston.

If you want to have a car there take the ferry from Woods Hole. I would guess that the costs for car rental and ferry might be the same as airfare and taxi/bus.

Thank you, oldemalloy. I appreciate your posting. I checked cape air, but not jet blue. That might be an option. The flights were twice as much as fares from chicago to boston. I might check out the TA forum; lots of activity there on MV.

I just for curiosity put in Oct 14-19 for BOS to MVY and while most fares were high, one was less tha n $100. Much less than car rental and ferry for two peoplle. I would grab it if it works for your dates.

Oh! That sounds great. Will have to look. I was lookign at before Columbus day/late sept, so maybe if I push back, fares may be better. Thank you!

You realize a good percentage of places will be closed. Flying in is good. Renting a car in MV is worth the money if only for 24 hours and have an adventure in Chappy and Gay Head. Or you could take bus to Woods Hole from Boston and stay a night at The Sands of Time before taking the ferry. This is a place I love. Basic Hotel/motel/inn no frills with a clean pool and rooms overlooking the ferries coming and going and the traffic that provides. Plus a stroll thru woods hole is always nice. Take the slow one and enjoy the ocean air. The fast ferries are nice if you've been an just want to arrive.

Edgartown is lovely with the aforementioned car ferry to Chappy. but OB has the gingerbread house/tabernackle community that you must take a stroll. I've stayed at The Kelly House over a decade ago as well as The big ocean front grande dame Harbour ,.......? And inns that have come and gone.

Depending on your lodging and transportation options, both rental and busses I think you would have enough exploring for 4 nights. I would. Just exploring the largest towns, Edgartown, Oak Bluffs and Vineyard Haven. I think a trip to the vineyard without a stop in Menemsha, Chappy and Gay Head. And if happening, the Tisbury Farmers/Crafts market and Chilmark Chocolates.

Good luck

Thank you, Inakauaidavidababy! I appreciate your posting. The idea of a lot of places being closed is a real deterrent. I'm going to have to research that on the tripadvisor forum and on google. If 70% of restaurants are closed, I'm going to have to rethink this. I had to go downtown for a hospital check up yesterday, and was shocked at how all my usual lunch places had gone out of business (no more Pret a Manger, Panera, Tazo cafe, etc.) My Lincoln Park neighborhood places had fared better. I know they couldn't afford to stay open with full service downtown, but somehow I held out hope that some of the larger chains would have had some skeleton presence, like catering/carryout, etc. If that happens in Chicago, where there were still a lot of essential businesses open, what must happen in a small place like MV?

But I do appreciate the information. Will be useful if we decide to go. And who knows what the delta variant will do come fall. My doctor told me to get all my medical checkups in asap because she fears for the unvaccinated with the covid variant being so contagious. Thanks, again!

And remember, there I always the chance that businesses will remain open longer then usual, if they have the help, to make up for some losses.
Shoulder season is disappearing as people like to travel in the off season.

Ferries - we have taken both the Steamship Authority out of Woods Hole, and the Island Queen out of Falmouth. If you are not taking a car, the Island Queen is much easier - a smaller ferry that leaves from Falmouth with a huge parking lot a few blocks away. It goes to Oak Bluffs, the most interesting town on the island. There is a nice beach right in town, as well as the gingerbread cottages, lots of shops and restaurants. We always brought our bikes (also easy to rent in town) and did the beautiful bike trail from Oak Bluffs to Edgartown - an easy jaunt along the sea, about 7 miles. With 4 nights, you could also spend a night or two in Falmouth, which has the longest beach frontage on the cape, as well as very picturesque Woods Hole. Lots of interesting restaurants and shops in Falmouth & Woods Hole as well as the picture perfect Nobska Lighthouse, SPOHR gardens, The Nob walking trail, and the Woods Hole Aquarium. Late Sept weather can be anything from 70's and sunny, to 50's and blustery, so be perepared - you might even be able to wade out into the sea. Falmouth is always busy, so I can't imagine many restaurants being closed - not sure about oak Bluffs and Edgartown. You can easily fill 4 days on MV and Falmouth!