Posted September 22, 2020
By NATALIE ABATEMARCO
NANTUCKET, Mass. — Because the island encompasses only 105 square miles, two days is a great amount of time to enjoy the beauty here. Just wandering the centuries-old streets and ending up at a waterfront eatery is a day well spent. A good amount of time in Nantucket can be spent just taking in the beauty it radiates on its own. Streets paved with aged stone lined by hydrangeas are what make up the magic of Nantucket. Known for being a quaint, isolated island with beautiful beaches surrounding its edges, Nantucket has evolved into a hotspot for travelers of all ages. Cobblestones and charming cottages are not the only attractions on the island; fantastic restaurants, gorgeous beaches, and bike trails are also important components of a stay in Nantucket. If you are visiting, be sure to bring lots of cash. Nantucket was settled in 1642, and the shops seem to remain in that era when it comes to credit card usage. I learned this the hard way.
Checking In, 12 p.m.
The best location to spend your 48 hours would be near Main Street, in the heart of the island. Hotel Pippa is one fantastic place to stay; it is a sleek modern “hotel” within a two-story house. Somehow, Hotel Pippa retains the classic Nantucket look while instilling a chic hint of 2020 right on the corner of Centre and Chestnut Streets. There are various places to stay in this vicinity that all give an old town feel to your trip.
Bike ride to Siasconset, 12 – 1 p.m.
If you’re feeling up for an adventure, the best way to see most of the island in a day (and an excuse to ditch your Peloton), would be to bike to Siasconset. A string of bike rentals can be found along Broad Street and Sea Street, which most likely open between 9 a.m.-10 a.m. As soon as you feel ready to take on the 8.3-mile ride to Siasconset, you should head to a rental station and be on your way! Be sure to pack your beach bag/towel, sunscreen, cash, and plenty of water for your journey. Depending on the weather, it can be a hot one. The bike rental shop will provide you with a map (if they don’t, ask for one). This will be your simple guide to Siasconset and will provide two routes you can choose from. Don’t worry, once you turn onto the bike path on Milestone Road, you will follow straight for miles.
Lunch at Claudette’s, 1 p.m.
Be sure to check out the Sconset Footbridge and wander past it to see the most adorable cottages on the island. You won’t get lost, so wander where you wish! Your journey will most likely warrant a snack or lunch. Head to Claudette’s Sandwich shop to reward yourself with a delicious sandwich of your choice. If you want to do it right, make sure you order the “House Sauce” on your sandwich, as well as “The Works.” You can thank me later.
Sconset Beach & Bluff Walk, 1 – 4 p.m.
After returning your bike rental and cleaning up, there are tons of places to reward yourself again for dinner. If you’re looking for views, Galley Beach is the way to go. Be sure to make a reservation ahead of time, these kinds of views are very popular. The restaurant is a chic take on Nantucket, beachfront, and allows you to dine with your toes in the sand. What could beat that? If Galley Beach is booked or not your style, you are bound to enjoy The Club Car or Brant Point Grill for different views and food.
Dinner at Galley Beach, 7 – 8 p.m.
If you’re feeling up for an adventure, the best way to see most of the island in a day (and an excuse to ditch your Peloton), would be to bike to Siasconset. A string of bike rentals can be found along Broad Street and Sea Street, which most likely open between 9-10. As soon as you feel ready to take on the 8.3-mile ride to Siasconset, you should head to a rental station and be on your way! Be sure to pack your beach bag/towel, sunscreen, cash and plenty of water. Depending on the weather, it can be a hot one! The bike rental shop will provide you with a map (if they don’t, ask for one). This will be your simple guide to Siasconset and will provide two routes you can choose from. Don’t worry, once you turn onto the bike path on Milestone Road, you will follow straight for miles!
Breakfast, 10 a.m.
After waking up to the crisp Nantucket air (not humid like most islands), head over to Provisions for a grab-and-go-breakfast. Day two may entail a bit of soreness in the legs after that 16-mile bike ride. If this is the case, catch the shuttle right outside of Force Five WaterSports on Washington Street to Surfside Beach. Linger on a bench right outside of the shop until the shuttle arrives and get off on the last stop. This should cost about $3, so be sure to have cash on hand to buy a ticket for the 10-minute ride.
Surfside Beach 11 a.m. – 3 p.m.
Enjoy a relaxing day at the family friendly Surfside Beach and treat yourself to a snack from the snack shack at the bus stop. Whether it be ice cream or a taco, the shack certainly provides during a hot day at the beach. Keep an eye on the shuttle schedule online to catch a shuttle back to Washington Street. These times vary seasonally but typically will leave you stranded after 5 p.m. If this is the case, it is only a 3.5-mile walk, and may just earn you your 10,000 steps for the day.
Browsing Nantucket, 5 – 7 p.m.
Spend the rest of the evening browsing the shops Nantucket has to offer before heading to eat at Breeze. There are tons of gift shops, boutiques and neat stores to check out before their early closing time. Be sure to grab some Nantucket garb and a souvenir knick-knack before heading to dinner.
Breakfast at Black-Eyed Susan’s, 8 a.m.
A must for visitors is to start the day right at Black Eyed Susan’s (10 India St., Nantucket, MA 02554). Enjoy a sourdough french toast with orange Jack Daniels butter (my personal favorite) or an omelet of any sort at the countertop (to see your breakfast in action). Although it opens at 7 a.m., the place is a true Nantucket restaurant, with only about eight tables in a small room. Waits can be quite long if you’re cranky and hungry after the clock strikes 9 a.m., so be sure to start the day as soon as possible! Due to COVID-19, there may be even less seating, so be sure to arrive before 9 a.m. to avoid a long wait.
An island stroll, 9 – 10 a.m.
Most other shops don’t open until around 10 a.m. as Nantucket does have the island time excuse. Use this time to familiarize yourself with the town. Start on Easton Street and make your way towards Main Street. This shouldn’t take long considering that the main town only covers about half of a mile. Feel free to wander and explore the aged buildings and amiable cabins.
If You Go
Plane or ferry ticket prices vary upon location and season (https://www.nantucket-ma.gov/891/Travel-by-Ferry), be sure to carry cash to get yourself from the airport to your hotel. This will most likely cost about $20. You can find a taxi lined up outside of the airport or wait for an Uber, which may take longer.
Expect to spend about $300 to $800 on your night stay at many of the hotels or inns. Prices will vary depending on season or location. Upscale options are available as well as bed and breakfasts. (Hotel Pippa https://hotelpippa.com)
The Nantucket Bike Shop (10 Broad St., Nantucket, MA 02554 and 37 Straight Wharf, Nantucket, MA 02554) has basic bike rentals for about $40 per day, but hourly rates are available upon request. You can call 800-770-3088 for more information or explore other rentals on the island.
Many restaurants for dinner time cost around $30-$50 for a meal. Keep this in mind during your stay. Breakfasts and lunches are available at small shops for cheap as well.
Beach entry is free at Sconset and Surfside Beach but bring cash to the Surfside Shack for a snack and enough money for the shuttle. ($3 each way). Short term passes are also available ($8 for 1-day). Check out https://nrtawave.com/ for more information.